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

General Information of Drug (ID: DR1541)
Drug Name
Tegaserod
Synonyms
Tegaserod; Tegaserod (USAN/INN); SDZ-HTF-919; Spectrum5_001691; Tegaserod maleate; tegaserodum; 1-(((5-Methoxyindol-3-yl)methylene)amino)-3-pentylguanidine; 1-[[(Z)-(5-methoxyindol-3-ylidene)methyl]amino]-2-pentylguanidine; 145158-71-0; 2-[(5-methoxy-2,3-dihydro-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide; 458VC51857; AC1NSFYX; AC1O2UE0; AC1OBC57; CAS-145158-71-0; CHEBI:51043; CHEMBL76370; DSSTox_CID_25955; DSSTox_GSID_45955; DSSTox_RID_81251; MLS001401406; NCGC00095192-01; SMR000471618; UNII-458VC51857
Indication Irritable bowel syndrome [ICD11: DD91] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 301.39 Topological Polar Surface Area 87.8
Heavy Atom Count 22 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
135409453
ChEBI ID
CHEBI:51043
CAS Number
145158-71-0
TTD Drug ID
D00XWD
Formula
C16H23N5O
Canonical SMILES
CCCCCN=C(N)NN=CC1=CNC2=C1C=C(C=C2)OC
InChI
1S/C16H23N5O/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15-7-6-13(22-2)9-14(12)15/h6-7,9-11,19H,3-5,8H2,1-2H3,(H3,17,18,21)/b20-11+
InChIKey
IKBKZGMPCYNSLU-RGVLZGJSSA-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
O-desmethyl tegaserod DM000470 N. A. Unclear 1 [2]
Tegaserod metabolite M43.2 DM000467
156613978
Conjugation - N-Glucuronidation 1 [4]
Tegaserod metabolite M43.8 DM000468
156614020
Conjugation - N-Glucuronidation 1 [4]
Tegaserod metabolite M45.3 DM000469
146019367
Conjugation - N-Glucuronidation 1 [4]
Unclear DM009999 N. A. Hydrolysis - Hydrolysis 1 [4]
Unclear DM009999 N. A. Oxidation - Oxidation 2 [4]
5-methoxyindole-3-carboxylic acid DM000466
259191
Conjugation - Conjugation 3 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002357 Tegaserod Tegaserod metabolite M43.2 Conjugation - N-Glucuronidation Unclear [4]
MR002358 Tegaserod Tegaserod metabolite M43.8 Conjugation - N-Glucuronidation Unclear [4]
MR002359 Tegaserod Tegaserod metabolite M45.3 Conjugation - N-Glucuronidation Unclear [4]
MR002360 Tegaserod O-desmethyl tegaserod Unclear CYP2D6 [2]
MR002361 Tegaserod . Hydrolysis - Hydrolysis Non-ME [4]
MR002356 . . Oxidation - Oxidation Unclear [4]
MR002355 . 5-methoxyindole-3-carboxylic acid Conjugation - Conjugation Unclear [4]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1362 Bacteroides caccae Not Available Not Available [3]
References
1 Tegaserod was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro metabolism of tegaserod in human liver and intestine: assessment of drug interactions. Drug Metab Dispos. 2001 Oct;29(10):1269-76.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Clinical pharmacokinetics of tegaserod, a serotonin 5-HT(4) receptor partial agonist with promotile activity Clin Pharmacokinet. 2002;41(13):1021-42. doi: 10.2165/00003088-200241130-00002.

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