CARBACHOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H15N2O2.Cl
Molecular Weight	182.6487
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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	147.1957
Charge	1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.4609
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/016968s029lbl.pdf

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

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor 153 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26535008 \| https://www.ncbi.nlm.nih.gov/pubmed/8401322 \| https://www.ncbi.nlm.nih.gov/pubmed/16879496 \| https://www.ncbi.nlm.nih.gov/pubmed/3689439	Agonist 2451
Acetylcholinesterase 196 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19006330 \| https://www.ncbi.nlm.nih.gov/pubmed/18602908	Substrate 608		6.0 mM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Elevated intraocular pressure 9 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/016968s029lbl.pdf	Preventing		Approved 7968	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 8.6486401E10

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00DELC
A2B Chem	AG24640
AA Blocks	AA00DE1W
AAA Chemistry	AR-1C8722
ABI Chem	AC1L1DXK
ABI Chem	AC1Q65QH
AbovChem LLC	HY-B1208
Acros Organics	10824
Alfa Chemistry	L06674
Angene	AGN-PC-0JK7E6
ApexBio Technology	B7196
BLD Pharm	BD01104798	http://www.bldpharm.com/products/462-58-8.html
Boerchem	BC224240	http://www.boerchem.com/?product_37788.html
Cayman Chemical	14486
ChemMol	44007155	http://www.chemmol.com/chemmol/44007155.html
ChemMol	49425868	http://www.chemmol.com/chemmol/49425868.html
ChemMol	99086802	http://www.chemmol.com/chemmol/99086802.html
ChemTik	CTK1D5875
Chemieliva Pharmaceutical Co., Ltd	PBCM1311157
Chemodex	C0306
Chemspace	CSSS00160769827	https://chem-space.com/CSSS00160769827
Compound Cloud	2551
Compound Cloud	5831
Enamine	BBV-39898943
Enamine	EN300-122286
Fluorochem	358106
Fluorochem	393337
Hangzhou Yuhao Chemical Technology	HL1007
Lab Network	LN01343758
MolPort	MolPort-003-666-136
MolPort	MolPort-044-724-528
Molnova	M14811
NCI Plated 2007	32865
Norris Pharm	NSZB-A219779
NovoSeek	2551
Princeton BioMolecular Research	OSSL_751146
Ryan Scientific	L-Adrenaline
Sigma Aldrich	1092009\|USP
Sigma Aldrich	C2409
Sigma Aldrich	C4382
Sigma Aldrich	PHR1511\|SIAL
Sigma Aldrich	Y0000113\|SIAL
Smolecule	S570329	https://www.smolecule.com/products/s570329
TargetMol	T0105
Tetrahedron	TS15068
TimTec	SBB057998
TimTec	ST50993883
TimTec	ST51007309
Tocris	2810
Toronto Research Chemicals	C175970
Toronto Research Chemicals	H939590
Vitas-M Laboratory	STL371210
Yuhao Chemical	HL1007	http://www.chemyuhao.com/51-83-2.html
ZINC	ZINC000003079342	http://zinc15.docking.org/substances/ZINC000003079342
eMolecules	193736093
eMolecules	260329458
eMolecules	300019310
eMolecules	489054
mcule	MCULE-5642570831	https://mcule.com/MCULE-5642570831/

PubMed

Title	Date	PubMed
Sustained atrial fibrillation induced by carbachol, methacholine and bethanechol.	1971 Apr	4397202
Motor disturbances produced by intrastriatal injection of cyclic AMP and cyclic GMP.	1976 Nov	189712
Midbrain interaction with the hypothalamus in expression of aggressive behavior in cats.	1977	563160
Muscarine- and carbachol-induced aggressions: fear and irritable kinds of aggressions.	1977 Dec 28	414283
Evidence that a nigral gabaergic--cholinergic balance controls posture.	1979 Jan 1	569589
[Effects of atropine and scopolamine on the aggressive behavior and convulsions induced by carbachol and eserine injected into the cerebral ventricles of the cat].	1980	6446956
Seizures induced by carbachol, morphine, and leucine-enkephalin: a comparison.	1983 Apr	6301361
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.	1983 Jan	6130710
Drug-induced modulation of locomotor hyperactivity induced by picrotoxin in nucleus accumbens.	1984 Oct	6504948
Subclassification of muscarinic receptors in the heart, urinary bladder and sympathetic ganglia in the pithed rat. Selectivity of some classical agonists.	1985 Dec	4094621
A crucial epileptogenic site in the deep prepiriform cortex.	1985 Oct 17-23	4058572
Cholinergic induction of seizures in the rat prefrontal cortex.	1986 Jun 23	3724361
Neuropeptide Y and calcitonin gene-related peptide: effects on glucagon and insulin secretion in the mouse.	1987	3329090
Cardiovascular effects of cholinergic agents in the ventral-lateral midbrain periaqueductal gray of the rat.	1987 Dec	3437936
Novel 'soft' anticholinergic agents.	1988 Feb	3255315
The effect of cholinergic stimulation in the nucleus accumbens on locomotor behavior.	1988 Feb 16	3359231
Anatomical analysis of frontal cortex sites at which carbachol induces motor seizures in the rat.	1988 May	3174734
Renal function during onset of carbachol-induced hypertension in conscious rats.	1990	2148214
Catalepsy induced by carbachol microinjected into the pontine reticular formation of rats.	1990 Jul 31	2234502
Excitatory modulation by a spinal cholinergic system of a descending sympathoexcitatory pathway in rats.	1992 Mar	1630594
Sites at which neuropeptide Y modulates parasympathetic control of heart rate in guinea pigs and rats.	1992 May 1	1619211
Regeneration of cardiomyocytes from bone marrow: Use of mesenchymal stem cell for cardiovascular tissue engineering.	2003 Mar	19002953
Pharmacokinetic and pharmacodynamic evaluations of the zwitterionic metabolite of a new series of N-substituted soft anticholinergics.	2005 Dec	16170596
Actin and non-muscle myosin II facilitate apical exocytosis of tear proteins in rabbit lacrimal acinar epithelial cells.	2005 Oct 15	16219687
Theoretical and experimental investigation of calcium-contraction coupling in airway smooth muscle.	2006	17272850
Case report: acute unintentional carbachol intoxication.	2006	16740173
Muscarinic acetylcholine receptors mediate oligodendrocyte progenitor survival through Src-like tyrosine kinases and PI3K/Akt pathways.	2006 Apr	16439036
Roles of protein kinase C, Ca2+, Pyk2, and c-Src in agonist activation of rat lacrimal gland p42/p44 MAPK.	2006 Aug	16877402
Novelty exploration elicits a reversal of acute stress-induced modulation of hippocampal synaptic plasticity in the rat.	2006 Dec 1	17008368
Muscarinic cholinoceptor activation modulates DNA synthesis and CD40 expression in fibroblast cells.	2006 Jul	16879495
[Effects of carbachol on apoptosis of intestinal epithelial cells after gut ischemia/reperfusion in rat].	2007 Aug	17708838
Gene transfer of neuronal nitric oxide synthase into intracardiac Ganglia reverses vagal impairment in hypertensive rats.	2007 Feb	17210833
Testosterone and progesterone rapidly attenuate plasma membrane Gbetagamma-mediated signaling in Xenopus laevis oocytes by signaling through classical steroid receptors.	2007 Jan	17021048
Endogenous RGS proteins modulate SA and AV nodal functions in isolated heart: implications for sick sinus syndrome and AV block.	2007 May	17277016
Myosin light chain kinase-independent inhibition by ML-9 of murine TRPC6 channels expressed in HEK293 cells.	2007 Sep	17603544
A novel assay of Gi/o-linked G protein-coupled receptor coupling to potassium channels provides new insights into the pharmacology of the group III metabotropic glutamate receptors.	2008 Apr	18171729
Metabotropic receptor-activated calcium increases and store-operated calcium influx in mouse Müller cells.	2008 Jul	18316702
Monitoring the reaction of carbachol with acetylcholinesterase by thioflavin T fluorescence and acetylthiocholine hydrolysis.	2008 Sep 25	18602908
Histamine H1 receptor induces cytosolic calcium increase and aquaporin translocation in human salivary gland cells.	2009 Aug	19443731
Prediction of functionally selective allosteric interactions at an M3 muscarinic acetylcholine receptor mutant using Saccharomyces cerevisiae.	2010 Aug	20466821
Aggravation of seizure-associated microvascular injuries by ibuprofen may involve multiple pathways.	2010 Dec	21121909
Structural and functional effects of developmental exposure to ethanol on the zebrafish heart.	2010 Jun	20374213
The validation of an in vitro colonic motility assay as a biomarker for gastrointestinal adverse drug reactions.	2010 Jun 15	20350559
Carbachol induces headache, but not migraine-like attacks, in patients with migraine without aura.	2010 Mar	19614687
Zinc oxide nanoparticle disruption of store-operated calcium entry in a muscarinic receptor signaling pathway.	2010 Oct	20708676
Molecular basis of inhibition of substrate hydrolysis by a ligand bound to the peripheral site of acetylcholinesterase.	2010 Sep 6	20493829
Antispasmodic effects of eugenol on rat airway smooth muscle.	2011 Dec	21077946
TRPC5 channel sensitivities to antioxidants and hydroxylated stilbenes.	2011 Feb 18	21127073
Interaction of bispyridinium compounds with the orthosteric binding site of human α7 and Torpedo californica nicotinic acetylcholine receptors (nAChRs).	2011 Sep 25	21703337
Characterisation of acetylcholinesterase release from neuronal cells.	2013 Mar 25	23047022

Patents

Sample Use Guides

In Vivo Use Guide

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 Vitro Use Guide

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 Jun 25 20:52:11 UTC 2021` Edited by `admin` on `Fri Jun 25 20:52:11 UTC 2021`
Record UNII	8Y164V895Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARBACHOL

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 [MART.]

Common Name

English

NSC-32865

Code

English

CARBACHOL [EP]

Common Name

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 [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