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Alendronic acid

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Alendronic acid Basic information

Product Name:
Alendronic acid
Synonyms:
  • 4-AMINO-1-HYDROXY-1,1-BUTYLIDINEDIPHOSPHONIC ACID
  • (4-AMINO-1-HYDROXY-1-PHOSPHONOBUTYL)PHOSPHONIC ACID
  • (4-AMINO-1-HYDROXYBUTYLIDENE)-BIS-(PHOSPHONIC ACID)
  • (4-AMINO-1-HYDROXYBUTYLIDENE)DIPHOSPHONIC ACID
  • ALENDRONATE
  • ALENDRONIC ACID
  • (4-amino-1-hydroxybutylidene)bis-phosphonicaci
  • 4-amino-1-hydroxybutylidene-1,1-bis(phosphonicacid)
CAS:
66376-36-1
MF:
C4H13NO7P2
MW:
249.1
EINECS:
204-352-8
Product Categories:
  • Miscellaneous Biochemicals
  • (intermediate of alendronate sodium)
Mol File:
66376-36-1.mol
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Alendronic acid Chemical Properties

Melting point:
230-235°C
Boiling point:
616.7±65.0 °C(Predicted)
Density 
1.857±0.06 g/cm3(Predicted)
storage temp. 
Store at -20°C
Water Solubility 
Insoluble in water
solubility 
Aqueous Base (Sparingly), Methanol (Slightly), Water (Very Slightly)
form 
powder to crystal
pka
pK1 2.72 ±0.05; pK2 8.73 ±0.05; pK3 10.5 ±0.1; pK4 11.6 ±0.1 at 25°, (0.1M KCl)
color 
White to Light yellow
Merck 
14,229
Stability:
Hygroscopic
EPA Substance Registry System
Phosphonic acid, P,P'-(4-amino-1-hydroxybutylidene)bis- (66376-36-1)
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Safety Information

RIDADR 
1759
RTECS 
SZ6521833
HS Code 
2931.90.9051
HazardClass 
8
PackingGroup 
III
Hazardous Substances Data
66376-36-1(Hazardous Substances Data)
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Alendronic acid Usage And Synthesis

Originator

Adronat ,Neopharmed ,Italy

Uses

Alendronate acid is an inhibitor of FDPS.

Definition

ChEBI: A 1,1-bis(phosphonic acid) that is methanebis(phosphonic acid) in which the two methylene hydrogens are replaced by hydroxy and 3-aminopropyl groups.

Manufacturing Process

4-Amino-1-hydroxybutylidene-1,1-diphosphonic acid (ABDT).
Orthosphophorous acid (102.7 g; 1.25 moles) is introduced into a 2 liter-flask with condenser, stirrer and dropping funnel, placed on a thermostatized bath; the air is then removed with a nitrogen stream which is continued during all the reaction. The acid is melted by heating the bath to 95°C. When melting is complete, 4-aminobutyric acid (103.3; 1 mole) is added under stirring which is continued till obtaining a doughy fluid. Phosphorous trihalide (176 ml; 2 moles) is added dropwise causing the mixture to boil and evolution of gaseous hydrochloric acid which is damped by means of a suitable trap. The addition rate is adjusted so as to keep a constant reflux for about 60 minutes. When the addition is nearly over, the mixture swells, slowly hardening. Stirring is continued as long as possible, whereafter the mixture is heated for further 3 hours. Without cooling, but removing the bath, water (300 ml) is added, first slowly and then quickly. Heating and stirring are started again. Decolorizing charcoal is added and the mixture is boiled for about 5 minutes, then hotfiltered on paper and the filtrate is refluxed for 6 hours. After cooling is slowly poured in stirred methanol (1500 ml) causing thereby the separation of a white solid which collected and dried (161 g; 64.6%). The structure of ABDT is confirmed by IR spectrum, proton magnetic and nuclear magnetic resonance spectrum and elemental analysis.
The sodium salt of this acid may be prepared by adding of equivalent of sodium hydroxide.

Therapeutic Function

Antiosteoporotic

Hazard

A reproductive hazard.

Clinical Use

Bisphosphonate:
Treatment and prophylaxis of osteoporosis

Drug interactions

Potentially hazardous interactions with other drugs
Calcium salts: reduced absorption of alendronate.

Metabolism

Alendronate transiently distributes to soft tissues but is then rapidly redistributed to bone or excreted in the urine. There is no evidence that alendronate is metabolised in animals or humans. Following a single intravenous dose of [14C]-alendronate, approximately 50% of the radioactivity was excreted in the urine within 72 hours and little or no radioactivity was recovered in the faeces.

Alendronic acid Preparation Products And Raw materials

Raw materials

Alendronic acidSupplier

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