Drug Information

General Information
Drug ID
DR00037
Drug Name
Cimetidine
Synonyms
1-Cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine; 1-Cyano-2-methyl-3-[2-[[(5-methylimidazol-4-yl)methyl]thio]ethyl]guanidine; 1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine; 2-Cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidine; 2-Cyano-1-methyl-3-[2-(5-methyl-1H-imidazol-4-yl-methylthio)ethyl]guanidine; 2-cyano-1-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine; 2-cyano-1-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]thio}ethyl)guanidine; Acibilin; Acinil; Altramet; Biomet400; Brumetidina; C 4522; CIMETIDINE A/AB; Ci metum; Cimal; Cimetadine; Cimetag; Cimetidina; Cimetidina [INN-Spanish]; Cimetidine (JP15/USP/INN); Cimetidine Hcl; Cimetidine [USAN:INN:BAN:JAN]; Cimetidinum; Cimetidinum [INN-Latin]; Cimetum; DRG-0150; Dyspamet; Edalene; Eureceptor; Evicer; FPF 1002; Gastrobitan; Gastromet; Histodil; Magicul; Metracin; N''-Cyano-N-methyl-N'-[2-[(5-methyl-1H-imidazol-4-yl)methylthio]ethyl]guanidine; N''-cyano-N-methyl-N'-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)-ethyl)guanidine; N''-cyano-N-methyl-N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]thio}ethyl)guanidine; N-Cyano-N'-Methyl-N''-(2-(((5-Methyl-1H-Imidazol-4-YL)Methyl)Thio)Ethyl) Guanidine; N-Cyano-N'-methyl-N''-(2-(((5-methyl-1 H-imidazol-4-yl) methyl)thio)ethyl)guanidine; N-Cyano-N'-methyl-N''-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)guanidine; N-Cyano-N'-methyl-[2-[[[5-methyl-1H-imidazol-4-yl]methyl]thio]ethyl]guanidine; N-cyano-N'-methyl-N''-(2-([(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl)ethyl)guanidine; N-cyano-N'-methyl-N''-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]thio}ethyl)guanidine; Peptol; SK&F-92334; SKF 92334; SKF-92334; Sigmetadine; Tagamet; Tagamet (TN); Tagamet HB (TN); Tagamet HB200 (TN); Tagamet Hb; Tagamet Hb 200; Tagamet, SKF-92334, Tratul, Tametin, Dyspamet, Acinil, Cimetidine; Tametin; Tratul; Ulcedin; Ulcedine; Ulcestop; Ulcimet; Ulcofalk; Ulcomedina; Ulcomet; Ulhys; Valmagen; Venopex
Drug Type
Small molecular drug
Indication Acid reflux disorder [ICD11:DA22] Approved [1]
Therapeutic Class
Antiulcer Agents
Structure
3D MOL 2D MOL
Formula
C10H16N6S
Canonical SMILES
CC1=C(N=CN1)CSCCNC(=NC)NC#N
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
CAS Number
CAS 51481-61-9
Pharmaceutical Properties Molecular Weight 252.34 Topological Polar Surface Area 114
Heavy Atom Count 17 Rotatable Bond Count 7
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
XLogP
0.4
PubChem CID
2756
PubChem SID
10321166 ,10524846 ,11110948 ,11113773 ,11335341 ,11360580 ,11363389 ,11365951 ,11368513 ,11372297 ,11374462 ,11376675 ,11407328 ,11461552 ,11484620 ,11488598 ,11491204 ,11492627 ,11494309 ,11533056 ,12013445 ,14774387 ,15122273 ,15196790 ,17389962 ,17404856 ,22391437 ,24277766 ,24531048 ,26612025 ,26679798 ,26747359 ,26747360 ,26751956 ,26751957 ,29221911 ,4266417 ,4493559 ,460110 ,46487919 ,46505360 ,47275096 ,615111 ,6699439 ,6897918 ,7847361 ,7978946 ,8147032 ,8149633 ,9167
ChEBI ID
ChEBI:3699
TTD Drug ID
D02DPA
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
2-Oct Transporter Info Organic cation transporter 2 Substrate [3]
BCRP Transporter Info Breast cancer resistance protein Substrate [4]
MATE1 Transporter Info Multidrug and toxin extrusion protein 1 Substrate [5]
MATE2 Transporter Info Multidrug and toxin extrusion protein 2 Substrate [5]
OAT3 Transporter Info Organic anion transporter 3 Substrate [6]
P-GP Transporter Info P-glycoprotein 1 Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data 2-Oct Transporter Info Km =60 microM Human embryonic kidney cells (HEK293)-OCT2 [2]
2-Oct Transporter Info Km =72.6 microM Human embryonic kidney cells (HEK293)-OCT2 [8]
MATE1 Transporter Info Km =170 microM Human embryonic kidney cells (HEK293)-MATE1 [5]
MATE2 Transporter Info Km =120 microM Human embryonic kidney cells (HEK293)-MATE2K [5]
MATE2 Transporter Info Km =370 microM Human embryonic kidney cells (HEK293)-MATE2K [9]
OAT3 Transporter Info Km =174 microM Chinese hamster ovary (CHO) cells-OAT3 [6]
OAT3 Transporter Info Km =113 microM Human embryonic kidney cells (HEK293)-OAT3 [10]
OAT3 Transporter Info Km =149 microM Human embryonic kidney cells (HEK293)-OAT3 [11]
OAT3 Transporter Info Km =57.4 microM Oocytes-OAT3 [12]
References
1 Cimetidine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Identification of novel substrates and structure-activity relationship of cellular uptake mediated by human organic cation transporters 1 and 2. J Med Chem. 2013 Sep 26;56(18):7232-42.
3 Elevated systemic elimination of cimetidine in rats with acute biliary obstruction: the role of renal organic cation transporter OCT2. Drug Metab Pharmacokinet. 2010;25(4):328-34.
4 Progesterone acts via progesterone receptors A and B to regulate breast cancer resistance protein expression. Mol Pharmacol. 2008 Mar;73(3):613-5.
5 Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71.
6 Transport of the dipeptidyl peptidase-4 inhibitor sitagliptin by human organic anion transporter 3, organic anion transporting polypeptide 4C1, and multidrug resistance P-glycoprotein. J Pharmacol Exp Ther. 2007 May;321(2):673-83.
7 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
8 A species difference in the transport activities of H2 receptor antagonists by rat and human renal organic anion and cation transporters. J Pharmacol Exp Ther. 2005 Oct;315(1):337-45.
9 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. 2006 Aug;17(8):2127-35.
10 Inhibition of oat3-mediated renal uptake as a mechanism for drug-drug interaction between fexofenadine and probenecid. Drug Metab Dispos. 2006 May;34(5):743-7.
11 Is the monkey an appropriate animal model to examine drug-drug interactions involving renal clearance? Effect of probenecid on the renal elimination of H2 receptor antagonists. J Pharmacol Exp Ther. 2006 Mar;316(3):1187-94.
12 Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86.

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