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Identification
NameCarbachol
Accession NumberDB00411  (APRD00845, DB02487)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
(2-Carbamoyloxyethyl)trimethylammonium chlorideNot AvailableNot Available
(2-Hydroxyethyl)trimethyl ammonium chloride carbamateNot AvailableNot Available
(2-Hydroxyethyl)trimethylammonium chloride carbamateNot AvailableNot Available
2-((Aminocarbonyl)oxy)-N,N,N-trimethylethanaminium chlorideNot AvailableNot Available
2-((Aminocarbonyl)oxy)-N,N,N-trimethylethanaminum chlorideNot AvailableNot Available
Carbachol chlorideNot AvailableNot Available
CarbacholumNot AvailableNot Available
CarbacolNot AvailableNot Available
CarbamylcholineNot AvailableNot Available
Choline carbamate chlorideNot AvailableNot Available
Choline chloride, carbamateNot AvailableNot Available
Choline chlorine carbamateNot AvailableNot Available
KarbacholNot AvailableNot Available
Karbamoylcholin chloridNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Miostatsolution.1 mg/mLophthalmicAlcon Laboratories, Inc.1974-04-15Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Carbacholtablet2 mgoralMylan Pharmaceuticals UlcNot AvailableNot AvailableCanada
Over the Counter ProductsNot Available
International Brands
NameCompany
CarbastatNovartis
CarbopticNutraMax
Isopto CarbacholAlcon Laboratories, Inc.
MioticolFarmigea
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number51-83-2
WeightAverage: 182.649
Monoisotopic: 182.082205441
Chemical FormulaC6H15ClN2O2
InChI KeyAIXAANGOTKPUOY-UHFFFAOYSA-N
InChI
InChI=1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H
IUPAC Name
2-(trimethylazaniumyl)ethyl carbamate chloride
SMILES
[Cl-].C[N+](C)(C)CCOC(N)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassQuaternary ammonium salts
Sub ClassCholines
Direct ParentCholines
Alternative Parents
Substituents
  • Choline
  • Hydrocarbon derivative
  • Organic chloride salt
  • Organic salt
  • Organooxygen compound
  • Amine
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationPrimarily used in the treatment of glaucoma, but is also used during ophthalmic surgery.
PharmacodynamicsCarbachol 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).
Mechanism of actionCarbachol 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.
AbsorptionNot well absorbed in the gastro-intestinal tract, and does not cross the blood-brain barrier.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral, mouse: LD50 = 15 mg/kg; Oral, rat: LD50 = 40 mg/kg.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7542
Blood Brain Barrier+0.9727
Caco-2 permeable+0.5111
P-glycoprotein substrateNon-substrate0.6062
P-glycoprotein inhibitor INon-inhibitor0.9569
P-glycoprotein inhibitor IINon-inhibitor0.9545
Renal organic cation transporterNon-inhibitor0.8526
CYP450 2C9 substrateNon-substrate0.7825
CYP450 2D6 substrateNon-substrate0.7825
CYP450 3A4 substrateSubstrate0.5643
CYP450 1A2 substrateNon-inhibitor0.8329
CYP450 2C9 substrateNon-inhibitor0.8895
CYP450 2D6 substrateNon-inhibitor0.9204
CYP450 2C19 substrateNon-inhibitor0.8551
CYP450 3A4 substrateNon-inhibitor0.9515
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9416
Ames testNon AMES toxic0.667
CarcinogenicityNon-carcinogens0.5998
BiodegradationNot ready biodegradable0.9151
Rat acute toxicity2.6763 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9765
hERG inhibition (predictor II)Non-inhibitor0.8719
Pharmacoeconomics
Manufacturers
  • Pharmafair inc
  • Novartis pharmaceuticals corp
  • Alcon laboratories inc
Packagers
Dosage forms
FormRouteStrength
Solutionophthalmic.1 mg/mL
Tabletoral2 mg
Prices
Unit descriptionCostUnit
Isopto Carbachol 3% Solution 15ml Bottle61.76USD bottle
Carbachol 99% powder53.1USD g
Isopto Carbachol 1.5% Solution 15ml Bottle48.64USD bottle
Isopto Carbachol 1.5% Solution 30ml Bottle44.99USD bottle
Miostat vial32.4USD ml
Isopto carbachol 3% drops3.51USD ml
Isopto carbachol 1.5% drops3.07USD ml
Isopto Carbachol 3 % Solution0.91USD ml
Isopto Carbachol 1.5 % Solution0.76USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point208-210Major, R.T. and Bonnett, H.T.; U.S. Patent 2,374,367; April 24,1945; assigned to Merck & Co., Inc.
water solubility1 g/mlNot Available
logP-3.78Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.948 mg/mLALOGPS
logP-3.5ALOGPS
logP-4.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)15.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.02 m3·mol-1ChemAxon
Polarizability16.02 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.39 KB)
SpectraNot Available
References
Synthesis Reference

Major, R.T. and Bonnett, H.T.; U.S. Patent 2,374,367; April 24,1945; assigned to Merck &
Co., Inc.

General ReferenceNot Available
External Links
ATC CodesN07AB01S01EB02
AHFS Codes
  • 12:04.00
  • 52:20.00
PDB Entries
FDA labelDownload (79.4 KB)
MSDSDownload (64.9 KB)
Interactions
Drug Interactions
Drug
TacrineThe acetylcholinesterase inhibitor, Tacrine, may increase the cholinergic effects of Carbachol, a cholinergic agonist. Monitor for increased cholinergic effects.
Food InteractionsNot Available

Targets

1. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

References:

  1. Weiner DM, Goodman MW, Colpitts TM, Feddock MA, Duggento KL, Nash NR, Levey AI, Brann MR: Functional screening of drug target genes: m1 muscarinic acetylcholine receptor phenotypes in degenerative dementias. Am J Pharmacogenomics. 2004;4(2):119-28. Pubmed

2. Muscarinic acetylcholine receptor M2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

References:

  1. Peter JC, Wallukat G, Tugler J, Maurice D, Roegel JC, Briand JP, Hoebeke J: Modulation of the M2 muscarinic acetylcholine receptor activity with monoclonal anti-M2 receptor antibody fragments. J Biol Chem. 2004 Dec 31;279(53):55697-706. Epub 2004 Oct 14. Pubmed
  2. May LT, Lin Y, Sexton PM, Christopoulos A: Regulation of M2 muscarinic acetylcholine receptor expression and signaling by prolonged exposure to allosteric modulators. J Pharmacol Exp Ther. 2005 Jan;312(1):382-90. Epub 2004 Aug 27. Pubmed
  3. Sawatzky DA, Kingham PJ, Durcan N, McLean WG, Costello RW: Eosinophil-induced release of acetylcholine from differentiated cholinergic nerve cells. Am J Physiol Lung Cell Mol Physiol. 2003 Dec;285(6):L1296-304. Epub 2003 Aug 29. Pubmed
  4. Sterin-Borda L, Joensen L, Bayo-Hanza C, Esteva M, Borda E: Therapeutic use of muscarinic acetylcholine receptor peptide to prevent mice chagasic cardiac dysfunction. J Mol Cell Cardiol. 2002 Dec;34(12):1645-54. Pubmed
  5. Zuchner T, Schliebs R, Perez-Polo JR: Down-regulation of muscarinic acetylcholine receptor M2 adversely affects the expression of Alzheimer’s disease-relevant genes and proteins. J Neurochem. 2005 Oct;95(1):20-32. Pubmed

3. Neuronal acetylcholine receptor subunit alpha-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-2 Q15822 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. An MC, Lin W, Yang J, Dominguez B, Padgett D, Sugiura Y, Aryal P, Gould TW, Oppenheim RW, Hester ME, Kaspar BK, Ko CP, Lee KF: Acetylcholine negatively regulates development of the neuromuscular junction through distinct cellular mechanisms. Proc Natl Acad Sci U S A. 2010 Jun 8;107(23):10702-7. Epub 2010 May 24. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. Cytosolic phospholipase A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytosolic phospholipase A2 P47712 Details

References:

  1. Konrad RJ, Jolly YC, Major C, Wolf BA: Carbachol stimulation of phospholipase A2 and insulin secretion in pancreatic islets. Biochem J. 1992 Oct 1;287 ( Pt 1):283-90. Pubmed
  2. Enyedi P, Fredholm BB: Calcium-dependent enhancement by carbachol of the VIP-induced cyclic AMP accumulation in cat submandibular gland. Acta Physiol Scand. 1984 Apr;120(4):523-8. Pubmed
  3. Grosfils K, Gomez F, Dehaye JP: Inhibition by mepacrine and amylase secretion from intact and permeabilized rat pancreatic acini. Biochem Biophys Res Commun. 1992 Apr 15;184(1):408-13. Pubmed
  4. Ying Z, Tojo H, Nonaka Y, Okamoto M: Cloning and expression of phospholipase A2 from guinea pig gastric mucosa, its induction by carbachol and secretion in vivo. Eur J Biochem. 1993 Jul 1;215(1):91-7. Pubmed
  5. Strosznajder J, Strosznajder RP: Guanine nucleotides and fluoride enhance carbachol-mediated arachidonic acid release from phosphatidylinositol. Evidence for involvement of GTP-binding protein in phospholipase A2 activation. J Lipid Mediat. 1989 Jul-Aug;1(4):217-29. Pubmed
  6. Hirasawa N, Santini F, Beaven MA: Activation of the mitogen-activated protein kinase/cytosolic phospholipase A2 pathway in a rat mast cell line. Indications of different pathways for release of arachidonic acid and secretory granules. J Immunol. 1995 May 15;154(10):5391-402. Pubmed
  7. Strosznajder J, Samochocki M: Carbachol-stimulated release of arachidonic acid and eicosanoids from brain cortex synaptoneurosome lipids of adult and aged rats. Adv Exp Med Biol. 1992;318:251-8. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 02, 2014 12:59