121268-17-5 Usage
Description
Alendronate sodium, also known as Fosamax, is an aminobisphosphonate compound that has been effectively used for the treatment of osteolysis, Paget's disease, and osteoporosis. It is a white crystalline solid with the chemical name ChEBI: A hydride that is the trihydrate of alendronate sodium.
Uses
Used in Pharmaceutical Industry:
Alendronate sodium is used as a bone resorption inhibitor for the treatment of osteoporosis and Paget's disease. It inhibits bone resorption and increases bone density, helping to prevent fractures and improve overall bone health.
Alendronate sodium is used as a farnesyl diphosphate synthase inhibitor and CD45 protein tyrosine phosphatase inhibitor for the treatment of osteolysis. It acts as a robust inhibitor of bone resorption and induces apoptosis in affected cells.
Alendronate sodium is used as a dopamine receptor agonist for the treatment of Parkinson's disease. It helps alleviate symptoms and improve the quality of life for patients suffering from this neurodegenerative disorder.
Alendronate sodium is used as an inhibitor of CD45RC and MMP, interfering with the mevalonate pathway and inhibiting the migration and invasion of PC-3 cells (sc-2220), which can be beneficial in cancer treatment.
Originator
Adronat ,Neopharmed ,Italy
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
Biochem/physiol Actions
Alendronate sodium trihydrate is a bone resorption inhibitor; farnesyl diphosphate synthase inhibitor (IC50 = 460 nM); CD45 protein tyrosine phosphatase inhibitor.
Check Digit Verification of cas no
The CAS Registry Mumber 121268-17-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,1,2,6 and 8 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 121268-17:
(8*1)+(7*2)+(6*1)+(5*2)+(4*6)+(3*8)+(2*1)+(1*7)=95
95 % 10 = 5
So 121268-17-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H13NO7P2.4Na/c5-3-1-2-4(6,13(7,8)9)14(10,11)12;;;;/h6H,1-3,5H2,(H2,7,8,9)(H2,10,11,12);;;;/q;4*+1/p-4
121268-17-5Relevant articles and documents
Synthesis and biological evaluation of new bisphosphonate-dextran conjugates targeting breast primary tumor
Migianu-Griffoni, Evelyne,Chebbi, Imene,Kachbi, Souad,Monteil, Maelle,Sainte-Catherine, Odile,Chaubet, Frederic,Oudar, Olivier,Lecouvey, Marc
, p. 224 - 230 (2014)
Bisphosphonates (BPs) have interesting antitumor effects as well in vitro as in vivo, despite their poor bioavailability in the organism after oral ingestion. To overcome this problem and reduce drug doses and secondary effects, we report the chemical synthesis of new bioconjugates. They were built with a nitrogen-containing BP as the drug covalently coupled to the carboxymethyldextran. This polysaccharide was used as a carrier, in order to increase BP lifetime in bloodstream and to target tumor cells which have a strong affinity with dextran. The efficiency of our vectorization system was biologically proved in vitro and in vivo on mammalian carcinoma models in mice.
Investigation of the effect of medium in the preparation of alendronate: till now the best synthesis in the presence of an ionic liquid additive
Nagy, Dávid Illés,Grün, Alajos,Garadnay, Sándor,Greiner, István,Keglevich, Gy?rgy
, (2017)
The synthesis of the drug alendronate from γ-aminobutyric acid and phosphorus trichloride/phosphorous acid as the P-reagents is revisited using methanesulfonic acid and sulfolane as solvents and ionic liquids (ILs) as additives according to a novel approach. Besides elaborating efficient synthetic methods with a record yield of up to 80%, the misleading literature data were also clarified. It is a novel trend to use ILs as only catalysts or additives and not as solvents.
The synthesis of risedronic acid and alendronate applying phosphorus oxychloride and phosphorous acid in methanesulfonic acid
Grün, Alajos,Kovács, Rita,Garadnay, Sándor,Greiner, István,Keglevich, Gy?rgy
, p. 253 - 258 (2015/04/14)
The synthesis of risedronic acid and alendronate from 3-pyridylacetic acid and γ-aminobutyric acid, respectively, using phosphorus oxychloride and phosphorous acid as the P-reagents and methanesulfonic acid as the solvent was optimized, and the role of phosphorus oxychloride and phosphorous acid in the reaction was clarified.