methanesulfonic acid ethyl 3-{1-[2-({[4-({[(hexyloxy)carbonyl]amino}methanimidoyl)phenyl]amino}methyl)-1-methyl-1H-1,3-benzodiazol-5-yl]-N-(pyridin-2-yl)formamido}propanoate

• ChemBase ID: 165346
• Molecular Formular: C35H45N7O8S
• Molecular Mass: 723.8389
• Monoisotopic Mass: 723.30503244
• SMILES: c1cnc(cc1)N(CCC(=O)OCC)C(=O)c1ccc2c(c1)nc(n2C)CNc1ccc(cc1)C(=N)NC(=O)OCCCCCC.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.CCCCCCOC(=O)NC(=N)c1ccc(cc1)NCc1nc2c(n1C)ccc(c2)C(=O)N(c1ccccn1)CCC(=O)OCC
• InChI: InChI=1S/C34H41N7O5.CH4O3S/c1-4-6-7-10-21-46-34(44)39-32(35)24-12-15-26(16-13-24)37-23-30-38-27-22-25(14-17-28(27)40(30)3)33(43)41(20-18-31(42)45-5-2)29-11-8-9-19-36-29;1-5(2,3)4/h8-9,11-17,19,22,37H,4-7,10,18,20-21,23H2,1-3H3,(H2,35,39,44);1H3,(H,2,3,4)
• InChIKey: XETBXHPXHHOLOE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methanesulfonic acid ethyl 3-{1-[2-({[4-({[(hexyloxy)carbonyl]amino}methanimidoyl)phenyl]amino}methyl)-1-methyl-1H-1,3-benzodiazol-5-yl]-N-(pyridin-2-yl)formamido}propanoate
• IUPAC Traditional name: methanesulfonic acid ethyl 3-{1-[2-({[4-({[(hexyloxy)carbonyl]amino}methanimidoyl)phenyl]amino}methyl)-1-methyl-1,3-benzodiazol-5-yl]-N-(pyridin-2-yl)formamido}propanoate
• Synonyms: N-[[2-[[[4-[[[(Hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-β-alanine Ethyl Ester Methanesulfonate; BIBR 1048MS; Pradaxa; Dabigatran Etexilate Mesylate

Database IDs

• CAS Number: 872728-81-9
• PubChem SID: 162259479
• PubChem CID: 11434065

CALCULATED PROPERTIES

• Acid pKa: 10.171733
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 4.975725
• LogD (pH = 7.4): 4.9874597
• Log P: 4.9882693
• Molar Refractivity: 186.9218 cm^3
• Polarizability: 68.01786 Å^3
• Polar Surface Area: 151.53 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: >132°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D100150

Nonpeptide, direct thrombin inhibitor. Antithrombotic.

REFERENCES

• Hauel, N., et al.: J. Med. Chem., 45, 1757 (2002)
• Mungall, D., et al.: Curr. Opin. Invest. Drugs, 3, 095 (2002)
• Stangier, J., et al.: J. Clin. Pharmacol., 45, 555 (2002)