Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C2HBrClF3 |
| Molecular Weight | 197.382 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
FC(F)(F)C(Cl)Br
InChI
InChIKey=BCQZXOMGPXTTIC-UHFFFAOYSA-N
InChI=1S/C2HBrClF3/c3-1(4)2(5,6)7/h1H
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.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2093872 |
|||
Target ID: CHEMBL2094124 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | FLUOTHANE Approved UseINDICATIONS. Halothane is indicated for the induction and maintenance of general anesthesia. Launch Date1958 |
Doses
| Dose | Population | Adverse events |
|---|---|---|
4 % single, respiratory Overdose |
unhealthy, 3 |
Disc. AE: Change in ECG, Blood pressure systolic decreased... AEs leading to discontinuation/dose reduction: Change in ECG Sources: Blood pressure systolic decreased |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Blood pressure systolic decreased | Disc. AE | 4 % single, respiratory Overdose |
unhealthy, 3 |
| Change in ECG | Disc. AE | 4 % single, respiratory Overdose |
unhealthy, 3 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical 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 victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
Page: 7.0 |
yes | |||
Page: 101.0 |
yes | |||
Page: 148.0 |
yes | |||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Interaction of anesthetics with the Rho GTPase regulator Rho GDP dissociation inhibitor. | 2008-09-09 |
|
| Trifluoroacetylated IgG4 antibodies in a child with idiosyncratic acute liver failure after first exposure to halothane. | 2008-08 |
|
| Stimulatory effect of Eucalyptus essential oil on innate cell-mediated immune response. | 2008-04-18 |
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| Cardiomyocyte formation by skeletal muscle-derived multi-myogenic stem cells after transplantation into infarcted myocardium. | 2008-03-12 |
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| Disruption of FAK signaling: a side mechanism in cytotoxicity. | 2008-03-12 |
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| Inhalation anaesthesia: from diethyl ether to xenon. | 2008 |
|
| A novel approach to detect hot-spots in large-scale multivariate data. | 2007-09-11 |
|
| Transgenic upregulation of IK1 in the mouse heart is proarrhythmic. | 2007-09 |
|
| Reduced cardiovascular reactivity to stress but not feeding in renin enhancer knockout mice. | 2007-08 |
|
| Therapeutic potential of neuronal two-pore domain potassium-channel modulators. | 2007-07 |
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| Inhaled anesthetic modulation of amyloid beta(1-40) assembly and growth. | 2007-07 |
|
| Detrimental effects of halothane narcosis on damage after endothelin-1-induced MCAO. | 2007-05-15 |
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| Halothane induced fulminant hepatic failure. | 2007-02 |
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| The common chemical motifs within anesthetic binding sites. | 2007-02 |
|
| Halothane induces oxidative stress and NF-kappaB activation in rat liver: protective effect of propofol. | 2006-10-03 |
|
| Switch from planktonic to sessile life: a major event in pneumococcal pathogenesis. | 2006-09 |
|
| A guest molecule-host cavity fitting algorithm to mine PDB for small molecule targets. | 2006-08 |
|
| Free radical theory of autoimmunity. | 2006-06-07 |
|
| Clinical observations surrounding an increased incidence of postanesthetic myopathy in halothane-anesthetized horses. | 2006-03 |
|
| Functional hyperemic response in the rat visual cortex under halothane anesthesia. | 2006-02-06 |
|
| Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978. | 2006-01 |
|
| Identification of the central imidazoline receptor subtype involved in modulation of halothane-epinephrine arrhythmias in rats. | 2005-12 |
|
| Fenamates and diltiazem modulate lipid-sensitive mechano-gated 2P domain K(+) channels. | 2005-12 |
|
| The role of surfactant protein D in the colonisation of the respiratory tract and onset of bacteraemia during pneumococcal pneumonia. | 2005-10-28 |
|
| Fulminant hepatic failure following halothane anaesthesia. | 2005-10 |
|
| Fulminant drug-induced hepatic failure leading to death or liver transplantation in Sweden. | 2005-09 |
|
| Truncated human serum albumin retains general anaesthetic binding activity. | 2005-05-15 |
|
| Reproducible loss of CA1 neurons following carotid artery occlusion combined with halothane-induced hypotension. | 2005-02-08 |
|
| 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 |
|
| Differential protective effects of volatile anesthetics against renal ischemia-reperfusion injury in vivo. | 2004-12 |
|
| Halothane induced hepatitis: case report. | 2004-10 |
|
| Functional characterization of malignant hyperthermia-associated RyR1 mutations in exon 44, using the human myotube model. | 2004-07 |
|
| Development of a halothane-adrenaline arrhythmia model using in vivo Guinea pigs. | 2004-06 |
|
| Biological activity of bacterial lectins and their molecular complexes with heterocyclic bis-adducts. | 2004-01-16 |
|
| [Halothane-induced hepatitis. 8 case reports]. | 2003-11 |
|
| In vivo measurement of bending stiffness in fracture healing. | 2003-03-28 |
|
| [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 |
|
| Molecular mimicry of trifluoroacetylated human liver protein adducts by constitutive proteins and immunochemical evidence for its impairment in halothane hepatitis. | 1992-12-01 |
|
| Isoflurane does not increase the incidence of intraoperative myocardial ischaemia compared with halothane during vascular surgery. | 1992-12 |
|
| Muscle rigidity following halothane anesthesia in two patients with Freeman-Sheldon syndrome. | 1992-09 |
|
| The calcium-binding protein calreticulin is covalently modified in rat liver by a reactive metabolite of the inhalation anesthetic halothane. | 1992-05-01 |
|
| Nalidixic acid-induced hemolytic anemia complicating halothane-induced hepatitis. | 1992-05 |
|
| Halothane hepatitis 28 years after primary exposure. | 1992-04 |
|
| Screening for antibodies associated with halothane hepatitis. | 1991-12 |
|
| Is premedication with oral glycopyrrolate as effective as oral atropine in attenuating cardiovascular depression in infants receiving halothane for induction of anesthesia? | 1991-09 |
|
| Severe bradycardia and sinus arrest after administration of vecuronium, fentanyl and halothane. A case report. | 1991-08-17 |
|
| Steal-prone coronary anatomy and myocardial ischemia associated with four primary anesthetic agents in humans. | 1991-01 |
|
| Use of structural alterations in the synthesis of halothane metabolite antigens to mimic halothane-induced immunogen. | 1990 |
Patents
Sample Use Guides
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.
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WHO-ATC |
N01AB01
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WHO-ESSENTIAL MEDICINES LIST | 1.1.1 | ||
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NCI_THESAURUS |
C245
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WHO-VATC |
QN01AB01
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LIVERTOX |
NBK548151
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1303501
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HALOTHANE
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205-796-5
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m5907
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5615
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C47554
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143490
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Halothane
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HALOTHANE
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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. | ||
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DB01159
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CHEMBL931
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE TOXIC (PARENT)
