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Oncovin

PubChem CID
5388992
Structure
Oncovin_small.png
Molecular Formula
Synonyms
  • Vincristine sulfate
  • 2068-78-2
  • Vincristine sulfate salt
  • Oncovin
  • Vincristine sulphate
Molecular Weight
923.0 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Parent Compound
Dates
  • Create:
    2005-06-29
  • Modify:
    2024-12-06
Description
Vincristine Sulfate can cause developmental toxicity according to state or federal government labeling requirements.
Vincristine sulfate appears as an anticancer drug. White to slightly yellow, amorphous or crystalline powder. Sensitive to light. Odorless. pH (0.1% solution) 3.5 - 4.5. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Vincristine Sulfate is the sulfate salt of a natural alkaloid isolated from the plant Catharanthus roseus (Vinca rosea L.) with antimitotic and antineoplastic activities. Vincristine binds irreversibly to microtubules and spindle proteins in S phase of the cell cycle and interferes with the formation of the mitotic spindle, thereby arresting tumor cells in metaphase. This agent also depolymerizes microtubules and may also interfere with amino acid, cyclic AMP, and glutathione metabolism; calmodulin-dependent Ca(2+)-activated ATPase activity; cellular respiration; and nucleic acid and lipid biosynthesis.
See also: Vincristine Sulfate (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Oncovin.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, mixture or salt

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate;sulfuric acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C46H56N4O10.H2O4S/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6;1-5(2,3)4/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3;(H2,1,2,3,4)/t28-,37-,38+,39+,42-,43+,44+,45-,46-;/m0./s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

AQTQHPDCURKLKT-PNYVAJAMSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC[C@@]1(C[C@H]2C[C@@](C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O.OS(=O)(=O)O
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C46H56N4O10.H2O4S
C46H58N4O14S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2068-78-2

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 UN Number

2.3.5 ChEMBL ID

2.3.6 KEGG ID

2.3.7 NCI Thesaurus Code

2.3.8 RXCUI

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • cellcristin
  • Citomid
  • Farmistin
  • Leurocristine
  • Oncovin
  • Oncovine
  • Onkocristin
  • PFS, Vincasar
  • Sulfate, Vincristine
  • Vincasar
  • Vincasar PFS
  • Vincristin Bristol
  • Vincristin medac
  • Vincristine
  • Vincristine Sulfate
  • Vincrisul
  • Vintec

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
923.0 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
16
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
922.36702371 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
922.36702371 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
254Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
65
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1830
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
9
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
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
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Vincristine sulfate appears as an anticancer drug. White to slightly yellow, amorphous or crystalline powder. Sensitive to light. Odorless. pH (0.1% solution) 3.5 - 4.5. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

3.2.2 Melting Point

531 °F approximately (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

3.2.3 Solubility

greater than or equal to 10 mg/mL at 75 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Antimitotic Agents
Human drug -> Discontinued; Active ingredient (VINCRISTINE SULFATE)
Human drug -> Discontinued

4 Spectral Information

4.1 IR Spectra

4.1.1 FTIR Spectra

Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
217980
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Classes

Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Antimitotic Agents

7.2 FDA Approved Drugs

7.3 FDA Orange Book

7.4 FDA National Drug Code Directory

7.5 Drug Labels

Drug and label
Active ingredient and drug

7.6 Cancer Drugs

Drug Name
Vincristine Sulfate
FDA Approved
Yes
Drug Use

Vincristine sulfate is approved to treat adults and children with:

• Acute leukemia.

Vincristine sulfate is sometimes used to treat adults and children with other types of cancer, including:

• Hodgkin lymphoma.

• Neuroblastoma.

• Non-Hodgkin lymphoma (NHL).

• Rhabdomyosarcoma.

• Wilms tumor.

Vincristine sulfate is also being studied in the treatment of other types of cancer.

7.7 Clinical Trials

7.7.1 ClinicalTrials.gov

7.7.2 EU Clinical Trials Register

7.7.3 NIPH Clinical Trials Search of Japan

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Tubulin Modulators
Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)
Antineoplastic Agents, Phytogenic
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

8.2 FDA Pharmacological Classification

Non-Proprietary Name
VINCRISTINE SULFATE
Pharmacological Classes
Vinca Alkaloids [CS]; Vinca Alkaloid [EPC]

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Health Hazard
Signal
Danger
GHS Hazard Statements

H300 (91.3%): Fatal if swallowed [Danger Acute toxicity, oral]

H341 (89.1%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

H361 (91.3%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Precautionary Statement Codes

P203, P264, P270, P280, P301+P316, P318, P321, P330, 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 46 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.

10.1.2 Hazard Classes and Categories

Acute Tox. 2 (91.3%)

Muta. 2 (89.1%)

Repr. 2 (91.3%)

10.1.3 Health Hazards

SYMPTOMS: The following symptoms of exposure have occurred during intravenous use. Symptoms of exposure include bone marrow depression, peripheral neuropathy, colicky abdominal pain, constipation and alopecia. Other symptoms include neuromuscular and neurological disturbances, gastrointestinal upset and leucopenia. It has caused impaired walking, convulsions, hypertension, inappropriate antidiuretic hormone (ADH) secretion, jaw pain, paresthesias in the fingers and toes, sensory impairment, headache, loss of deep tendon reflexes, parotid gland pain, optic atrophy and blindness. It has also caused acute uric acid nephropathy, myocardial infarction, ocular toxicity (ptosis, other ocular muscle paresis, and 5th and 7th nerve involvement); laryngeal nerve paralysis causing hoarseness or cough, depression of the Achilles tendon reflex, muscle pain, weakness, motor weakness, quadriparesis, numbness and tingling of the fingers and toes, malaise, depression, psychoses, neuromyopathy, peripheral neuritis, adynamic ileus, and permanent central nervous system damage. Exposure may cause paresthesia, foot drop, ataxia, athetosis, thrombocytosis and coma. Exposure may also cause granulocytopenia, thrombocytopenia, hypoplasia of all elements of bone marrow, nausea, vomiting, anorexia, neuritic pain and motor difficulties. Other effects may include cranial nerve neuropathy including optic nerve neuropathy and injury to the retina; cataracts, facial paralysis, diplopia and corneal hypesthesia. It may cause anemia, polyuria, dysuria, fever, tingling and numbness of the extremities, abdominal obstruction, ischemic cardiac toxicity and syndrome of hyponatremia. It may also cause diarrhea, sensory loss, slapping gait, muscle wasting, generalized sensorimotor dysfunction, paralytic ileus, abdominal cramps, rash, oral ulceration, intestinal necrosis and/or perforation, urinary retention due to bladder atony cranial nerve manifestations including isolated paresis and/or paralysis of muscles controlled by cranial motor nerves; pharyngeal pain, bone pain, back pain, limb pain, myalgias, renal or adrenal disease, hypotension, dehydration, azotemia and clinical edema. Effects on the autonomic nervous system have been reported. It may cause irritation of the skin, and congenital malformation in the fetus.

ACUTE/CHRONIC HAZARDS: This compound is highly toxic and may be fatal if inhaled, swallowed or absorbed through the skin. It may cause irritation of the skin. When heated to decomposition it emits very toxic fumes of carbon monoxide, carbon dioxide, nitrogen oxides and sulfur oxides. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.1.4 Fire Hazards

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.2 First Aid Measures

10.2.1 First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING. Strychnine is an exceptionally toxic poison but inducing vomiting may cause a seizure. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.3 Fire Fighting

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.4 Accidental Release Measures

10.4.1 Isolation and Evacuation

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

10.5 Handling and Storage

10.5.1 Nonfire Spill Response

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.6 Exposure Control and Personal Protection

10.6.1 Personal Protective Equipment (PPE)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.7 Stability and Reactivity

10.7.1 Air and Water Reactions

Very hygroscopic. Water soluble.

10.7.2 Reactive Group

Alcohols and Polyols

Amides and Imides

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Salts, Acidic

10.7.3 Reactivity Profile

Sensitive to hydrolysis, oxidation and heat. Incompatible with strong oxidizing agents. (NTP, 1992).
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.8 Transport Information

10.8.1 DOT Label

Poison

10.9 Regulatory Information

California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Developmental Toxicity

Authoritative List - Prop 65

Report - regardless of intended function of ingredient in the product

10.10 Other Safety Information

Chemical Assessment

IMAP assessments - Vincaleukoblastine, 22-oxo-, sulfate (1:1) (salt): Human health tier I assessment

IMAP assessments - Vincaleukoblastine, 22-oxo-, sulfate (1:1) (salt): Environment tier I assessment

11 Toxicity

11.1 Toxicological Information

11.1.1 Carcinogen Classification

IARC Carcinogenic Agent
Vincristine sulfate
IARC Carcinogenic Classes
Group 3: Not classifiable as to its carcinogenicity to humans
IARC Monographs

Volume 26: (1981) Some Antineoplastic and Immunosuppressive Agents

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

11.1.2 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Most sources consider breastfeeding to be contraindicated during maternal antineoplastic drug therapy. It is probably impractical to resume breastfeeding after vincristine therapy because of the drug's long half-life. Chemotherapy may adversely affect the normal microbiome and chemical makeup of breastmilk.

◉ Effects in Breastfed Infants

In a 4-month-old, neutropenia was probably caused by cyclophosphamide in a mother 9 days after the last of 6 weekly doses of 800 mg cyclophosphamide intravenously, 2 mg vincristine intravenously and daily doses of 30 mg of prednisolone orally. Neutropenia persisted at least 12 days and was accompanied by a brief episode of diarrhea. The contribution of vincristine to the neutropenia cannot be determined.

A woman was diagnosed with B-cell lymphoma at 27 weeks of pregnancy. Labor was induced at 34 4/7 weeks and treatment was begun with a standard regimen of rituximab, cyclophosphamide, doxorubicin, vincristine, and prednisone in unspecified doses on a 21-day cycle, starting on day 2 postpartum. She pumped and discarded her milk and fed her infant donor milk for the first 10 days of each cycle and then breastfed her infant for the remaining 10 days before the next treatment cycle. The 10-day period of breastfeeding abstinence was determined by using about 3 half-lives of vincristine. After completion of 4 cycles of chemotherapy, her infant was reportedly healthy and developing without any complications.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

11.1.3 Acute Effects

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Chemical Co-Occurrences in Literature

12.5 Chemical-Gene Co-Occurrences in Literature

12.6 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 NCI Thesaurus Tree

16.3 ChemIDplus

16.4 CAMEO Chemicals

16.5 UN GHS Classification

16.6 International Agency for Research on Cancer (IARC) Classification

16.7 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Vincaleukoblastine, 22-oxo-, sulfate (1:1) (salt)
    https://services.industrialchemicals.gov.au/search-assessments/
  2. CAMEO Chemicals
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    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  3. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. 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
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. California Office of Environmental Health Hazard Assessment (OEHHA)
  8. NCI Thesaurus (NCIt)
    LICENSE
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    https://www.cancer.gov/policies/copyright-reuse
  9. California Safe Cosmetics Program (CSCP) Product Database
  10. ChEMBL
    LICENSE
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    http://www.ebi.ac.uk/Information/termsofuse.html
  11. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  12. DailyMed
  13. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  14. Drugs and Lactation Database (LactMed)
  15. Drugs@FDA
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  16. EU Clinical Trials Register
  17. FDA Orange Book
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  18. International Agency for Research on Cancer (IARC)
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    https://publications.iarc.fr/Terms-Of-Use
    IARC Classification
    https://www.iarc.fr/
  19. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  20. National Drug Code (NDC) Directory
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  21. NCI Cancer Drugs
  22. NIPH Clinical Trials Search of Japan
  23. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  24. SpectraBase
  25. Springer Nature
  26. 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
    Antineoplastic Agents, Phytogenic
    https://www.ncbi.nlm.nih.gov/mesh/68000972
  27. PubChem
  28. GHS Classification (UNECE)
  29. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  30. PATENTSCOPE (WIPO)
CONTENTS