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Fosamax

PubChem CID
16760285
Structure
Fosamax_small.png
Fosamax_3D_Structure.png
Molecular Formula
Synonyms
  • ALENDRONATE SODIUM
  • 129318-43-0
  • Fosamax
  • Binosto
  • Fosamac
Molecular Weight
271.08 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2007-11-13
  • Modify:
    2025-01-18
Description
Alendronate Sodium is the sodium salt of alendronate, a second generation bisphosphonate and synthetic analog of pyrophosphate with bone anti-resorption activity. Alendronate sodium binds to and inhibits the activity of geranyltranstransferase (farnesyl pyrophosphate synthetase), an enzyme involved in terpenoid biosynthesis. Inhibition of this enzyme prevents the biosynthesis of isoprenoid lipids (FPP and GGPP) that are donor substrates of farnesylation and geranylgeranylation during the post-translational modification of small GTPase signalling proteins, which is important in the process of osteoclast turnover. As a result, osteoclast activity is inhibited and bone resorption and turnover are reduced.
ALENDRONATE SODIUM is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1995 and has 4 approved and 2 investigational indications.
A nonhormonal medication for the treatment of postmenopausal osteoporosis in women. This drug builds healthy bone, restoring some of the bone loss as a result of osteoporosis.
See also: Alendronate Sodium (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Fosamax.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(4-amino-1-hydroxy-1-phosphonobutyl)-hydroxyphosphinate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C4H13NO7P2.Na/c5-3-1-2-4(6,13(7,8)9)14(10,11)12;/h6H,1-3,5H2,(H2,7,8,9)(H2,10,11,12);/q;+1/p-1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

CAKRAHQRJGUPIG-UHFFFAOYSA-M
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C(CC(O)(P(=O)(O)O)P(=O)(O)[O-])CN.[Na+]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C4H12NNaO7P2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

129318-43-0

2.3.2 Deprecated CAS

1159882-48-0

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 NCI Thesaurus Code

2.3.7 RXCUI

2.3.8 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 4-Amino-1-Hydroxybutylidene 1,1-Biphosphonate
  • Alendronate
  • Alendronate Monosodium Salt, Trihydrate
  • Alendronate Sodium
  • Aminohydroxybutane Bisphosphonate
  • Fosamax
  • MK 217
  • MK-217
  • MK217

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
271.08 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
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
270.99867000 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
270.99867000 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
164 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
293
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
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
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 Collision Cross Section

155.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Breast Feeding; Lactation; Bisphosphonates; Bone Density Conservation Agents; Diphosphonates
Human drug -> Prescription; Discontinued
Human drugs -> Drugs for treatment of bone diseases -> Human pharmacotherapeutic group -> EMA Drug Category

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Indication

Treatment of postmenopausal osteoporosis in patients at risk of vitamin-D insufficiency. Adrovance reduces the risk of vertebral and hip fractures.

6.2 Drug Classes

Breast Feeding; Lactation; Bisphosphonates; Bone Density Conservation Agents; Diphosphonates

6.3 FDA Medication Guides

Drug
Active Ingredient
ALENDRONATE SODIUM
Form;Route
SOLUTION;ORAL
Company
MERCK
Date
11/30/15
Drug
Active Ingredient
ALENDRONATE SODIUM
Form;Route
TABLET;ORAL
Company
MERCK AND CO INC
Date
8/16/19

6.4 Clinical Trials

6.4.1 ClinicalTrials.gov

6.4.2 EU Clinical Trials Register

6.4.3 NIPH Clinical Trials Search of Japan

6.5 EMA Drug Information

Medicine
Category
Human drugs
Therapeutic area
Osteoporosis, Postmenopausal
Pharmacotherapeutic Classes
Drugs for treatment of bone diseases
Status
This medicine is authorized for use in the European Union
Company
N.V. Organon
Market Date
2007-01-04

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Bone Density Conservation Agents
Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation Agents.)

7.2 ATC Code

M05BB03

8 Use and Manufacturing

8.1 Uses

8.1.1 Use Classification

Human drugs -> Drugs for treatment of bone diseases -> Human pharmacotherapeutic group -> EMA Drug Category

8.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Phosphonic acid, P,P'-(4-amino-1-hydroxybutylidene)bis-, sodium salt (1:1): ACTIVE
EPA TSCA Regulatory Flag
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

9 Toxicity

9.1 Toxicological Information

9.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Limited evidence indicates that breastfeeding after cessation of long-term bisphosphonate treatment appears to have no adverse effects on the infant. Because no information is available on the use of alendronate during breastfeeding, an alternate drug may be preferred, especially while nursing a newborn or preterm infant. However, absorption of alendronate by a breastfed infant is unlikely. If the mother receives a bisphosphonate during pregnancy or nursing, some experts recommend monitoring the infant's serum calcium during the first 2 months postpartum.

◉ Effects in Breastfed Infants

Because alendronate can persist in the body for years after long-term administration, the following cases may be relevant. A woman received alendronate for 6 months, then pamidronate every 4 months for 1 year prior to conception. Her infant was breastfed (extent not stated) for 3 months. The infant had mild hypocalcemia at 2 months of age, but a normal calcium level and normal long bone development at 5 months of age.

◉ Effects on Lactation and Breastmilk

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

9.1.2 Acute Effects

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Thieme References

11.4 Chemical Co-Occurrences in Literature

11.5 Chemical-Gene Co-Occurrences in Literature

11.6 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 ChemIDplus

15.3 ChEMBL Target Tree

15.4 UN GHS Classification

15.5 CCSBase Classification

15.6 EPA DSSTox Classification

15.7 EPA TSCA and CDR Classification

15.8 FDA Drug Type and Pharmacologic Classification

15.9 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  2. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. EPA Chemicals under the TSCA
    Phosphonic acid, P,P'-(4-amino-1-hydroxybutylidene)bis-, sodium salt (1:1)
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  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. 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
  8. Drugs and Lactation Database (LactMed)
  9. 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
  10. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  11. EU Clinical Trials Register
  12. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  13. FDA Medication Guides
    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
  14. NCI Thesaurus (NCIt)
    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
  15. NIPH Clinical Trials Search of Japan
  16. 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
  17. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  18. Wikidata
  19. 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
    Bone Density Conservation Agents
    https://www.ncbi.nlm.nih.gov/mesh/68050071
  20. PubChem
  21. GHS Classification (UNECE)
  22. 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
  23. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  24. PATENTSCOPE (WIPO)
CONTENTS