Carbachol

Carbachol

Systematic (IUPAC) name
2-[(aminocarbonyl)oxy]-N,N,N-trimethylethanaminium chloride
Clinical data
Trade names	Miostat
AHFS/Drugs.com	monograph
Pregnancy cat.	C(US)
Legal status	?
Routes	Tablet, liquid, eye drops
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half-life	?
Excretion	?
Identifiers
CAS number	51-83-2 Y
ATC code	N07AB01 S01EB02 QA03AB92
PubChem	CID 5831
IUPHAR ligand	298
DrugBank	APRD00845
ChemSpider	5626 Y
UNII	8Y164V895Y Y
KEGG	D00524 Y
ChEBI	CHEBI:3385 Y
ChEMBL	CHEMBL14 Y
Chemical data
Formula	C6H15ClN2O2
Mol. mass	182.696 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H Y Key:AIXAANGOTKPUOY-UHFFFAOYSA-N Y
N(what is this?)  (verify)

Carbachol (Carbastat, Carboptic, Isopto Carbachol, Miostat), also known as carbamylcholine, is a 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. 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. 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.

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

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).

Indications

Carbachol is primarily used in the treatment of glaucoma, 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 cataract surgery.

Topical ocular administration is used to decrease intraocular pressure in people with primary open-angle glaucoma. 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

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 vs systemic administration). ^[1]

References

1. ^ Champe and Harvey (2009). "Lippincott's Illustrated Review: Pharmacology 4th edition." pp. 49

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

• RxList.com - Carbachol