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Details

Stereochemistry RACEMIC
Molecular Formula C2HBrClF3
Molecular Weight 197.3811
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HALOTHANE

SMILES

C(C(F)(F)F)(Br)Cl

InChI

InChIKey=BCQZXOMGPXTTIC-UHFFFAOYSA-N
InChI=1S/C2HBrClF3/c3-1(4)2(5,6)7/h1H

HIDE SMILES / InChI
Halothane, USP is an inhalation anesthetic chemically designated 2-Bromo-2-chloro-1,1,1-trifluoroethane. Halothane, sold under the brand name Fluothane among others, is a general anesthetic. It can be used to start or maintain anesthesia. One of its benefits is that it does not increase the production of saliva which can be particularly useful in those who are difficult to intubate. Side effects include an irregular heartbeat, decreased effort to breath (respiratory depression), and liver problems. It should not be used in people with porphyria or a history of malignant hyperthermia either in themselves or their family members. It is unclear whether use during pregnancy is harmful to the baby, and it is not generally recommended for use during a cesarean section. Fluothane is no longer commercially available in the United States.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FLUOTHANE

Approved Use

INDICATIONS. Halothane is indicated for the induction and maintenance of general anesthesia.

Launch Date

-3.72643201E11
Doses

Doses

DosePopulationAdverse events​
4 % single, respiratory (min)
Overdose
Dose: 4 %
Route: respiratory
Route: single
Dose: 4 %
Sources: Page: p.212
unhealthy, 3
n = 1
Health Status: unhealthy
Condition: anesthesia for dental disorder
Age Group: 3
Sex: F
Population Size: 1
Sources: Page: p.212
Disc. AE: Change in ECG, Blood pressure systolic decreased...
AEs leading to
discontinuation/dose reduction:
Change in ECG
Blood pressure systolic decreased
Sources: Page: p.212
AEs

AEs

AESignificanceDosePopulation
Blood pressure systolic decreased Disc. AE
4 % single, respiratory (min)
Overdose
Dose: 4 %
Route: respiratory
Route: single
Dose: 4 %
Sources: Page: p.212
unhealthy, 3
n = 1
Health Status: unhealthy
Condition: anesthesia for dental disorder
Age Group: 3
Sex: F
Population Size: 1
Sources: Page: p.212
Change in ECG Disc. AE
4 % single, respiratory (min)
Overdose
Dose: 4 %
Route: respiratory
Route: single
Dose: 4 %
Sources: Page: p.212
unhealthy, 3
n = 1
Health Status: unhealthy
Condition: anesthesia for dental disorder
Age Group: 3
Sex: F
Population Size: 1
Sources: Page: p.212
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
yes (co-administration study)
Comment: plasma concentration of chlorzoxazone (substrate) increased 2.5-fold after 3 h of halothane inhalation in rabbits
Drug as victimTox targets
PubMed

PubMed

TitleDatePubMed
Myocardial function and metabolism in the conscious dog and during halothane anesthesia.
1976 May
Use of structural alterations in the synthesis of halothane metabolite antigens to mimic halothane-induced immunogen.
1990
Severe bradycardia and sinus arrest after administration of vecuronium, fentanyl and halothane. A case report.
1991 Aug 17
Screening for antibodies associated with halothane hepatitis.
1991 Dec
Steal-prone coronary anatomy and myocardial ischemia associated with four primary anesthetic agents in humans.
1991 Jan
Is premedication with oral glycopyrrolate as effective as oral atropine in attenuating cardiovascular depression in infants receiving halothane for induction of anesthesia?
1991 Sep
Halothane hepatitis 28 years after primary exposure.
1992 Apr
Isoflurane does not increase the incidence of intraoperative myocardial ischaemia compared with halothane during vascular surgery.
1992 Dec
Molecular mimicry of trifluoroacetylated human liver protein adducts by constitutive proteins and immunochemical evidence for its impairment in halothane hepatitis.
1992 Dec 1
[Neuromyopathy induced by halothane anesthesia and muscle relaxants for status asthmaticus--report of 2 patients].
1992 Mar
Nalidixic acid-induced hemolytic anemia complicating halothane-induced hepatitis.
1992 May
Chemical hepatitis associated with occupational exposure to halothane in a research laboratory.
1992 Oct
Muscle rigidity following halothane anesthesia in two patients with Freeman-Sheldon syndrome.
1992 Sep
[Heart rhythm variability as a criterion for selecting anesthesia for maxillofacial surgical procedures in children].
2003
Calcium release from sarcoplasmic reticulum is facilitated in human myotubes derived from carriers of the ryanodine receptor type 1 mutations Ile2182Phe and Gly2375Ala.
2003 Fall
Concordance between trifluoroacetic acid and hepatic protein trifluoroacetylation after disulfiram inhibition of halothane metabolism in rats.
2003 Jul
In vivo measurement of bending stiffness in fracture healing.
2003 Mar 28
[Halothane-induced hepatitis. 8 case reports].
2003 Nov
Trifluoroacetylated proteins in liver and plasma of guinea pigs treated with HCFC-123 and halothane.
2003 Sep 15
Biological activity of bacterial lectins and their molecular complexes with heterocyclic bis-adducts.
2003 Sep-Oct
Differential protective effects of volatile anesthetics against renal ischemia-reperfusion injury in vivo.
2004 Dec
Functional characterization of malignant hyperthermia-associated RyR1 mutations in exon 44, using the human myotube model.
2004 Jul
Development of a halothane-adrenaline arrhythmia model using in vivo Guinea pigs.
2004 Jun
Halothane induced hepatitis: case report.
2004 Oct
Gas-phase positive ion chemistry of 1-bromo-1-chloro-2,2,2-trifluoroethane (halothane) upon electron ionization within an ion trap mass spectrometer.
2005
Positive and negative ion chemistry of the anesthetic halothane (1-bromo-1-chloro-2,2,2-trifluoroethane) in air plasma at atmospheric pressure.
2005
Identification of the central imidazoline receptor subtype involved in modulation of halothane-epinephrine arrhythmias in rats.
2005 Dec
Reproducible loss of CA1 neurons following carotid artery occlusion combined with halothane-induced hypotension.
2005 Feb 8
Truncated human serum albumin retains general anaesthetic binding activity.
2005 May 15
Fulminant hepatic failure following halothane anaesthesia.
2005 Oct
Fulminant drug-induced hepatic failure leading to death or liver transplantation in Sweden.
2005 Sep
A guest molecule-host cavity fitting algorithm to mine PDB for small molecule targets.
2006 Aug
Functional hyperemic response in the rat visual cortex under halothane anesthesia.
2006 Feb 6
Clinical observations surrounding an increased incidence of postanesthetic myopathy in halothane-anesthetized horses.
2006 Mar
Halothane induces oxidative stress and NF-kappaB activation in rat liver: protective effect of propofol.
2006 Oct 3
Switch from planktonic to sessile life: a major event in pneumococcal pathogenesis.
2006 Sep
Reduced cardiovascular reactivity to stress but not feeding in renin enhancer knockout mice.
2007 Aug
Halothane induced fulminant hepatic failure.
2007 Feb
The common chemical motifs within anesthetic binding sites.
2007 Feb
Therapeutic potential of neuronal two-pore domain potassium-channel modulators.
2007 Jul
Inhaled anesthetic modulation of amyloid beta(1-40) assembly and growth.
2007 Jul
Detrimental effects of halothane narcosis on damage after endothelin-1-induced MCAO.
2007 May 15
Transgenic upregulation of IK1 in the mouse heart is proarrhythmic.
2007 Sep
A novel approach to detect hot-spots in large-scale multivariate data.
2007 Sep 11
Inhalation anaesthesia: from diethyl ether to xenon.
2008
Stimulatory effect of Eucalyptus essential oil on innate cell-mediated immune response.
2008 Apr 18
Trifluoroacetylated IgG4 antibodies in a child with idiosyncratic acute liver failure after first exposure to halothane.
2008 Aug
Cardiomyocyte formation by skeletal muscle-derived multi-myogenic stem cells after transplantation into infarcted myocardium.
2008 Mar 12
Disruption of FAK signaling: a side mechanism in cytotoxicity.
2008 Mar 12
Interaction of anesthetics with the Rho GTPase regulator Rho GDP dissociation inhibitor.
2008 Sep 9
Patents

Patents

Sample Use Guides

In Vivo Use Guide
The induction dose varies from patient to patient. The maintenance dose varies from 0.5 to 1.5%. Halothane may be administered with either oxygen or a mixture of oxygen and nitrous oxide.
Route of Administration: Respiratory
Mechanically dissociated rat hippocampal CA3 neurons was used for evaluation of halothane effects on synaptic and extrasynaptic GABAA and glutamate receptor responses. All receptor mediated currents were recorded in whole-cell patch recording under the voltage clamp condition at a holding potential of 0mV for GABAergic inhibitory postsynaptic currents or -65 mV for glutamatergic excitatory postsynaptic currents (EPSCs). Halothane solution (up to 20mM) was continuously applied to the isolated neuron by Y-tube system using silicon tubing directly connected to the glass test tube and all well sealed with parafilm to avoid any evaporation and loss of anesthetic.
Name Type Language
HALOTHANE
EP   GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
HALOTHANE [HSDB]
Common Name English
HALOTHANE [WHO-IP]
Common Name English
HALOTHANE [USP MONOGRAPH]
Common Name English
HALOTHANE [EP MONOGRAPH]
Common Name English
NSC-143490
Code English
HALOTHANE [ORANGE BOOK]
Common Name English
2-BROMO-2-CHLORO-1,1,1-TRIFLUOROETHANE
Common Name English
ETHANE, 2-BROMO-2-CHLORO-1,1,1-TRIFLUORO-,(+/-)-
Common Name English
HALOTHANE [WHO-DD]
Common Name English
HALOTHANE [EP]
Common Name English
HALOTHANUM [WHO-IP LATIN]
Common Name English
HALOTHANE [INN]
Common Name English
FREON 123B1
Code English
(+/-)-2-BROMO-2-CHLORO-1,1,1-TRIFLUOROETHANE
Systematic Name English
FLUOTHANE
Brand Name English
HALOTHANE [MI]
Common Name English
HALOTHANE [VANDF]
Common Name English
HALOTHANE [GREEN BOOK]
Common Name English
HALOTHANE [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC N01AB01
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 1.1.1
NCI_THESAURUS C245
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
WHO-VATC QN01AB01
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
LIVERTOX 477
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
Code System Code Type Description
WIKIPEDIA
HALOTHANE
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
PUBCHEM
3562
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-796-5
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
EPA CompTox
151-67-7
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
IUPHAR
2401
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PRIMARY
MERCK INDEX
M5907
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PRIMARY Merck Index
NCI_THESAURUS
C47554
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
HSDB
6753
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
FDA UNII
UQT9G45D1P
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PRIMARY
INN
697
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PRIMARY
RXCUI
5095
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY RxNorm
MESH
D006221
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
DRUG CENTRAL
1356
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
LACTMED
Halothane
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
HALOTHANE
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY Description: A colourless, mobile, heavy liquid; odour, characteristic, resembling that of chloroform. Miscibility: Miscible with 400 parts of water; miscible with ethanol (~750 g/l) TS, ether R, and trichloroethylene R. Category: General anaesthetic. Storage: Halothane should be kept in a well-closed container, protected from light, and stored at a temperature not exceeding 25?C. Additional information: Halothane is a noninflammable liquid. Halothane contains not less than 0.08 mg/g and not more than 0.12 mg/g of thymol, as a stabilizer.
DRUG BANK
DB01159
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
EVMPD
SUB08009MIG
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
USP_CATALOG
1303501
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY USP-RS
CAS
151-67-7
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY
ChEMBL
CHEMBL931
Created by admin on Fri Jun 25 20:52:33 UTC 2021 , Edited by admin on Fri Jun 25 20:52:33 UTC 2021
PRIMARY