Compound Detail

CHEMBL550

PILOCARPINE

💊 Approved Drug

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💊 Approved Drug

CC[C@@H]1C(=O)OC[C@@H]1Cc1cncn1C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL550
Name	PILOCARPINE
Phase	Approved
Structure Type	MOL
InChI Key	QCHFTSOMWOSFHM-WPRPVWTQSA-N
Therapeutic	✓ Yes

Known Names

Ocucarpine Ocusert pilo Ocusert pilo-20 Ocusert pilo-40 Pilocarpine Pilocarpinum Pilocarpol Pilokarpin Spersacarpine Syncarpine

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

208.3

MW (Da)

1.16

ALogP

HBA

HBD

44.1

PSA (Å²)

0.70

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1974
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Topical

Flags

Natural Product

USAN Stem

-pine

Extended Properties

Molecular Formula	C11H16N2O2
MW	208.26
Aromatic Rings	1
Heavy Atoms	15
NP-Likeness	1.25

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Muscarinic acetylcholine receptor M3 agonist	AGONIST	Muscarinic acetylcholine receptor M3	✓	✓
Muscarinic acetylcholine receptor M1 agonist	AGONIST	Muscarinic acetylcholine receptor M1	✓	✓

Indications

Glaucoma Glaucoma, Angle-Closure Glaucoma, Open-Angle Miosis Ocular Hypertension Sjogren's Syndrome Xerostomia Presbyopia Dry Eye Syndromes Urinary Incontinence Myopia

ATC Classification

N07AX01

pilocarpine

Level 1: NERVOUS SYSTEM

Level 2: OTHER NERVOUS SYSTEM DRUGS

S01EB01

pilocarpine

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

S01EB51

pilocarpine, combinations

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

Activity Summary

Ki 15 meas. best 7.58

EC50 10 meas. best 7.76

IC50 9 meas. best 7.17

Kd 5 meas. best 5.57

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Muscarinic acetylcholine receptor M1 CHEMBL216	EC50	7.76	6.2475	17.5	4
Unchecked CHEMBL612545	Ki	7.58	7.58	26.0	1
Muscarinic acetylcholine receptor CHEMBL1907609	IC50	7.17	6.1275	68.0	4
Unchecked CHEMBL612545	IC50	7.17	6.145	67.0	2
Muscarinic acetylcholine receptor CHEMBL1907609	Ki	7.08	6.1175	82.9	4
Muscarinic acetylcholine receptor M5 CHEMBL2035	EC50	6.2	6.2	631.0	1
Muscarinic acetylcholine receptor M1 CHEMBL276	IC50	6.02	5.685	960.0	2
Muscarinic acetylcholine receptor M2 CHEMBL211	EC50	6.0	5.1	1000.0	2
Cytochrome P450 2A13 CHEMBL3542436	Ki	5.85	5.85	1400.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	EC50	5.84	5.84	1445.4	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Kd	5.57	5.57	2691.5	2
Muscarinic acetylcholine receptor DM1 CHEMBL2366467	Ki	5.55	5.54	2800.0	2
Cytochrome P450 2A6 CHEMBL5282	Ki	5.52	5.52	3000.0	1
Cytochrome P450 2A13 CHEMBL3542436	Kd	5.52	5.52	3000.0	1
Muscarinic acetylcholine receptor M1 CHEMBL276	Ki	5.51	5.51	3100.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	EC50	5.48	5.48	3311.3	1
Cytochrome P450 2A6 CHEMBL5282	Kd	5.44	5.44	3600.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	5.18	5.14	6606.9	2
Muscarinic acetylcholine receptor M1 CHEMBL3733	EC50	5.16	5.16	6900.0	1
Muscarinic acetylcholine receptor M2 CHEMBL309	IC50	5.06	5.06	8800.0	1
Muscarinic acetylcholine receptor M2 CHEMBL309	Ki	5.01	5.01	9800.0	1
Muscarinic acetylcholine receptor M2 CHEMBL309	Kd	5.0	5.0	10000.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	4.99	4.99	10232.9	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	4.92	4.92	12022.6	1

Pharmacokinetic Data

Parameter	Value	Units	Species
KA	1.8	uM	Cavia porcellus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Muscarinic acetylcholine receptor M1	EC50	=	17.5	nM	7.76	Agonist activity at human m1 muscarinic acetylcholine receptor expressed in HEK2...	25765911
Unchecked	Ki	=	26.0	nM	7.58	Binding affinity against muscarinic acetylcholine receptor from rat brain crude ...	7739014
Unchecked	IC50	=	67.0	nM	7.17	In vitro inhibition of [3H]Oxo-Mas binding to M1 and M4 receptors in rat brain h...	9784113
Muscarinic acetylcholine receptor	IC50	=	68.0	nM	7.17	Binding affinity against muscarinic receptor in rat brain membranes using oxotre...	9873644
Muscarinic acetylcholine receptor	IC50	=	80.0	nM	7.1	Ability to displace [3H]cis--2-methyl-5-((dimethylamino)methyl)-1,3-di oxolane f...	1732522
Muscarinic acetylcholine receptor	Ki	=	82.9	nM	7.08	Inhibition of [3H]OXO-M binding against muscarinic acetylcholine receptor in rat...	1956033
Muscarinic acetylcholine receptor M5	EC50	=	630.96	nM	6.2	Partial agonist activity at N-terminal FLAG tagged/C-terminal NanoLuc tagged hum...	37042802
Muscarinic acetylcholine receptor M1	EC50	=	812.83	nM	6.09	Partial agonist activity at N-terminal FLAG tagged/C-terminal NanoLuc tagged hum...	37042802
Muscarinic acetylcholine receptor M1	EC50	=	831.76	nM	6.08	Partial agonist activity at human muscarinic M1 acetylcholine receptor expressed...	25478907
Muscarinic acetylcholine receptor M1	IC50	=	960.0	nM	6.02	Ability to displace [3H]pirenzepine (pir) from muscarinic acetylcholine receptor...	1732522
Muscarinic acetylcholine receptor	Ki	=	1010.0	nM	6.0	Inhibition of [3H]QNB binding against muscarinic acetylcholine receptor in rat b...	1956033
Muscarinic acetylcholine receptor M2	EC50	=	1000.0	nM	6.0	Partial agonist activity at C-terminal NanoLuc tagged human muscarinic M2 recept...	37042802
Muscarinic acetylcholine receptor	Ki	=	1110.0	nM	5.96	The compound was tested for inhibition of [3H]NMS binding against muscarinic ace...	1956033
Cytochrome P450 2A13	Ki	=	1400.0	nM	5.85	Competitive inhibition of CYP2A13 (unknown origin)	22696418
Muscarinic acetylcholine receptor M3	EC50	=	1445.44	nM	5.84	Partial agonist activity at C-terminal NanoLuc tagged human muscarinic M3 recept...	37042802
Muscarinic acetylcholine receptor M1	Kd	=	2691.53	nM	5.57	Displacement of [3H]NMS from human muscarinic M1 acetylcholine receptor expresse...	25478907
Muscarinic acetylcholine receptor M1	Kd	=	2691.53	nM	5.57	Binding affinity to muscarinic M1 acetylcholine receptor (unknown origin)	25478907
Muscarinic acetylcholine receptor DM1	Ki	=	2800.0	nM	5.55	Displacement of [3H]AF-DX 384 from Drosophila melanogaster mAChR by scintillatio...	17319687
Muscarinic acetylcholine receptor DM1	Ki	=	2980.0	nM	5.53	Displacement of [3H]QNB from Drosophila melanogaster mAChR by scintillation coun...	17319687
Cytochrome P450 2A13	Kd	=	3000.0	nM	5.52	Binding affinity to CYP2A13 (unknown origin) assessed as type 2 interaction as i...	22696418

Literature References

PubMed	DOI	Target Context	# Activities
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
17319687	10.1021/jf0631934	Musca domestica	10
25478907	10.1021/jm500860w	Muscarinic acetylcholine receptor M1	7
1732522	10.1021/jm00079a002	Muscarinic acetylcholine receptor M1	4
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2A	3
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M1	3
37468498	10.1038/s41467-023-40064-9	Histamine H1 receptor	3
1732546	10.1021/jm00080a014	Muscarinic acetylcholine receptor	3
1732522	10.1021/jm00079a002	Muscarinic acetylcholine receptor	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	3
9873644	10.1016/s0960-894x(98)00509-5	Muscarinic acetylcholine receptor M1	3
2319559	10.1021/jm00166a008	Muscarinic acetylcholine receptor	3
7739014	10.1021/jm00009a016	Muscarinic acetylcholine receptor	3
1956033	10.1021/jm00115a003	Muscarinic acetylcholine receptor	3
2213823	10.1021/jm00172a003	Muscarinic acetylcholine receptor	3
9784113	10.1021/jm981048e	Mus musculus	3
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	3

Data from ChEMBL 36 via Core Engine