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

General Information of Drug (ID: DR5811)
Drug Name
Tiotropium
Synonyms
186691-13-4; UNII-0EB439235F; 0EB439235F; [3H]tiotropium; (1r,2r,4s,5s,7s)-7-{[hydroxy(Dithiophen-2-Yl)acetyl]oxy}-9,9-Dimethyl-3-Oxa-9-Azoniatricyclo[3310~2,4~]nonane; NCGC00167971-01; 0HK; (1R,2R,4S,5S)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3310^{2,4}]nonan-9-ium; GTPL367; SCHEMBL4662461; GTPL8592; DTXSID5044281; CHEMBL3305968; Spiriva (TN); Tiotropium bromide [USAN:INN]; (1A,2A,4A,5A,7A)-7-[(Hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatri-cyclo[331024]nonane bromide; (1a,2,4,5a,7)-7-[(2-Hydroxy-2,2-di-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[33102,4]nonane bromide; 7-{[hydroxy(dithiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclo[33102,4]nonane bromide
Indication Chronic obstructive pulmonary disease [ICD11: CA22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 392.5 Topological Polar Surface Area 116
Heavy Atom Count 26 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5487427
ChEBI ID
CHEBI:90960
CAS Number
186691-13-4
TTD Drug ID
D0P1WA
Formula
C19H22NO4S2+
Canonical SMILES
C[N+]1([C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)C(C4=CC=CS4)(C5=CC=CS5)O)C
InChI
InChI=1S/C19H22NO4S2/c1-20(2)12-9-11(10-13(20)17-16(12)24-17)23-18(21)19(22,14-5-3-7-25-14)15-6-4-8-26-15/h3-8,11-13,16-17,22H,9-10H2,1-2H3/q+1/t11?,12-,13+,16-,17+
InChIKey
LERNTVKEWCAPOY-FPISHFTHSA-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
Dithienylglycolic Acid DM004655
12723754
Unclear - Unclear 1 [3] , [2]
N-methylscopine DM004656
16656111
Unclear - Unclear 1 [3] , [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010765 Tiotropium Dithienylglycolic Acid Unclear - Unclear CYP3A4 ... [3], [2]
MR010766 Tiotropium N-methylscopine Unclear - Unclear CYP3A4 ... [3], [2]
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]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 367).
2 Tiotropium bromide. A review of its use as maintenance therapy in patients with COPD. Treat Respir Med. 2004;3(4):247-68.
3 Quantitative determination of pentazocine in plasma and of pentazocine and metabolites in urine

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