(3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acid

• ChemBase ID: 167
• Molecular Formular: C3H11NO7P2
• Molecular Mass: 235.069462
• Monoisotopic Mass: 235.00107496
• SMILES: P(=O)(O)(O)C(P(=O)(O)O)(O)CCN
• Canonical SMILES: NCCC(P(=O)(O)O)(P(=O)(O)O)O
• InChI: InChI=1S/C3H11NO7P2/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)
• InChIKey: WRUUGTRCQOWXEG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acid
• IUPAC Traditional name: pamidronate
• Brand Name: Amidronate; Aminomux; Aredia
• Synonyms: Pamidronic AcidSee P172500; Pamidronic acid; Acide pamidronique [INN-French]; Acido pamidronico [INN-Spanish]; Acidum pamidronicum [INN-Latin]; APD; Pamidronate Disodium; Pamidronic acid; Pamidronate

Database IDs

• CAS Number: 40391-99-9
• PubChem SID: 160963630; 46504823
• PubChem CID: 4674

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.6686214
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -6.578678
• LogD (pH = 7.4): -6.911782
• Log P: -4.536483
• Molar Refractivity: 42.6188 cm^3
• Polarizability: 17.42429 Å^3
• Polar Surface Area: 161.31 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.41
• LOG S: -1.17
• Solubility (Water): 1.58e+01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Hydrophobicity(logP): -4.7

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

DrugBank - DB00282

• Drug Groups: approved
• Description: Pamidronic acid (INN) or pamidronate disodium (USAN), marketed as pamidronate disodium pentahydrate under the brand name Aredia, is a bisphosphonate. [Wikipedia]
• Indication: For the treatment of moderate or severe hypercalcemia associated with malignancy
• Pharmacology: Pamidronate is in a class of drugs called bisphosphonates. Pamidronate reduces breakdown of the bones. Pamidronate is used in the treatment of Paget's disease of bone; to reduce high levels of calcium in the blood associated with malignancy (cancer); and to reduce the breakdown of bone due to metastases of breast cancer or multiple myeloma.
• Toxicity: Side effects include an allergic reaction, kidney problems, seizures, low levels of calcium, magnesium, or phosphorus in the blood
• Affected Organisms: Humans and other mammals
• Biotransformation: Pamidronate is not metabolized and is exclusively eliminated by renal excretion
• Absorption: Plasma concentration rises rapidly upon IV administration.
• Half Life: The mean ± SD elimination half-life is 28 ± 7 hours
• Protein Binding: Approximately 54% to human serum proteins.
• Elimination: Pamidronate is not metabolized and is exclusively eliminated by renal excretion.
• Clearance: * 107 +/- 50 mlL/min
• References: Zarychanski R, Elphee E, Walton P, Johnston J: Osteonecrosis of the jaw associated with pamidronate therapy. Am J Hematol. 2006 Jan;81(1):73-5. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - P172490

A biphosphonate bone resorption inhibitor.

REFERENCES

• Zarychanski R, Elphee E, Walton P, Johnston J: Osteonecrosis of the jaw associated with pamidronate therapy. Am J Hematol. 2006 Jan;81(1):73-5. Pubmed
• Sissons, C.H., et al.: Oral Microbiol. Immunol., 15, 317 (2000)
• Chen, J.X., et al.: J. Cell Physiol., 186, 116 (2001)