cimetidine   Click here for help

GtoPdb Ligand ID: 1231

Synonyms: cimetidine HCl | Tagamet®
Approved drug
cimetidine is an approved drug (FDA (1977))
Compound class: Synthetic organic
Comment: Cimetidine is a histamine H2 receptor antagonist.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 114.19
Molecular weight 252.12
XLogP 1.02
No. Lipinski's rules broken 0
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Canonical SMILES N#CNC(=NC)NCCSCc1nc[nH]c1C
Isomeric SMILES N#CNC(=NC)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)
1. Beukers MW, Klaassen CH, De Grip WJ, Verzijl D, Timmerman H, Leurs R. (1997)
Heterologous expression of rat epitope-tagged histamine H2 receptors in insect Sf9 cells.
Br J Pharmacol, 122 (5): 867-74. [PMID:9384502]
2. Cappelli A, Manini M, Valenti S, Castriconi F, Giuliani G, Anzini M, Brogi S, Butini S, Gemma S, Campiani G et al.. (2013)
Synthesis and structure-activity relationship studies in serotonin 5-HT1A receptor agonists based on fused pyrrolidone scaffolds.
Eur J Med Chem, 63: 85-94. [PMID:23466604]
3. Engel K, Wang J. (2005)
Interaction of organic cations with a newly identified plasma membrane monoamine transporter.
Mol Pharmacol, 68 (5): 1397-407. [PMID:16099839]
4. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H. (1999)
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
J Biol Chem, 274 (19): 13675-80. [PMID:10224140]
5. Masuda S, Terada T, Yonezawa A, Tanihara Y, Kishimoto K, Katsura T, Ogawa O, Inui K. (2006)
Identification and functional characterization of a new human kidney-specific H+/organic cation antiporter, kidney-specific multidrug and toxin extrusion 2.
J Am Soc Nephrol, 17 (8): 2127-35. [PMID:16807400]
6. Ohta KY, Inoue K, Hayashi Y, Yuasa H. (2006)
Molecular identification and functional characterization of rat multidrug and toxin extrusion type transporter 1 as an organic cation/H+ antiporter in the kidney.
Drug Metab Dispos, 34 (11): 1868-74. [PMID:16928787]
7. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K. (2007)
Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters.
Biochem Pharmacol, 74 (2): 359-71. [PMID:17509534]
8. Tsuda M, Terada T, Ueba M, Sato T, Masuda S, Katsura T, Inui K. (2009)
Involvement of human multidrug and toxin extrusion 1 in the drug interaction between cimetidine and metformin in renal epithelial cells.
J Pharmacol Exp Ther, 329 (1): 185-91. [PMID:19164462]
9. Wang J. (2016)
The plasma membrane monoamine transporter (PMAT): Structure, function, and role in organic cation disposition.
Clin Pharmacol Ther, 100 (5): 489-499. [PMID:27506881]