Alendronic acid

Base Information

• Chemical Name: Alendronic acid
• CAS No.: 66376-36-1
• Molecular Formula: C4H13NO7P2
• Molecular Weight: 249.097
• Hs Code.: 2931900090
• European Community (EC) Number: 613-929-7,689-696-0
• UNII: X1J18R4W8P
• DSSTox Substance ID: DTXSID5022568
• Nikkaji Number: J363.022F
• Wikipedia: Alendronic_acid
• Wikidata: Q420057
• NCI Thesaurus Code: C61625
• RXCUI: 236083
• Pharos Ligand ID: 941BJ1UYW842
• Metabolomics Workbench ID: 37924
• ChEMBL ID: CHEMBL870
• Mol file: 66376-36-1.mol

Synonyms:4-Amino-1-Hydroxybutylidene 1,1-Biphosphonate;Alendronate;Alendronate Monosodium Salt, Trihydrate;Alendronate Sodium;Aminohydroxybutane Bisphosphonate;Fosamax;MK 217;MK-217;MK217

Chemical Property of Alendronic acid

Chemical Property:

• Appearance/Colour: white fine powder
• Melting Point: 230-235 °C
• Boiling Point: 616.7 °C at 760 mmHg
• 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)
• Flash Point: 326.7 °C
• PSA: 180.93000
• Density: 1.857 g/cm³
• LogP: -0.57290
• Water Solubility.: Insoluble in water
• XLogP3: -6.5
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 249.01672575
• Heavy Atom Count: 14
• Complexity: 257

Purity/Quality:

99% ^*data from raw suppliers

Alendronic Acid >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC(O)(P(=O)(O)O)P(=O)(O)O)CN
• Recent ClinicalTrials: Setrusumab vs Bisphosphonates in Subjects 2 to <5 Years of Age With Osteogenesis Imperfecta
• Recent EU Clinical Trials: Denosumab (DMAB) Discontinuation and Switching Study in Glucocorticoid-Induced Osteoporosis (GIOP): A Pilot Study
• Recent NIPH Clinical Trials: Evaluation of Falls and Frailty; Eldecalcitol Clinical Trial (EFFECT) study
• Clinical Use: Bisphosphonate: Treatment and prophylaxis of osteoporosis
• Drug interactions: Potentially hazardous interactions with other drugs Calcium salts: reduced absorption of alendronate.

Technology Process of Alendronic acid

There total 12 articles about Alendronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

4-amino-n-butyric acid (56-12-2) → 4-amino-1-hydroxybutylidenebisphosphonic acid (66376-36-1)

Guidance literature:

4-amino-n-butyric acid; With phosphonic Acid; phosphorus trichloride; In methoxybenzene; at 60 - 105 ℃; for 5.66667 - 5.75h;

With water; In methoxybenzene; at 110 - 115 ℃; for 5 - 6h; Reflux;

Reference yield: 86.0%

→ 4-amino-1-hydroxybutylidenebisphosphonic acid (66376-36-1)

Guidance literature:

Reference yield: 82.0%

[4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-1-hydroxy-1-phosphonobutyl]phosphonic acid (948317-79-1) → 4-amino-1-hydroxybutylidenebisphosphonic acid (66376-36-1)

Guidance literature:

With hydrazine hydrate; In water; at 20 ℃; for 0.5h;

DOI:10.1002/ejoc.200601067

upstream raw materials:

4-amino-n-butyric acid

tetramethyl (4-phthalimido-1-hydroxybutylidene)bisphosphonate

4-phthalimidobutyryl chloride

2-pyrrolidinon

Refernces

• 1、 Xu, Guangyu,Xie, Yuyuan,Wu, Xihan. "A facile and direct synthesis of alendronate from pyrrolidone". . p. 185 - 187. Retrieved 2004.
• 2、 Alanne, Aino-Liisa,Ylisirnioe, Markku,Turhanen, Petri,Peraeniemi, Sirpa,Vepsaelaeinen, Jouko,Hyvoenen, Helena,Lahtinen, Manu,Kolehmainen, Erkki. "Systematic study of the physicochemical properties of a homologous series of aminobisphosphonates". . p. 10928 - 10945,18. Retrieved 2012.
• 3、 Iben Ayad,Belda Marín,Colaco,Lefevre,Méthivier,Ould Driss,Landoulsi,Guénin. ""water soluble" palladium nanoparticle engineering for C-C coupling, reduction and cyclization catalysis". supporting information. p. 6646 - 6657. Retrieved 2019/12/26.
• 4、 Savino, Salvatore,Toscano, Annamaria,Purgatorio, Rosa,Profilo, Emanuela,Laghezza, Antonio,Tortorella, Paolo,Angelelli, Mariacristina,Cellamarea, Saverio,Scala, Rosa,Tricarico, Domenico,Thomas Marobbio, Carlo Marya,Perna, Filippo,Vitale, Paola,Agamennone, Mariangela,Dimiccoli, Vincenzo,Tolomeo, Anna,Scilimati, Antonio. "Novel bisphosphonates with antiresorptive effect in bone mineralization and osteoclastogenesis". . p. 184 - 200. Retrieved 2018/09/18.