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

General Information of Drug (ID: DR2187)
Drug Name
Nizatidine
Synonyms
Naxidine; Niatidine; Nizatidina; Nizatidina [Spanish]; Nizatidine (JAN/USP/INN); Nizatidine [USAN:BAN:INN:JAN]; Nizatidinum; Nizatidinum [Latin]; Nizaxid; Acinon; Acinon (TN); Antizid; Axid (TN); Axid Ar; Calmaxid; Cronizat; Distaxid; Galitidin; Gastrax; LY 139037; LY-139037; Panaxid; Splendil ER; Tazac (TN); Ulcosol; ZE-101; ZL-101; Zanizal; (E)-1-N'-[2-[[2-(dimethylaminomethyl)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-1-N-methyl-2-nitroethene-1,1-diamine; (E)-N-[2-[[2-(dimethylaminomethyl)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-N'-methyl-2-nitroethene-1,1-diamine; (E)-N-{2-[({2-[(dimethylamino)methyl]-1,3-thiazol-4-yl}methyl)thio]ethyl}-N'-methyl-2-nitroethene-1,1-diamine; Axid; N-(2-(((2-((Dimethylamino)methyl)-4-thiazolyl)methyl)thio)ethyl)-N'-methyl-2-nitro-1,1-ethenediamine; N-(4-(6-Methylamino-7-nitro-2-thia-5-aza-6-hepten-1-yl)-2-thiazolylmethyl)-N,N-dimethylamin; Nizax; Tazac; Ulxid; Zinga
Indication Peptic ulcer [ICD11: DA61] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 331.5 Topological Polar Surface Area 140
Heavy Atom Count 21 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
3033637
PubChem SID
9479 ; 7847506 ; 7980136 ; 10047729 ; 11112849 ; 12012865 ; 14801956 ; 26719892 ; 36077514 ; 46386765 ; 46507554 ; 48395159 ; 48416335 ; 49648463 ; 49968698 ; 57352747 ; 80039644 ; 85175204 ; 85209480 ; 92308159 ; 92308434 ; 92711372 ; 93166919 ; 103091650 ; 103157346 ; 103189241 ; 111634652 ; 117377111 ; 117480196 ; 119526527 ; 124658842 ; 124801333 ; 124882685 ; 126630925 ; 131269073 ; 131326051 ; 134337651 ; 135011516 ; 135692320 ; 137005454 ; 142971063 ; 144075999 ; 144089140 ; 152040062 ; 160963930 ; 172080209 ; 177748315 ; 178103822 ; 179116550 ; 179148990
ChEBI ID
CHEBI:7601
CAS Number
76963-41-2
TTD Drug ID
D0Q9DK
Formula
C12H21N5O2S2
Canonical SMILES
CNC(=C[N+](=O)[O-])NCCSCC1=CSC(=N1)CN(C)C
InChI
1S/C12H21N5O2S2/c1-13-11(6-17(18)19)14-4-5-20-8-10-9-21-12(15-10)7-16(2)3/h6,9,13-14H,4-5,7-8H2,1-3H3/b11-6+
InChIKey
SGXXNSQHWDMGGP-IZZDOVSWSA-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
N2-monodes-methylnizatidine DM002221
13121939
Oxidation - N-Demethylation 1 [3] , [4]
Nizatidine N2-oxide metabolite DM002222
91810595
Oxidation - N-Oxidation 1 [5]
Nizatidine sulfoxide metabolite DM002223
71751150
Oxidation - Sulfoxidation 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001772 Nizatidine N2-monodes-methylnizatidine Oxidation - N-Demethylation Unclear [3], [4]
MR001773 Nizatidine Nizatidine N2-oxide metabolite Oxidation - N-Oxidation Unclear [5]
MR001774 Nizatidine Nizatidine sulfoxide metabolite Oxidation - Sulfoxidation 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]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [2]
⏷ Show the Full List of 7  DME(s)
References
1 Nizatidine 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 Hemofiltrability of histamine H2-receptor antagonist, nizatidine, and its metabolites in patients with renal failure J Clin Pharmacol. 1993 Apr;33(4):324-9. doi: 10.1002/j.1552-4604.1993.tb04664.x.
4 Determination of nizatidine and two of its main metabolites in human serum using high-performance liquid chromatography J Chromatogr. 1990 Aug 3;529(2):369-76. doi: 10.1016/s0378-4347(00)83843-8.
5 Nizatidine, an H2-blocker. Its metabolism and disposition in man Drug Metab Dispos. 1986 Mar-Apr;14(2):175-82.

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