methanesulfonic acid 4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoate

• ChemBase ID: 155029
• Molecular Formular: C21H26N4O8S
• Molecular Mass: 494.51814
• Monoisotopic Mass: 494.14713481
• SMILES: CN(C)C(=O)COC(=O)Cc1ccc(cc1)OC(=O)c1ccc(cc1)NC(=N)N.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.CN(C(=O)COC(=O)Cc1ccc(cc1)OC(=O)c1ccc(cc1)NC(=N)N)C
• InChI: InChI=1S/C20H22N4O5.CH4O3S/c1-24(2)17(25)12-28-18(26)11-13-3-9-16(10-4-13)29-19(27)14-5-7-15(8-6-14)23-20(21)22;1-5(2,3)4/h3-10H,11-12H2,1-2H3,(H4,21,22,23);1H3,(H,2,3,4)
• InChIKey: FSEKIHNIDBATFG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methanesulfonic acid 4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoate; 4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoate; methanesulfonic acid
• IUPAC Traditional name: camostat; methanesulfonic acid
• Synonyms: 4-[[4-[(Aminoiminomethyl)amino]benzoyl]oxy]benzeneacetic acid 2-(dimethylamino)-2-oxoethyl ester methanesulfonate; FOY 305; FOY-S 980; Foipan mesylate; Camostat mesylate; Camostat Mesilate (FOY-305)

Database IDs

• CAS Number: 59721-29-8
• MDL Number: MFCD00941410
• PubChem SID: 162249167
• PubChem CID: 5284360

CALCULATED PROPERTIES

• Acid pKa: 19.543585
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.81215864
• LogD (pH = 7.4): 0.3649923
• Log P: 1.5107094
• Molar Refractivity: 117.7716 cm^3
• Polarizability: 40.389175 Å^3
• Polar Surface Area: 134.81 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥24 mg/mL
• Apperance: white to tan powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38-50
• Safety Statements: 26-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335-H400
• GHS Precautionary statements: P261-P273-P305 + P351 + P338
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: HCV Protease

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Mesilate
• Empirical Formula (Hill Notation): C20H22N4O5·CH3SO3H

DETAILS

Sigma Aldrich - SML0057

Biochem/physiol Actions
Camostat is a synthetic, orally bioavailble serine protease inhibitor.