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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/03 12:43:49」(JST)

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Terbutaline (trade names Brethine, Bricanyl, Brethaire, or Terbulin) is a β₂-adrenergic receptor agonist, used as a "reliever" inhaler in the management of asthma symptoms and as a tocolytic (anti-contraction medication) to delay preterm labor for up to 48 hours. This time can then be used to administer steroid injections to the mother which help fetal lung maturity and reduce complications of prematurity.^[1] It should not be used to prevent preterm labor or delay labor more than 48–72 hours. In February 2011, the Food and Drug Administration has ordered to put a boxed warning on the drug's label. Pregnant women should not be given injections of the drug terbutaline for the prevention of preterm labor or for long-term (beyond 48–72 hours) management of preterm labor, and should not be given oral terbutaline for any type of prevention or treatment of preterm labor "due to the potential for serious internal heart problems and death."^[2]^[3]

The American College of Obstetricians and Gynecologists also discourages the use of terbutaline for preventing preterm labor.

Terbutaline is currently on the World Anti-Doping Agency's list of prohibited drugs for Olympic athletes, except when administered by inhalation and a Therapeutic Use Exemption (TUE) has been obtained in advance.

Uses

Terbutaline is used as a fast-acting bronchodilator (often used as a short-term asthma treatment) and as a tocolytic^[4] to delay premature labor. The inhaled form of terbutaline starts working within 15 minutes and can last up to 6 hours.

Terbutaline as a treatment for premature labor is an off-label use not approved by the FDA. It is a pregnancy category C medication and is routinely prescribed to stop contractions. After successful intravenous tocolysis, little evidence exists that oral terbutaline is effective.^[5] However, following uterine inversion in the third stage of labor. Terbutaline (or either Halothane or magnesium sulfate) can be used to relax the uterus if necessary prior to uterine replacement.

Structure activity relationships

The tertiary butyl group in terbutaline makes it more selective for β2-receptors. Since there is no hydroxy group on position 4 of the benzene ring, the molecule is less susceptible to metabolism by the enzyme catechol-O-methyl transferase.^[6]

Side effects

Adult - tachycardia, anxiety, nervousness, tremors, headache, hyperglycemia, hypokalemia, hypertension and, rarely, pulmonary edema.^[7]
Fetal - tachycardia and hypoglycemia.^[8]

Chemistry

It is synthesized by brominating 3,5-dibenzyloxyacetophenone into the appropriate 3,5-dibenzyloxybromoacetophenone, which is reacted with N-benzyl-N-tert-butylamine, giving the aminoketone. Reduction of this product by hydrogen over a palladium catalyst leads to terbutaline.^[9]^[10]^[11]

References

^ WHO. "Antenatal administration of corticosteroids for women at risk of preterm birth". WHO. Retrieved 2013-03-25.
^ "Most Popular E-mail Newsletter". USA Today. 18 February 2011.
^ http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm243840.htm
^ Mohamed Ismail NA, Ibrahim M, Mohd Naim N, Mahdy ZA, Jamil MA, Mohd Razi ZR (September 2008). "Nifedipine versus terbutaline for tocolysis in external cephalic version". Int J Gynaecol Obstet 102 (3): 263–6. doi:10.1016/j.ijgo.2008.04.010. PMID 18554601.
^ Goldenberg, RL (November 2002). "High-Risk Pregnancy Series: An Expert's View". Obstetrics & Gynecology 100 (5): 1020–1037. doi:10.1016/S0029-7844(02)02212-3.
^ Medicinal Chemistry of Adrenergics and Cholinergics
^ Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 7. ISBN 1-59541-101-1.
^ [1], 5 Minute Consult (Original Source: UpToDate "Terbutaline: Drug information").
^ Draco Lunts Farmcetiska Actiebolag, GB 1199630 (1967)
^ Draco Lunts Farmcetiska Actiebolag, BE 704932 (1968)
^ A. L. Swensson, I. K. Weterlin, U.S. Patent 3,937,838 (1976)

UpToDate Contents

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1. 切迫早産の予防 inhibition of acute preterm labor
2. 喘息におけるβ刺激剤：急性期投与および予防的使用 beta agonists in asthma acute administration and prophylactic use
3. 妊産婦の施設間搬送 inter facility maternal transport
4. 小児における急性重症喘息の増悪：集中治療室（ICU）でのマネージメント acute severe asthma exacerbations in children intensive care unit management
5. 切迫早産予防後の妊婦のマネージメント management of pregnant women after inhibition of acute preterm labor

English Journal

A sensitive determination of terbutaline in pharmaceuticals and urine samples using a composite electrode based on zirconium oxide nanoparticles.

Baytak AK1, Teker T1, Duzmen S1, Aslanoglu M2.
Materials science & engineering. C, Materials for biological applications.Mater Sci Eng C Mater Biol Appl.2016 Oct 1;67:125-31. doi: 10.1016/j.msec.2016.05.008. Epub 2016 May 4.
An accurate and precise determination of terbutaline has been carried out using a glassy carbon electrode (GCE) modified with a composite of multi-walled carbon nanotubes (MWCNTs) and nanoparticles of zirconium oxide (ZrO2NPs). Energy dispersive X-ray and scanning electron microscopic techniques wer
PMID 27287106

Comparison of the cohesion-adhesion balance approach to colloidal probe atomic force microscopy and the measurement of Hansen partial solubility parameters by inverse gas chromatography for the prediction of dry powder inhalation performance.

Jones MD1, Buckton G2.
International journal of pharmaceutics.Int J Pharm.2016 Jul 25;509(1-2):419-30. doi: 10.1016/j.ijpharm.2016.06.002. Epub 2016 Jun 2.
The abilities of the cohesive-adhesive balance approach to atomic force microscopy (AFM) and the measurement of Hansen partial solubility parameters by inverse gas chromatography (IGC) to predict the performance of carrier-based dry powder inhaler (DPI) formulations were compared. Five model drugs (
PMID 27265314

Fast analysis of terbutaline in pharmaceuticals using multi-walled nanotubes modified electrodes from recordable compact disc.

Felix FS1, Daniel D2, Matos JR1, Lucio do Lago C1, Angnes L3.
Analytica chimica acta.Anal Chim Acta.2016 Jul 20;928:32-8. doi: 10.1016/j.aca.2016.04.045. Epub 2016 Apr 28.
In this study, homemade disposable gold electrodes made from recordable compact disks were modified with carbon nanotubes for amperometric quantification of terbutaline sulfate in pharmaceutical products. A flow cell using an impingent jet of solution on the electrode surface was build and used for
PMID 27251854

Japanese Journal

成人気管支喘息におけるブデソニド/ホルモテロールを定期吸入に加えて頓用吸入する治療法の有効性及び安全性の検討 : 国際共同第Ⅲ相試験における日本人患者の成績

川合満,斉藤武文,植山茂宏
アレルギー・免疫 19(8), 1296-1309, 2012-08
NAID 40019388285

日本人成人気管支喘息患者におけるテルブタリンとサルブタモールの単回投与の有用性の比較

福嶋康之,本間哲也,大田和枝 [他]
アレルギ-・免疫 18(9), 1360-1368, 2011-09
NAID 40018958757

A Case of Idiopathic Systemic Capillary Leak Syndrome with High Serum Levels of G-CSF on Exacerbation (増悪時に血清顆粒球コロニー刺激因子高値を示した特発性全身性毛細血管漏出症候群の1症例)

中川直樹,Ota Hisanobu,Tanabe Yasuko,Kabara Maki,Matsuki Motoki,Chinda Junko,Sakamoto Naka,Fujino Takayuki,Takehara Naofumi,Takeuchi Toshiharu,Kawabe Jun-ichi,Sato Nobuyuki,Kawamura Yuichiro,Fukuhara Takashi,Ikuta Katsuya,Kikuchi Kenjiro,Hasebe Naoyuki
Internal Medicine 50(6), 597-600, 2011
… 著者最終原稿版積極的輸液蘇生を要し、corticosteroid、terbutaline、theophyllineにより治療成功した全身性毛細血管漏出症候群(SCLS)の28歳女性症例について検討した。 …
NAID 130000649892

Related Pictures

★リンクテーブル★

リンク元	「テルブタリン」
拡張検索	「terbutaline sulfate」

「テルブタリン」

Terbutaline
Systematic (IUPAC) name
	(RS)-5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a682144
Pregnancy; category	C;
Legal status	UK: Prescription-only (POM);
Routes of; administration	SQ, Oral, Inhaled
Pharmacokinetic data
Protein binding	25%
Metabolism	GI tract (oral), liver; CYP450: unknown
Biological half-life	11-16 hours
Excretion	urine 90% (60% unchanged), bile/faeces
Identifiers
CAS Registry Number	23031-25-6
ATC code	R03AC03 R03CC03
PubChem	CID: 5403
IUPHAR/BPS	560
DrugBank	DB00871
ChemSpider	5210
UNII	N8ONU3L3PG
KEGG	D08570
ChEBI	CHEBI:9449
ChEMBL	CHEMBL1760
Chemical data
Formula	C12H19NO3
Molecular mass	225.284 g/mol
	SMILES Oc1cc(cc(O)c1)C(O)CNC(C)(C)C ;
	InChI InChI=1S/C12H19NO3/c1-12(2,3)13-7-11(16)8-4-9(14)6-10(15)5-8/h4-6,11,13-16H,7H2,1-3H3 ; Key:XWTYSIMOBUGWOL-UHFFFAOYSA-N ;
(what is this?) (verify)

　　[★]

英: terbutaline
化: 硫酸テルブタリン, terbutaline sulfate
商: ブリカニール、コンボン、Brethine
関: アドレナリン受容体、アセチルコリン受容体

化合物：硫酸テルブタリン
βアドレナリン受容体作動薬

β₂受容体刺激薬

適応

気道閉塞性障害の緩解：気管支喘息、小児喘息、肺気腫、急性気管支炎、慢性気管支炎、肺結核、珪肺結核
気管支痙攣の緩解　　：気管支喘息、気管支炎、喘息様気管支炎

副作用

β1受容体も刺激するので心拍数↑

肺水腫

日本での報告例はない

K⁺減少

強心配糖体や利尿薬を服用の患者で問題となる

高血糖

肝臓に発現しているβ2受容体に作用→グリコーゲン分解→血糖値↑

「terbutaline sulfate」

　　[★] テルブタリン。硫酸テルブタリン

[1] WHO. "Antenatal administration of corticosteroids for women at risk of preterm birth". WHO. Retrieved 2013-03-25.

[2] "Most Popular E-mail Newsletter". USA Today. 18 February 2011.

[3] ttp://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm243840.htm

[pmid18554601-4] Mohamed Ismail NA, Ibrahim M, Mohd Naim N, Mahdy ZA, Jamil MA, Mohd Razi ZR (September 2008). "Nifedipine versus terbutaline for tocolysis in external cephalic version". Int J Gynaecol Obstet 102 (3): 263–6. doi:10.1016/j.ijgo.2008.04.010. PMID 18554601.

[5] Goldenberg, RL (November 2002). "High-Risk Pregnancy Series: An Expert's View". Obstetrics & Gynecology 100 (5): 1020–1037. doi:10.1016/S0029-7844(02)02212-3.

[6] Medicinal Chemistry of Adrenergics and Cholinergics

[pharmnemonics-7] Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 7. ISBN 1-59541-101-1.

[8] [1], 5 Minute Consult (Original Source: UpToDate "Terbutaline: Drug information").

[9] Draco Lunts Farmcetiska Actiebolag, GB 1199630 (1967)

[10] Draco Lunts Farmcetiska Actiebolag, BE 704932 (1968)

[11] A. L. Swensson, I. K. Weterlin, U.S. Patent 3,937,838 (1976)

匿名

検索

案内

案内

terbutaline