SynCED: Pilocarpine

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:20 UTC

Update Date

2026-05-14 16:57:42 UTC

Accession Number

CHEM002341

Identification

Common Name

Pilocarpine

Class

Small Molecule

Description

Pilocarpine is only found in individuals that have used or taken this drug. It is a slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma. [PubChem]Pilocarpine is a cholinergic parasympathomimetic agent. It increase secretion by the exocrine glands, and produces contraction of the iris sphincter muscle and ciliary muscle (when given topically to the eyes) by mainly stimulating muscarinic receptors.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Cholinergic Agent
Drug
Ester
Ether
Metabolite
Miotic
Muscarinic Agonist
Organic Compound
PFAS
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3S,4R)-3-Ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone	ChEBI
(3S-cis)-3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone	ChEBI
Ocusert pilo-20	Kegg
Adsorbocarpine	HMDB
beta-Pilocarpine hydrochloride	HMDB
Pilocarpin	HMDB
Pilocarpine chloride	HMDB
Pilocarpine HCL	HMDB
Pilocarpine hydrochloride	HMDB
Pilocarpine monohydrochloride	HMDB
Pilocarpine muriate	HMDB
Pilokarpin	HMDB
Pilokarpin monohydrochloride	HMDB
Spersacarpine	HMDB
Spersacarpine hydrochloride	HMDB
Hydrochloride, pilocarpine	HMDB
Isopilocarpine	HMDB
Nitrate, pilocarpine	HMDB
Pilocarpine mononitrate, (3S-cis)-isomer	HMDB
Pilocarpine, monohydrochloride, (3S-cis)-isomer	HMDB
Salagen	HMDB
Ocusert	HMDB
Isoptocarpine	HMDB
Pilocarpine nitrate	HMDB
Pilocarpine	ChEBI

Chemical Formula

C₁₁H₁₆N₂O₂

Average Molecular Mass

208.257 g/mol

Monoisotopic Mass

208.121 g/mol

CAS Registry Number

54-71-7

IUPAC Name

(3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one

Traditional Name

pilocarpine

SMILES

CC[C@H]1[C@@H](CC2=CN=CN2C)COC1=O

InChI Identifier

InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1

InChI Key

QCHFTSOMWOSFHM-WPRPVWTQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Gamma butyrolactone
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pilocarpine (CHEBI:8207 )
Imidazole alkaloids (C07474 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	204-205°C
Boiling Point	Not Available
Solubility	1E+006 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	2.07 g/L	ALOGPS
logP	1.15	ALOGPS
logP	0.95	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	6.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.53 m³·mol⁻¹	ChemAxon
Polarizability	22.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Oral ; eye contact. There was a decrease in the rate of absorption of pilocarpine from SALAGEN Tablets when taken with a high fat meal by 12 healthy male volunteers

Mechanism of Toxicity

Pilocarpine is a cholinergic parasympathomimetic agent. It increase secretion by the exocrine glands, and produces contraction of the iris sphincter muscle and ciliary muscle (when given topically to the eyes) by mainly stimulating muscarinic receptors.

Metabolism

Possibly occurs at the neuronal synapses and in the plasma Half Life: 0.76 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of radiation-induced dry mouth (xerostomia) and symptoms of dry mouth in patients with Sjögrens syndrome.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Overdosage should be treated with atropine titration (0. 5 mg to 1. 0 mg given subcutaneously or intravenously) and supportive measures to maintain respiration and circulation. Epinephrine (0. 3 mg to 1. 0 mg, subcutaneously or intramuscularly) may also be of value in the presence of severe cardiovascular depression or bronchoconstriction. (2)

Concentrations

Not Available

External Links

DrugBank ID

DB01085

HMDB ID

HMDB0015217

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID