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 8297		0.061 µM [IC50]
cellular respiration 1 Target ID: GO:0045333 Sources: http://egypt.msd-animal-health.com/products/butalex/butalex.aspx	Inhibitor 8297

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 8429	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 1132	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

PubMed

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

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 `Sat Dec 16 17:04:49 GMT 2023` Edited by `admin` on `Sat Dec 16 17:04:49 GMT 2023`
Record UNII	0354RT7LG4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUPARVAQUONE

Official 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

BUTALEX

Brand Name

English

BW-720C

Code

English

BUPARVAQUONE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QP51AX22