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]
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) 2
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
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
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]

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]
Molecular Interaction Atlas (MIA) 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
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.