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a nonflammable inhalation anesthetic that produces general anesthesia; used along with analgesics and muscle relaxants for many types of surgical procedures

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/02/01 12:53:59」(JST)

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Halothane (trademarked as Fluothane) is an inhalational general anesthetic. Its IUPAC name is 2-bromo-2-chloro-1,1,1-trifluoroethane. It is the only inhalational anesthetic agent containing a bromine atom; several other halogenated anesthesia agents lack the bromine atom and do contain the fluorine and chlorine atoms present in halothane. It is colorless and pleasant-smelling, but unstable in light. It is packaged in dark-colored bottles and contains 0.01% thymol as a stabilizing agent. Halothane is a core medicine in the World Health Organization's "Essential Drugs List", which is a list of minimum medical needs for a basic health care system.^[2] Its use in developed countries, however, has been almost entirely superseded by newer inhalational anaesthetic agents.

Anesthetic properties[edit]

It is a potent anesthetic with a minimum alveolar concentration of 0.74. Its blood/gas partition coefficient of 2.4 makes it an agent with moderate induction and recovery time. It is not a good analgesic and its muscle relaxation effect is moderate.^[3]

Availability[edit]

It is available as a volatile liquid, at 30, 50, 200, and 250 ml per container.^[4]

History[edit]

This halogenated hydrocarbon was first synthesized by C. W. Suckling of Imperial Chemical Industries in 1951 and was first used clinically by M. Johnstone in Manchester in 1956. Halothane became popular as a nonflammable general anasthetic replacing other volatile anesthetics such as diethyl ether and cyclopropane. Use of the anesthetic was phased out during the 1980s and 1990s as newer anesthetic agents became popular. Halothane retains some use in veterinary surgery and in the Third World because of its lower cost.

Halothane was given to many millions of adult and pediatric patients worldwide from its introduction in 1956 through the 1980s. Its properties include cardiac depression at high levels, cardiac sensitization to catecholamines such as norepinephrine, and potent bronchial relaxation. Its lack of airway irritation made it a common inhalation induction agent in pediatric anesthesia. Due to its cardiac depressive effect, it was contraindicated in patients with cardiac failure. Halothane was also contraindicated in patients susceptible to cardiac arrhythmias, or in situations related to high catecholamine levels such as pheochromocytoma.

Side effects[edit]

Repeated exposure to halothane in adults was noted in rare cases to result in severe liver injury. This occurred in about one in 10,000 exposures. The resulting syndrome was referred to as halothane hepatitis, and is thought to result from the metabolism of halothane to trifluoroacetic acid via oxidative reactions in the liver. About 20% of inhaled halothane is metabolized by the liver and these products are excreted in the urine. The hepatitis syndrome had a mortality rate of 30% to 70%. Concern for hepatitis resulted in a dramatic reduction in the use of halothane for adults. It was replaced in the 1980s by enflurane and isoflurane. By 2005, the common volatile anesthetics in use were isoflurane, sevoflurane, and desflurane. Since the risk of halothane hepatitis in children was substantially lower than in adults, halothane continued to be used in pediatrics in the 1990s. However, by 2000, sevoflurane had largely replaced the use of halothane in children.

Halothane sensitises the heart to catecholamines, so it is liable to cause cardiac arrhythmias, occasionally fatal, particularly if hypercapnia has been allowed to develop. This seems to be especially problematic in dental anaesthesia.

Like all the potent inhalational anaesthetic agents, it is a potent trigger for malignant hyperthermia. Similarly, it relaxes uterine smooth muscle and this may increase blood loss during delivery or termination of pregnancy.

Chemical and physical properties[edit]

Boiling point:	50.2°C	(at 101.325 kPa)
Density:	1.868 g/cm³	(at 20°C)
Molecular Weight:	197.4 u
Vapor pressure:	244 mmHg	(at 20°C)
	288 mmHg	(at 24 °C)
MAC:	0.75	vol %
Blood:gas partition coefficient:	2.3
Oil:gas partition coefficient:	224

Chemically, halothane is an alkyl halide (not an ether like many other anesthetics).^[5] The structure has one stereocenter, so (R)- and (S)-optical isomers occur.

Synthesis[edit]

The commercial synthesis of halothane starts from trichloroethylene, which is reacted with hydrogen fluoride in the presence of antimony trichloride at 130°C to form 2-chloro-1,1,1-trifluoroethane. This is then reacted with bromine at 450°C to produce halothane.^[6]

Related substances[edit]

Attempts to find anesthetics with less metabolism led to halogenated ethers such as enflurane and isoflurane. The incidence of hepatic reactions with these agents is lower. The exact degree of hepatotoxic potential of enflurane is debated, although it is minimally metabolized. Isoflurane is essentially not metabolized and reports of associated liver injury are quite rare. Small amounts of trifluoroacetic acid can be formed from both halothane and isoflurane metabolism and possibly accounts for cross sensitization of patients between these agents.

The main advantage of the more modern agents is lower blood solubility, resulting in faster induction of and recovery from anaesthesia.

References[edit]

^ DrugBank: DB01159 (Halothane)
^ "WHO Model List of Essential Medicines" (PDF). World Health Organization. March 2011. Retrieved 2011-08-22.
^ Halothane.
^ National formulary of India, 4th Ed. New Delhi, India, Indian Pharmacopoeia commission; 2011: 411
^ "DrugBank: Halothane (DB01159)". 17 December 2010.
^ Suckling et al.,"PROCESS FOR THE PREPARATION OF 1,1,1-TRIFLUORO-2-BROMO-2-CHLOROETHANE", US patent 2921098, granted January 1960 , assigned to Imperial Chemical Industries

UpToDate Contents

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1. ハロタン肝炎 halothane hepatitis
2. 全身麻酔の導入 induction of general anesthesia
3. 重症筋無力症患者に対する麻酔 anesthesia for the patient with myasthenia gravis
4. 小児における、アデノイド切除同時施行例を含む扁桃摘出に対する麻酔 anesthesia for tonsillectomy with or without adenoidectomy in children
5. 悪性高熱症：臨床診断および急性期のマネージメント malignant hyperthermia clinical diagnosis and management of acute crisis

English Journal

Dysregulation of a potassium channel, THIK-1, targeted by caspase-8 accelerates cell shrinkage.

Sakamaki K1, Ishii TM2, Sakata T3, Takemoto K4, Takagi C5, Takeuchi A6, Morishita R7, Takahashi H8, Nozawa A8, Shinoda H9, Chiba K10, Sugimoto H3, Saito A3, Tamate S11, Satou Y12, Jung SK13, Matsuoka S14, Koyamada K15, Sawasaki T8, Nagai T16, Ueno N5.
Biochimica et biophysica acta.Biochim Biophys Acta.2016 Nov;1863(11):2766-2783. doi: 10.1016/j.bbamcr.2016.08.010. Epub 2016 Aug 23.
Activation of caspases is crucial for the execution of apoptosis. Although the caspase cascade associated with activation of the initiator caspase-8 (CASP8) has been investigated in molecular and biochemical detail, the physiological role of CASP8 is not fully understood. Here, we identified a two-p
PMID 27566292

New insights into the elucidation of angiotensin-(1-7) in vivo antiarrhythmic effects and its related cellular mechanisms.

Joviano-Santos JV1, Santos-Miranda A2, Joca HC2, Cruz JS2, Ferreira AJ3.
Experimental physiology.Exp Physiol.2016 Oct 12. doi: 10.1113/EP085884. [Epub ahead of print]
Angiotensin (Ang)-(1-7) has been proved to have cardio-protective effects. However, the effects of this peptide on in vivo cardiac arrhythmias and details regarding its mechanisms of action are still undetermined. The aim of this study was to investigate the protective effects of Ang-(1-7) against c
PMID 27730696

Anesthesia specific differences in a cardio-pulmonary resuscitation rat model; halothane versus sevoflurane.

Esser T1, Keilhoff G2, Ebmeyer U1.
Brain research.Brain Res.2016 Oct 7. pii: S0006-8993(16)30695-3. doi: 10.1016/j.brainres.2016.10.003. [Epub ahead of print]
OBJECTIVE: Our asphyxia cardiac arrest (ACA) rat model is well established. The original model was designed in the 1990th using halothane and nitrous oxide for pre-insult anesthesia. Because of its hepato-toxicity and its potential to induce severe liver failures, halothane is no longer used in clin
PMID 27725150

Japanese Journal

Fluvoxamine by itself has potential to directly induce long QT syndrome at supra-therapeutic concentrations

Yamazaki-Hashimoto Yukiko,Nakamura Yuji,Ohara Hiroshi [他],Cao Xin,Kitahara Ken,Izumi-Nakaseko Hiroko,Ando Kentaro,Yamazaki Hiroshi,Ikeda Takanori,Yamazaki Junichi,Sugiyama Atsushi
The Journal of Toxicological Sciences 40(1), 33-42, 2015
… We examined electropharmacological effects of fluvoxamine together with its pharmacokinetic profile by using the halothane-anesthetized dogs (n = 4). …
NAID 130004904019

The Conventional Antihistamine Drug Cyproheptadine Lacks QT-interval–Prolonging Action in Halothane-Anesthetized Guinea Pigs: Comparison With Hydroxyzine

Kobayashi Kazuko,Omuro Naoki,Takahara Akira
Journal of Pharmacological Sciences 124(1), 92-98, 2014
… Since information is limited regarding the in vivo electrophysiological effects of cyproheptadine, we assessed it using the halothane-anesthetized guinea-pig model, which was compared with effects of another antihistamine drug, hydroxyzine. …
NAID 130003382628

Effects of the Fluoroquinolone Antibacterial Drug Ciprofloxacin on Ventricular Repolarization in the Halothane-Anesthetized Guinea Pig

Matsuo Kazuhiro,Fujiwara Kaori,Omuro Naoki [他],KIMURA Itsuki,KOBAYASHI Kazuko,YOSHIO Takashi,TAKAHARA Akira
Journal of pharmacological sciences 122(3), 205-212, 2013-07-20
… In this study using the halothane-anesthetized guinea pig, we assessed whether ciprofloxacin has a proarrhythmic activity. …
NAID 10031185414

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★リンクテーブル★

リンク元	「薬理学」「ハロタン」

「薬理学」

Halothane
Systematic (IUPAC) name
	2-Bromo-2-chloro-1,1,1-trifluoroethane
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Legal status	?
Pharmacokinetic data
Metabolism	Hepatic (CYP2E1)
Excretion	Renal
Identifiers
CAS number	151-67-7
ATC code	N01AB01
PubChem	CID 3562
IUPHAR ligand	2401
DrugBank	DB01159
ChemSpider	3441
UNII	UQT9G45D1P
KEGG	D00542
ChEBI	CHEBI:5615
ChEMBL	CHEMBL931
Chemical data
Formula	C2HBrClF3
Mol. mass	197.381 g/mol
	SMILES C(C(F)(F)F)(Cl)Br;
	InChI InChI=1S/C2HBrClF3/c3-1(4)2(5,6)7/h1H ; Key:BCQZXOMGPXTTIC-UHFFFAOYSA-N ;
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　　[★]

英: pharmacology
関: drug entries

定義

生物系と化学物質の選択的な相互作用を研究する学問 (SPC.2)

生物系と薬の相互作用

薬の生物系に対する相互作用：薬理作用 <-化学の視点
生物系の薬に対する相互作用：薬物動態 <-生物の視点

薬品の命名

Ending of the drug name	Category	Example
～afil	Erectile dysfunction	sildenafil
～ane	Inhalatinal general anesthetic	halothane
～azepam	Benzodiaizepine	diazepam
～azine	Phenothiazine (neuroleptic, antiemetic)	chlorpromazine
～azole	Ailtifungal	ketoconazole
～barbital	Barbiturate	phenobarbital
～caine	Local anesthetic	lidocaine
～cillin	Penicillin	methicillin
～cycline	Antibiotic, protein syntlesis inhibitor	tetracycline
～ipramine	TCA	iimipramine
～navir	Protease inhibitor	saquinavir
～olol	β-antagonist	propranolol
～operidol	Butyrophenone ( neuroleptic )	haloperidol
～oxin	Cardiac glycoside ( inotropic agent )	digoxin
～phylline	Methylxanthine	theophylline
～pril	ACE inhibitor	captopril
～terol	β₂ agonist	albuterol
～tidine	H₂ antagonist	cimtidine
～triptyline	TCA	amitriptyline
～tropine	Pituitary hormone	somatotropine
～zosin	a₁ antagonist	prazosin

薬一覧

薬物代謝

薬理動態

神経伝達物質

貧血治療薬

甲状腺関連物質

甲状腺ホルモン製剤

レボチロキシン levothyroxine
リオチニシン liothyronine

抗甲状腺薬

痛風治療薬

痛風発作予防薬

コルヒチン colchicine

尿酸排泄促進薬

尿酸生成抑制薬

アロプリノール allopurinol

「ハロタン」

　　[★]

英: halothane
ラ: Halothanum
同: ハロセン
商: フローセン Fluothane
関: 麻酔薬

[show details]

ハロセン : 約 2,980 件
ハローセン : 約 578 件
ハロタン : 約 17,800 件

吸入型全身麻酔薬。

参考

フローセン

http://www.info.pmda.go.jp/go/pack/1112700X1038_1_09/1112700X1038_1_09?view=body

臨床関連

ハロタン肝炎

[1] DrugBank: DB01159 (Halothane)

[essentialWHO-2] "WHO Model List of Essential Medicines" (PDF). World Health Organization. March 2011. Retrieved 2011-08-22.

[3] Halothane.

[4] National formulary of India, 4th Ed. New Delhi, India, Indian Pharmacopoeia commission; 2011: 411

[5] "DrugBank: Halothane (DB01159)". 17 December 2010.

[6] Suckling et al.,"PROCESS FOR THE PREPARATION OF 1,1,1-TRIFLUORO-2-BROMO-2-CHLOROETHANE", US patent 2921098, granted January 1960 , assigned to Imperial Chemical Industries

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案内

halothane