Drug/Small Molecule:
carbachol

2D structure

Overview

IUPAC Name: 2-carbamoyloxyethyl-trimethylazanium
Trade Names: CB; Carbachol USP27; Carbachol chloride; Carbachol hydrochloride; Carbacholin; Carbacholine; Carbacholine chloride; Carbacolina; Carbaminocholine chloride; Carbaminoylcholine chloride; Carbamiotin; Carbamoylcholine chloride; Carbamoylcholine-hydrochloride; Carbamylcholine chloride; Carbastat; Carbastat intraocular; Carbochol; Carbocholin; Carbocholine; Carboptic; Carbyl; Carcholin; Choline carbamate chloride; Choline chloride carbamate; Choline chloride, carbamoyl-; Choline chlorine carbamate; Choline, chloride, carbamate; Coletyl; Doryl; Isopto Carbachol; Jestryl; Karbachol; Karbamoylcholin chlorid; Lentin; Lentine; Miostat; Mistura C; Moryl; P. V. Carbachol; Rilentol; Vasoperif
PharmGKB Accession Id: PA448784

Description

A slowly hydrolyzed cholinergic agonist that acts at both muscarinic and nicotinic receptors. [PubChem]

Indication

Primarily used in the treatment of glaucoma, but is also used during ophthalmic surgery.

ATC Therapeutic Categories

  • N07AB:Choline esters
  • S01EB:Parasympathomimetics

Pharmacology and Interactions

Mechanism Of Action

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.

Pharmacology

Carbachol is a potent cholinergic (parasympathomimetic) agent which produces constriction of the iris and ciliary body resulting in reduction in intraocular pressure. The exact mechanism by which carbachol lowers intraocular pressure is not precisely known. 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).

Absorption, Distribution, Metabolism, Elimination & Toxicity

Absorption

Not well absorbed in the gastro-intestinal tract, and does not cross the blood-brain barrier.

Toxicity

Oral, mouse: LD50 = 15 mg/kg; Oral, rat: LD50 = 40 mg/kg.

Chemical Properties

Chemical Formula:

C6H15N2O2

SMILES Code:

C[N+](C)(C)CCOC(=O)N.[Cl-]

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

147.1955 / 147.1134

Curated Information

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
No phenotype data Genotype Data Available Literature annotations available Not annotated
ACHE
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No phenotype data Genotype Data Available Literature annotations available Not annotated
CHAT
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No phenotype data No genotype data Literature annotations available Not annotated
CHGA
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
CHRNA3
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
CHRNA7
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
CHRNB4
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
DDC
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Pathways
No phenotype data Genotype Data Available Literature annotations available Not annotated
SLC18A3
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Pathways
No phenotype data No genotype data No literature annotations Not annotated
SLC5A7
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Pathways

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00411
KEGG Drug ID:
D00524
PubChem Compound ID:
2551
PubChem Substance ID:
7978854

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
The PharmGKB is financially supported by the NIH/ NIGMS and is managed at Stanford University (U01GM61374).
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