1-methyl-2-[2-(thiophen-2-yl)ethenyl]-1,4,5,6-tetrahydropyrimidine; 4-[(3-carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid

• ChemBase ID: 129188
• Molecular Formular: C34H30N2O6S
• Molecular Mass: 594.6768
• Monoisotopic Mass: 594.18245769
• SMILES: O=C(O)c1cc2c(cccc2)c(c1O)Cc1c2c(cc(C(=O)O)c1O)cccc2.N1=C(/C=C/c2sccc2)N(C)CCC1
• Canonical SMILES: OC(=O)c1cc2ccccc2c(c1O)Cc1c(O)c(cc2c1cccc2)C(=O)O.CN1CCCN=C1/C=C/c1cccs1
• InChI: InChI=1S/C23H16O6.C11H14N2S/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29;1-13-8-3-7-12-11(13)6-5-10-4-2-9-14-10/h1-10,24-25H,11H2,(H,26,27)(H,28,29);2,4-6,9H,3,7-8H2,1H3
• InChIKey: AQXXZDYPVDOQEE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-2-[2-(thiophen-2-yl)ethenyl]-1,4,5,6-tetrahydropyrimidine; 4-[(3-carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid; 1-methyl-2-[(E)-2-(thiophen-2-yl)ethenyl]-1,4,5,6-tetrahydropyrimidine; 4-[(3-carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid
• IUPAC Traditional name: pamoic acid; pyrantel
• Synonyms: Pyrantel pamoate; Pyrantel embonate; Pyrantel pamoate; 1-Methyl-2-(2-[2-thienyl]ethenyl)-1,4,5,6-tetrahydropyrimidine compound with 4,4′-methylenebis(3-hydroxy-2-naphthoic acid); 4,4'-Methylenebis[3-hydroxy-2-naphthalenecarboxylic Acid compound with 1,4,5,6-Tetrahydro-1-methyl-2-[(1E)-2-(2-thienyl)ethenyl]pyrimidine; Antiminth; 1,4,5,6-Tetrahydro-1-methyl-2-[(1E)-2-(2-thienyl)ethenyl]pyrimidine 4,4'-Methylenebis[3-hydroxy-2-naphthalenecarboxylate]; CP 10423-16; Cobantril; Combantrin; Early Bird; Embovin; Helmex; Helmintox; Nemocid; Piranver; 含 4,4′-亚甲基双(3-羟基-2-萘甲酸) 的 1-甲基-2-(2-[2-噻吩基]乙烯基)-1,4,5,6-四氢嘧啶化合物; 双羟萘酸噻嘧啶

Database IDs

• CAS Number: 22204-24-6
• EC Number: 244-837-1
• MDL Number: MFCD00072037
• Beilstein Number: 9034755
• PubChem SID: 162223485; 24898655; 24870378
• PubChem CID: 5281033
• CHEMBL: 1673147
• Chemspider ID: 4444501
• MeSH Name: Pyrantel+pamoate
• Wikipedia Title: Pyrantel_pamoate

CALCULATED PROPERTIES

• Acid pKa: 2.3815763
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.5700001
• LogD (pH = 7.4): -0.95232564
• Log P: 6.0520287
• Molar Refractivity: 107.1698 cm^3
• Polarizability: 42.550995 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Grade: VETRANAL™, analytical standard
• Ignition Residue: <0.5%
• Impurities: <0.0005% Phosphorus (P); <0.1% Insoluble matter
• Cation Traces: Al: <0.0005%; Ca: <0.002%; Cu: <0.0005%; Fe: <0.001%; K: <0.005%; Mg: <0.0005%; Na: <0.01%; Pb: <0.001%; Zn: <0.0005%
• Antion Traces: chloride (Cl-): <0.5%
• Linear Formula: C11H14N2S · C23H16O6

DETAILS

Sigma Aldrich - P6210

Application
Pyrantel pamoate is used as a deworming agent in domesticated animals such as horses, hamsters, sheep, pigs, cats, and dogs1. It is a combination of pyrantel and pamoic acid. It is used to study mechanisms underlying gut dysfunction in a murine model2. It has been used as an anthelmintic treatment of children in Bangladesh and has been studied for it′s effect on host physiology, growth, and biochemical status3.
Biochem/physiol Actions
Pyrantel pamoate is a nematode muscle cell-associated nicotinic agonist for the acetylcholine (ACh) receptor. Cholinesterase inhibitor.

Sigma Aldrich - 46702

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - P840575

An antiparasitic agent used in the treatment of intestinal parasites such as hookworms and roundworms (Ascaris lumbricoides, aka ascarids in humans) in domesticated animals such as horses, cattle, sheep, pigs, cats, dogs, and many other species.

REFERENCES

• Becher, A.M. et al.: Vet. Parasitol., 171, 116 (2010)
• Barr, S.C. et al.: Am. J. Vet. Res., 59, 1134 (2010)