Compound Detail

CHEMBL14

CARBACHOL

💊 Approved Drug

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💊 Approved Drug

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

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL14
Name	CARBACHOL
Phase	Approved
Structure Type	MOL
InChI Key	AIXAANGOTKPUOY-UHFFFAOYSA-N
Therapeutic	✓ Yes
Parent Compound	CHEMBL965
Active Moiety	CHEMBL965

Known Names

Carbachol Carbachol chloride Carbacol Carbastat Doryl Miostat NSC-32865

Targets

281

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

147.2

MW (Da)

-0.21

ALogP

HBA

HBD

52.3

PSA (Å²)

0.56

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1972
Availability	Prescription
Chirality	Achiral

Routes of Administration

Parenteral

Flags

Natural Product

Extended Properties

Molecular Formula	C6H15ClN2O2
MW	182.65
Aromatic Rings	0
Heavy Atoms	10
NP-Likeness	1.00

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Muscarinic acetylcholine receptor M3 agonist	AGONIST	Muscarinic acetylcholine receptor M3	✓	✓

Indications

Cataract Glaucoma Miosis Presbyopia

ATC Classification

N07AB01

carbachol

Level 1: NERVOUS SYSTEM

Level 2: OTHER NERVOUS SYSTEM DRUGS

S01EB02

carbachol

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

Activity Summary

Ki 124 meas. best 8.89

EC50 94 meas. best 9.96

IC50 56 meas. best 9.4

Kd 7 meas. best 4.85

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cavia porcellus CHEMBL369	EC50	9.96	7.3444	0.1	9
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	9.4	6.96	0.4	4
Muscarinic acetylcholine receptor CHEMBL1907609	Ki	8.89	6.5631	1.3	16
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	8.42	6.7471	3.8	7
Muscarinic acetylcholine receptor M2 CHEMBL309	Ki	8.4	6.76	4.0	4
Muscarinic acetylcholine receptor M3 CHEMBL320	EC50	8.37	6.9862	4.3	21
Muscarinic acetylcholine receptor CHEMBL1907609	IC50	8.17	6.3362	6.7	13
Acetylcholinesterase CHEMBL3198	Ki	8.1	6.14	8.0	2
Muscarinic acetylcholine receptor M2 CHEMBL3197	Ki	8.1	6.14	8.0	2
Muscarinic acetylcholine receptor M1 CHEMBL3733	Ki	7.7	7.0867	19.9	3
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	7.7	6.4254	20.0	13
Muscarinic acetylcholine receptor M3 CHEMBL245	EC50	7.68	6.3655	21.0	11
Muscarinic acetylcholine receptor M1 CHEMBL276	IC50	7.64	5.695	23.0	4
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	7.62	5.7	24.0	11
Muscarinic acetylcholine receptor M1 CHEMBL276	Ki	7.51	6.35	31.0	5
Muscarinic acetylcholine receptor M2 CHEMBL309	IC50	7.47	6.1475	34.0	4
Muscarinic acetylcholine receptor M4 CHEMBL1821	EC50	7.35	6.0467	44.7	6
Unchecked CHEMBL612545	EC50	7.2	6.3967	63.0	3
Muscarinic acetylcholine receptor M2 CHEMBL211	EC50	7.13	6.2343	74.0	7
A9 CHEMBL614518	IC50	7.0	7.0	100.0	1
Muscarinic acetylcholine receptor CHEMBL2094109	EC50	7.0	6.7233	100.0	3
Muscarinic acetylcholine receptor M3 CHEMBL5498	EC50	6.92	6.92	120.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	6.77	4.8842	170.0	12
Muscarinic acetylcholine receptors; M2 & M3 CHEMBL2095187	EC50	6.72	6.72	190.0	1
Neuronal acetylcholine receptor; alpha2/beta2 CHEMBL1907592	Ki	6.68	6.68	210.0	1
Muscarinic acetylcholine receptor M4 CHEMBL317	IC50	6.64	6.64	230.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	EC50	6.6	5.2846	250.0	13
Aorta CHEMBL613606	EC50	6.52	6.4	300.0	3
Unchecked CHEMBL612545	Ki	6.48	5.77	334.0	3
Muscarinic acetylcholine receptor M5 CHEMBL2035	EC50	6.44	5.648	360.0	5
Neuronal acetylcholine receptor CHEMBL2094110	Ki	6.35	6.35	450.0	1
Oryctolagus cuniculus CHEMBL374	IC50	6.34	6.34	460.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	6.34	5.5767	457.1	3
Cavia porcellus CHEMBL369	IC50	6.3	6.3	500.0	1
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907596	Ki	6.23	6.23	590.0	1
Unchecked CHEMBL612545	IC50	6.19	5.106	647.0	5
Muscarinic acetylcholine receptor M1 CHEMBL276	EC50	6.19	6.19	650.0	1
Muscarinic acetylcholine receptor M3 CHEMBL320	Ki	6.16	5.4045	700.0	20
Aorta CHEMBL613606	IC50	6.1	6.1	790.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	6.06	5.55	880.0	2
Muscarinic acetylcholine receptor M1/M5 chimeric protein CHEMBL2111417	EC50	6.0	5.0333	1000.0	3
Neuronal acetylcholine receptor; alpha3/beta2 CHEMBL1907587	Ki	5.96	5.96	1100.0	1
Neuronal acetylcholine receptor; alpha4/beta4 CHEMBL1907595	Ki	5.89	5.89	1300.0	1
Muscarinic acetylcholine receptor M4 CHEMBL317	Ki	5.58	5.58	2600.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	5.37	4.5489	4265.8	9
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907593	Ki	5.32	5.32	4800.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	5.2	4.5767	6309.6	9
Acetylcholine receptor subunit alpha CHEMBL3097	IC50	5.12	5.12	7640.0	2
Muscarinic acetylcholine receptor M3 CHEMBL5105	EC50	5.0	5.0	9900.0	1
Muscarinic acetylcholine receptor M1/M5 chimeric protein CHEMBL2111417	Ki	4.9	4.6	12589.2	3

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cavia porcellus	EC50	=	0.11	nM	9.96	Concentration that elicits 50% of its own maximum contractile response in guinea...	3346881
Muscarinic acetylcholine receptor M4	IC50	=	0.4	nM	9.4	Compound was evaluated for its binding affinity at human muscarinic receptor m4 ...	9873472
Cavia porcellus	EC50	=	0.9	nM	9.05	Concentration that elicits 50% of its own maximum contractile response in guinea...	3346881
Muscarinic acetylcholine receptor	Ki	=	1.3	nM	8.89	In vitro binding affinity for muscarinic receptor by displacing [3H]oxotremorine...	7990109
Muscarinic acetylcholine receptor M2	IC50	=	3.8	nM	8.42	Compound was evaluated for its binding affinity at human muscarinic receptor m2 ...	9873472
Muscarinic acetylcholine receptor	Ki	=	4.0	nM	8.4	Binding activity to the muscarinic acetylcholine receptor in rat cortex, assayed...	2258905
Muscarinic acetylcholine receptor M2	Ki	=	4.0	nM	8.4	Binding affinity at [3H]CD radiolabeled muscarinic M2 receptor in rat cortex.	8246221
Muscarinic acetylcholine receptor M3	EC50	=	4.3	nM	8.37	Agonist activity at rat M3'(3C)-Xa receptor F92C/F550C mutant expressed in afric...	17623649
Muscarinic acetylcholine receptor	IC50	=	6.7	nM	8.17	Binding affinity towards muscarinic receptor using [3H]cis-methyldioxolane (CMD)...	-
Muscarinic acetylcholine receptor	IC50	=	6.7	nM	8.17	Compound was evaluated for inhibition of [3H]cis-methyldioxolane binding to labe...	-
Muscarinic acetylcholine receptor	IC50	=	6.7	nM	8.17	Binding affinity against muscarinic receptor using radioligand [3H]cis-methyldio...	-
Muscarinic acetylcholine receptor	IC50	=	6.7	nM	8.17	Stimulations of inositol phosphate(PI) accumulation in transfected CHO cells in ...	9651157
Muscarinic acetylcholine receptor M2	Ki	=	8.0	nM	8.1	Ability to displace [3H]oxotremorine ([3H]OXO-M) from mouse cerebral cortex	1507203
Acetylcholinesterase	Ki	=	8.0	nM	8.1	Compound was evaluated for the binding affinity by displacing [3H]oxotremorine f...	1552502
Muscarinic acetylcholine receptor	Ki	=	9.0	nM	8.05	Binding affinity against Muscarinic acetylcholine receptor using [3H]-OXO-M as t...	9784090
Muscarinic acetylcholine receptor	Ki	=	12.0	nM	7.92	The binding affinity was measured as inhibition of binding of [3H]- oxotremorine...	10891110
Muscarinic acetylcholine receptor M2	IC50	=	12.59	nM	7.9	Inhibitory activity was evaluated against Muscarinic acetylcholine receptor M2 e...	13678406
Muscarinic acetylcholine receptor	Ki	=	13.11	nM	7.88	Inhibition of [3H]- Oxo-M binding to muscarinic acetylcholine receptor of rat he...	1613746
Muscarinic acetylcholine receptor	Ki	=	13.1	nM	7.88	Inhibition of [3H]OXO-M binding against muscarinic acetylcholine receptor in rat...	1956033
Muscarinic acetylcholine receptor	IC50	=	16.5	nM	7.78	Ability to displace [3H]cis--2-methyl-5-((dimethylamino)methyl)-1,3-di oxolane f...	1732522

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	436
17623649	10.1074/jbc.m704875200	Muscarinic acetylcholine receptor M3	72
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
9111297	10.1021/jm960467d	Muscarinic acetylcholine receptor M1	8
3346881	10.1021/jm00398a031	Cavia porcellus	8
9622546	10.1021/jm9705115	Muscarinic acetylcholine receptor M1	7
9622546	10.1021/jm9705115	Muscarinic acetylcholine receptor M2	6
18543900	10.1021/jm800145d	Unchecked	6
9111297	10.1021/jm960467d	Muscarinic acetylcholine receptor M2	6
11741475	10.1021/jm0102405	Muscarinic acetylcholine receptor M1	6
17149881	10.1021/jm0606995	Muscarinic acetylcholine receptor M1/M5 chimeric protein	6
9111297	10.1021/jm960467d	Muscarinic acetylcholine receptor M3	6
15050613	10.1016/j.bmcl.2003.09.105	Unchecked	5
16539379	10.1021/jm0510878	Muscarinic acetylcholine receptor M2	5
8246221	10.1021/jm00075a007	Muscarinic acetylcholine receptor M2	5
10891110	10.1021/jm9904001	Muscarinic acetylcholine receptor	5
17149881	10.1021/jm0606995	Muscarinic acetylcholine receptor M1	5
2258905	10.1021/jm00174a015	Muscarinic acetylcholine receptor	5
18077164	10.1016/j.bmcl.2007.11.073	Unchecked	5
17084634	10.1016/j.bmc.2006.10.040	Muscarinic acetylcholine receptor M3	5

Data from ChEMBL 36 via Core Engine