4-({2-butyl-5-[(1E)-2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid; methanesulfonic acid

• ChemBase ID: 154681
• Molecular Formular: C24H28N2O7S2
• Molecular Mass: 520.61832
• Monoisotopic Mass: 520.13379325
• SMILES: CCCCc1ncc(n1Cc1ccc(cc1)C(=O)O)/C=C(\Cc1cccs1)/C(=O)O.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.CCCCc1ncc(n1Cc1ccc(cc1)C(=O)O)/C=C(/C(=O)O)\Cc1cccs1
• InChI: InChI=1S/C23H24N2O4S.CH4O3S/c1-2-3-6-21-24-14-19(12-18(23(28)29)13-20-5-4-11-30-20)25(21)15-16-7-9-17(10-8-16)22(26)27;1-5(2,3)4/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29);1H3,(H,2,3,4)
• InChIKey: DJSLTDBPKHORNY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({2-butyl-5-[(1E)-2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid; methanesulfonic acid; 4-({2-butyl-5-[2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid; methanesulfonic acid
• IUPAC Traditional name: eprosartan; methanesulfonic acid
• Synonyms: (E)-α-[[2-Butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-2-thiophenepropanoic Acid Methanesulfonate; (αE)-α-[[2-Butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-2-thiophenepropanoic Acid Monomethanesulfonate; Eprosartan methanesulfonate; SKF 108566; Eprosartan Mesylate; Eprosartan Monomethanesulfonate; SKF-108566J; Teveten; Eprosartan mesylate

Database IDs

• CAS Number: 144143-96-4
• MDL Number: MFCD08141807
• PubChem SID: 162248819
• PubChem CID: 5282474

CALCULATED PROPERTIES

• Acid pKa: 3.6324818
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.6257877
• LogD (pH = 7.4): 0.3021144
• Log P: 3.7972305
• Molar Refractivity: 117.0243 cm^3
• Polarizability: 44.08464 Å^3
• Polar Surface Area: 92.42 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: room temp

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥98% (HPLC); 95+%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C23H24N2O4S · CH4O3S

DETAILS

Sigma Aldrich - E2535

Biochem/physiol Actions
Angiotensin II type 1 (AT1) receptor antagonist; anti-hypertensive.

Toronto Research Chemicals - E590105

Eprosartan Mesylate is an angiotensin II receptor antagonists. Eprosartan Mesylate is used as an antihypertensive agent.

REFERENCES

• Sheng, J. et al.: J. Pharmac. Sci., 88., 1021 (1999)
• Punzi, H.A. et al.: J. Hum. Hypertens., 18, 655 (1999)