[dichloro(phosphono)methyl]phosphonic acid

• ChemBase ID: 601
• Molecular Formular: CH4Cl2O6P2
• Molecular Mass: 244.892382
• Monoisotopic Mass: 243.88601647
• SMILES: ClC(Cl)(P(=O)(O)O)P(=O)(O)O
• Canonical SMILES: ClC(P(=O)(O)O)(P(=O)(O)O)Cl
• InChI: InChI=1S/CH4Cl2O6P2/c2-1(3,10(4,5)6)11(7,8)9/h(H2,4,5,6)(H2,7,8,9)
• InChIKey: ACSIXWWBWUQEHA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [dichloro(phosphono)methyl]phosphonic acid
• IUPAC Traditional name: clodronate
• Brand Name: Acide Clodronique [INN-French]; Acido Clodronico [INN-Spanish]; Acidum Clodronicum [INN-Latin]; Bonefos; Clasteon; Dichloromethanediphosphonic acid; Dichloromethylidene diphosphonate; Loron; Ostac
• Synonyms: clodronate; Clodronate

Database IDs

• CAS Number: 10596-23-3
• PubChem SID: 160964064; 46508646
• PubChem CID: 25419

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.6193091
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.6775923
• LogD (pH = 7.4): -5.0399384
• Log P: -0.06669456
• Molar Refractivity: 38.2136 cm^3
• Polarizability: 15.668829 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.16
• LOG S: -1.52
• Solubility (Water): 7.47e+00 g/l

PROPERTIES

Physical Property

• Solubility: 395 mg/L
• Hydrophobicity(logP): -2.4

DETAILS

DrugBank - DB00720

• Drug Groups: approved; investigational
• Description: A diphosphonate which affects calcium metabolism. It inhibits bone resorption and soft tissue calcification. [PubChem]
• Indication: For the management of hypercalcemia of malignancy and as an adjunct in the management of osteolysis resulting from bone metastases of malignant tumors.
• Pharmacology: Clodronate is a first generation (non-nitrogenous) bisphosphonate in the same family as etidronate and tiludronate. Clodronate affects calcium metabolism and inhibits bone resorption and soft tissue calcification. Of the clodronate that is resorbed (from oral preparation) or infused (for intravenous drugs), about 50% is excreted unchanged by the kidney. The remainder has a very high affinity for bone tissue, and is rapidly absorbed onto the bone surface. Clodronate has been shown to prevent or delay skeletal-related events and decrease bone pain as well as normalize calcium levels in the presence of hypercalcemia.
• Toxicity: Decreases in serum calcium following substantial overdosage may be expected in some patients. Signs and symptoms of hypocalcemia also may occur in some of these patients.
• Affected Organisms: Humans and other mammals
• Biotransformation: Clodronate is not metabolized in humans.
• Absorption: After oral administration, absorption is estimated at 1–3% of the ingested dose because of the low uptake from the gastrointestinal tract.
• Half Life: Approximately 13 hours.
• Protein Binding: 2%-36%
• External Links: Wikipedia