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Alendronic acid

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CAS:66376-36-1
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Products Intro: Product Name:(4-Amino-1-hydroxybutane-1,1-diyl)diphosphonic Acid
CAS:66376-36-1
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Products Intro: Product Name:ALENDRONIC ACID
CAS:66376-36-1
Purity:99% Package:1kg

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  • Alendronic Acid
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  • 2026-03-06
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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
Alendronic acid Structure
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
pkapK1 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 SystemPhosphonic acid, P,P'-(4-amino-1-hydroxybutylidene)bis- (66376-36-1)
Safety Information
RIDADR 1759
RTECS SZ6521833
HS Code 2931.90.9051
HazardClass 8
PackingGroup III
Hazardous Substances Data66376-36-1(Hazardous Substances Data)
MSDS Information
Alendronic acid Usage And Synthesis
Chemical PropertiesWhite to Light yellow powder to crystal.
OriginatorAdronat ,Neopharmed ,Italy
UsesAlendronate acid is an inhibitor of FDPS.
IndicationsAlendronic acid is a bisphosphonate used to treat and prevent osteoporosis and corticosteroid-induced osteoporosis.
PreparationSynthesis of Alendronic Acid: 1 mol of 4-aminobutyric acid was added to 1.5 mol of molten phosphoric acid at 95°C, followed by dropwise addition of 2 mol of phosphorus trihalide over 60 minutes. After the reaction mixture hardened, heating was continued for an additional 3 hours. The mixture was then hydrolyzed by adding 300 mL of water. Following cooling, the solution was poured into 1500 mL of methanol, and the resulting precipitate was collected to yield alendronic acid in 64.6% yield.
DefinitionChEBI: Alendronic acid is 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. It has a role as an EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor and a bone density conservation agent. It is a 1,1-bis(phosphonic acid) and a primary amino compound. It is a conjugate acid of an alendronate(1-).
Manufacturing Process4-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 FunctionAntiosteoporotic
HazardA reproductive hazard.
Clinical UseBisphosphonate:
Treatment and prophylaxis of osteoporosis
Drug interactionsPotentially hazardous interactions with other drugs
Calcium salts: reduced absorption of alendronate.
MetabolismAlendronate 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.
References[1] DÁVID ILLÉS NAGY. Synthesis of Hydroxymethylenebisphosphonic Acid Derivatives in Different Solvents.[J]. Molecules, 2016, 21 8. DOI:10.3390/molecules21081046.
[2] E. A. VOLOSNIKOVA. The synthesis of TNF-alpha conjugates with alendronic acid[J]. Russian Journal of Bioorganic Chemistry, 2017, 42 6: 638-645. DOI:10.1134/S1068162016060145.
[3] MOHAMED F. MADY* Malcolm A K Rocio Ortega. Exploring Modified Alendronic Acid as a New Inhibitor for Calcium-Based Oilfield Scales[J]. Energy & Fuels, 2022, 36 4: 1863-1873. DOI:10.1021/acs.energyfuels.1c03936.
Alendronic acid Preparation Products And Raw materials
Raw materialsPhosphoric acid-->4-Aminobutyric acid-->Phosphorus trichloride-->Orthophosphorus acid
Tag:Alendronic acid(66376-36-1) Related Product Information
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