CARBACHOL

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 Search

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	ClH
Molecular Weight	36.461
Charge	0
Count

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

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

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 160 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 2662
Acetylcholinesterase 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19006330 \| https://www.ncbi.nlm.nih.gov/pubmed/18602908	Substrate 656		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 8360	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

Avoidance learning: long-lasting deficits after temporal lobe seizure.	1969 Dec 12	5350349
[Tremor following intracerebral carbachol injection. 1.Carbachol sensitivity of various brain structures].	1975	1189819
Motor disturbances produced by intrastriatal injection of cyclic AMP and cyclic GMP.	1976 Nov	189712
Muscarine- and carbachol-induced aggressions: fear and irritable kinds of aggressions.	1977 Dec 28	414283
[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
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	6499920
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
Interactions between limbic, thalamo-striatal-cortical, and central autonomic pathways during epileptic seizure progression.	1999 Aug 16	10404113
Myoclonic and tonic seizures elicited by microinjection of cholinergic drugs into the inferior colliculus.	1999 Sep-Oct	10667095
Chick optic lobe contains a developmentally regulated alpha2alpha5beta2 nicotinic receptor subtype.	2000 Aug	10908297
The role of endogenous human Trp4 in regulating carbachol-induced calcium oscillations in HEK-293 cells.	2002 Apr 19	11830588
The relationship between hippocampal acetylcholine release and cholinergic convulsant sensitivity in withdrawal seizure-prone and withdrawal seizure-resistant selected mouse lines.	2002 Aug	12198388
Design, pharmacokinetic, and pharmacodynamic evaluation of soft anticholinergics based on tropyl alpha-phenylcyclopentylacetate.	2002 Feb	11878186
Impaired parasympathetic heart rate control in mice with a reduction of functional G protein betagamma-subunits.	2002 Feb	11788391
Physiological antagonism between ventricular beta 1-adrenoceptors and alpha 1-adrenoceptors but no evidence for beta 2- and beta 3-adrenoceptor function in murine heart.	2002 May	12010770
Zebrafish M2 muscarinic acetylcholine receptor: cloning, pharmacological characterization, expression patterns and roles in embryonic bradycardia.	2002 Nov	12411408
Type 5 adenylyl cyclase disruption alters not only sympathetic but also parasympathetic and calcium-mediated cardiac regulation.	2003 Aug 22	12869393
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	14645658
Ameliorative effect of NC-1900, a new AVP4-9 analog, through vasopressin V1A receptor on scopolamine-induced impairments of spatial memory in the eight-arm radial maze.	2003 Mar	12646291
Design, pharmacokinetic, and pharmacodynamic evaluation of a new class of soft anticholinergics.	2003 Oct	14620526
Crucial role of histamine for regulation of gastric acid secretion ascertained by histidine decarboxylase-knockout mice.	2003 Oct	12893847
TNF-alpha hyperpolarizes membrane potential and potentiates the response to nicotinic receptor stimulation in cultured rat myenteric neurones.	2004 May	15086448
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
Endogenous RGS proteins modulate SA and AV nodal functions in isolated heart: implications for sick sinus syndrome and AV block.	2007 May	17277016
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
Enhanced proliferation of SNU-407 human colon cancer cells by muscarinic acetylcholine receptors.	2008 Nov 30	19017493
The cholinomimetic agent carbachol induces headache in healthy subjects.	2009 Feb	19143771
Carbachol induces headache, but not migraine-like attacks, in patients with migraine without aura.	2010 Mar	19614687
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 `Wed Jul 05 22:42:36 UTC 2023` Edited by `admin` on `Wed Jul 05 22:42:36 UTC 2023`
Record UNII	8Y164V895Y
Record Status	`Validated (UNII)`
Record Version

Download

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 [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