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convert into a sulfate
a salt or ester of sulphuric acid (同)sulphate

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/22 18:17:00」(JST)

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Terbutaline (trade names "Bronclyn",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, hypotension 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

Evaluation and treatment of accidental autoinjection of epinephrine.

Peyko V, Cohen V, Jellinek-Cohen SP, Pearl-Davis M.SourceVincent Peyko, Pharm.D., is Postgraduate Year 2 Infectious Diseases Pharmacy Resident, James J. Peters Veterans Affairs Medical Center, Bronx, NY; at the time of writing he was Postgraduate Year 1 Pharmacy Resident, Department of Pharmaceutical Services, Maimonides Medical Center, Brooklyn, NY. Victor Cohen, Pharm.D., BCPS, CGP, is Associate Professor of Pharmacy Practice, Arnold and Marie Schwartz College of Pharmacy and Health Sciences, Long Island University, Brooklyn. Samantha P. Jellinek-Cohen, Pharm.D., BCPS, CGP, is Assistant Clinical Professor, College of Pharmacy and Health Sciences, St. John's University, Queens, NY. Michelle Pearl-Davis, D.O., is Associate Director, Emergency Ultrasound, Department of Emergency Medicine, Maimonides Medical Center.
American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists.Am J Health Syst Pharm.2013 May 1;70(9):778-781.
PURPOSE: A case of accidental autoinjection of epinephrine is described.SUMMARY: A 47-year-old man arrived at the emergency department after accidental injection of epinephrine with an autoinjector into his left thumb. His vital signs were stable at admission. The patient was allergic to nuts and th
PMID 23592360

Revealing binding interaction between seven drugs and immobilized β2 -adrenoceptor by high-performance affinity chromatography using frontal analysis.

Xin-Feng Z, Jing-Jing H, Qian L, Lu-Sha W, Jian-Bin Z, Xiao-Hui Z, Zi-Jian L, You-Yi Z.SourceCollege of Life Sciences, Northwest University, Xi'an, 710069, China.
Journal of molecular recognition : JMR.J Mol Recognit.2013 May;26(5):252-7. doi: 10.1002/jmr.2271.
The development of new approaches to study the affinity between ligands and G-protein-coupled receptors proves to be of growing interest for pharmacologists, chemists, and biologists. The aim of this work was to determine the binding of seven drugs to β2 -adrenoceptors by frontal analysis using imm
PMID 23526777

In vitro characterisation of terbutaline sulphate particles prepared by thermal ink-jet spray freeze drying.

Sharma G, Mueannoom W, Buanz AB, Taylor KM, Gaisford S.SourceUCL School of Pharmacy, University College London, 29-39 Brunswick Square, London WC1N 1AX, UK.
International journal of pharmaceutics.Int J Pharm.2013 Apr 15;447(1-2):165-70. doi: 10.1016/j.ijpharm.2013.02.045. Epub 2013 Feb 27.
Thermal ink-jet spray freeze-drying (TIJ-SFD) was used to produce inhalable particles of terbutaline sulphate, the aerosolisation properties of which were compared to the commercial Bricanyl(®) formulation. Scanning electron micrograph images showed the particles to be spherical, highly porous and
PMID 23454848

Japanese Journal

Stability Indicating HPTLC Method for Determination of Terbutaline Sulfate in Bulk and from Submicronized Dry Powder Inhalers

FAIYAZUDDIN Md.,AHMAD Sayeed,IQBAL Zeenat,TALEGAONKAR Sushma,AHMAD Farhan Jalees,BHATNAGAR Aseem,KHAR Roop Krishen
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 26(4), 467-472, 2010-04-10
NAID 10026783020

Determination of terbutaline sulfate by capillary electrophoresis with chemiluminescence detection

LI Shuting,WANG Janshi,ZHAO Shulin
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 877(3), 155-158, 2009-01-15
NAID 10028011812

Related Pictures

★リンクテーブル★

リンク元	「テルブタリン」
関連記事	「sulfate」「sulfated」「sulfa」

「テルブタリン」

Terbutaline
	Terbutaline (top),; and (R)-(−)-terbutaline (bottom)
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;
Routes of; administration	Oral (tablets, oral solution), inhalational (DPI, nebulizer solution), SQ
Legal status
Legal status	UK: POM (Prescription only);
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 Number	23031-25-6
ATC code	R03AC03 (WHO) R03CC03
PubChem	CID 5403
IUPHAR/BPS	560
DrugBank	DB00871
ChemSpider	5210
UNII	N8ONU3L3PG
KEGG	D08570
ChEBI	CHEBI:9449
ChEMBL	CHEMBL1760
Chemical data
Formula	C12H19NO3
Molar mass	225.284 g/mol
Chirality	Racemic mixture
	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↑

「sulfate」

　　[★]

n.

(官能基やイオンを表して)硫酸、(化合物)硫酸塩、硫酸エステル、硫酸化する

関: H2SO4、inorganic sulfate、sulfate ester、sulfated、sulfation、sulfuric acid、sulfuric acid ester、sulphate、sulphuric acid

「sulfated」

　　[★]

adj.

硫酸化の

関: sulfate、sulfation、sulphate

「sulfa」

　　[★]

スルファ、サルファ

[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)

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案内

案内

terbutaline sulfate