Ibandronic Acid

Base Information

• Chemical Name: Ibandronic Acid
• CAS No.: 114084-78-5
• Molecular Formula: C9H23NO7P2
• Molecular Weight: 333.259
• Hs Code.: 2931900090
• European Community (EC) Number: 682-157-0,688-095-0
• UNII: UMD7G2653W
• DSSTox Substance ID: DTXSID5048340
• Nikkaji Number: J476.066B
• Wikipedia: Ibandronic_acid
• Wikidata: Q166825
• NCI Thesaurus Code: C65874
• RXCUI: 115265
• Pharos Ligand ID: R4XFHQG7PJRN
• Metabolomics Workbench ID: 43018
• ChEMBL ID: CHEMBL997
• Mol file: 114084-78-5.mol

Synonyms:(1-hydroxy-3-(methylpentylamino)propylidene)bisphosphonate;1-hydroxy-3-(methylpentylamino)propylidenebisphosphonate;BM 21.0955;BM 210955;BM-21.0955;BM-210955;BM21.0955;BM210955;Bondronat;Boniva;Bonviva;ibandronate;ibandronate sodium;Ibandronate Sodium Anhydrous;ibandronic acid;ibandronic acid, sodium salt, monohydrate;RPR 102289A;RPR-102289A;RPR102289A

Chemical Property of Ibandronic Acid

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 2.88E-16mmHg at 25°C
• Melting Point: 113-115 ºC
• Refractive Index: 1.537
• Boiling Point: 587.8 ºC at 760 mm
• PKA: 1.60±0.10(Predicted)
• Flash Point: 309.3 ºC
• PSA: 158.15000
• Density: 1.449 g/cm³
• LogP: 0.50000
• Storage Temp.: -20°C Freezer
• Solubility.: Aqueous Base (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -4.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 319.09497607
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

99% ^*data from raw suppliers

Ibandronic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCN(C)CCC(O)(P(=O)(O)O)P(=O)(O)O
• Recent ClinicalTrials: Use of Ibandronate in Diabetic Patients
• Recent EU Clinical Trials: Treatment of Osteogenesis Imperfecta with Parathyroid hormone and Zoledronic acid
• Recent NIPH Clinical Trials: The combination therapy with Eldecalcitol and Ibandronate sodium
• Description: This third generation biphosphonate was launched in Austria and Germany for the treatment of bone disorders such as hypercalcemia in malignancy and ostedysis, Paget's disease and osteoporosis. It does not effect bone mineralization, therefore, the potential risk of osteomalacia is prevented. This was a problem with first generation derivatives. While the exact mode of action is not understood, they are inhibitors of osteroclast mediated bone resorption. These compounds strongly interact with hydroxyapatite crystals and have a half-life in the skeleton of several years. Despite this observation ibandronate was well tolerated and safe.
• Uses: A biphosphonate bone resorption inhibitor. A labeled biphosphonate bone resorption inhibitor. A bisphosphonate antiresorptive agent. Bone resorption inhibitor. Labelled Ibandronic Acid (I120000). A bisphosphonate antiresorptive agent. Bone resorption inhibitor.
• Clinical Use: Bisphosphonate: Reduction of bone damage in bone metastases in breast cancer Hypercalcaemia of malignancy Postmenopausal osteoporosis
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Ibandronic Acid

There total 5 articles about Ibandronic 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%

N-(n-pentyl)-N-methyl-3-aminopropionic acid (287395-61-3) → ibandronic acid (114084-78-5)

Guidance literature:

With phosphonic Acid; 1-butyl-3-methylimidazolium Tetrafluoroborate; phosphorus trichloride; at 75 ℃; for 3h; Reagent/catalyst; Green chemistry;

DOI:10.1080/10426507.2018.1555537

Reference yield: 59.0%

→ ibandronic acid (114084-78-5)

Guidance literature:

Reference yield:

3-[N-(methylpentyl)amino]propionic acid hydrochloride → ibandronic acid (114084-78-5)

Guidance literature:

3-[N-(methylpentyl)amino]propionic acid hydrochloride; With phosphorous acid; In toluene; at 70 - 75 ℃;

With phosphorus trichloride; In toluene; at 80 - 85 ℃;

With water; Reflux;

upstream raw materials:

N-(n-pentyl)-N-methyl-3-aminopropionic acid

3-(N-methyl-N-pentylamino) propionic acid hydrochloride

Downstream raw materials:

ibandronate monosodium

ibandronic acid monosodium salt

Refernces

• 1、 -. "PROCESS FOR MAKING 1-HYDROXYALKYLIDENE-1,1-BIPHOSPHONIC ACIDS". Page/Page column 4. . Retrieved 2010/02/17.
• 2、 -. "PROCESS FOR THE SYNTHESIS OF IBANDRONATE SODIUM". Page/Page column 7. . Retrieved 2010/08/07.