Details of the Drug

General Information of Drug (ID: DMV9ADG)

Drug Name

Pilocarpine

Synonyms

Adsorbocarpine; Almocarpine; Epicar; Isopilocarpine; Isoptocarpine; Miocarpine; Ocusert; Pilagan; Pilocarpin; Pilocarpol; Pilokarpin; Pilokarpol; Pilostat; Salagen; Spersacarpine; Syncarpine; Amistura P; Isopto carpine; Minims Pilocarpine; Ocusert pilo; Pilocarpine HCl; Pilocarpine chloride; Pilocarpine nitrate; Ocusert P 20;Beta-Pilocarpine hydrochloride; Diocarpine (TN); Isopto Carpine (TN); Mi-Pilo; Miocarpine (TN); Ocu-Carpine; Ocusert Pilo-40; Ocusert pilo-20; Pilocarpine (TN); Pilopine HS (TN); Piloptic-1; Piloptic-2; Piloptic-3; Piloptic-4; Piloptic-6; Salagen (TN); Scheinpharm (TN); Timpilo (TN); Ocusert Pilo-20 (TN); Ocusert pilo-20 (TN); P.V. Carpine Liquifilm; Pilocarpine (JAN/USP); Pilocarpine [USAN:BAN:JAN]; Piloptic-1/2; Pilocarpine Mononitrate, (3S-cis)-Isomer; Pilocarpine, Monohydrochloride, (3S-cis)-Isomer; Imidazole-5-butyric acid, alpha-ethyl-beta-(hydroxymethyl)-1-methyl-, gamma-lactone; (+)-Pilocarpine; (3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydrofuran-2(3H)-one; (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one; (3S,4R)-3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone; (3S-cis)-3-Ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone; (3S-cis)-3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone; 3-Ethyl-4-(3-methyl-3H-imidazol-4-ylmethyl)dihydrofuran-2-one; 3-Ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydro-2(3H)-furanone; 3-Ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydrofuran-2(3H)-one; 3-ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)dihydro-2(3H)-furanone; 3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one

Indication

Disease Entry	ICD 11	Status	REF
Glaucoma/ocular hypertension	9C61	Approved	[1], [2]

Therapeutic Class

Cholinergic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

208.26

Topological Polar Surface Area (xlogp)

1.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Half-life: The concentration or amount of drug in body reduced by one-half in 0.76 hours [3]
Metabolism: The drug is metabolized via plasma [4]

Chemical Identifiers

Formula: C11H16N2O2
IUPAC Name: (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one
Canonical SMILES: CC[C@H]1[C@H](COC1=O)CC2=CN=CN2C
InChI: 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
InChIKey: QCHFTSOMWOSFHM-WPRPVWTQSA-N

Cross-matching ID

PubChem CID: 5910
ChEBI ID: CHEBI:8207
CAS Number: 92-13-7
DrugBank ID: DB01085
TTD ID: D06HLY
VARIDT ID: DR00888
INTEDE ID: DR1285
ACDINA ID: D00530

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Muscarinic acetylcholine receptor M5 (CHRM5)	TTH18TF	ACM5_HUMAN	Agonist	[5], [6]

------------------------------------------------------------------------------------

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[7]
Cytochrome P450 2A6 (CYP2A6)	DEJVYAZ	CP2A6_HUMAN	Substrate	[8]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Pilocarpine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Mepyramine	DMB4SFH	Moderate	Antagonize the effect of Pilocarpine when combined with Mepyramine.	Allergic/hypersensitivity disorder [4A80-4A8Z]	[35]
Phenyltoloxamine	DMKAEQW	Moderate	Antagonize the effect of Pilocarpine when combined with Phenyltoloxamine.	Allergic/hypersensitivity disorder [4A80-4A8Z]	[35]
Desipramine	DMT2FDC	Moderate	Antagonize the effect of Pilocarpine when combined with Desipramine.	Attention deficit hyperactivity disorder [6A05]	[35]
Umeclidinium	DM4E8O9	Moderate	Antagonize the effect of Pilocarpine when combined with Umeclidinium.	Chronic obstructive pulmonary disease [CA22]	[36]
Tiotropium	DMFDC0Q	Moderate	Antagonize the effect of Pilocarpine when combined with Tiotropium.	Chronic obstructive pulmonary disease [CA22]	[36]
Revefenacin	DMMP5SI	Moderate	Antagonize the effect of Pilocarpine when combined with Revefenacin.	Chronic obstructive pulmonary disease [CA22]	[36]
OPC-34712	DMHG57U	Moderate	Antagonize the effect of Pilocarpine when combined with OPC-34712.	Depression [6A70-6A7Z]	[35]
Clomipramine	DMINRKW	Moderate	Antagonize the effect of Pilocarpine when combined with Clomipramine.	Depression [6A70-6A7Z]	[35]
Doxepin	DMPI98T	Moderate	Antagonize the effect of Pilocarpine when combined with Doxepin.	Depression [6A70-6A7Z]	[35]
Mepenzolate	DM8YU2F	Moderate	Antagonize the effect of Pilocarpine when combined with Mepenzolate.	Digestive system disease [DE2Z]	[36]
Solifenacin	DMG592Q	Moderate	Antagonize the effect of Pilocarpine when combined with Solifenacin.	Functional bladder disorder [GC50]	[36]
Belladonna	DM2RBWK	Moderate	Antagonize the effect of Pilocarpine when combined with Belladonna.	Infectious gastroenteritis/colitis [1A40]	[36]
ITI-007	DMUQ1DO	Moderate	Antagonize the effect of Pilocarpine when combined with ITI-007.	Insomnia [7A00-7A0Z]	[35]
Siponimod	DM2R86O	Major	Increased risk of atrioventricular block by the combination of Pilocarpine and Siponimod.	Multiple sclerosis [8A40]	[37]
Fingolimod	DM5JVAN	Moderate	Increased risk of atrioventricular block by the combination of Pilocarpine and Fingolimod.	Multiple sclerosis [8A40]	[38]
Ozanimod	DMT6AM2	Moderate	Increased risk of bradycardia by the combination of Pilocarpine and Ozanimod.	Multiple sclerosis [8A40]	[39]
Phenindamine	DMDTC7R	Moderate	Antagonize the effect of Pilocarpine when combined with Phenindamine.	Nasopharyngitis [CA00]	[35]
Cyclizine	DM9G7BS	Moderate	Antagonize the effect of Pilocarpine when combined with Cyclizine.	Nausea/vomiting [MD90]	[36]
Flavoxate	DMKV4NL	Moderate	Antagonize the effect of Pilocarpine when combined with Flavoxate.	Pain [MG30-MG3Z]	[36]
Orphenadrine	DMW542E	Moderate	Antagonize the effect of Pilocarpine when combined with Orphenadrine.	Parkinsonism [8A00]	[35]
Methylscopolamine	DM5VWOB	Moderate	Antagonize the effect of Pilocarpine when combined with Methylscopolamine.	Peptic ulcer [DA61]	[36]
Levomepromazine	DMIKFEL	Moderate	Antagonize the effect of Pilocarpine when combined with Levomepromazine.	Psychotic disorder [6A20-6A25]	[35]
Quetiapine	DM1N62C	Moderate	Antagonize the effect of Pilocarpine when combined with Quetiapine.	Schizophrenia [6A20]	[35]
Aripiprazole	DM3NUMH	Moderate	Antagonize the effect of Pilocarpine when combined with Aripiprazole.	Schizophrenia [6A20]	[35]
Molindone	DMAH70G	Moderate	Antagonize the effect of Pilocarpine when combined with Molindone.	Schizophrenia [6A20]	[35]
Thiothixene	DMDINC4	Moderate	Antagonize the effect of Pilocarpine when combined with Thiothixene.	Schizophrenia [6A20]	[35]
Pimozide	DMW83TP	Moderate	Antagonize the effect of Pilocarpine when combined with Pimozide.	Schizophrenia [6A20]	[35]
Chlorpheniramine	DM5URA2	Moderate	Antagonize the effect of Pilocarpine when combined with Chlorpheniramine.	Vasomotor/allergic rhinitis [CA08]	[35]
Trimeprazine	DMEMV9D	Moderate	Antagonize the effect of Pilocarpine when combined with Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[35]
Acrivastine	DMTIGA0	Moderate	Antagonize the effect of Pilocarpine when combined with Acrivastine.	Vasomotor/allergic rhinitis [CA08]	[35]
-----------


⏷ Show the Full List of 30 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
FD&C blue no. 2	E00446	2723854	Colorant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
--------------------


⏷ Show the Full List of 8 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Pilocarpine 5 mg tablet	5 mg	Oral Tablet	Oral
Pilocarpine 7.5 mg tablet	7.5 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 305).
2	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 020619.
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
5	Retinoic acid prevents virus-induced airway hyperreactivity and M2 receptor dysfunction via anti-inflammatory and antiviral effects. Am J Physiol Lung Cell Mol Physiol. 2009 Aug;297(2):L340-6.
6	Muscarinic activation attenuates abnormal processing of beta-amyloid precursor protein induced by cobalt chloride-mimetic hypoxia in retinal gangli... Biochem Biophys Res Commun. 2009 Jun 19;384(1):110-3.
7	The inhibition of CYP enzymes in mouse and human liver by pilocarpine. Br J Pharmacol. 1995 Feb;114(4):832-6.
8	Structural comparison of cytochromes P450 2A6, 2A13, and 2E1 with pilocarpine. FEBS J. 2012 May;279(9):1621-31.
9	Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
10	Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
11	Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
12	Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
13	Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
14	Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
15	Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
16	The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
17	Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
18	Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63.
19	Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
20	Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9.
21	Psychotropic drug interactions with valproate. Clin Neuropharmacol. 2005 Mar-Apr;28(2):96-101.
22	The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94.
23	Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
24	CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine delta-5'(1')iminium ion. J Pharmacol Exp Ther. 2012 Nov;343(2):307-15.
25	Muscarinic cholinergic and histamine H1 receptor binding of phenothiazine drug metabolites. Life Sci. 1988;43(5):405-12.
26	Design, synthesis, and neurochemical evaluation of 5-(3-alkyl-1,2,4- oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidines as M1 muscarinic receptor agonists. J Med Chem. 1993 Apr 2;36(7):842-7.
27	Medicinal plants in therapy. Bull World Health Organ. 1985;63(6):965-81.
28	Additive protective effects of donepezil and nicotine against salsolinol-induced cytotoxicity in SH-SY5Y cells. Neurotox Res. 2009 Oct;16(3):194-204.
29	Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8.
30	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7354).
31	Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
32	Comparison of pharmacological effects of L- and DL-n-butyl-scopolamine in rat uterus. Yao Xue Xue Bao. 1994;29(1):24-7.
33	Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34.
34	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 467).
35	Multum Information Services, Inc. Expert Review Panel.
36	Benjamin KW "Toxicity of ocular medications." Int Ophthalmol Clin 19 (1979): 199-255. [PMID: 376469]
37	Cerner Multum, Inc. "Australian Product Information.".
38	Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
39	Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.