Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2272)
Drug Name
Cimetidine
Synonyms
Cimetadine; Cimetag; Cimetidina; Cimetidina [INN-Spanish]; Cimetidine (JP15/USP/INN); Cimetidine Hcl; Cimetidine [USAN:INN:BAN:JAN]; Cimetidinum; Cimetidinum [INN-Latin]; Cimetum; Dyspamet; Edalene; Eureceptor; Evicer; Gastrobitan; Acibilin; Acinil; Altramet; Biomet400; Brumetidina; CIMETIDINE A/AB; Gastromet; Histodil; Magicul; Metracin; Peptol; SK&F-92334; SKF 92334; SKF-92334; Sigmetadine; Tagamet; Tagamet (TN); Tagamet HB (TN); Tagamet HB200 (TN); Tagamet Hb; Tagamet Hb 200; Tametin; Tratul; Ulcedin; Ulcedine; Ulcestop; Ulcimet; Ulcofalk; Ulcomedina; Ulcomet; Valmagen; Venopex; 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; C 4522; Ci metum; Cimal; DRG-0150; FPF 1002; 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; Tagamet, SKF-92334, Tratul, Tametin, Dyspamet, Acinil, Cimetidine; Ulhys
Indication Duodenal ulcer [ICD11: DA63] Approved [1]
Structure
3D MOL 2D MOL
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
Cross-matching ID
PubChem CID
2756
PubChem SID
9167 ; 460110 ; 615111 ; 4266417 ; 4493559 ; 6699439 ; 6897918 ; 7847361 ; 7978946 ; 8147032 ; 8149633 ; 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 ; 46487919 ; 46505360 ; 47275096
ChEBI ID
ChEBI:3699
CAS Number
51481-61-9
TTD Drug ID
D02DPA
Formula
C10H16N6S
Canonical SMILES
CC1=C(N=CN1)CSCCNC(=NC)NC#N
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Cimetidine sulfoxide metabolite DM001847
62949
Oxidation - 6-Hydroxylation 1 [3] , [4]
Hydroxymethyl cimetidine DM001848
162879
Unclear 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000659 Cimetidine Cimetidine sulfoxide metabolite Oxidation - 6-Hydroxylation Unclear [3], [4]
MR000660 Cimetidine Hydroxymethyl cimetidine Unclear Unclear [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [2]
References
1 Cimetidine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
3 Cimetidine sulfoxidation in small intestinal microsomes Drug Metab Dispos. 1998 Sep;26(9):940-2.
4 An improved high performance liquid chromatographic method for determination of cimetidine and its major metabolite in plasma Arch Invest Med (Mex). 1989 Oct-Dec;20(4):309-13.
5 Clinical pharmacokinetics of cimetidine Clin Pharmacokinet. 1983 Nov-Dec;8(6):463-95. doi: 10.2165/00003088-198308060-00001.

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