Details of the Drug

General Information of Drug (ID: DMG2X3E)

Drug Name

Pyrantel

Synonyms

PYRANTEL; Pyrequan; 15686-83-6; Strongid; Pirantele [DCIT]; Pyrantelum; Pirantel; Pyrantel [INN:BAN]; Pyrantelum [INN-Latin]; Pirantel [INN-Spanish]; UNII-4QIH0N49E7; HSDB 3252; EINECS 239-774-1; CHEBI:8654; 4QIH0N49E7; (E)-1-Methyl-2-(2-(thiophen-2-yl)vinyl)-1,4,5,6-tetrahydropyrimidine; E-1,4,5,6-Tetrahydro-1-methyl-2-(2-(2-thienyl)vinyl)pyrimidine; Pirantele; 1-methyl-2-[(E)-2-(2-thienyl)vinyl]-5,6-dihydro-4H-pyrimidine; Pyrimidine, 1,4,5,6-tetrahydro-1-methyl-2-(2-(2-thienyl)vinyl)-, (E)-; Pin-X

Indication

Disease Entry	ICD 11	Status	REF
Worm infection	1F90.Z	Approved	[1]
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Affected Organisms

Humans

ATC Code

P02CC01: Pyrantel

P02CC: Tetrahydropyrimidine derivatives

P02C: ANTINEMATODAL AGENTS

P02: ANTHELMINTICS

P: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

206.31

Logarithm of the Partition Coefficient (xlogp)

1.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Elimination: Approximately 50% of an oral dose is excreted unchanged in feces; 7% excreted in urine as unchanged drug and metabolites [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.75 +/- 0.19 hours [4]
Metabolism: The drug is metabolized via the liver [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 55.08 micromolar/kg/day [6]
Water Solubility: The ability of drug to dissolve in water is measured as 0.5 mg/mL [2]

Chemical Identifiers

Formula: C11H14N2S
IUPAC Name: 1-methyl-2-[(E)-2-thiophen-2-ylethenyl]-5,6-dihydro-4H-pyrimidine
Canonical SMILES: CN1CCCN=C1/C=C/C2=CC=CS2
InChI: InChI=1S/C11H14N2S/c1-13-8-3-7-12-11(13)6-5-10-4-2-9-14-10/h2,4-6,9H,3,7-8H2,1H3/b6-5+
InChIKey: YSAUAVHXTIETRK-AATRIKPKSA-N

Cross-matching ID

PubChem CID: 708857
ChEBI ID: CHEBI:8654
CAS Number: 15686-83-6
UNII: 4QIH0N49E7
DrugBank ID: DB11156
TTD ID: D03PTH
INTEDE ID: DR1371
ACDINA ID: D00569

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[7]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 1B1 (CYP1B1)	OTYXFLSD	CP1B1_HUMAN	Gene/Protein Processing	[8]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Gene/Protein Processing	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

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

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Calcium hydrogenphosphate	E00294	24441	Diluent
Carmellose sodium	E00625	Not Available	Disintegrant
Magnesium stearate	E00208	11177	lubricant
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Pyrantel 180 mg tablet	180 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	BDDCS applied to over 900 drugs
3	Pyrantel Pamoate Monograph
4	The kinetic disposition of pyrantel citrate and pamoate and their efficacy against pyrantel-resistant Oesophagostomum dentatum in pigs. Int J Parasitol. 1996 Dec;26(12):1375-80.
5	MSD vet manual
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42.
8	Association of CYP1A1 and CYP1B1 inhibition in in vitro assays with drug-induced liver injury. J Toxicol Sci. 2021;46(4):167-176. doi: 10.2131/jts.46.167.
9	Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5.