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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 of BUPARVAQUONE

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Cytochrome bc1 complex (Leishmania)
0.061 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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.
Primary
Butalex

Approved Use

Unknown
Curative
Butalex

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The activity of hydroxynaphthoquinones against Leishmania donovani.
1992 Dec
Effectiveness of liposomal buparvaquone in an experimental hamster model of Leishmania (L.) infantum chagasi.
2012 Mar
Repurposing of antiparasitic drugs: the hydroxy-naphthoquinone buparvaquone inhibits vertical transmission in the pregnant neosporosis mouse model.
2016 Feb 17
Patents

Sample Use Guides

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 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
  • Download
Name Type Language
BUPARVAQUONE
INN   MART.   MI  
INN  
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
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C73276
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID4057849
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
PRIMARY
INN
5549
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
PRIMARY
SMS_ID
100000088465
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
PRIMARY
EVMPD
SUB05980MIG
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
PRIMARY
CAS
88426-33-9
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
PRIMARY
MERCK INDEX
m2765
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
PRIMARY Merck Index
FDA UNII
0354RT7LG4
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL292009
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
PRIMARY
MESH
C046326
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
PRIMARY
WIKIPEDIA
Buparvaquone
Created by admin on Sat Dec 16 17:04:49 GMT 2023 , Edited by admin on Sat Dec 16 17:04:49 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY