(E)-1-cyano-2-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

• ChemBase ID: 126598
• Molecular Formular: C10H16N6S
• Molecular Mass: 252.33924
• Monoisotopic Mass: 252.11571554
• SMILES: N#CN/C(=N/C)/NCCSCc1nc[nH]c1C
• Canonical SMILES: N#CN/C(=N/C)/NCCSCc1nc[nH]c1C
• InChI: InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)
• InChIKey: AQIXAKUUQRKLND-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (E)-1-cyano-2-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
• IUPAC Traditional name: (E)-1-cyano-2-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
• Brand Name: Tagamet
• Synonyms: Cimetidine

Database IDs

• CAS Number: 51481-61-9
• PubChem SID: 162220928
• PubChem CID: 2756
• CHEBI ID: 3699
• ATC CODE: A02BA01
• CHEMBL: 30
• Chemspider ID: 2654
• DrugBank ID: DB00501
• IUPHAR ligand ID: 1231
• KEGG ID: D00295
• Unique Ingredient Identifier: 80061L1WGD
• Wikipedia Title: Cimetidine
• Medline Plus: a682256

CALCULATED PROPERTIES

• Acid pKa: 13.3825
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.0659736
• LogD (pH = 7.4): -0.21997932
• Log P: -0.109356105
• Molar Refractivity: 70.3171 cm^3
• Polarizability: 25.88721 Å^3
• Polar Surface Area: 88.89 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral, parenteral
• Bioavailability: 60–70%
• Excretion: Renal
• Half Life: 2 hours
• Metabolism: Hepatic
• Protein Bound: 15–20%
• Legal Status: OTC/?-only (U.S., depending on dosage strength); POM (UK); S4 (Australia)
• Pregnancy Category: B (US); B1 (Australia)
• US Licence: Cimetidine