ChemicalBook > CAS DataBase List > Alendronic acid

Alendronic acid

Product Name
Alendronic acid
CAS No.
66376-36-1
Chemical Name
Alendronic acid
Synonyms
ALENDRONATE;Bisphosphonate;Alendronate Sodium Hydrate;ABDP;R3-RM2;Onclast;Aledronate;alendronicaci;ALENDRONIC ACID;Alendronic Acid >
CBNumber
CB3380835
Molecular Formula
C4H13NO7P2
Formula Weight
249.1
MOL File
66376-36-1.mol
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Alendronic acid Property

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)
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)
form 
powder to crystal
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

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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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TCI Chemical
Product number
A2120
Product name
Alendronic Acid
Purity
>98.0%(T)
Packaging
5g
Price
$67
Updated
2025/07/31
TCI Chemical
Product number
A2120
Product name
Alendronic Acid
Purity
>98.0%(T)
Packaging
25g
Price
$199
Updated
2025/07/31
Chem-Impex
Product number
37567
Product name
Alendronicacid,98%(Assaybytitration)
Purity
98%(Assaybytitration)
Packaging
25G
Price
$217.28
Updated
2021/12/16
Matrix Scientific
Product number
099914
Product name
(4-Amino-1-hydroxybutane-1,1-diyl)diphosphonic acid
Purity
95+%
Packaging
10g
Price
$68
Updated
2021/12/16
Biosynth Carbosynth
Product number
FA38407
Product name
Alendronic acid
Packaging
250g
Price
$312.5
Updated
2021/12/16
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Alendronic acid Chemical Properties,Usage,Production

Chemical Properties

White to Light yellow powder to crystal.

Originator

Adronat ,Neopharmed ,Italy

Uses

Alendronate acid is an inhibitor of FDPS.

Preparation

Synthesis 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.

Definition

ChEBI: 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-).

Indications

Alendronic acid is a bisphosphonate used to treat and prevent osteoporosis and corticosteroid-induced osteoporosis.

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.

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 materials

Preparation Products

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View Lastest Price from Alendronic acid manufacturers

Shaanxi Dideu New Materials Co. Ltd
Product
Alendronic acid 66376-36-1
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10000KGS
Release date
2025-05-15
Moxin Chemicals
Product
Alendronic Acid 66376-36-1
Price
US $0.00-0.00/mg
Min. Order
10mg
Purity
98
Supply Ability
10000000
Release date
2025-02-21
Dideu Industries Group Limited
Product
Alendronic acid 66376-36-1
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons min
Release date
2021-07-28

66376-36-1, Alendronic acidRelated Search:


  • 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)
  • 4-Amino-1-hydroxybutane-1,1-diphosphonic Acid
  • ABDP
  • Onclast
  • AlendronateSodium/AlendronicAcid
  • 1-Hydroxy-4-aminobutylidenebisphosphonic acid
  • 4-Amino-1-hydroxy-1,1-butanediylbisphosphonic acid
  • 4-Amino-1-hydroxybutane-1,1-diylbis(phosphonic acid)
  • Bisphosphonate
  • Alendronate Sodium Hydrate
  • Aledronate
  • Phosphonic acid, (4-aMino-1-hydroxybutylidene)bis-
  • (4-aMino-1-hydroxybutane-1,1-diyl)diphosphonic acid
  • Phosphonic acid,P,P'-(4-aMino-1-hydroxybutylidene)bis-
  • Alendronic Acid &gt
  • alendronicaci
  • Alendronic acid USP/EP/BP
  • R3-RM2
  • Alendronic AcidQ: What is Alendronic Acid Q: What is the CAS Number of Alendronic Acid Q: What is the storage condition of Alendronic Acid Q: What are the applications of Alendronic Acid
  • (4-amino-1-hydroxybutylidene)bis- phosphonic aci 4-amino-1-hydroxybutylidene- 1,1-bis(phosphonic acid) alendronate alendronic acid
  • 66376-36-1
  • 66736-36-1
  • C4H13NO7P2
  • Miscellaneous Biochemicals
  • (intermediate of alendronate sodium)