180064-38-4

Basic information

• Product Name: PHOSPHONIC ACID, (1-HYDROXY-2-IMIDAZO(1,2-A)PYRIDIN-3-YLETHYLIDENE)BIS-
• Synonyms: PHOSPHONIC ACID, (1-HYDROXY-2-IMIDAZO(1,2-A)PYRIDIN-3-YLETHYLIDENE)BIS-;1-Hydroxy-2-(imidazo[1,2-a]pyridin-3-yl)ethane-1,1-bis(phosphonic acid);Minodronic acid;(1-Hydroxy-2-imidazo[1,2-A]pyridin-3-yl-1-ethyl)-1,1-bisphos phonate;Nsc725590;Bonoteo;BPH 261;ONO 5920
• CAS NO: 180064-38-4
• Molecular Formula: C9H12N2O7P2
• Molecular Weight: 322.148302
• EINECS: 1592732-453-0
• Mol File: 180064-38-4.mol
• Article Data: 0

Chemical Properties

• Appearance: /
• Density: 1.973 g/cm³
• Refractive Index: 1.744
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.48±0.10(Predicted)
• CAS DataBase Reference: PHOSPHONIC ACID, (1-HYDROXY-2-IMIDAZO(1,2-A)PYRIDIN-3-YLETHYLIDENE)BIS-(CAS DataBase Reference)
• NIST Chemistry Reference: PHOSPHONIC ACID, (1-HYDROXY-2-IMIDAZO(1,2-A)PYRIDIN-3-YLETHYLIDENE)BIS-(180064-38-4)
• EPA Substance Registry System: PHOSPHONIC ACID, (1-HYDROXY-2-IMIDAZO(1,2-A)PYRIDIN-3-YLETHYLIDENE)BIS-(180064-38-4)

Safety Data

• Hazardous Substances Data: 180064-38-4(Hazardous Substances Data)

Usage

Description

Minodronic acid hydrate, a third-generation bisphosphonate, was approved and launched in Japan for the oral treatment of osteoporosis. Osteoporosis is a skeletal disorder characterized by low bone mass and structural deterioration of bone tissue resulting in bone fragility and increased susceptibility to fractures, particularly of the hip, spine, and wrist. It is the most common type of metabolic bone disease and a major health concern affecting 200 million women worldwide. Minodronic acid is the newest nitrogen-containing bisphosphonate to reach the market. In vitro, it inhibits recombinant human FPP synthase activity with similar potency as zoledronic acid (IC50 = 3 nM for both agents). The most common adverse events associated with minodronic acid included stomach and abdominal discomfort, abdominal pain, decrease in blood calcium level, and gastritis. The chemical synthesis of minodronic acid starts with a condensation reaction of 2-aminopyridine with ethyl 4-bromo-3-oxobutyrate by means of sodium bicarbonate to produce 2-(imidazo[1,2-a]pyridin-3-yl)acetic acid ethyl ester, which is hydrolyzed to the corresponding carboxylic acid with potassium hydroxide. Treatment of the carboxylic acid intermediate with phosphorus acid and phosphorus trichloride followed by hydrolysis with hydrochloric acid gives minodronic acid.

Originator

Astellas Pharma (Japan)

Uses

Minodronic acid is developed for osteoporosis treatment.

Brand name

Recalbon, Bonoteo

InChI:InChI=1/C9H12N2O7P2/c12-9(19(13,14)15,20(16,17)18)5-7-6-10-8-3-1-2-4-11(7)8/h1-4,6,12H,5H2,(H2,13,14,15)(H2,16,17,18)