halothane   Click here for help

GtoPdb Ligand ID: 2401

Synonyms: Fluothane®
Approved drug
halothane is an approved drug (FDA (1958))
Compound class: Synthetic organic
Comment: Halothane is a volatile anaesthetic which causes rapid anaesthesia, but requires use of additional nitrous oxide and/or neuromuscular blocking agents to be fully effective.
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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
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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Click here for structure editor
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 0
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 0
Molecular weight 195.89
XLogP 3.16
No. Lipinski's rules broken 0
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 ClC(C(F)(F)F)Br
Isomeric SMILES ClC(C(F)(F)F)Br
InChI InChI=1S/C2HBrClF3/c3-1(4)2(5,6)7/h1H
InChI Key BCQZXOMGPXTTIC-UHFFFAOYSA-N
References
1. Blin S, Chatelain FC, Feliciangeli S, Kang D, Lesage F, Bichet D. (2014)
Tandem pore domain halothane-inhibited K+ channel subunits THIK1 and THIK2 assemble and form active channels.
J Biol Chem, 289 (41): 28202-12. [PMID:25148687]
2. Gray AT, Zhao BB, Kindler CH, Winegar BD, Mazurek MJ, Xu J, Chavez RA, Forsayeth JR, Yost CS. (2000)
Volatile anesthetics activate the human tandem pore domain baseline K+ channel KCNK5.
Anesthesiology, 92 (6): 1722-30. [PMID:10839924]
3. Kelemen B, Lisztes E, Vladár A, Hanyicska M, Almássy J, Oláh A, Szöllősi AG, Pénzes Z, Posta J, Voets T et al.. (2020)
Volatile anaesthetics inhibit the thermosensitive nociceptor ion channel transient receptor potential melastatin 3 (TRPM3).
Biochem Pharmacol, 174: 113826. [PMID:31987857]
4. Kulkarni RS, Zorn LJ, Anantharam V, Bayley H, Treistman SN. (1996)
Inhibitory effects of ketamine and halothane on recombinant potassium channels from mammalian brain.
Anesthesiology, 84 (4): 900-9. [PMID:8638845]
5. Lazarenko RM, Willcox SC, Shu S, Berg AP, Jevtovic-Todorovic V, Talley EM, Chen X, Bayliss DA. (2010)
Motoneuronal TASK channels contribute to immobilizing effects of inhalational general anesthetics.
J Neurosci, 30 (22): 7691-704. [PMID:20519544]
6. Lesage F, Terrenoire C, Romey G, Lazdunski M. (2000)
Human TREK2, a 2P domain mechano-sensitive K+ channel with multiple regulations by polyunsaturated fatty acids, lysophospholipids, and Gs, Gi, and Gq protein-coupled receptors.
J Biol Chem, 275 (37): 28398-405. [PMID:10880510]
7. Meadows HJ, Randall AD. (2001)
Functional characterisation of human TASK-3, an acid-sensitive two-pore domain potassium channel.
Neuropharmacology, 40 (4): 551-9. [PMID:11249964]
8. Patel AJ, Honoré E, Lesage F, Fink M, Romey G, Lazdunski M. (1999)
Inhalational anesthetics activate two-pore-domain background K+ channels.
Nat Neurosci, 2 (5): 422-6. [PMID:10321245]
9. Patel AJ, Honoré E, Maingret F, Lesage F, Fink M, Duprat F, Lazdunski M. (1998)
A mammalian two pore domain mechano-gated S-like K+ channel.
EMBO J, 17 (15): 4283-90. [PMID:9687497]
10. Talley EM, Bayliss DA. (2002)
Modulation of TASK-1 (Kcnk3) and TASK-3 (Kcnk9) potassium channels: volatile anesthetics and neurotransmitters share a molecular site of action.
J Biol Chem, 277 (20): 17733-42. [PMID:11886861]
11. Washburn CP, Sirois JE, Talley EM, Guyenet PG, Bayliss DA. (2002)
Serotonergic raphe neurons express TASK channel transcripts and a TASK-like pH- and halothane-sensitive K+ conductance.
J Neurosci, 22 (4): 1256-65. [PMID:11850453]
12. Weigl LG, Schreibmayer W. (2001)
G protein-gated inwardly rectifying potassium channels are targets for volatile anesthetics.
Mol Pharmacol, 60 (2): 282-9. [PMID:11455015]