U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H15N2O2.Cl
Molecular Weight 182.649
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBACHOL

SMILES

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

InChI

InChIKey=AIXAANGOTKPUOY-UHFFFAOYSA-N
InChI=1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H

HIDE SMILES / InChI

Molecular Formula C6H15N2O2
Molecular Weight 147.1955
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Carbachol is a potent cholinergic (parasympathomimetic) agent which produces constriction of the iris and ciliary body resulting in reduction in intraocular pressure.

CNS Activity

Curator's Comment: Carbachol does not pass the blood-brain-barrier (BBB) however it produces cholinergic effects on brain blood vessels from the luminal side, whereas the effects on dural and extracranial vessels are from both the luminal and abluminal side since they are devoid of BBB

Originator

Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1550933/

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
MIOSTAT

Approved Use

Intraocular use for obtaining miosis during surgery. In addition, MIOSTAT (carbachol intraocular solution, USP) reduces the intensity of intraocular pressure elevation in the first 24 hours after cataract surgery.

Launch Date

1972
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Avoidance learning: long-lasting deficits after temporal lobe seizure.
1969 Dec 12
Sustained atrial fibrillation induced by carbachol, methacholine and bethanechol.
1971 Apr
Motor disturbances produced by intrastriatal injection of cyclic AMP and cyclic GMP.
1976 Nov
Drug-induced modulation of locomotor hyperactivity induced by picrotoxin in nucleus accumbens.
1984 Oct
Cardiovascular characterization of UL-FS 49, 1,3,4,5-tetrahydro-7,8-dimethoxy-3-[3-][2-(3,4-dimethoxyphenyl)ethyl] methylimino]propyl]-2H-3-benzazepin-2-on hydrochloride, a new "specific bradycardic agent".
1984 Sep 3
Neuropeptide Y and calcitonin gene-related peptide: effects on glucagon and insulin secretion in the mouse.
1987
Cardiovascular effects of cholinergic agents in the ventral-lateral midbrain periaqueductal gray of the rat.
1987 Dec
Spinal cholinergic neurons and the expression of morphine withdrawal symptoms in the rat.
1987 Mar
The effect of cholinergic stimulation in the nucleus accumbens on locomotor behavior.
1988 Feb 16
Renal function during onset of carbachol-induced hypertension in conscious rats.
1990
Similarities between the akinesia induced by carbachol microinjections into the pontine reticular formation and neuroleptic catalepsy.
1992
Sites at which neuropeptide Y modulates parasympathetic control of heart rate in guinea pigs and rats.
1992 May 1
Chick optic lobe contains a developmentally regulated alpha2alpha5beta2 nicotinic receptor subtype.
2000 Aug
Regional differences in functional receptor distribution and calcium mobilization in the intact human lens.
2001 Sep
The role of endogenous human Trp4 in regulating carbachol-induced calcium oscillations in HEK-293 cells.
2002 Apr 19
Zebrafish M2 muscarinic acetylcholine receptor: cloning, pharmacological characterization, expression patterns and roles in embryonic bradycardia.
2002 Nov
Type 5 adenylyl cyclase disruption alters not only sympathetic but also parasympathetic and calcium-mediated cardiac regulation.
2003 Aug 22
Impaired gastric secretion and lack of trophic responses to hypergastrinemia in M3 muscarinic receptor knockout mice.
2003 Dec
Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells.
2003 Dec
Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells.
2003 Jun 12
Effects of ML-7 and Y-27632 on carbachol- and endothelin-1-induced contraction of bovine trabecular meshwork.
2005 Jun
Theoretical and experimental investigation of calcium-contraction coupling in airway smooth muscle.
2006
Gene transfer of neuronal nitric oxide synthase into intracardiac Ganglia reverses vagal impairment in hypertensive rats.
2007 Feb
Metabotropic receptor-activated calcium increases and store-operated calcium influx in mouse Müller cells.
2008 Jul
Monitoring the reaction of carbachol with acetylcholinesterase by thioflavin T fluorescence and acetylthiocholine hydrolysis.
2008 Sep 25
Muscarinic receptors prevent oxidative stress-mediated apoptosis induced by domoic acid in mouse cerebellar granule cells.
2009 Apr
Histamine H1 receptor induces cytosolic calcium increase and aquaporin translocation in human salivary gland cells.
2009 Aug
Prediction of functionally selective allosteric interactions at an M3 muscarinic acetylcholine receptor mutant using Saccharomyces cerevisiae.
2010 Aug
Structural and functional effects of developmental exposure to ethanol on the zebrafish heart.
2010 Jun
Molecular basis of inhibition of substrate hydrolysis by a ligand bound to the peripheral site of acetylcholinesterase.
2010 Sep 6
TRPC5 channel sensitivities to antioxidants and hydroxylated stilbenes.
2011 Feb 18
Patents

Patents

Sample Use Guides

MIOSTAT (CARBACHOL INTRAOCULAR SOLUTION, USP) 0.01% Aseptically remove the sterile vial from the blister package by peeling the backing paper and dropping the vial onto a sterile tray. Withdraw the contents into a dry sterile syringe, and replace the needle with an atraumatic cannula prior to intraocular instillation. No more than one-half milliliter should be gently instilled into the anterior chamber for the production of satisfactory miosis. It may be instilled before or after securing sutures. Miosis is usually maximal within two to five minutes after application.
Route of Administration: Other
In the dose-course studies, carbachol showed significant increase in phosphorylation of MYPT1 at Thr696 (p-MYPT1) from concentrations of 15-100 μM based on Western blot results (p < 0.05, ANOVA test). In the time-course studies, treatment of cells with 15 μM of carbachol significantly enhanced the expression of p-MYPT1 from 3 to 15 h (p < 0.05, ANOVA test) and induced the expression of Rho A from 10 to 120 min (p < 0.05, ANOVA test).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:11:00 GMT 2023
Edited
by admin
on Fri Dec 15 15:11:00 GMT 2023
Record UNII
8Y164V895Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBACHOL
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
CARBACHOL [USP-RS]
Common Name English
CARBACHOL [EP MONOGRAPH]
Common Name English
CARBACHOLINE CHLORIDE
Systematic Name English
MIOSTAT
Brand Name English
CARBACHOL [EP IMPURITY]
Common Name English
CARBACHOL [MART.]
Common Name English
NSC-32865
Code English
ETHANAMINIUM, 2-((AMINOCARBONYL)OXY)-N,N,N-TRIMETHYL-, CHLORIDE
Systematic Name English
CARBACHOL [VANDF]
Common Name English
CARBACHOL [HSDB]
Common Name English
Choline chloride, carbamate
Systematic Name English
CARBACHOL CHLORIDE
Common Name English
CARBASTAT
Brand Name English
Carbachol [WHO-DD]
Common Name English
CARBACHOL [JAN]
Common Name English
carbachol [INN]
Common Name English
CARBACHOL [MI]
Common Name English
CARBACHOL [USP MONOGRAPH]
Common Name English
CARBACHOL [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29705
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
WHO-ATC S01EB02
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
WHO-ATC N07AB01
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
NDF-RT N0000175884
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
WHO-VATC QS01EB02
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
WHO-VATC QA03AB92
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
Code System Code Type Description
PUBCHEM
5831
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
NCI_THESAURUS
C47430
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
DRUG BANK
DB00411
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
NSC
32865
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
DAILYMED
8Y164V895Y
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
DRUG CENTRAL
488
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PRIMARY
EVMPD
SUB06087MIG
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PRIMARY
IUPHAR
298
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PRIMARY
MERCK INDEX
m3051
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PRIMARY Merck Index
MESH
D002217
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
ChEMBL
CHEMBL965
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PRIMARY
EPA CompTox
DTXSID9022730
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
CHEBI
3385
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
CAS
51-83-2
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
HSDB
6373
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
RS_ITEM_NUM
1092009
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
RXCUI
1999
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY RxNorm
INN
383
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
FDA UNII
8Y164V895Y
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
LACTMED
Carbachol
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
SMS_ID
100000081628
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-127-3
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
WIKIPEDIA
Carbachol
Created by admin on Fri Dec 15 15:11:01 GMT 2023 , Edited by admin on Fri Dec 15 15:11:01 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
TARGET -> AGONIST
TARGET -> AGONIST
TARGET -> AGONIST
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Duration of Action PHARMACOKINETIC INTRAOCULAR ADMINISTRATION
PHARMACOKINETIC