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[3-Amino-1-hydroxy-1-[hydroxy(oxido)phosphoryl]propyl]-hydroxyphosphinate

PubChem CID
10236235
Structure
[3-Amino-1-hydroxy-1-[hydroxy(oxido)phosphoryl]propyl]-hydroxyphosphinate_small.png
[3-Amino-1-hydroxy-1-[hydroxy(oxido)phosphoryl]propyl]-hydroxyphosphinate_3D_Structure.png
Molecular Formula
Synonyms
  • Aredia
  • PAMIDRONATE DISODIUM
  • Sodium;(3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acid
  • [3-amino-1-hydroxy-1-[hydroxy(oxido)phosphoryl]propyl]-hydroxyphosphinate
  • NSC720699
Molecular Weight
258.06 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2006-10-25
  • Modify:
    2025-01-18
Description
Pamidronate Disodium is the disodium salt of the synthetic bisphosphonate pamidronate. Although its mechanism of action is not completely understood, pamidronate appears to adsorb to calcium phosphate crystals in bone, blocking their dissolution by inhibiting osteoclast-mediated bone resorption. This agent does not inhibit bone mineralization and formation.
An aminobisphosphonate that inhibits BONE RESORPTION and is used for the treatment of osteolytic lesions, bone pain, and severe HYPERCALCEMIA associated with malignancies.
See also: Pamidronate Disodium (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
[3-Amino-1-hydroxy-1-[hydroxy(oxido)phosphoryl]propyl]-hydroxyphosphinate.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C3H11NO7P2.Na/c4-2-1-3(5,12(6,7)8)13(9,10)11;/h5H,1-2,4H2,(H2,6,7,8)(H2,9,10,11);/q;+1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

AFICAMMULQSNNG-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

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

2.2 Molecular Formula

C3H11NNaO7P2+
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

57248-88-1

2.3.2 KEGG ID

2.3.3 NCI Thesaurus Code

2.3.4 NSC Number

2.3.5 RXCUI

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (3-amino-1-hydroxypropylidene)-1,1-biphosphonate
  • 1 Hydroxy 3 aminopropane 1,1 diphosphonic acid
  • 1-hydroxy-3-aminopropane-1,1-diphosphonic acid
  • AHPrBP
  • amidronate
  • Amino 1 hydroxypropane 1,1 diphosphonate
  • amino-1-hydroxypropane-1,1-diphosphonate
  • aminohydroxypropylidene diphosphonate
  • aminopropanehydroxydiphosphonate
  • Aredia
  • pamidronate
  • pamidronate calcium
  • pamidronate disodium
  • pamidronate monosodium
  • Pamidronic Acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
258.06 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
257.99084497 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
257.99084497 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
161 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
14
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
1
Reference
Computed by PubChem
Property Name
Complexity
Property Value
243
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
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
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 Chemical Classes

3.2.1 Drugs

3.2.1.1 Human Drugs
Human drug -> Prescription; Discontinued
Human drug -> Prescription; Discontinued; Active ingredient (PAMIDRONATE DISODIUM)

5 Chemical Vendors

6 Drug and Medication Information

6.1 FDA Approved Drugs

6.2 FDA Orange Book

6.3 FDA National Drug Code Directory

6.4 Drug Labels

Drug and label
Active ingredient and drug

6.5 Cancer Drugs

Brand Name(s)
Aredia
FDA Approved
Yes
Drug Use

Pamidronate disodium is approved to be given with chemotherapy to treat bone damage caused by:

• breast cancer that has spread to bone

• multiple myeloma that has spread to bone

Pamidronate disodium is also approved to treat:

• hypercalcemia (high blood levels of calcium) caused by malignant cancer

Pamidronate disodium is also being studied in the treatment of other types of cancer.

6.6 Clinical Trials

6.6.1 ClinicalTrials.gov

6.6.2 NIPH Clinical Trials Search of Japan

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 FDA Pharmacological Classification

Non-Proprietary Name
PAMIDRONATE DISODIUM
Pharmacological Classes
Bisphosphonate [EPC]; Diphosphonates [CS]

8 Use and Manufacturing

8.1 Uses

8.1.1 Use Classification

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

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Gene Co-Occurrences in Literature

9.5 Chemical-Disease Co-Occurrences in Literature

10 Biological Test Results

10.1 BioAssay Results

11 Classification

11.1 MeSH Tree

12 Information Sources

  1. ClinicalTrials.gov
    LICENSE
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  2. DailyMed
  3. Drugs@FDA
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  4. 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
  5. FDA Orange Book
    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
  6. 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
  7. 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
  8. NCI Cancer Drugs
  9. NCI Thesaurus (NCIt)
    LICENSE
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    https://www.cancer.gov/policies/copyright-reuse
  10. NIPH Clinical Trials Search of Japan
  11. 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
  12. 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
  13. PubChem
CONTENTS