clotrimazole   Click here for help

GtoPdb Ligand ID: 2330

Synonyms: Canesten® | Lotrimin®
Approved drug PDB Ligand
clotrimazole is an approved drug (FDA (1975))
Compound class: Synthetic organic
Comment: Clotrimazole is an anti-fungal agent.
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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: clotrimazole

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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 1
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 17.82
Molecular weight 344.11
XLogP 6.14
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 Clc1ccccc1C(n1cncc1)(c1ccccc1)c1ccccc1
Isomeric SMILES Clc1ccccc1C(n1cncc1)(c1ccccc1)c1ccccc1
InChI InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H
InChI Key VNFPBHJOKIVQEB-UHFFFAOYSA-N
References
1. Bertilsson G, Heidrich J, Svensson K, Asman M, Jendeberg L, Sydow-Bäckman M, Ohlsson R, Postlind H, Blomquist P, Berkenstam A. (1998)
Identification of a human nuclear receptor defines a new signaling pathway for CYP3A induction.
Proc Natl Acad Sci USA, 95 (21): 12208-13. [PMID:9770465]
2. Ghanshani S, Coleman M, Gustavsson P, Wu AC, Gargus JJ, Gutman GA, Dahl N, Mohrenweiser H, Chandy KG. (1998)
Human calcium-activated potassium channel gene KCNN4 maps to chromosome 19q13.2 in the region deleted in diamond-blackfan anemia.
Genomics, 51 (1): 160-1. [PMID:9693050]
3. Hill K, McNulty S, Randall AD. (2004)
Inhibition of TRPM2 channels by the antifungal agents clotrimazole and econazole.
Naunyn Schmiedebergs Arch Pharmacol, 370 (4): 227-37. [PMID:15549272]
4. Ishii TM, Silvia C, Hirschberg B, Bond CT, Adelman JP, Maylie J. (1997)
A human intermediate conductance calcium-activated potassium channel.
Proc Natl Acad Sci USA, 94 (21): 11651-6. [PMID:9326665]
5. Kanno Y, Tanuma N, Takahashi A, Inouye Y. (2013)
TO901317, a potent LXR agonist, is an inverse agonist of CAR.
J Toxicol Sci, 38 (3): 309-15. [PMID:23665929]
6. Logsdon NJ, Kang J, Togo JA, Christian EP, Aiyar J. (1997)
A novel gene, hKCa4, encodes the calcium-activated potassium channel in human T lymphocytes.
J Biol Chem, 272 (52): 32723-6. [PMID:9407042]
7. Moore LB, Parks DJ, Jones SA, Bledsoe RK, Consler TG, Stimmel JB, Goodwin B, Liddle C, Blanchard SG, Willson TM, Collins JL, Kliewer SA. (2000)
Orphan nuclear receptors constitutive androstane receptor and pregnane X receptor share xenobiotic and steroid ligands.
J Biol Chem, 275 (20): 15122-7. [PMID:10748001]
8. Nina DUllrich. (2005)
PhD Thesis.  In  TRPM4 and TRPM5: Functional characterisation and comparison of two novel Ca2+-activated cation channels of the TRPM subfamily (Faculteit Geneeskunde, Dept. Moleculaire Celbiologie, KU Leuven) .
9. Wulff H, Miller MJ, Hansel W, Grissmer S, Cahalan MD, Chandy KG. (2000)
Design of a potent and selective inhibitor of the intermediate-conductance Ca2+-activated K+ channel, IKCa1: a potential immunosuppressant.
Proc Natl Acad Sci USA, 97 (14): 8151-6. [PMID:10884437]