ブチルスコポラミン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/05/08 07:06:13」(JST)
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Butylscopolamine
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Systematic (IUPAC) name |
[7(S)-(1α,2β,4β,5α,7β)]-9-butyl-7-(3-hydroxy-
1-oxo-2-phenylpropoxy)-9-methyl-3-oxa-
9-azonitricyclo[3.3.1.0(2,4)]nonane |
Clinical data |
Pregnancy cat. |
B2 (AU) |
Legal status |
Pharmacy Only (S2) (AU) GSL (UK) |
Routes |
Oral, rectal, intravenous |
Pharmacokinetic data |
Bioavailability |
<1% |
Protein binding |
Low |
Half-life |
5 hours |
Excretion |
Renal (50%) and fecal |
Identifiers |
CAS number |
149-64-4 |
ATC code |
A03BB01 |
PubChem |
CID 160883 |
ChemSpider |
16736107 Y |
UNII |
2Z3E1OF81V Y |
Chemical data |
Formula |
C21H30NO4+ |
Mol. mass |
360.467 g/mol |
SMILES |
eMolecules & PubChem |
InChI
-
InChI=1S/C21H30NO4.BrH/c1-3-4-10-22(2)17-11-15(12-18(22)20-19(17)26-20)25-21(24)16(13-23)14-8-6-5-7-9-14;/h5-9,15-20,23H,3-4,10-13H2,1-2H3;1H/q+1;/p-1/t15-,16-,17-,18+,19-,20+,22?;/m1./s1 Y
Key:HOZOZZFCZRXYEK-GSWUYBTGSA-M Y
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Y (what is this?) (verify)
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Butylscopolamine, also known as scopolamine butylbromide, butylhyoscine and hyoscine butylbromide, is a peripherally acting antimuscarinic, anticholinergic agent[1] used as an abdominal-specific antispasmodic. It is a quaternary ammonium compound and a semisynthetic derivative of scopolamine. It is marketed under the trade name Buscopan by Boehringer Ingelheim GmbH, Germany, who also offer a combination of butylscopolamine and paracetamol, marketed under the name Buscopan Plus (in some countries, Buscopan Compositum).
Butylscopolamine is used to treat pain and discomfort caused by abdominal cramps, menstrual cramps, or other spasmodic activity in the digestive system. It is also effective at preventing bladder spasms. It is not an analgesic in the normal sense, since it doesn't 'mask' or 'cover over' the pain, but rather works to prevent painful cramps and spasms from occurring in the first place. The attachment of the butyl-bromide moiety effectively prevents the movement of this drug across the blood-brain barrier, effectively minimising undesirable CNS side-effects associated with scopolamine/hyoscine.
Contents
- 1 Medical uses
- 2 Abuse
- 3 References
- 4 External links
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Medical uses
Butylscopolamine is used to treat cramping abdominal pain with some success.[2]
Hyoscine butylbromide is effective in significantly reducing the duration of the first stage of labour, and it is not associated with any obvious adverse outcomes in mother or neonate.[3][4]
Abuse
Butylscopolamine is not centrally active and has a low incidence of abuse.
References
- ^ Murakami, M.; Tomiyama, Y.; Hayakawa, K.; Akahane, M.; Ajisawa, Y.; Park, Y. C.; Ohnishi, N.; Sugiyama, T.; Kurita, T. (2000). "Effects of β-Adrenergic Stimulation on the Acutely Obstructed Ureter in Dogs" (pdf). Journal of Pharmacology and Experimental Therapeutics 292 (1): 67–75. PMID 10604932. http://jpet.aspetjournals.org/content/292/1/67.full.pdf.
- ^ Tytgat, G. N. (2007). "Hyoscine Butylbromide: A Review of its Use in the Treatment of Abdominal Cramping and Pain". Drugs 67 (9): 1343–1357. PMID 17547475.
- ^ BJOG. 2007 Dec;114(12):1542-6. Epub 2007 Sep 27.The effect of hyoscine butylbromide on the first stage of labour in term pregnancies.Samuels LA, Christie L, Roberts-Gittens B, Fletcher H, Frederick J.
- ^ Samuels LA, Christie L, Roberts-Gittens B, Fletcher H, Frederick J. (2007 Sep 27.). "The effect of hyoscine butylbromide on the first stage of labour in term pregnancies". BJOG. 12 114 (1542): 6. http://www.ncbi.nlm.nih.gov/pubmed/17903230.
External links
- "Buscopan/Buscapina". Boehringer Ingelheim. http://www.buscopan.com.
Drugs for functional gastrointestinal disorders (A03)
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Drugs for
functional bowel disorders |
Antimuscarinics
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Tertiary
amino group
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- Oxyphencyclimine
- Camylofin
- Mebeverine
- Trimebutine
- Rociverine
- Dicycloverine
- Dihexyverine
- Difemerine
- Piperidolate
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Quaternary ammonium
compounds
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- Benzilone
- Mepenzolate
- Pipenzolate
- Glycopyrronium
- Oxyphenonium
- Penthienate
- Methantheline
- Propantheline
- Otilonium bromide
- Tridihexethyl
- Isopropamide
- Hexocyclium
- Poldine
- Bevonium
- Diphemanil
- Tiemonium iodide
- Prifinium bromide
- Timepidium bromide
- Fenpiverinium
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Phosphodiesterase inhibitors
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- Papaverine
- Drotaverine
- Moxaverine
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Acting on serotonin receptors
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- 5-HT3 antagonists
- 5-HT4 agonists
- Mosapride
- Prucalopride
- Tegaserod
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Other
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- Alverine
- Caroverine
- Chlorbenzoxamine
- Diisopromine
- Dimethylaminopropionylphenothiazine
- Fenpiprane
- Fenoverine
- Idanpramine
- Isometheptene
- Phloroglucinol
- Pinaverium
- Proxazole
- Silicones
- Tiropramide
- Trepibutone
- Trimethyldiphenylpropylamine
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Belladonna and derivatives
(antimuscarinics) |
- tertiary amines: Atropine
- Hyoscyamine
- quaternary ammonium compounds:
- Scopolamine
- Butylscopolamine
- Methylscopolamine
- Methylatropine
- Fentonium
- Cimetropium bromide
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Propulsives |
- primarily dopamine antagonists
- Metoclopramide/Bromopride
- Clebopride
- Domperidone
- Alizapride
- 5-HT4 agonists
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anat(t, g, p)/phys/devp/enzy
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noco/cong/tumr, sysi/epon
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proc, drug(A2A/2B/3/4/5/6/7/14/16), blte
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UpToDate Contents
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English Journal
- Effect of N-butylscopolammonium bromide on equine ileal smooth muscle activity in an ex vivo model.
- Hart KA1, Sherlock CE1, Davern AJ1, Lewis TH1, Robertson TP1.
- Equine veterinary journal.Equine Vet J.2015 Jul;47(4):450-5. doi: 10.1111/evj.12293. Epub 2014 May 26.
- REASONS FOR PERFORMING STUDY: N-butylscopolammonium bromide (NBB) is an anticholinergic agent used to treat spasmodic colic in horses. Intestinal smooth muscle spasm also occurs in horses with intraluminal intestinal obstructions, such as ileal impactions. The antispasmodic effects of NBB may be use
- PMID 24779926
- Microangiopathy triggers, and inducible nitric oxide synthase exacerbates dextran sulfate sodium-induced colitis.
- Saijo H1, Tatsumi N2, Arihiro S3, Kato T4, Okabe M2, Tajiri H5, Hashimoto H2.
- Laboratory investigation; a journal of technical methods and pathology.Lab Invest.2015 Jul;95(7):728-48. doi: 10.1038/labinvest.2015.60. Epub 2015 May 4.
- Ulcerative colitis (UC) is a representative clinical manifestation of inflammatory bowel disease that causes chronic gastrointestinal tract inflammation. Dextran sulfate sodium (DSS)-induced colitis mice have been used to investigate UC pathogenesis, and in this UC model, disturbance and impairment
- PMID 25938626
- Motility mapping as evaluation tool for bowel motility: initial results on the development of an automated color-coding algorithm in cine MRI.
- Hahnemann ML1, Nensa F, Kinner S, Gerken G, Lauenstein TC.
- Journal of magnetic resonance imaging : JMRI.J Magn Reson Imaging.2015 Feb;41(2):354-60. doi: 10.1002/jmri.24557. Epub 2014 Jan 8.
- PURPOSE: To develop and implement an automated algorithm for visualizing and quantifying bowel motility using cine magnetic resonance imaging (MRI).MATERIALS AND METHODS: Four healthy volunteers as well as eight patients with suspected or diagnosed inflammatory bowel disease (IBD) underwent MR exami
- PMID 24399576
Japanese Journal
- Influence of N-butylscopolamine on SUV in FDG PET of the bowel
- SANGHERA Bal,EMMOTT Jennifer,WELLSTED David,CHAMBERS Jane,WONG Wai-Lup
- Annals of nuclear medicine 23(5), 471-478, 2009-07-01
- NAID 10025136753
- ブチルスコポラミン投与により抑制された胃運動に対する足三里穴鍼通電刺激の効果
- 清水 奈宇留,智原 栄一
- 自律神経 = The Autonomic nervous system 45(6), 233-241, 2008-12-15
- NAID 10024836811
- ドンペリドンと臭化ブチルスコポラミンの同時経口投与が低カロリー飲料の胃排出に与える影響について
- 白崎 由佳子
- 日本臨床生理学会雑誌 = Japanese journal of applied physiology 38(6), 299-302, 2008-12-01
- NAID 10025635565
Related Links
- It is marketed under the trade name Buscopan by Boehringer Ingelheim GmbH, Germany, who also offer a combination of butylscopolamine and paracetamol, marketed under the name Buscopan Plus (in some countries as Buscapina, ...
- Butylscopolamine is a medicine available in a number of countries worldwide. A list of US medications equivalent to Butylscopolamine is available on the Drugs. com website.
Related Pictures
★リンクテーブル★
[★]
- 英
- butylscopolamine、scopolamine butylbromide、butylscopolammonium bromide
- 化
- ブチルスコポラミン臭化物 scopolamine butylbromide、臭化ブチルスコポラミン butylscopolamine bromide、ヒヨスチン-N-ブチルブロミド hyoscine-N-butylbromide
- 商
- スコルパン、スパスモパン、スポラミン、ブスコパン、ブスコム、ブスフォリロン、ブスポン、ブチブロン、ブチルミン、リラダン
- 関
- ムスカリン性受容体
[★]
ブチルスコポラミン。臭化ブチルスコポラミン、ブチルスコポラミン臭化物、butylscopolamine、scopolamine butylbromide
[★]
- 関
- butylscopolamine、butylscopolammonium bromide