関: carbachol

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/04/01 06:48:06」(JST)

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Carbachol (Carbastat, Carboptic, Isopto Carbachol, Miostat), also known as carbamylcholine, is a cholinomimetic drug that binds and activates the acetylcholine receptor. Thus it is classified as a cholinergic agonist. It is primarily used for various ophthalmic purposes, such as for treating glaucoma, or for use during ophthalmic surgery. It is generally administered as an ophthalmic solution (i.e. eyedrops).

Chemistry and pharmacology

Carbachol is a choline carbamate and a positively charged quaternary ammonium compound.^[1] It is not well absorbed in the gastro-intestinal tract and does not cross the blood–brain barrier. It is usually administered topical ocular or through intraocular injection.^[1] Carbachol is not easily metabolized by cholinesterase, it has a two to 5 minute onset of action and its duration of action is 4 to 8 hours with topical administration and 24 hours for intraocular administration. Since carbachol is poorly absorbed through topical administration, benzalkonium chloride is mixed in to promote absorption.^[1]

Carbachol is a parasympathomimetic that stimulates both muscarinic and nicotinic receptors.^[1] In topical ocular and intraocular administration its principal effects are miosis and increased aqueous humour outflow.^[1]

In the cat and rat, carbachol is well known for its ability to induce rapid eye movement (REM) sleep when microinjected into the pontine reticular formation. Carbachol elicits this REM sleep-like state via activation of postsynaptic muscarinic cholinergic receptors (mAChRs).^[1]

A recent review indicates that carbachol is a strong promoter of ICC activity, which is mediated through the calcium-activated chloride channel, anoctamin 1.^[2]

Indications

Carbachol is primarily used in the treatment of glaucoma, but it is also used during ophthalmic surgery.^[1] Carbachol eyedrops are used to decrease the pressure in the eye for people with glaucoma. It is sometimes used to constrict the pupils during cataract surgery.

Topical ocular administration is used to decrease intraocular pressure in people with primary open-angle glaucoma. Intraocular administration is used to produce miosis after lens implantation during cataract surgery. Carbachol can also be used to stimulate bladder emptying if the normal emptying mechanism is not working properly.

In most countries carbachol is only available by prescription. Outside the United States, it is also indicated for urinary retention as an oral (2 mg) tablet.^[1]^[3]

Contraindications

Use of carbachol, as well as all other muscarinic receptor agonists, is contraindicated in patients with asthma, coronary insufficiency, gastroduodenal ulcers, and incontinence. The parasympathomimetic action of this drug will exacerbate the symptoms of these disorders.

Overdose

The effects of a systemic overdose will probably be similar to the effects of a nerve agent (they both act on the cholinergic system, increasing cholinergic transmission), but its toxicity is much weaker and it is easier to antagonize in overdose. When administered ocularly there is little risk of such effects, since the doses are much smaller (see topical versus systemic administration).^[4]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h "Carbachol". PubChem Compound. Retrieved 6 March 2014.
^ Sanders KM, Zhu MH, Britton F, Koh SD, Ward SM (February 2012). "Anoctamins and gastrointestinal smooth muscle excitability". Exp. Physiol. 97 (2): 200–206. doi:10.1113/expphysiol.2011.058248. PMC 3272164. PMID 22002868.
^ "Carbachol generics". ndrugs. Retrieved 6 March 2014.
^ Richard A. Harvey; Pamela C. Champe, eds. (2009). Lippincott's Illustrated Review: Pharmacology (4th ed.). Lippincott Williams & Wilkins. p. 49. ISBN 978-0781771559.

External links

RxList.com - Carbachol
International Carbachol brands and dosage forms
PMC overdose case reports (humans)

English Journal

Monitoring intracellular calcium in response to GPCR activation using thin-film silicon photodiodes with integrated fluorescence filters.

Martins SA, Moulas G, Trabuco JR, Monteiro GA, Chu V, Conde JP, Prazeres DM.SourceINESC Microsistemas e Nanotecnologias (INESC MN), Rua Alves Redol 9, 1000-029 Lisbon, Portugal; IN-Institute of Nanoscience and Nanotechnology, Rua Alves Redol 9, 1000-029 Lisbon, Portugal; IBB-Institute for Biotechnology and Bioengineering, Instituto Superior Técnico, Avenida Rovisco Pais, 1049-001 Lisbon, Portugal.
Biosensors & bioelectronics.Biosens Bioelectron.2014 Feb 15;52:232-8. doi: 10.1016/j.bios.2013.08.037. Epub 2013 Sep 5.
G-protein coupled receptor (GPCRs) drug discovery is a thriving strategy in the pharmaceutical industry. The standard approach uses living cells to test millions of compounds in a high-throughput format. Typically, changes in the intracellular levels of key elements in the signaling cascade are moni
PMID 24055937

Two-dimensional surface plasmon resonance imager: An approach to study neuronal differentiation.

Mir TA, Shinohara H.SourceBiological Information Systems Science, Graduate School of Innovative Life Science for Education, University of Toyama, Toyama 930-8555, Japan. Electronic address: mirtanveer0699@gmail.com.
Analytical biochemistry.Anal Biochem.2013 Dec 1;443(1):46-51. doi: 10.1016/j.ab.2013.08.008. Epub 2013 Aug 19.
There is a growing demand for the development of a new bioanalytical technique that is capable of monitoring neuronal differentiation noninvasively, in real time, and without any fluorescent probes. In a previous article, we demonstrated that a high-resolution two-dimensional surface plasmon resonan
PMID 23969011

Design, synthesis and binding affinity of acetylcholine carbamoyl analogues.

Bolchi C, Valoti E, Binda M, Fasoli F, Ferrara R, Fumagalli L, Gotti C, Matucci R, Vistoli G, Pallavicini M.SourceDipartimento di Scienze Farmaceutiche, Università di Milano, via Mangiagalli 25, I-20133 Milano, Italy.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2013 Dec 1;23(23):6481-5. doi: 10.1016/j.bmcl.2013.09.023. Epub 2013 Sep 18.
A series of acetylcholine carbamoyl analogues, cyclised at the carbamate moiety or at the cationic head or at both, were tested for binding affinity at muscarinic and neuronal nicotinic receptors (nAChRs). While no muscarinic affinity was found, submicromolar Ki values, similar to that of carbachol,
PMID 24128660

Japanese Journal

Electrophysiological Properties of Prion-Positive Cardiac Progenitors Derived From Murine Embryonic Stem Cells

Fujii Hiroshi,Ikeuchi Yu,Kurata Yasutaka,Ikeda Nobuhito,Bahrudin Udin,Li Peili,Nakayama Yuji,Endo Ryo,Hasegawa Akira,Morikawa Kumi,Miake Junichiro,Yoshida Akio,Hidaka Kyoko,Morisaki Takayuki,Ninomiya Haruaki,Shirayoshi Yasuaki,Yamamoto Kazuhiro,Hisatome Ichiro
Circulation Journal 2012(0), 2012
… PrP-positive cells with automaticity showed positive and negative chronotropic responses to isoproterenol and carbamylcholine, respectively. …
NAID 130001870101

P-080 フェニレフリン、イソプロテレノール、カルバコール投与によるラット唾液タンパク分泌(ポスターセッション,2010年度日本味と匂学会第44回大会)

安松啓子,勝川秀夫,硲哲崇
日本味と匂学会誌 17(3), 395-396, 2010-12
NAID 110008451369

Polycyclic N-Heterocyclic Compounds. Part 64: Synthesis of 5-Amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c]isoquinolines and Related Compounds. Evaluation of Their Bronchodilator Activity and Effects on Lipoprotein Lipase mRNA Expression

Okuda Kensuke,Deguchi Hiroshi,Kashino Setsuo,Hirota Takashi,Sasaki Kenji
Chemical and Pharmaceutical Bulletin 58(5), 685-689, 2010
… Effects of the newly synthesized compounds on carbamylcholine chloride-induced contractions of trachea and lipoprotein lipase mRNA expression were also evaluated and found one promising bronchodilator. …
NAID 130000255829

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★リンクテーブル★

リンク元	「カルバコール」「カルバミルコリン」

「カルバコール」

Carbachol
Systematic (IUPAC) name
	2-[(Aminocarbonyl)oxy]-N,N,N-trimethylethanaminium chloride
Clinical data
Trade names	Miostat
AHFS/Drugs.com	monograph
Pregnancy; category	US: C (Risk not ruled out); ;
Routes of; administration	Oral-Tablet, Injectable-solution, Topical-eye drops
Legal status	℞ (Prescription only);
Pharmacokinetic data
Bioavailability	low
Metabolism	?
Biological half-life	?
Excretion	?
Identifiers
CAS Number	51-83-2
ATC code	N07AB01 (WHO) S01EB02 QA03AB92
PubChem	CID 5831
IUPHAR/BPS	298
DrugBank	DB00411
ChemSpider	5626
UNII	8Y164V895Y
KEGG	D00524
ChEBI	CHEBI:3385
ChEMBL	CHEMBL14
Chemical data
Formula	C6H15ClN2O2
Molar mass	182.696 g/mol
	SMILES [Cl-].O=C(OCC[N+](C)(C)C)N ;
	InChI InChI=1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H ; Key:AIXAANGOTKPUOY-UHFFFAOYSA-N ;
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