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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
0.061 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Butalex
Primary
Butalex
Curative
Butalex

PubMed

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
Record UNII
0354RT7LG4
Record Status Validated (UNII)
Record Version