Drug Information

General Information
Drug ID
DR00017
Drug Name
Tiotropium
Synonyms
(1A,2A,4A,5A,7A)-7-[(Hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatri-cyclo[3.3.1.02.4]nonane bromide; (1a,2,4,5a,7)-7-[(2-Hydroxy-2,2-di-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide; 7-((Hydroxybis(2-thienyl)acetyl)oxy)-9,9-dimethyl-3-oxa-9-azoniatricyclo(3.3.1.0(2,4))nonane bromide; 7-{[hydroxy(dithiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide; BA 679 BR; BA 679BR; BA-679 BR; BA-679-BR; Spiriva; Spiriva (TN); Spiriva Handihaler; Spiriva Respimat; TIOTROPIUM BROMIDE; Tiotropium bromide [USAN:INN]
Drug Type
Small molecular drug
Indication Chronic obstructive pulmonary disease [ICD11:CA22] Approved [1]
Therapeutic Class
Bronchodilator Agents
Structure
3D MOL 2D MOL
Formula
C19H22NO4S2+
Canonical SMILES
C[N+]1(C2CC(CC1C3C2O3)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
CAS Number
CAS 186691-13-4
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
XLogP
2.3
PubChem CID
5487427
PubChem SID
134356992 ,135200496 ,135651266 ,140035980 ,140036001 ,172914590 ,175268858 ,176484519 ,176485044 ,176485084 ,180123694 ,180371973 ,223404197 ,223404198 ,223573677 ,230569065 ,242495157 ,242656157 ,244840198 ,249309736 ,252166793 ,39473136 ,50113015 ,51387641 ,58832470
ChEBI ID
CHEBI:90960
TTD Drug ID
D0P1WA
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
OCTN2 Transporter Info Organic cation/carnitine transporter 2 Substrate [3]
References
1 Tiotropium was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Identification of novel substrates and structure-activity relationship of cellular uptake mediated by human organic cation transporters 1 and 2. J Med Chem. 2013 Sep 26;56(18):7232-42.
3 Transport of ipratropium, an anti-chronic obstructive pulmonary disease drug, is mediated by organic cation/carnitine transporters in human bronchial epithelial cells: implications for carrier-mediated pulmonary absorption. Mol Pharm. 2010 Feb 1;7(1):187-95.

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