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Details

Stereochemistry ACHIRAL
Molecular Formula C6H15N2O2.Cl
Molecular Weight 182.649
Optical Activity NONE
Defined Stereocenters 0 / 1
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 / 1
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
Spasmolytic constituents of Cedrus deodara (Roxb.) Loud: pharmacological evaluation of himachalol.
1975 Feb
Evidence that a nigral gabaergic--cholinergic balance controls posture.
1979 Jan 1
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.
1983 Jan
Drug-induced modulation of locomotor hyperactivity induced by picrotoxin in nucleus accumbens.
1984 Oct
Neuropeptide Y and calcitonin gene-related peptide: effects on glucagon and insulin secretion in the mouse.
1987
Spinal cholinergic neurons and the expression of morphine withdrawal symptoms in the rat.
1987 Mar
Novel 'soft' anticholinergic agents.
1988 Feb
Anatomical analysis of frontal cortex sites at which carbachol induces motor seizures in the rat.
1988 May
Plasma catecholamines and alpha 1-adrenoceptor function in hemodialysis-associated hypotension.
1990
Dopaminergic drugs influence the intensity of catalepsy induced by microinjections of carbachol into the reticular formation.
1990 Nov 13
Studies on the development of tolerance and potential spinal neurotoxicity after chronic intrathecal carbachol-antinociception in the rat.
1991 Feb
Positive and negative feedback regulation of choline acetyltransferase mRNA levels in Drosophila: a study using temperature-sensitive mutants and embryo cell cultures.
1992 Apr
Vagus nerve modulates secretin binding sites in the rat forestomach.
1999 Apr
Myoclonic and tonic seizures elicited by microinjection of cholinergic drugs into the inferior colliculus.
1999 Sep-Oct
Carbachol blocks beta-amyloid fragment 31-35-induced apoptosis in cultured cortical neurons.
2000 Apr
Low-affinity M(2) receptor binding state mediates mouse atrial bradycardia: comparative effects of carbamylcholine and the M(1) receptor agonists sabcomeline and xanomeline.
2001 Mar
The role of endogenous human Trp4 in regulating carbachol-induced calcium oscillations in HEK-293 cells.
2002 Apr 19
Design, pharmacokinetic, and pharmacodynamic evaluation of soft anticholinergics based on tropyl alpha-phenylcyclopentylacetate.
2002 Feb
Impaired parasympathetic heart rate control in mice with a reduction of functional G protein betagamma-subunits.
2002 Feb
Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells.
2003 Jun 12
Design, pharmacokinetic, and pharmacodynamic evaluation of a new class of soft anticholinergics.
2003 Oct
Crucial role of histamine for regulation of gastric acid secretion ascertained by histidine decarboxylase-knockout mice.
2003 Oct
Cyclic AMP/protein kinase a signal attenuates Ca(2+)-induced fibroblast growth factor-1 synthesis in rat cortical neurons.
2004 Aug 15
Post-seizures amygdaloallocortical microvascular lesion leading to atrophy and memory impairment.
2005 Aug
Pharmacokinetic and pharmacodynamic evaluations of the zwitterionic metabolite of a new series of N-substituted soft anticholinergics.
2005 Dec
[Effects of carbachol on apoptosis of peripheral white blood cells and expression of cytokines in rats suffering from gut ischemia/reperfusion injury].
2005 Feb
Neuronal nitric oxide synthase activity in rat urinary bladder detrusor: participation in M3 and M4 muscarinic receptor function.
2005 Jul
Effects of ML-7 and Y-27632 on carbachol- and endothelin-1-induced contraction of bovine trabecular meshwork.
2005 Jun
Actin and non-muscle myosin II facilitate apical exocytosis of tear proteins in rabbit lacrimal acinar epithelial cells.
2005 Oct 15
Case report: acute unintentional carbachol intoxication.
2006
Muscarinic acetylcholine receptors mediate oligodendrocyte progenitor survival through Src-like tyrosine kinases and PI3K/Akt pathways.
2006 Apr
Novelty exploration elicits a reversal of acute stress-induced modulation of hippocampal synaptic plasticity in the rat.
2006 Dec 1
Muscarinic cholinoceptor activation modulates DNA synthesis and CD40 expression in fibroblast cells.
2006 Jul
Myosin light chain kinase-independent inhibition by ML-9 of murine TRPC6 channels expressed in HEK293 cells.
2007 Sep
Structural and functional effects of developmental exposure to ethanol on the zebrafish heart.
2010 Jun
The validation of an in vitro colonic motility assay as a biomarker for gastrointestinal adverse drug reactions.
2010 Jun 15
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 Mon Mar 31 17:49:17 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:17 GMT 2025
Record UNII
8Y164V895Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBASTAT
Preferred Name English
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
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 Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
WHO-ATC S01EB02
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
WHO-ATC N07AB01
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
NDF-RT N0000175884
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
WHO-VATC QS01EB02
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
WHO-VATC QA03AB92
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
Code System Code Type Description
PUBCHEM
5831
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
NCI_THESAURUS
C47430
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
DRUG BANK
DB00411
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
NSC
32865
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
DAILYMED
8Y164V895Y
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
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
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY Merck Index
MESH
D002217
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL965
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID9022730
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
CHEBI
3385
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
CAS
51-83-2
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
HSDB
6373
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
RS_ITEM_NUM
1092009
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
RXCUI
1999
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY RxNorm
INN
383
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
FDA UNII
8Y164V895Y
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
LACTMED
Carbachol
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
SMS_ID
100000081628
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-127-3
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
PRIMARY
WIKIPEDIA
Carbachol
Created by admin on Mon Mar 31 17:49:17 GMT 2025 , Edited by admin on Mon Mar 31 17:49:17 GMT 2025
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