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Revision as of 09:33, 27 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit		Latest revision as of 06:50, 25 October 2024 edit undo76.174.0.57 (talk) Cats (source: https://doi.org/10.2174/138161206778522056).
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			{{Short description|Chemical compound}}
			{{Use dmy dates|date=March 2014}}
	{{Drugbox		{{Drugbox
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 443497130		| verifiedrevid = 457629915
	| IUPAC_name = 2--''N,N,N''-trimethylethanaminium chloride		| IUPAC_name = 2--''N'',''N'',''N''-trimethylethanaminium chloride
	| image = Carbachol chloride.svg		| image = Carbachol chloride.svg
	<!--Clinical data-->		<!--Clinical data-->| tradename = Miostat
			| Drugs.com = {{drugs.com|monograph|carbachol}}
	| tradename = Miostat
			| DailyMedID = Carbachol
	| Drugs.com = {{drugs.com|monograph|carbachol}}
			| pregnancy_AU = B2
	| pregnancy_US = C
	| legal_status = ?		| pregnancy_US = C
			| legal_status = Rx-only
	| routes_of_administration = Tablet, liquid, eye drops
			| routes_of_administration = ] (])<br />Solution for injection<br />] (])
	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->| bioavailability = Low
	| bioavailability = ?		| metabolism =
			| elimination_half-life =
	| metabolism = ?
			| excretion = <!--Identifiers-->
	| elimination_half-life = ?
			| CAS_number_Ref = {{cascite|correct|??}}
	| excretion = ?
			| CAS_number = 51-83-2
			| ATC_prefix = N07
			| ATC_suffix = AB01
			| ATC_supplemental = {{ATC|S01|EB02}} {{ATCvet|A03|AB92}}
			| PubChem = 5831
			| IUPHAR_ligand = 298
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
			| DrugBank = DB00411
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID = 5626
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 8Y164V895Y
			| KEGG_Ref = {{keggcite|correct|kegg}}
			| KEGG = D00524
			| ChEBI_Ref = {{ebicite|correct|EBI}}
			| ChEBI = 3385
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| PDB_ligand = CCE
			| ChEMBL = 14
			<!--Chemical data-->| C = 6
	<!--Identifiers-->
			| H = 15
	| CASNo_Ref = {{cascite|correct|CAS}}
			| N = 2
	| CAS_number_Ref = {{cascite|correct|??}}
			| O = 2
	| CAS_number = 51-83-2
			| Cl = 1
	| ATC_prefix = N07
			| smiles = .O=C(OCC(C)(C)C)N
	| ATC_suffix = AB01
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| ATC_supplemental = {{ATC|S01|EB02}} {{ATCvet|A03|AB92}}
			| StdInChI = 1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H
	| PubChem = 5831
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| IUPHAR_ligand = 298
			| StdInChIKey = AIXAANGOTKPUOY-UHFFFAOYSA-N
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB00411
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 5626
	| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 8Y164V895Y
	| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D00524
	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 3385
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 14
	<!--Chemical data-->
	| C=6 | H=15 | N=2 | O=2 | Cl = 1
	| molecular_weight = 182.696 g/mol
	| smiles = .O=C(OCC(C)(C)C)N
	| InChI = 1/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H
	| InChIKey = AIXAANGOTKPUOY-UHFFFAOYAV
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = AIXAANGOTKPUOY-UHFFFAOYSA-N
	}}		}}
	'''Carbachol''' ('''Carbastat''', '''Carboptic''', '''Isopto Carbachol''', '''Miostat'''), also known as '''carbamylcholine''', is a ] that binds and activates the ]. Thus it is classified as a ] ]. It is primarily used for various ] purposes, such as for treating ], or for use during ophthalmic surgery. It is generally administered as an ophthalmic solution (i.e. ]s).		'''Carbachol''', also known as '''carbamylcholine''' and sold under the brand name '''Miostat''' among others, is a ] ] that binds and activates ]. Thus it is classified as a ]. It is primarily used for various ] purposes, such as for treating ], or for use during ophthalmic surgery. It is generally administered as an ophthalmic solution (i.e., ]s).
			Carbachol produces effects comparable to those of ] if a massive overdose is administered (as may occur following industrial and shipping accidents) and therefore it is classified as an ] in the United States as defined in Section 302 of the U.S. ] (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.<ref name="gov-right-know">{{Cite web | publisher = ] | title = 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities | url = http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | edition = 1 July 2008 | access-date = 29 October 2011 | archive-url = https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | archive-date = 25 February 2012 | url-status = dead }}</ref>
			It is on the ].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref>
	== Chemistry and pharmacology ==		== Chemistry and pharmacology ==
			Carbachol is a ] ] and a positively charged quaternary ammonium compound.<ref name="PubChem">{{cite web | url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=2551 | title = Carbachol | work = PubChem Compound| access-date = 6 March 2014}}</ref> It is not well absorbed in the ] and does not cross the ]. It is usually administered topical ocular or through intraocular injection.<ref name="PubChem" /> Carbachol is not easily metabolized by ], it has a 2 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, ] is mixed in to promote absorption.<ref name="PubChem" />
			Carbachol is a ] that ] both ] and ] receptors.<ref name="PubChem" /> In topical ocular and intraocular administration its principal effects are ] and increased ] outflow.<ref name="PubChem" />
	Carbachol is a ] ] and a positively charged quaternary ammonium compound. It is not well absorbed in the ] and does not cross the ]. It is usually administered topical ocular or through intraocular injection. Carbachol is not easily metabolized by ], 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, ] is mixed in to promote absorption.
			In the ] and ], carbachol is well known for its ability to induce ] (REM) sleep when microinjected into the ] formation. Carbachol elicits this REM sleep-like state via activation of postsynaptic muscarinic ] receptors (]).<ref name="PubChem" />
	Carbachol is a ] that ] both ] and ] receptors. In topical ocular and intraocular administration its principal effects are ] and increased ] outflow.
			A recent review indicates that carbachol is a strong promoter of ] activity, which is mediated through the ], ].<ref name="pmid22002868">{{cite journal | vauthors = Sanders KM, Zhu MH, Britton F, Koh SD, Ward SM | title = Anoctamins and gastrointestinal smooth muscle excitability | journal = Experimental Physiology | volume = 97 | issue = 2 | pages = 200–206 | date = February 2012 | pmid = 22002868 | pmc = 3272164 | doi = 10.1113/expphysiol.2011.058248 }}</ref>
	In the ] and ], carbachol is well-known for its ability to induce ] (REM) sleep when microinjected into the ] formation. Carbachol elicits this REM sleep-like state via activation of postsynaptic muscarinic ] receptors (]).
			===Synthesis===
			Carbachol may be prepared in a 2 step process beginning with the reaction of ] with ] to form a 2-chloroethyl-], which is then ] by a reaction with ].
	== Indications ==		== Indications ==
			Carbachol is primarily used in the treatment of ], but it is also used during ophthalmic surgery.<ref name="PubChem" /> Carbachol eyedrops are used to decrease the pressure in the eye for people with glaucoma. It is sometimes used to constrict the pupils during ] surgery.
			Topical ocular administration is used to decrease intraocular pressure in people with primary open-angle ]. Intraocular administration is used to produce miosis after lens implantation during cataract surgery. Carbachol can also be used to stimulate bladder emptying to treat the condition of underactive bladder.<ref>{{cite journal | vauthors = Moro C, Phelps C, Veer V, Clark J, Glasziou P, Tikkinen KA, Scott AM | title = The effectiveness of parasympathomimetics for treating underactive bladder: A systematic review and meta-analysis | journal = Neurourology and Urodynamics | volume = 41 | issue = 1 | pages = 127–139 | date = January 2022 | pmid = 34816481 | doi = 10.1002/nau.24839 | s2cid = 244530010 | url = https://pure.bond.edu.au/ws/files/118955227/AM_The_effectiveness_of_parasympathomimetics_for_treating.pdf }}</ref>
	Carbachol is primarily used in the treatment of ], but it is also used during ophthalmic surgery. Carbachol eyedrops are used to decrease the pressure in the eye for people with glaucoma. It is sometimes used to constrict the pupils during ] surgery.
			In most countries carbachol is only available by prescription. Outside the United States, it is also indicated for urinary retention as an oral (2&nbsp;mg) tablet.<ref name="PubChem" /><ref name="ndrugs">{{cite web | url = http://www.ndrugs.com/?s=Carbachol | title = Carbachol generics| work =ndrugs | access-date = 6 March 2014}}</ref>
	Topical ocular administration is used to decrease intraocular pressure in people with primary open-angle ]. Intracellular 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.
	== Contraindications ==		== Contraindications ==
			Use of carbachol, as well as all other ], is contraindicated in patients with ], ], gastroduodenal ], and ].{{fact|date=November 2018}} The ] action of this drug will exacerbate the ] of these disorders.{{fact|date=November 2018}}
	Use of carbachol, as well as all other ], is contraindicated in patients with ], ], gastroduodenal ], and ]. The ] action of this drug will exacerbate the ] of these disorders.
	== Overdose ==		== Overdose ==
			The effects of a systemic overdose will probably be similar to the effects of a ] (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).<ref name="Lippencott's">{{cite book | veditors = Harvey RA, Champe PC |year=2009 |title=Lippincott's Illustrated Review: Pharmacology |edition=4th |publisher=Lippincott Williams & Wilkins |page=49 |isbn=978-0-7817-7155-9}}</ref>
	The effects of a systemic overdose will probably be similar to the effects of a ] (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 vs systemic administration). <ref name="Lippencott's">Champe and Harvey (2009). "Lippincott's Illustrated Review: Pharmacology 4th edition." pp. 49</ref>
	== References ==		== References ==
	{{Reflist|2}}		{{Reflist}}
	== Further reading ==
	* Brenner, G. M. (2000). ''Pharmacology.'' Philadelphia, PA: W.B. Saunders Company. ISBN 0-7216-7757-6
	* Canadian Pharmacists Association (2000). ''Compendium of pharmaceuticals and specialties'' (25th ed.). Toronto, ON: Webcom. ISBN 0-919115-76-4
	* Carbachol (1998). ''MedlinePlus''. Retrieved June 27, 2004, from http://www.nlm.nih.gov/medlineplus/druginfo/uspdi/202110.html
	* Carbachol (2003). ''RxList''. Retrieved June 27, 2004, from http://www.rxlist.com/cgi/generic2/carbachol.htm
	* National Institute for Occupational Safety and Health. (2002). Choline, chloride, carbamate. In ''The registry of toxic effects of chemical substances.'' Retrieved June 27, 2004, from http://www.cdc.gov/niosh/rtecs/gad59f8.html
	* Carbachol Chloride (2004). ''Hazardous Substances Data Bank''. Retrieved July 16, 2004, from http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?hsdbb.htm (search carbachol).
	== External links ==		== External links ==
			* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/carbachol | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Carbachol }}
	*
	{{Opthalmologicals}}		{{Opthalmologicals}}
			{{Acetylcholine receptor modulators}}
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