dutasteride   Click here for help

GtoPdb Ligand ID: 7457

Synonyms: Avodart® | GG-745 | GI-198745
Approved drug
dutasteride is an approved drug (FDA (2001))
Compound class: Natural product or derivative
Comment: Dutasteride is a 5α-reductase inhibitor, which inhibits conversion of testosterone to dihydrotestosterone (DHT). There are three 5α-reductase isozymes: SRD5A1, SRD5A2 and SRD5A3, all of which are inhibited by dutasteride [1-2].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: dutasteride

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 58.2
Molecular weight 528.22
XLogP 6.77
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C1C=CC2(C(N1)CCC1C2CCC2(C1CCC2C(=O)Nc1cc(ccc1C(F)(F)F)C(F)(F)F)C)C
Isomeric SMILES O=C1C=C[C@]2([C@H](N1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)Nc1cc(ccc1C(F)(F)F)C(F)(F)F)C)C
InChI InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1
InChI Key JWJOTENAMICLJG-QWBYCMEYSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (2001))
IUPAC Name Click here for help
(1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
International Nonproprietary Names Click here for help
INN number INN
7586 dutasteride
Synonyms Click here for help
Avodart® | GG-745 | GI-198745
Database Links Click here for help
CAS Registry No. 164656-23-9
ChEBI CHEBI:521033
ChEMBL Ligand CHEMBL1200969
DrugBank Ligand DB01126
DrugCentral Ligand 973
GtoPdb PubChem SID 187051760
PubChem CID 6918296
Search Google for chemical match using the InChIKey JWJOTENAMICLJG-QWBYCMEYSA-N
Search Google for chemicals with the same backbone JWJOTENAMICLJG
Search PubMed clinical trials dutasteride
Search PubMed titles dutasteride
Search PubMed titles/abstracts dutasteride
UniChem Compound Search for chemical match using the InChIKey JWJOTENAMICLJG-QWBYCMEYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JWJOTENAMICLJG-QWBYCMEYSA-N
Wikipedia Dutasteride