PONAZURIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H14F3N3O6S
Molecular Weight	457.38
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(=O)NC(=O)N(C1=O)C2=CC=C(OC3=CC=C(C=C3)S(=O)(=O)C(F)(F)F)C(C)=C2

InChI

InChIKey=VBUNOIXRZNJNAD-UHFFFAOYSA-N

InChI=1S/C18H14F3N3O6S/c1-10-9-11(24-16(26)22-15(25)23(2)17(24)27)3-8-14(10)30-12-4-6-13(7-5-12)31(28,29)18(19,20)21/h3-9H,1-2H3,(H,22,25,26)

HIDE SMILES / InChI

Molecular Formula	C18H14F3N3O6S
Molecular Weight	457.38
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://web.archive.org/web/20170721093649/http://marquis.merial.com:80/Pages/marquis-Label.aspx
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/24679485

Ponazuril, sold by the Bayer Corporation under the trade name Marquis, was the first FDA-approved treatment for equine protozoal myeloencephalitis (EPM) in horse, caused by Sarcocystis neurona. Also this drug was used in animals such as cats, dogs against coccidia, an intestinal parasite. Coccidia treatment is far shorter than treatment for EPM.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Equine protozoal myeloencephalitis 3 Sources: https://web.archive.org/web/20170721093649/http://marquis.merial.com:80/Pages/marquis-Label.aspx	Curative		Approved 8429	MARQUIS Approved Use MARQUIS (ponazuril) is indicated for the treatment of equine protozoal myeloencephalitis (EPM) caused by Sarcocystis neurona.
Coccidiosis 45 Sources: http://www.ncbi.nlm.nih.gov/pubmed/24679485	Curative		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Detection, quantifications, and pharmacokinetics of ponazuril in healthy swine.	2014 Dec	24731142
Pharmacokinetics of single-dose oral ponazuril in weanling goats.	2016 Jun	26542450
Efficacy of treatment of elevated coccidial oocyst counts in goats using amprolium versus ponazuril.	2016 Mar 15	26872920

Patents

Sample Use Guides

In Vivo Use Guide

horses: paste to treat one 1,200 lb (544 kg) horse for seven days, at a dose rate of 5 mg/kg (2.27 mg/lb) body weight

Route of Administration: Oral

In Vitro Use Guide

Ponazuril inhibited T. equi in erythrocyte culture at all concentrations tested but parasite elimination required at least 500 μg/mL. The high dose of ponazuril required for in vitro inhibition likely limits its ability to control or clear T. equi infection in vivo.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:37:51 GMT 2023` Edited by `admin` on `Fri Dec 15 16:37:51 GMT 2023`
Record UNII	JPW84AS66U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PONAZURIL

Official Name

English

1-METHYL-3-(4-(P-((TRIFLUOROMETHYL)SULFONYL)PHENOXY)-M-TOLYL)-S-TRIAZINE-2,4,6(1H,3H,5H)-TRIONE

Common Name

English

ponazuril [INN]

Common Name

English

PONAZURIL [MI]

Common Name

English

PONAZURIL [GREEN BOOK]

Common Name

English

TOLTRAZURIL SULFONE

Common Name

English

Classification Tree Code System Code

WHO-VATC

QP51AJ04