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

General Information of Drug (ID: DR1600)
Drug Name
Tiotropium Bromide
Synonyms
Tiopropium; Tiotropium (Bromide); UNII-XX112XZP0J; XX112XZP0J; (1R,2R,4S,5S,7S)-7-(2-Hydroxy-2,2-di(thiophen-2-yl)acetoxy)-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0; (1R,2R,4S,5S,7s)-7-(2-Hydroxy-2,2-di(thiophen-2-yl)acetoxy)-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-ium bromide; 136310-93-5; BA 679BR; Spiriva Handihaler; Spiriva Respimat; TIOTROPIUM BROMIDE
Indication Chronic obstructive pulmonary disease [ICD11: CA22] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 472.4 Topological Polar Surface Area 116
Heavy Atom Count 27 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
5487426
PubChem SID
12014767 ; 16431254 ; 16516650 ; 37101841 ; 57364284 ; 78006594 ; 92309156 ; 92714242 ; 93302582 ; 121264529 ; 125003137 ; 126592377 ; 126624303 ; 126655544 ; 134224129 ; 134337655 ; 135087660 ; 135693784 ; 136376471 ; 136946674 ; 144206151 ; 152059683 ; 152258759 ; 152343784 ; 160647604 ; 162038024 ; 162170559 ; 164194996 ; 164814954 ; 172440019 ; 172440020 ; 172919722 ; 174476476 ; 175268305 ; 180673829 ; 184811782 ; 187072489 ; 196106129 ; 198991441 ; 223658400 ; 226399777 ; 226763578 ; 233206887 ; 241032671 ; 242592071 ; 249845981 ; 250203609 ; 251916428 ; 251917775 ; 252039050
ChEBI ID
CHEBI:90959
CAS Number
136310-93-5
TTD Drug ID
D0Z7AB
Formula
C19H22BrNO4S2
Canonical SMILES
C[N+]1(C2CC(CC1C3C2O3)OC(=O)C(C4=CC=CS4)(C5=CC=CS5)O)C.[Br-]
InChI
1S/C19H22NO4S2.BrH/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;1H/q+1;/p-1/t11?,12-,13+,16-,17+;
InChIKey
DQHNAVOVODVIMG-RGECMCKFSA-M
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
Hydrolysis - Hydrolyzation 1 [4]
N-methylscopine DM004656
16656111
Hydrolysis - Hydrolyzation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005000 Tiotropium Bromide Dithienylglycolic Acid Hydrolysis - Hydrolyzation Unclear [4]
MR005001 Tiotropium Bromide N-methylscopine Hydrolysis - Hydrolyzation Unclear [4]
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
[3]
References
1 Tiotropium Bromide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Tiotropium rromide/olodaterol (Stiolto Respimat): once-daily combination therapy for the maintenance of COPD. P T. 2016 Feb;41(2):97-102.
3 Tiotropium bromide. A review of its use as maintenance therapy in patients with COPD. Treat Respir Med. 2004;3(4):247-68.
4 Biochemical properties, pharmacokinetics and pharmacological response of tiotropium in chronic obstructive pulmonary disease patients

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