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Identification
NameCarbachol
Accession NumberDB00411  (APRD00845, DB02487)
TypeSmall Molecule
GroupsApproved
DescriptionA slowly hydrolyzed cholinergic agonist that acts at both muscarinic and nicotinic receptors. [PubChem]
Structure
Thumb
Synonyms
(2-Carbamoyloxyethyl)trimethylammonium chloride
(2-Hydroxyethyl)trimethyl ammonium chloride carbamate
(2-Hydroxyethyl)trimethylammonium chloride carbamate
2-((Aminocarbonyl)oxy)-N,N,N-trimethylethanaminium chloride
2-((Aminocarbonyl)oxy)-N,N,N-trimethylethanaminum chloride
Carbachol chloride
Carbacholum
Carbacol
Carbamylcholine
Choline carbamate chloride
Choline chloride, carbamate
Choline chlorine carbamate
Karbachol
Karbamoylcholin chlorid
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Carbacholtablet2 mgoralMylan Pharmaceuticals Ulc1995-12-312015-11-03Canada
Carbachol Injection Liq Sc 0.25mg/mlliquid.25 mgsubcutaneousBioniche Pharma (Canada) Ltd1995-12-312014-11-24Canada
Carbachol Intraocular Solution 0.01%liquid0.1 mgintraocularSabex IncNot applicableNot applicableCanada
Carbachol Tab 2mgtablet2 mgoralAllen & Hanburys A Glaxo Canada Ltd. Co.1951-12-311996-09-10Canada
Carbastatsolution0.01 %intraocularNovartis Ophthalmics Novartis Pharmaceuticals (Canada) Inc1996-10-222004-07-13Canada
Isopto Carbachol 1.5%liquid1.5 %ophthalmicAlcon Canada Inc1951-12-312012-08-14Canada
Isopto Carbachol 3%liquid3 %ophthalmicAlcon Canada Inc1951-12-312013-02-28Canada
Miostatsolution.1 mg/mLophthalmicAlcon Laboratories, Inc.1974-04-15Not applicableUs
Miostat Ophthalmic Liq 0.01%solution.01 %intraocularAlcon Canada Inc1980-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CarbopticNutraMax
Isopto CarbacholAlcon Laboratories, Inc.
MioticolFarmigea
Brand mixturesNot Available
SaltsNot Available
Categories
UNII8Y164V895Y
CAS number51-83-2
WeightAverage: 182.649
Monoisotopic: 182.082205441
Chemical FormulaC6H15ClN2O2
InChI KeyInChIKey=AIXAANGOTKPUOY-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.
Related Articles
AbsorptionNot well absorbed in the gastro-intestinal tract, and does not cross the blood-brain barrier.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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 inhibitorNon-inhibitor0.8895
CYP450 2D6 inhibitorNon-inhibitor0.9204
CYP450 2C19 inhibitorNon-inhibitor0.8551
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pharmafair inc
  • Novartis pharmaceuticals corp
  • Alcon laboratories inc
Packagers
Dosage forms
FormRouteStrength
Liquidsubcutaneous.25 mg
Liquidintraocular0.1 mg
Tabletoral2 mg
Solutionintraocular0.01 %
Liquidophthalmic1.5 %
Liquidophthalmic3 %
Solutionophthalmic.1 mg/mL
Solutionintraocular.01 %
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 ReferencesNot 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
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when 1,10-Phenanthroline is combined with Carbachol.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Carbachol.
AlprenololThe risk or severity of adverse effects can be increased when Alprenolol is combined with Carbachol.
AmbenoniumThe risk or severity of adverse effects can be increased when Ambenonium is combined with Carbachol.
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Carbachol.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Carbachol.
BefunololThe risk or severity of adverse effects can be increased when Befunolol is combined with Carbachol.
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Carbachol.
BevantololThe risk or severity of adverse effects can be increased when Bevantolol is combined with Carbachol.
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Carbachol.
BopindololThe risk or severity of adverse effects can be increased when Bopindolol is combined with Carbachol.
BufuralolThe risk or severity of adverse effects can be increased when Bufuralol is combined with Carbachol.
BupranololThe risk or severity of adverse effects can be increased when Bupranolol is combined with Carbachol.
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Carbachol.
CarvedilolThe risk or severity of adverse effects can be increased when Carvedilol is combined with Carbachol.
CeliprololThe risk or severity of adverse effects can be increased when Celiprolol is combined with Carbachol.
CimetropiumCarbachol may decrease the anticholinergic activities of Cimetropium.
CoumaphosThe risk or severity of adverse effects can be increased when Coumaphos is combined with Carbachol.
DecamethoniumThe risk or severity of adverse effects can be increased when Decamethonium is combined with Carbachol.
DemecariumThe risk or severity of adverse effects can be increased when Demecarium is combined with Carbachol.
DichlorvosThe risk or severity of adverse effects can be increased when Dichlorvos is combined with Carbachol.
DonepezilThe risk or severity of adverse effects can be increased when Donepezil is combined with Carbachol.
EchothiophateThe risk or severity of adverse effects can be increased when Echothiophate is combined with Carbachol.
EdrophoniumThe risk or severity of adverse effects can be increased when Edrophonium is combined with Carbachol.
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Carbachol.
FenthionThe risk or severity of adverse effects can be increased when Fenthion is combined with Carbachol.
GalantamineThe risk or severity of adverse effects can be increased when Galantamine is combined with Carbachol.
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Gallamine Triethiodide is combined with Carbachol.
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Ginkgo biloba is combined with Carbachol.
Huperzine AThe risk or severity of adverse effects can be increased when Huperzine A is combined with Carbachol.
IndenololThe risk or severity of adverse effects can be increased when Indenolol is combined with Carbachol.
IsoflurophateThe risk or severity of adverse effects can be increased when Isoflurophate is combined with Carbachol.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Carbachol.
LevobunololThe risk or severity of adverse effects can be increased when Levobunolol is combined with Carbachol.
MalathionThe risk or severity of adverse effects can be increased when Malathion is combined with Carbachol.
MefloquineThe risk or severity of adverse effects can be increased when Mefloquine is combined with Carbachol.
MemantineThe risk or severity of adverse effects can be increased when Memantine is combined with Carbachol.
MetipranololThe risk or severity of adverse effects can be increased when Metipranolol is combined with Carbachol.
MetoprololThe risk or severity of adverse effects can be increased when Metoprolol is combined with Carbachol.
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Carbachol.
NadololThe risk or severity of adverse effects can be increased when Nadolol is combined with Carbachol.
NeostigmineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Carbachol.
OxprenololThe risk or severity of adverse effects can be increased when Oxprenolol is combined with Carbachol.
PenbutololThe risk or severity of adverse effects can be increased when Penbutolol is combined with Carbachol.
PhysostigmineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Carbachol.
PindololThe risk or severity of adverse effects can be increased when Pindolol is combined with Carbachol.
PractololThe risk or severity of adverse effects can be increased when Practolol is combined with Carbachol.
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Carbachol.
PyridostigmineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Carbachol.
RivastigmineThe risk or severity of adverse effects can be increased when Rivastigmine is combined with Carbachol.
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Carbachol.
TacrineThe risk or severity of adverse effects can be increased when Tacrine is combined with Carbachol.
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Carbachol.
TrichlorfonThe risk or severity of adverse effects can be increased when Trichlorfon is combined with Carbachol.
TubocurarineThe risk or severity of adverse effects can be increased when Tubocurarine is combined with Carbachol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
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:15059034 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
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:15485827 ]
  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:15333678 ]
  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:12948933 ]
  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:12505062 ]
  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:16181410 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Drug binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular Weight:
59764.82 Da
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:17139284 ]
  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:17016423 ]
  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. doi: 10.1073/pnas.1004956107. Epub 2010 May 24. [PubMed:20498043 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Phospholipase a2 activity
Specific Function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular Weight:
85238.2 Da
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:1417779 ]
  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:6091414 ]
  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:1373616 ]
  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:8344290 ]
  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:2519894 ]
  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:7730640 ]
  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:1636494 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23