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

• ChemBase ID: 384
• Molecular Formular: C10H16N6S
• Molecular Mass: 252.33924
• Monoisotopic Mass: 252.11571554
• SMILES: S(Cc1nc[nH]c1C)CCN/C(=N/C)/NC#N
• 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: (Z)-1-cyano-2-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
• IUPAC Traditional name: tagamet HB
• Brand Name: Acibilin; Acinil; Cimal; Cimetag; Cimetum; Dyspamet; Edalene; Eureceptor; Gastromet; Peptol; Tagamet; Tagamet HB; Tagamet HB 200; Tametin; Tratul; Ulcedin; Ulcedine; Ulcerfen; Ulcimet; Ulcofalk; Ulcomedina; Ulcomet; Ulhys
• Synonyms: Cimetidine Hcl; Cimetidine A/AB; Cimetidine

Database IDs

• CAS Number: 51481-61-9
• PubChem SID: 160963847; 46505360
• PubChem CID: 2756

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 0.44
• LOG S: -2.49
• Solubility (Water): 8.16e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.5 g/100 mL
• Hydrophobicity(logP): 1

DETAILS

DrugBank - DB00501

• Drug Groups: approved
• Description: A histamine congener, it competitively inhibits histamine binding to histamine H2 receptors. Cimetidine has a range of pharmacological actions. It inhibits gastric acid secretion, as well as pepsin and gastrins output. It also blocks the activity of cytochrome P-450 which might explain proposals for use in neoadjuvant therapy. [PubChem]
• Indication: For the treatment and the management of acid-reflux disorders (GERD), peptic ulcer disease, heartburn, and acid indigestion.
• Pharmacology: Cimetidine 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. It is used to treat gastrointestinal disorders such as gastric or duodenal ulcer, gastroesophageal reflux disease, and pathological hypersecretory conditions. Cimetidine inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Other actions of Cimetidine include an increase in gastric bacterial flora such as nitrate-reducing organisms.
• Toxicity: Symptoms of overdose include nausea, vomiting, diarrhea, increased saliva production, difficulty breathing, and a fast heartbeat.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Rapid 60-70%
• Half Life: 2 hours
• Protein Binding: 15-20%
• Elimination: The principal route of excretion of cimetidine is the urine.
• References: Michnovicz JJ, Galbraith RA: Cimetidine inhibits catechol estrogen metabolism in women. Metabolism. 1991 Feb;40(2):170-4. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Michnovicz JJ, Galbraith RA: Cimetidine inhibits catechol estrogen metabolism in women. Metabolism. 1991 Feb;40(2):170-4. Pubmed