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Anavar

PubChem CID
249098
Structure
Anavar_small.png
Molecular Formula
Synonyms
  • 53-39-4
  • Anavar
  • 17-epi-Oxandrolone
  • 1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one
  • 17-.beta.-hydroxy-17-methyl-2-oxa-androstan-3-one
Molecular Weight
306.4 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-02-01
Description
A synthetic hormone with anabolic and androgenic properties.
See also: Oxandrolone (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Anavar.png

1.2 3D Status

Conformer generation is disallowed since too many undefined stereo centers

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C19H30O3/c1-17-11-22-16(20)10-12(17)4-5-13-14(17)6-8-18(2)15(13)7-9-19(18,3)21/h12-15,21H,4-11H2,1-3H3
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

QSLJIVKCVHQPLV-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

CC12CCC3C(C1CCC2(C)O)CCC4C3(COC(=O)C4)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C19H30O3
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 CAS

53-39-4

2.3.2 European Community (EC) Number

2.3.3 NSC Number

2.3.4 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Anavar
  • Oxandrin
  • Oxandrolone
  • SC 11585
  • SC-11585
  • SC11585

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
306.4 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
3.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
306.21949481 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
306.21949481 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
46.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
22
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
503
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
7
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

3.2 Experimental Properties

3.2.1 Color / Form

Crystals
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1239
Crystallized from 2-propanol
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 10th ed. Volumes 1-3 New York, NY: John Wiley & Sons Inc., 1999., p. 257
WHITE, CRYSTALLINE POWDER
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 931

3.2.2 Odor

ODORLESS
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 931

3.2.3 Melting Point

235-238 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1239

3.2.4 Solubility

PRACTICALLY INSOL IN WATER; SPARINGLY SOL IN ALC, ACETONE; FREELY SOL IN CHLOROFORM
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 931

3.2.5 Stability / Shelf Life

Stable in air but darkens when exposed to light
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 931

3.2.6 Optical Rotation

Specific optical rotation: -23 deg at 25 °C/D
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1239

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 5
View All
NIST Number
352198
Library
Main library
Total Peaks
244
m/z Top Peak
71
m/z 2nd Highest
43
m/z 3rd Highest
93
Thumbnail
Thumbnail
2 of 5
View All
NIST Number
123945
Library
Replicate library
Total Peaks
42
m/z Top Peak
43
m/z 2nd Highest
71
m/z 3rd Highest
81
Thumbnail
Thumbnail

4.2 UV Spectra

Max absorption: 2.87 nm; 5.79 nm
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 898

6 Chemical Vendors

7 Drug and Medication Information

7.1 Therapeutic Uses

Anabolic Steroids
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
Oxandrolone ... /is/ indicated in conditions such as chronic infections, extensive surgery, (corticosteroid-induced myopathy, decubitus ulcers, burns, /NOT included in US product labeling/) or severe trauma, which require reversal of catabolic processes or protein-sparing effects. /This agent is/ ... adjunct to, and not replacement for, conventional treatment of these disorders. /Included in US product labeling/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 140
Oxandrolone is used in the treatment of the short stature that accompanies Turner's syndrome (gonadal dysgenesis in females). Although the therapy is controversial, recent experimental reports seem to indicate that oxandrolone may be as effective as growth hormone and that oxandrolone may increase the efficacy of growth hormone therapy. /NOT included in US product labeling/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 140
Anabolic steroids may be used in children as an adjunct in the treatment of growth failure caused by pituitary growth hormone (GH) deficiency (pituitary dwarfism) or if the response to human growth hormone administration is inadequate. /Anabolic steroids; NOT included in US product labeling/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 140
For more Therapeutic Uses (Complete) data for OXANDROLONE (6 total), please visit the HSDB record page.

7.2 Drug Warnings

Peliosis hepatis, a condition in which liver and sometimes splenic tissue is replaced with blood-filed cysts, has occurred in patients receiving androgenic anabolic steroids. These cysts are sometimes present with minimal hepatic dysfunction and have been associated with liver failure. They are often not recognized until life-threatening liver failure or intro-abdominal hemorrhage develops. Withdrawal of drug usually results in complete disappearance of lesions. /Anabolic steroids/
Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 334
Liver cell tumors: Most often these tumors are benign and androgen-dependent, but fatal malignant tumors have occurred. Withdrawal of drug often results in regression or cessation of tumor progression. However, hepatic tumors associated with androgens or anabolic steroids are much more vascular than other hepatic tumors and may be silent until life-threatening intra-abdominal hemorhage develops. /Anabolic steroids/
Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 324
Use of anabolic steroids by athletes is not recommended. Objective evidence is conflicting and inconclusive as to whether these medications significantly increase athletic performance by increasing muscle strength. Weight gains reported by athletes are due in part to fluid retention, which is a potentially hazardous side effect of anabolic steroid therapy. The risk of other unwanted effects, such as testicular atrophy and suppression of spermatogenesis in males; menstrual disturbances and virilization, such as deepening of voice, development of acne, and unnatural growth of body hair in females; peliosis hepatis or other hepatotoxicity; and hepatic cancer outweigh and possible benefit received from anabolic steroids and make their use in athletes inappropriate. /Anabolic steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 140
Anabolic steroids are not recommended for use during pregnancy, since studies in animals have shown that anabolic steroids cause masculinization of the fetus. Risk-benefit must be carefully considered. /Anabolic steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141
For more Drug Warnings (Complete) data for OXANDROLONE (22 total), please visit the HSDB record page.

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Androgens
Compounds that interact with ANDROGEN RECEPTORS in target tissues to bring about the effects similar to those of TESTOSTERONE. Depending on the target tissues, androgenic effects can be on SEX DIFFERENTIATION; male reproductive organs, SPERMATOGENESIS; secondary male SEX CHARACTERISTICS; LIBIDO; development of muscle mass, strength, and power. (See all compounds classified as Androgens.)
Anabolic Agents
These compounds stimulate anabolism and inhibit catabolism. They stimulate the development of muscle mass, strength, and power. (See all compounds classified as Anabolic Agents.)

8.2 Absorption, Distribution and Excretion

It is not known whether anabolic steroids are distributed into breast milk. /Anabolic steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141

8.3 Metabolism / Metabolites

The metabolism of 17 alpha-methyl-17 beta-hydroxy-2-oxa-5 alpha-androstan-3-one (oxandrolone) in man has been investigated by gas chromatography/mass spectrometry. After oral administration of a 10 mg dose to man, five metabolites were detected in the free fraction of the urinary samples. Oxandrolone, the major compound excreted in urine, was detected within 72 hr after administration. During this period 35.8 and 8.4% of the administered dose was excreted as unchanged oxandrolone and 17-epioxandrolone, respectively. In addition, minute amounts of 16 alpha- and 16 beta-hydroxyoxandrolone and a delta-hydroxy acid resulting from the hydrolysis of the lactone group of oxandrolone were detected in the urine samples 8-60 hr after administration.
Masse R et al; Biomed Environ Mass Spectrom 18 (6): 429-38 (1989)

8.4 Biological Half-Life

Biphasic: 1st phase - 0.55 hours. 2nd phase - 9 hours.
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141

8.5 Mechanism of Action

Reverses catabolic processes and negative nitrogen balance by promoting protein anabolism and stimulating appetite if there is concurrently a proper intake of calories and proteins. /Anabolic steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141
There was abs decrease in total serum cholesterol and redistribution of cholesterol, such that post-treatment low-density lipoprotein carried less cholesterol and high-density lipoprotein more cholesterol on percentage basis than found in pre-treatment values with oxandrolone.
FREEMAN MW ET AL; J GERONTOL 35(1) 31 (1980)

9 Use and Manufacturing

9.1 Uses

Use for weight gain after surgery, chronic illness or trauma
Physicians Desk Reference. 59th ed. Thomson PDR. Montvale, NJ 2005., p. 3019
Androgen
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 2001
MEDICATION

Use (kg) in USA (2002): 29

Consumption (g per capita) in the USA (2002): 0.000101

Calculated removal (%): 49.5

9.2 Methods of Manufacturing

Pappo, US 3128283 (1964 to Searle)
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1239
Methyldihydrotesterone is converted into corresponding 1,2-dehydro compound by bromination followed by dehydrobromination. Ring a is then ruptured through ozonization & subsequent hydrolysis to yield aldehyde-acid. Reduction of formyl group ... yields expected hydroxy acid ...which is lactonized to oxandrolone.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 931

9.3 Formulations / Preparations

Oxandrolone, NF, Anavar, tablets: 2.5 mg; oral: 5 to 10 mg daily /From Table/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1463

9.4 General Manufacturing Information

While data specific to oxandrolone were not available(SRC, 2005), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2).
(1) Heberer T; Tox Lett 131: 5-17 (2002)
(2) Koplin DW et al; Environ Sci Toxicol 36: 1202-211 (2002)
... Introduced primarily for use as anabolic agents with expectation that they would be relatively less androgenic than testosterone & its close relatives. None is free of androgenic activity in man, & in many instances androgenicity is much greater than results of animal tests had predicted. /Anabolic Steroids/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1459
Although not strictly speaking a steroid, its configuration is that of 17-methyl androgenic steroid. Its anabolic actions are strong relative to its androgenic actions.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 931
This is a controlled substance (anabolic steroid)... .
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1239
For more General Manufacturing Information (Complete) data for OXANDROLONE (6 total), please visit the HSDB record page.

10 Identification

10.1 Analytic Laboratory Methods

Analyte: oxandrolone; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards
U.S. Pharmacopeia. The United States Pharmacopeia, USP 28/The National Formulary, NF 23; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p1426 (2005)
Analyte: oxandrolone; matrix: chemical identification; procedure: thin-layer chromatography with comparison to standards
U.S. Pharmacopeia. The United States Pharmacopeia, USP 28/The National Formulary, NF 23; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p1426 (2005)
Analyte: oxandrolone; matrix: chemical purity; procedure: titration with potassium iodate
U.S. Pharmacopeia. The United States Pharmacopeia, USP 28/The National Formulary, NF 23; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p1426 (2005)
Analyte: oxandrolone; matrix: pharmaceutical preparation (tablets); procedure: thin-layer chromatography with comparison to standards (chemical identification)
U.S. Pharmacopeia. The United States Pharmacopeia, USP 28/The National Formulary, NF 23; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p1427 (2005)
Analyte: oxandrolone; matrix: pharmaceutical preparation (tablets); procedure: infrared absorption spectrophotometry with comparison to standards (chemical purity)
U.S. Pharmacopeia. The United States Pharmacopeia, USP 28/The National Formulary, NF 23; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p1427 (2005)

10.2 Clinical Laboratory Methods

Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry. All steroids within the study could be selectively detected in urine with detection limits of 0.1-2.0 ng/ml.
Leinonen A et al; Steroids 69 (2): 101-9 (2004)
Screening of anabolic steroids /including oxandrolone/ in horse urine by liquid chromatography-tandem mass spectrometry.
Yu NH et al; J Pharm Biomed Anal 37 (5): 1031-8 (2005)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Note
Pictograms displayed are for 98.3% (58 of 59) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 1.7% (1 of 59) of reports.
Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H312 (96.6%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H332 (96.6%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H351 (30.5%): Suspected of causing cancer [Warning Carcinogenicity]

H360 (94.9%): May damage fertility or the unborn child [Danger Reproductive toxicity]

Precautionary Statement Codes

P203, P261, P271, P280, P302+P352, P304+P340, P317, P318, P321, P362+P364, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 59 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 1 of 59 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 4 notifications provided by 58 of 59 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Acute Tox. 4 (96.6%)

Acute Tox. 4 (96.6%)

Carc. 2 (30.5%)

Repr. 1B (94.9%)

11.2 Accidental Release Measures

11.2.1 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

11.3 Regulatory Information

11.3.1 FDA Requirements

Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule III shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation containing any quantity of the following substances, including its salts, isomers, and salts of isomers whenever the existence of such salts of isomers is possible within the specific chemical designation. DEA Code #: 4000; Drug class: anabolic steroids.
21 CFR 1308.13(f); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 1, 2005: https://www.ecfr.gov
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl oxandrolone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
DHHS/FDA; Electronic Orange Book-Approved Drug Products with Therapeutic Equivalence Evaluations. Available from, as of June 1, 2005: https://www.fda.gov/cder/ob/

12 Toxicity

12.1 Toxicological Information

12.1.1 Toxicity Summary

IDENTIFICATION: Oxandrolone is an anabolic steroid for systemic use. Origin of the substance: Naturally-occurring anabolic steroids are synthesized in the testis, ovary and adrenal gland from cholesterol via pregnenolone. Synthetic anabolic steroids are based on the principal male hormone testosterone, modified in one of three ways: alkylation of the 17-carbon; esterification of the 17-OH group and modification of the steroid nucleus. This steroid is a white solid crystalline material. It is soluble in water, alcohol, acetone, chloroform and ether. The only legitimate therapeutic indications for anabolic steroids are: (a) replacement of male sex steroids in men who have androgen deficiency, for example as a result of loss of both testes; (b) the treatment of certain rare forms of aplastic anemia which are or may be responsive to anabolic androgens. (c) the drugs have been used in certain countries to counteract catabolic states, for example after major trauma. HUMAN EXPOSURE: Main risks and target organs: The main risks are those of excessive androgens: menstrual irregularities and virilization in women and impotence, premature cardiovascular disease and prostatic hypertrophy in men. Both men and women can suffer liver damage with oral anabolic steroids containing a substituted 17-alpha-carbon. Psychiatric changes can occur during use or after cessation of these agents. Summary of clinical effects: Acute overdosage can produce nausea and gastrointestinal upset. Chronic usage is thought to cause an increase in muscle bulk, and can cause an exaggeration of male characteristics and effects related to male hormones. Anabolic steroids can influence sexual function. They can also cause cardiovascular and hepatic damage. Acne and male-pattern baldness occur in both sexes; irregular menses, atrophy of the breasts, and clitoromegaly in women; and testicular atrophy and prostatic hypertrophy in men. Contraindications: Known or suspected cancer of the prostate or (in men) breast. Pregnancy or breast feeding or known cardiovascular disease is a relative contraindication. Routes of exposure: Oral: Anabolic steroids can be absorbed from the gastrointestinal tract, but many compounds undergo such extensive first-pass metabolism in the liver that they are inactive. Those compounds in which substitution of the 17-carbon protects the compound from the rapid hepatic metabolism are active orally. There are preparations of testosterone that can be taken sublingually. Parenteral: Intramuscular or deep subcutaneous injection is the principal route of administration of all the anabolic steroids except the 17-alpha-substituted steroids which are active orally. Absorption by route of exposure: The absorption after oral dosing is rapid for testosterone and probably for other anabolic steroids, but there is extensive first-pass hepatic metabolism for all anabolic steroids except those that are substituted at the 17-alpha position. The rate of absorption from subcutaneous or intramuscular depots depends on the product and its formulation. Absorption is slow for the lipid-soluble esters such as the cypionate or enanthate, and for oily suspensions. Distribution by route of exposure: The anabolic steroids are highly protein bound, and is carried in plasma by a specific protein called sex-hormone binding globulin. Biological half-life by route of exposure: The metabolism of absorbed drug is rapid, and the elimination half-life from plasma is very short. The duration of the biological effects is therefore determined almost entirely by the rate of absorption from subcutaneous or intramuscular depots, and on the de-esterification which precedes it. Metabolism: Free (de-esterified) anabolic androgens are metabolized by hepatic mixed function oxidases. Elimination by route of exposure: After administration of radiolabelled testosterone, about 90% of the radioactivity appears in the urine, and 6% in the feces; there is some enterohepatic recirculation. Mode of action: Toxicodynamics: The toxic effects are an exaggeration of the normal pharmacological effects. Pharmacodynamics: Anabolic steroids bind to specific receptors present especially in reproductive tissue, muscle and fat. The anabolic steroids reduce nitrogen excretion from tissue breakdown in androgen deficient men. They are also responsible for normal male sexual differentiation. The ratio of anabolic body-building effects to androgenic (virilizing) effects may differ among the members of the class, but in practice all agents possess both properties to some degree. There is no clear evidence that anabolic steroids enhance overall athletic performance. Carcinogenicity: Precocious prostatic cancer has been described after long-term anabolic steroid abuse. Cases where hepatic cancers have been associated with anabolic steroid abuse have been reported. Teratogenicity: Androgen ingestion by a pregnant mother can cause virilization of a female fetus. Main adverse effects: The adverse effects of anabolic steroids include weight gain, fluid retention, and abnormal liver function as measured by biochemical tests. Administration to children can cause premature closure of the epiphyses. Men can develop impotence and azoospermia. Women are at risk of virilization. Acute poisoning: Ingestion: Nausea and vomiting can occur. Parenteral exposure: Patients are expected to recover rapidly after acute overdosage, but there are few data. Body-builders use doses many times the standard therapeutic doses for these compounds but do not suffer acute toxic effects. Chronic poisoning: Ingestion: Hepatic damage, manifest as derangement of biochemical tests of liver function and sometimes severe enough to cause jaundice; virilization in women; prostatic hypertrophy, impotence and azoospermia in men; acne, abnormal lipids, premature cardiovascular disease (including stroke and myocardial infarction), abnormal glucose tolerance, and muscular hypertrophy in both sexes; psychiatric disturbances can occur during or after prolonged treatment. Parenteral exposure: Virilization in women; prostatic hypertrophy, impotence and azoospermia in men; acne, abnormal lipids, premature cardiovascular disease (including stroke and myocardial infarction), abnormal glucose tolerance, and muscular hypertrophy in both sexes. Psychiatric disturbances can occur during or after prolonged treatment. Hepatic damage is not expected from parenteral preparations. Course, prognosis, cause of death: Patients with symptoms of acute poisoning are expected to recover rapidly. Patients who persistently abuse high doses of anabolic steroids are at risk of death from premature heart disease or cancer, especially prostatic cancer. Non-fatal but long lasting effects include voice changes in women and fusion of the epiphyses in children. Other effects are reversible over weeks or months. Systematic description of clinical effects: Cardiovascular: Chronic ingestion of high doses of anabolic steroids can cause elevations in blood pressure, left ventricular hypertrophy and premature coronary artery disease. Neurological: Central nervous system: Stroke has been described in a young anabolic steroid abuser. Mania and psychotic symptoms of hallucination and delusion have been described in anabolic steroid abusers. They also described depression after withdrawal from anabolic steroids. There is also considerable debate about the effects of anabolic steroids on aggressive behavior and on criminal behavior. Mood swings were significantly more common in normal volunteers during the active phase of a trial comparing methyltestosterone with placebo. Gastrointestinal: Acute ingestion of large doses can cause nausea and gastrointestinal upset. Hepatic: Orally active (17-alpha substituted) anabolic steroids can cause abnormalities of hepatic function, manifest as abnormally elevated hepatic enzyme activity in biochemical tests of liver function, and sometimes as overt jaundice. The histological abnormality of peliosis hepatis has been associated with anabolic steroid use. Angiosarcoma and a case of hepatocellular carcinoma in an anabolic steroid user has been reported. Urinary: Men who take large doses of anabolic steroids can develop prostatic hypertrophy. Prostatic carcinoma has been described in young men who have abused anabolic steroids. Endocrine and reproductive systems: Small doses of anabolic steroids are said to increase libido, but larger doses lead to azoospermia and impotence. Testicular atrophy is a common clinical feature of long-term abuse of anabolic steroids, and gynecomastia can occur. Women develop signs of virilism, with increased facial hair, male pattern baldness, acne, deepening of the voice, irregular menses and clitoral enlargement. Eye, ear, nose, throat: local effects: Changes in the larynx in women caused by anabolic steroids can result in a hoarse, deep voice. The changes are irreversible. Hematological: Anabolic androgens stimulate erythropoiesis. Metabolic: Fluid and electrolyte disturbances: Sodium and water retention can occur, and result in edema; hypercalcemia is also reported. Insulin resistance with a fall in glucose tolerance, and hypercholesterolemia with a fall in high density lipoprotein cholesterol, have been reported.
International Programme on Chemical Safety; Poisons Information Monograph: Oxandrolone (PIM 913) (1998) Available from, as of April 7, 2009: https://www.inchem.org/pages/pims.html

12.1.2 Interactions

Anticoagulant effect may be increased during concurrent use with anabolic steroids, especially 17-alpha-alkylated compounds, because of decreased procoagulant factor concentration caused by alteration of procoagulant factor synthesis or catabolism and increased receptor affinity for the anticoagulant; anticoagulant dosage adjustment based on prothrombin time determinations may be required during and following concurrent use. /Anabolic steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141
Anabolic steroids may decrease blood glucose concentrations; diabetic patients should be closely monitored for signs of hypoglycemia and dosage of hypoglycemic agent adjusted as necessary. /Anabolic steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141
Concurrent use /of glucocorticoid corticosteroids, especially with significant mineralocorticoid activity; mineralocorticoid corticosteroids; corticotropin, especially prolonged therapeutic use; or sodium-containing medications or foods/ with anabolic steroids may increase the possibility of edema; in addition, concurrent use of glucocorticoids or corticotropin with anabolic steroids may promote development of severe acne. /Anabolic steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141
Concurrent use of anabolic steroids with somatrem or somatropin may accelerate epiphyseal maturation. /Anabolic steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141
For more Interactions (Complete) data for OXANDROLONE (6 total), please visit the HSDB record page.

12.1.3 Antidote and Emergency Treatment

Treatment of overdose is symptomatic and supportive. To decrease absorption: In acute oral overdose, decontamination includes induced emesis and/or gastric lavage. Monitoring: Hepatic function. ... /Anabolic steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 143
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 139
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 139

12.1.4 Human Toxicity Excerpts

/CASE REPORTS/ Liver cell tumors have been reported in patients receiving long-term therapy with androgenic anabolic steroids in high doses. Withdrawl of the drugs did not lead to regression of the tumors in all cases.
Physicians Desk Reference. 59th ed. Thomson PDR. Montvale, NJ 2005., p. 3020

12.1.5 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ In 2-year chronic oral rat studies, a dose related reduction of spermatogenesis and decreased organ weights (testes, prostate, seminar vesicles, ovaries, uterus, adrenals, and pituitary) were shown.
Physicians Desk Reference. 59th ed. Thomson PDR. Montvale, NJ 2005., p. 3020
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Animal studies have ... shown oxandrolone to cause embryotoxicity, fetotoxicity, and infertility, in addition to masculinization in offspring of animals receiving 9 times the human dose.
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141

12.1.6 Populations at Special Risk

Anabolic steroids are not recommended for use during pregnancy, since studies in animals have shown that anabolic steroids cause masculinization of the fetus. Risk-benefit must be carefully considered. /Anabolic steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141
Anabolic steroids should be used with caution in children and adolescents and only by specialists who are aware of their effects on bone maturation because of possible premature epiphyseal closure, precocious sexual development in males, and virilization in females. The epiphyseal maturation may be accelerated more rapidly than linear growth in children, and the effect may continue for 6 months after the medication has been discontinued. /Anabolic Steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141
Anabolic steroids may decrease blood glucose concentrations; diabetic patients should be closely monitored for signs of hypoglycemia and dosage of hypoglycemic agent adjusted as necessary. /Anabolic steroids/
Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141

12.2 Ecological Information

12.2.1 Environmental Fate / Exposure Summary

Oxandrolone's production and use for weight gain after surgery, chronic illness or trauma and as an androgen may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 4.7X10-10 mm Hg at 25 °C indicates oxandrolone will exist solely in the particulate phase in the atmosphere. Particulate-phase oxandrolone will be removed from the atmosphere by wet and dry deposition. Oxandrolone does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, oxandrolone is expected to have low mobility based upon an estimated Koc of 1,800. Volatilization from water or moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.3X10-8 atm-cu m/mole. Oxandrolone is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not available. If released into water, oxandrolone is expected to adsorb to suspended solids and sediment based upon the estimated Koc. An estimated BCF of 19 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to oxandrolone may occur through dermal contact with this compound at workplaces where oxandrolone is produced or used. Exposure to the drug among the general population may be limited to those taking oxandrin (a weight enhancer) that contains oxandrolone or those taking oxandrolone (an androgen) for performance enhancement. (SRC)

12.2.2 Artificial Pollution Sources

Oxandrolone's production and use for weight gain after surgery, chronic illness or trauma(1) and as an androgen(2) may result in its release to the environment through various waste streams(SRC).
(1) PDR; Physicians' Desk Reference. 59nd ed. Montvale, NJ: Medical Economics Co. p. 3019 (2005)
(2) O'Neil MJ, ed; The Merck Index. 13th ed. Whitehouse Station, NJ: Merck and Co., Inc. p. 1239 (2001)

12.2.3 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,800(SRC), determined from a structure estimation method(2), indicates that oxandrolone is expected to have low mobility in soil(SRC). Volatilization of oxandrolone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.3X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Oxandrolone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.7X10-10 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(4) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,800(SRC), determined from a structure estimation method(2), indicates that oxandrolone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.3X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 19(SRC), from an estimated log Kow of 2.6(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990)
(4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(7) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), oxandrolone, which has an estimated vapor pressure of 4.7X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase oxandrolone may be removed from the air by wet and dry deposition(SRC). Oxandrolone does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)

12.2.4 Environmental Abiotic Degradation

Oxandrolone is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(1). Oxandrolone does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5 (1990)

12.2.5 Environmental Bioconcentration

An estimated BCF of 19 was calculated for oxandrolone(SRC), using an estimated log Kow of 2.6(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

12.2.6 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of oxandrolone can be estimated to be 1,800(SRC). According to a classification scheme(2), this estimated Koc value suggests that oxandrolone is expected to have low mobility in soil.
(1) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(2) Swann RL et al; Res Rev 85: 17-28 (1983)

12.2.7 Volatilization from Water / Soil

The Henry's Law constant for oxandrolone is estimated as 2.3X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that oxandrolone is expected to be essentially nonvolatile from moist soil(SRC) and water surfaces(2). Oxandrolone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.7X10-10 mm Hg(SRC), determined from a fragment constant method(3).
(1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)

12.2.8 Probable Routes of Human Exposure

Occupational exposure to oxandrolone may occur through dermal contact with this compound at workplaces where oxandrolone is produced or used. Exposure to the drug among the general population may be limited to those taking oxandrin (a weight enhancer) that contains oxandrolone or those taking oxandrolone (an androgen) for performance enhancement. (SRC)

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Chemical Co-Occurrences in Literature

13.4 Chemical-Gene Co-Occurrences in Literature

13.5 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 UN GHS Classification

16.3 NORMAN Suspect List Exchange Classification

17 Information Sources

  1. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  2. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  3. Hazardous Substances Data Bank (HSDB)
  4. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    OXANDROLONE
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  5. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  6. SpectraBase
  7. Wikidata
  8. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  9. PubChem
  10. GHS Classification (UNECE)
  11. NCBI
CONTENTS