Oxantel

Oxantel
Clinical data
ATC code	P02CC02 (WHO) QP52AF03 (WHO);
Identifiers
	IUPAC name 3-[(E)-2-(1-Methyl-5,6-dihydro-4H-pyrimidin-2-yl)ethenyl]phenol;
CAS Number	36531-26-7 ;
PubChem CID	5281087;
ChemSpider	4444540 ;
UNII	94AJJ30D9E;
KEGG	D00806 ;
CompTox Dashboard (EPA)	DTXSID601016597 ;
Chemical and physical data
Formula	C13H16N2O
Molar mass	216.284 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCCN=C1/C=C/C2=CC(=CC=C2)O;
	InChI InChI=1S/C13H16N2O/c1-15-9-3-8-14-13(15)7-6-11-4-2-5-12(16)10-11/h2,4-7,10,16H,3,8-9H2,1H3/b7-6+ ; Key:VRYKTHBAWRESFI-VOTSOKGWSA-N ;
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Oxantel is an anthelmintic. It has typically been used in human and animal medicine as a treatment for intestinal worms.^[1] It has also been shown to inhibit fumarate reductase in some pathogenic bacteria.^[2]

Similarly to pyrantel, oxantel depolarises the neurons of gastrointestinal parasites 100x more than acetylcholine, causing sustained muscular contraction, causing the parasites to die by spastic paralysis. This anthelmintic is commonly used to treat domestic animals as well as livestock, and resistance has been reported in both groups of animals.^[3]

References

^ Palmeirim MS, Specht S, Scandale I, Gander-Meisterernst I, Chabicovsky M, Keiser J (June 2021). "Preclinical and Clinical Characteristics of the Trichuricidal Drug Oxantel Pamoate and Clinical Development Plans: A Review". Drugs. 81 (8): 907–921. doi:10.1007/s40265-021-01505-1. PMC 8144136. PMID 33929716.
^ Dashper S, O'Brien-Simpson N, Liu SW, Paolini R, Mitchell H, Walsh K, et al. (2014). "Oxantel disrupts polymicrobial biofilm development of periodontal pathogens". Antimicrobial Agents and Chemotherapy. 58 (1): 378–85. doi:10.1128/AAC.01375-13. PMC 3910723. PMID 24165189.
^ Kopp SR, Kotze AC, McCarthy JS, Traub RJ, Coleman GT (November 2008). "Pyrantel in small animal medicine: 30 years on". Veterinary Journal. 178 (2): 177–184. doi:10.1016/j.tvjl.2007.06.021. PMID 17720556.

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[pmid33929716-1] Palmeirim MS, Specht S, Scandale I, Gander-Meisterernst I, Chabicovsky M, Keiser J (June 2021). "Preclinical and Clinical Characteristics of the Trichuricidal Drug Oxantel Pamoate and Clinical Development Plans: A Review". Drugs. 81 (8): 907–921. doi:10.1007/s40265-021-01505-1. PMC 8144136. PMID 33929716.

[pmid24165189-2] Dashper S, O'Brien-Simpson N, Liu SW, Paolini R, Mitchell H, Walsh K, et al. (2014). "Oxantel disrupts polymicrobial biofilm development of periodontal pathogens". Antimicrobial Agents and Chemotherapy. 58 (1): 378–85. doi:10.1128/AAC.01375-13. PMC 3910723. PMID 24165189.

[3] Kopp SR, Kotze AC, McCarthy JS, Traub RJ, Coleman GT (November 2008). "Pyrantel in small animal medicine: 30 years on". Veterinary Journal. 178 (2): 177–184. doi:10.1016/j.tvjl.2007.06.021. PMID 17720556.

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[2]

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Clinical data

ATC code	P02CC02 (WHO) QP52AF03 (WHO)
Identifiers
IUPAC name 3-[(E)-2-(1-Methyl-5,6-dihydro-4H-pyrimidin-2-yl)ethenyl]phenol
CAS Number	36531-26-7^Y
PubChem CID	5281087
ChemSpider	4444540^N
UNII	94AJJ30D9E
KEGG	D00806^Y
CompTox Dashboard (EPA)	DTXSID601016597
Chemical and physical data
Formula	C₁₃H₁₆N₂O
Molar mass	216.284 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1CCCN=C1/C=C/C2=CC(=CC=C2)O
InChI InChI=1S/C13H16N2O/c1-15-9-3-8-14-13(15)7-6-11-4-2-5-12(16)10-11/h2,4-7,10,16H,3,8-9H2,1H3/b7-6+^N Key:VRYKTHBAWRESFI-VOTSOKGWSA-N^N
^NY (what is this?) (verify)