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

General Information of Drug (ID: DR1393)
Drug Name
Ranitidine
Synonyms
Radinat; Randin; Ranidine; Raniogas; Ranisen; Raniter; Ranitidin; Ranitidina; Ranitidina [INN-Spanish]; Ranitidine Base; Ranitidine HCL; Ranitidinum; Ranitidinum [INN-Latin]; Ranitiget; Rantacid; Rantidine; Raticina; Sampep; Sostril; Achedos; Acidex; Atural; Axoban; Coralen; Duractin; Ezopta; Gastrial; Gastrosedol; Istomar; Logast; Mauran; Microtid; Ptinolin; Quantor; Quicran; Taural; Ul-Pep; Ulceranin; Urantac; Verlost; Vesyca; Vizerul; Weichilin; Weidos; Xanidine; ZANTAC; Zantab; Zantadin; Zantic; ranitidine; 66357-35-5; Ranin; Ratic
Indication Peptic ulcer [ICD11: DA61] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 314.41 Topological Polar Surface Area 112
Heavy Atom Count 21 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
3001055
PubChem SID
615112 ; 7847488 ; 7980484 ; 8149747 ; 10036397 ; 10532147 ; 11111714 ; 11111715 ; 11113371 ; 14776753 ; 26612202 ; 26680173 ; 26748519 ; 26748520 ; 26753732 ; 34666962 ; 46505543 ; 47216723 ; 47515261 ; 47810695 ; 48184944 ; 49846707 ; 49968693 ; 50100822 ; 50107423 ; 50107424 ; 50139267 ; 50286426 ; 53790194 ; 57410138 ; 85209253 ; 85245763 ; 90341455 ; 92124471 ; 92307665 ; 92711914 ; 93166337 ; 99301528 ; 103091649 ; 103155999 ; 103173566 ; 104171226 ; 111610678 ; 117377112 ; 117814891 ; 118258804 ; 124551883 ; 124636867 ; 124881290 ; 124881291
ChEBI ID
ChEBI:8776
CAS Number
66357-35-5
TTD Drug ID
D0B8WN
Formula
C13H22N4O3S
Canonical SMILES
CNC(=C[N+](=O)[O-])NCCSCC1=CC=C(O1)CN(C)C
InChI
1S/C13H22N4O3S/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3/h4-5,9,14-15H,6-8,10H2,1-3H3/b13-9+
InChIKey
VMXUWOKSQNHOCA-UKTHLTGXSA-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
Desmethylranitidine DM015669
10380064
Oxidation - N-demethylation 1 [3]
Ranitidine N-Oxide DM015388
3033888
Oxidation - N-oxygenation 1 [3]
Ranitidine S-Oxide DM015389
3033889
Oxidation - S-oxygenation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013046 Ranitidine Desmethylranitidine Oxidation - N-demethylation CYP2C19 ... [3]
MR013047 Ranitidine Ranitidine N-Oxide Oxidation - N-oxygenation FMO3 [3]
MR013048 Ranitidine Ranitidine S-Oxide Oxidation - S-oxygenation FMO3 ... [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Dimethylaniline oxidase 5 (FMO5) DME0634 Homo sapiens
FMO5_HUMAN
1.14.13.8
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1418 Enterococcus faecalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1432 Hungatella hathewayi Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [5]
⏷ Show the Full List of 9  DME(s)
References
1 Ranitidine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Comparative in vitro and in vivo inhibition of cytochrome P450 CYP1A2, CYP2D6, and CYP3A by H2-receptor antagonists. Clin Pharmacol Ther. 1999 Apr;65(4):369-76.
3 Oxidation of ranitidine by isozymes of flavin-containing monooxygenase and cytochrome P450. Jpn J Pharmacol. 2000 Oct;84(2):213-20.
4 Drug metabolism by flavin-containing monooxygenases of human and mouse. Expert Opin Drug Metab Toxicol. 2017 Feb;13(2):167-181.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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