BUPARVAQUONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H26O3
Molecular Weight	326.4293
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)[C@H]1CC[C@H](CC2=C(O)C(=O)C3=CC=CC=C3C2=O)CC1

InChI

InChIKey=KLLIVCPQDTYMLC-HDJSIYSDSA-N

InChI=1S/C21H26O3/c1-21(2,3)14-10-8-13(9-11-14)12-17-18(22)15-6-4-5-7-16(15)19(23)20(17)24/h4-7,13-14,24H,8-12H2,1-3H3/t13-,14-

HIDE SMILES / InChI

Molecular Formula	C21H26O3
Molecular Weight	326.4293
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.interchemie.com/veterinary-medicines/butachem-50.html | http://egypt.msd-animal-health.com/products/butalex/butalex.aspx | https://www.ncbi.nlm.nih.gov/pubmed/14665744 | https://www.ncbi.nlm.nih.gov/pubmed/25941626

Buparvaquone is a second-generation hydroxynaphtaquinone with novel features that make it an effective compound for the therapy and prophylaxis of all forms of theileriosis. It has shown promising activities against Leishmania spp. and Neospora caninum infection. In combination with arteether it is effective against Babesia equi. Buparvaquone directly inhibits the respiration of Theileria parasites. Due to the inhibiting effects of theileriosis on the immune system, vaccination should be delayed until the animal has recovered from theileriosis. Localised, painless, oedematous swelling may occasionally be seen at the injection site.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome bc1 complex (Leishmania) 1 Target ID: Cytochrome bc1 complex (Leishmania) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27297476	Inhibitor 8504		0.061 µM [IC50]
cellular respiration 1 Target ID: GO:0045333 Sources: http://egypt.msd-animal-health.com/products/butalex/butalex.aspx	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Bovine theileriosis 1 Sources: http://egypt.msd-animal-health.com/products/butalex/butalex.aspx http://www.fivetanimalhealth.com/products/butalex	Curative	Approved 8583	Butalex Approved Use Indicated for the treatment of tick-transmitted theileriosis caused by the intracellular protozoan parasites Theileria parva (East Coast fever, Corridor disease, Zimbabwean theileriosis) and T. annulata (tropical theileriosis) in cattle.
Babesiosis 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14665744	Primary	Phase II 1147	Butalex Approved Use Unknown
Leishmaniasis 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1289357 https://www.ncbi.nlm.nih.gov/pubmed/22281156 https://www.ncbi.nlm.nih.gov/pubmed/26883424	Curative	Preclinical	Butalex Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
252.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16289157/	2.5 mg/kg bw single, intramuscular dose: 2.5 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered:		BUPARVAQUONE plasma	Bos taurus population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.102 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2896450/	2.5 mg/kg bw single, intramuscular dose: 2.5 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered:		BUPARVAQUONE plasma	Bos taurus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
4.156 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16289157/	2.5 mg/kg bw single, intramuscular dose: 2.5 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered:		BUPARVAQUONE plasma	Bos taurus population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.43 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2896450/	2.5 mg/kg bw single, intramuscular dose: 2.5 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered:		BUPARVAQUONE plasma	Bos taurus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
26.44 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2896450/	2.5 mg/kg bw single, intramuscular dose: 2.5 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered:		BUPARVAQUONE plasma	Bos taurus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71768#section=BioAssay-Results Page: 72.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71768#section=BioAssay-Results Page: 73.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71768#section=BioAssay-Results Page: 70.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71768#section=BioAssay-Results Page: 7.0	yes [IC50 1.9497 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71768#section=BioAssay-Results Page: 15.0	yes [IC50 9.7717 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71768#section=BioAssay-Results Page: 72.0

PubMed

Title	Date	PubMed
Repurposing of antiparasitic drugs: the hydroxy-naphthoquinone buparvaquone inhibits vertical transmission in the pregnant neosporosis mouse model.	2016-02-17	26883424
Effectiveness of liposomal buparvaquone in an experimental hamster model of Leishmania (L.) infantum chagasi.	2012-03	22281156
Clinical, haematological and therapeutic studies on tropical theileriosis in water buffaloes (Bubalus bubalis) in Egypt.	2007-05-31	17420101
In-vivo therapeutic efficacy trial with artemisinin derivative, buparvaquone and imidocarb dipropionate against Babesia equi infection in donkeys.	2003-11	14665744
The activity of hydroxynaphthoquinones against Leishmania donovani.	1992-12	1289357

Patents

Sample Use Guides

In Vivo Use Guide

Cattle: A single dose of 1 ml per 20 kg body weight. (2.5 mg buparvaquone/kg body weight). In severe and advanced cases, a second treatment may be required at 48-72 hrs after the initial injection at the same dose rate.

Route of Administration: Intramuscular

In Vitro Use Guide

In 4-day proliferation assays, buparvaquone efficiently inhibited Neospora caninum tachyzoite replication (IC50 = 4.9 nM; IC100 = 100 nM).

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:44:27 GMT 2025` Edited by `admin` on `Wed Apr 02 08:44:27 GMT 2025`
Record UNII	0354RT7LG4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUPARVAQUONE

Official Name

English

BUTALEX

Preferred Name

English

BUPARVAQUONE [MI]

Common Name

English

2-((4-TERT-BUTYLCYCLOHEXYL)METHYL)-3-HYDROXY-1,4-NAPHTHOQUINONE

Systematic Name

English

buparvaquone [INN]

Common Name

English

BW-720C

Code

English

BUPARVAQUONE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QP51AX22