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

• ChemBase ID: 6405
• Molecular Formular: C9H16N4S2
• Molecular Mass: 244.38014
• Monoisotopic Mass: 244.08163853
• SMILES: S(Cc1nc[nH]c1C)CCNC(=S)NC
• Canonical SMILES: CNC(=S)NCCSCc1nc[nH]c1C
• InChI: InChI=1S/C9H16N4S2/c1-7-8(13-6-12-7)5-15-4-3-11-9(14)10-2/h6H,3-5H2,1-2H3,(H,12,13)(H2,10,11,14)
• InChIKey: FPBPLBWLMYGIQR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-1-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)thiourea
• IUPAC Traditional name: metiamide; methiamide
• Synonyms: Methiamide; Metiamidum; Metiamida; Metiamide

Database IDs

• CAS Number: 34839-70-8
• PubChem SID: 160969712
• PubChem CID: 1548992
• CHEMBL: 275446
• Chemspider ID: 1265996
• DrugBank ID: DB08805
• Wikipedia Title: Metiamide

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.478477
• H Acceptors: 1
• H Donor: 3
• LogD (pH = 5.5): -0.5725445
• LogD (pH = 7.4): 0.23148139
• Log P: 0.3414594
• Molar Refractivity: 70.3953 cm^3
• Polarizability: 26.881952 Å^3
• Polar Surface Area: 52.74 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.5
• LOG S: -3.93
• Solubility (Water): 2.87e-02 g/l

DETAILS

DrugBank - DB08805

• Drug Groups: experimental
• Description: Metiamide is a histamine H2-receptor antagonist developed from another H2 antagonist, burimamide. It was an intermediate compound in the development of the successful anti-ulcer drug cimetidine.
• Indication: Potential in the treatment and the management of acid-reflux disorders (GERD), peptic ulcer disease, heartburn, and acid indigestion.
• Pharmacology: Metiamide is a histamine H₂-receptor antagonist. It reduces basal and nocturnal gastric acid secretion and a reduction in gastric volume, acidity, and amount of gastric acid released in response to stimuli including food, caffeine, insulin, betazole, or pentagastrin. Metiamide inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Other actions of Metiamide include an increase in gastric bacterial flora such as nitrate-reducing organisms.
• External Links: Wikipedia