{1-hydroxy-3-[methyl(pentyl)amino]-1-phosphonopropyl}phosphonic acid

• ChemBase ID: 591
• Molecular Formular: C9H23NO7P2
• Molecular Mass: 319.228942
• Monoisotopic Mass: 319.09497534
• SMILES: P(=O)(O)(O)C(P(=O)(O)O)(O)CCN(CCCCC)C
• Canonical SMILES: CCCCCN(CCC(P(=O)(O)O)(P(=O)(O)O)O)C
• InChI: InChI=1S/C9H23NO7P2/c1-3-4-5-7-10(2)8-6-9(11,18(12,13)14)19(15,16)17/h11H,3-8H2,1-2H3,(H2,12,13,14)(H2,15,16,17)
• InChIKey: MPBVHIBUJCELCL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {1-hydroxy-3-[methyl(pentyl)amino]-1-phosphonopropyl}phosphonic acid
• IUPAC Traditional name: ibandronate
• Brand Name: Boniva; Bonviva; Bondronat
• Synonyms: (1-Hydroxy-3-(methyl(pentyl)amino)propane-1,1-diyl)diphosphonic acid; Ibandronate sodium; Ibandronate sodium monohydrate; Ibandronic Acid; R484; ibandronate; Ibandronate; [1-HYDROXY-3-(METHYL-PENTYL-AMINO)-1-PHOSPHONO-PROPYL]-PHOSPHONIC ACID

Database IDs

• CAS Number: 114084-78-5
• MDL Number: MFCD00868772
• PubChem SID: 160964054; 46508134
• PubChem CID: 60852

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.6608223
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.524289
• LogD (pH = 7.4): -4.8642755
• Log P: -2.4814348
• Molar Refractivity: 71.1627 cm^3
• Polarizability: 28.144053 Å^3
• Polar Surface Area: 138.53 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.26
• LOG S: -1.38
• Solubility (Water): 1.34e+01 g/l

PROPERTIES

Physical Property

• Solubility: Freely soluble
• Hydrophobicity(logP): -2.1

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB04635

Drug information: experimental

DrugBank - DB00710

• Drug Groups: approved; investigational
• Description: Ibandronate is a nitrogen-containing bisphosphonate in the same class as alendronate and risedronate. Ibandronate inhibits osteoclast-mediated bone resorption. All of the bisphosphonates prevent the breakdown of bone by bone cells called osteoclasts. In persons who are at high risk for osteoporosis, bisphosphonates not only result in increased amounts of bone and bone strength, they also reduce the risk of hip fractures and other bone fractures.
• Indication: For the treatment and prevention of osteoporosis in postmenopausal women.
• Pharmacology: Ibandronate is a nitrogen-containing bisphosphonate in the same class as alendronate and risedronate. Ibandronate inhibits osteoclast-mediated bone resorption. All of the bisphosphonates prevent the breakdown of bone by bone cells called osteoclasts. In persons who are at high risk for osteoporosis, bisphosphonates not only result in increased amounts of bone and bone strength, they also reduce the risk of hip fractures and other bone fractures.
• Toxicity: LD₅₀ = 811 mg/kg (rat, oral), side effects include bronchitis, pneumonia and urinary tract infections.
• Affected Organisms: Humans and other mammals
• Biotransformation: No evidence of ibandronate being metabolized in humans.
• Absorption: Poorly absorbed (mean bioavailability following a 2.5 mg oral dose is about 0.6% compared to intravenous dosing). Absorption is impaired by any kind of food or drink other than plain water.
• Half Life: 10-60 hours
• Protein Binding: 90.9 to 99.5% over an ibandronate concentration range of 2 to 10 ng/mL
• Elimination: Ibandronate is eliminated by renal excretion. Unabsorbed ibandronate is eliminated unchanged in the feces.
• Distribution: * 90 L
• Clearance: * 84 to 160 mL/min [IV administration]
• References: Epstein S, Zaidi M: Biological properties and mechanism of action of ibandronate: application to the treatment of osteoporosis. Bone. 2005 Oct;37(4):433-40. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Epstein S, Zaidi M: Biological properties and mechanism of action of ibandronate: application to the treatment of osteoporosis. Bone. 2005 Oct;37(4):433-40. Pubmed