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

Topological Polar Surface Area (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
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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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	Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
9	Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):117-23.
10	CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
11	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.
12	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.
13	Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol. 2003 Apr;16(4):450-9.
14	Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
15	Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
16	Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
17	Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.