MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 412175 | Name: Bupravaquone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bupravaquone is a hydroxynaphthoquinone antiprotozoal drug related to parvaquone and atovaquone. It is a promising compound for the therapy and prophylaxis of all forms of theileriosis. Buparvaquone has been shown to have anti-leishmanial activity in vitro. It can be used to treat bovine East Coast fever protozoa in vitro, along with the only other substance known – Peganum harmala. It is the only really effective commercial therapeutic product against bovine theileriosis, where it has been used since the late 1980s.

Chemical Structure

Bupravaquone
Bupravaquone
CAS#86790-29-6

Theoretical Analysis

MedKoo Cat#: 412175

Name: Bupravaquone

CAS#: 86790-29-6

Chemical Formula: C20H24O3

Exact Mass: 312.1725

Molecular Weight: 312.41

Elemental Analysis: C, 76.89; H, 7.74; O, 15.36

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Bupravaquone; BW58C; BW-58: BW 58C
IUPAC/Chemical Name
1,4-Naphthalenedione, 2-(4-(1,1-dimethylethyl)cyclohexyl)-3-hydroxy-, trans-
InChi Key
NWCVRXADYNRXCT-JOCQHMNTSA-N
InChi Code
InChI=1S/C20H24O3/c1-20(2,3)13-10-8-12(9-11-13)16-17(21)14-6-4-5-7-15(14)18(22)19(16)23/h4-7,12-13,23H,8-11H2,1-3H3/t12-,13-
SMILES Code
O=C1C([C@H]2CC[C@H](C(C)(C)C)CC2)=C(O)C(C3=C1C=CC=C3)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 312.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Spahi S, Mutlu O, Sariyer E, Kocer S, Ugurel E, Turgut-Balik D. Hit identification against peptidyl-prolyl isomerase of Theileria annulata by combined virtual high-throughput screening and molecular dynamics simulation approach. Comput Biol Chem. 2020 Oct 2;89:107398. doi: 10.1016/j.compbiolchem.2020.107398. Epub ahead of print. PMID: 33059132. 2: Hines SA, Brandvold J, Mealey RH, Call DR, Graça T. Exposure to ambient air causes degradation and decreased in vitro potency of buparvaquone and parvaquone. Vet Parasitol X. 2020 Feb 7;3:100023. doi: 10.1016/j.vpoa.2020.100023. PMID: 32904749; PMCID: PMC7458381. 3: Lalatsa A, Statts L, Adriana de Jesus J, Adewusi O, Auxiliadora Dea-Ayuela M, Bolas-Fernandez F, Dalastra Laurenti M, Felipe Domingues Passero L, Serrano DR. Topical buparvaquone nano-enabled hydrogels for cutaneous leishmaniasis. Int J Pharm. 2020 Oct 15;588:119734. doi: 10.1016/j.ijpharm.2020.119734. Epub 2020 Aug 7. PMID: 32777535. 4: Ram PK, Singh SK, Srivastava A, Kumar G, Jaiswal AK, Yadav B, Garg SK. Effects of Injectable Trace Minerals (ITMs) on Th1/Th2 Cytokine Balance of Newborn Calves with Tropical Theileriosis. Biol Trace Elem Res. 2020 Jun 22. doi: 10.1007/s12011-020-02263-z. Epub ahead of print. PMID: 32572800. 5: Gharbi M, Darghouth MA, Elati K, Al-Hosary AAT, Ayadi O, Salih DA, El Hussein AM, Mhadhbi M, Khamassi Khbou M, Hassan SM, Obara I, Ahmed LS, Ahmed J. Current status of tropical theileriosis in Northern Africa: A review of recent epidemiological investigations and implications for control. Transbound Emerg Dis. 2020 Mar;67 Suppl 1:8-25. doi: 10.1111/tbed.13312. PMID: 32174036. 6: Lundström-Stadelmann B, Rufener R, Ritler D, Zurbriggen R, Hemphill A. The importance of being parasiticidal… an update on drug development for the treatment of alveolar echinococcosis. Food Waterborne Parasitol. 2019 Mar 14;15:e00040. doi: 10.1016/j.fawpar.2019.e00040. PMID: 32095613; PMCID: PMC7034016. 7: Salim B, Chatanga E, Jannot G, Mossaad E, Nakao R, Weitzman JB. Mutations in the TaPIN1 peptidyl prolyl isomerase gene in Theileria annulata parasites isolated in Sudan. Int J Parasitol Drugs Drug Resist. 2019 Dec;11:101-105. doi: 10.1016/j.ijpddr.2019.11.001. Epub 2019 Nov 26. PMID: 31794951; PMCID: PMC6904843. 8: Lawrence KE, Gedye K, Pomroy WE. A longitudinal study of the effect of Theileria orientalis Ikeda type infection on three New Zealand dairy farms naturally infected at pasture. Vet Parasitol. 2019 Dec;276:108977. doi: 10.1016/j.vetpar.2019.108977. Epub 2019 Nov 12. PMID: 31775104. 9: Jayalakshmi K, Selvaraj P, Veeraselvam M, Yogeshpriya S, Venkatesan M. Diabetic ketoacidosis in a buck: a case report. Iran J Vet Res. 2019 Summer;20(3):213-217. PMID: 31656528; PMCID: PMC6811715. 10: Maithania HV, Mohanty BS, Chaudhari PR, Samad A, Devarajan PV. Shape mediated splenotropic delivery of buparvaquone loaded solid lipid nanoparticles. Drug Deliv Transl Res. 2020 Feb;10(1):159-167. doi: 10.1007/s13346-019-00670-x. PMID: 31468307. 11: Bishop RP, Odongo DO, Dolan TT, Dolan RB, Skilton RA, Sayer PD. THEILERIOSIS IN MOUNTAIN BONGO REPATRIATED TO KENYA: A CLINICAL AND MOLECULAR INVESTIGATION. J Zoo Wildl Med. 2019 Jun 13;50(2):342-349. doi: 10.1638/2018-0110. PMID: 31260199. 12: Monteiro LM, Löbenberg R, Fotaki N, de Araújo GLB, Cotrim PC, Bou-Chacra N. Co-delivery of buparvaquone and polymyxin B in a nanostructured lipid carrier for leishmaniasis treatment. J Glob Antimicrob Resist. 2019 Sep;18:279-283. doi: 10.1016/j.jgar.2019.06.006. Epub 2019 Jun 13. PMID: 31202979. 13: Rashid M, Guan G, Luo J, Zhao S, Wang X, Rashid MI, Hassan MA, Mukhtar MU, Liu J, Yin H. Establishment and Expression of Cytokines in a Theileria annulata-Infected Bovine B Cell Line. Genes (Basel). 2019 Apr 30;10(5):329. doi: 10.3390/genes10050329. PMID: 31052316; PMCID: PMC6562936. 14: Marsolier J, Perichon M, Weitzman JB, Medjkane S. Secreted parasite Pin1 isomerase stabilizes host PKM2 to reprogram host cell metabolism. Commun Biol. 2019 Apr 30;2:152. doi: 10.1038/s42003-019-0386-6. PMID: 31044177; PMCID: PMC6491484. 15: Metwally DM, Al-Talhi RA, Barakat IAH, ElKhadragy MF. Effects of Eugenol on Haemoproteus columbae in domestic pigeons (Columba livia domestica) from Riyadh, Saudi Arabia. Biosci Rep. 2019 May 23;39(5):BSR20190409. doi: 10.1042/BSR20190409. PMID: 31028133; PMCID: PMC6533204. 16: Nyagwange J, Awino E, Tijhaar E, Svitek N, Pelle R, Nene V. Leveraging the Medicines for Malaria Venture malaria and pathogen boxes to discover chemical inhibitors of East Coast fever. Int J Parasitol Drugs Drug Resist. 2019 Apr;9:80-86. doi: 10.1016/j.ijpddr.2019.01.002. Epub 2019 Jan 25. PMID: 30771616; PMCID: PMC6376154. 17: Chatanga E, Mosssad E, Abdo Abubaker H, Amin Alnour S, Katakura K, Nakao R, Salim B. Evidence of multiple point mutations in Theileria annulata cytochrome b gene incriminated in buparvaquone treatment failure. Acta Trop. 2019 Mar;191:128-132. doi: 10.1016/j.actatropica.2018.12.041. Epub 2018 Dec 30. PMID: 30599177. 18: Chandratre GA, Jangir BL, Sharma M, Jakhar KK, Kumar T. Clinico- haematological alterations and therapeutic management of tick borne fever in cross bred cow. J Parasit Dis. 2018 Dec;42(4):643-645. doi: 10.1007/s12639-018-1034-7. Epub 2018 Oct 15. PMID: 30538366; PMCID: PMC6261148. 19: Rufener R, Dick L, D'Ascoli L, Ritler D, Hizem A, Wells TNC, Hemphill A, Lundström-Stadelmann B. Repurposing of an old drug: In vitro and in vivo efficacies of buparvaquone against Echinococcus multilocularis. Int J Parasitol Drugs Drug Resist. 2018 Dec;8(3):440-450. doi: 10.1016/j.ijpddr.2018.10.011. Epub 2018 Oct 31. PMID: 30396011; PMCID: PMC6216040. 20: Nayyar Ghauri H, Ijaz M, Farooqi SH, Ali A, Ghaffar A, Saleem S, Iqbal MK, Aziz MU, Ghani U, Ullah MR, Ahmad HM. A comprehensive review on past, present and future aspects of canine theileriosis. Microb Pathog. 2019 Jan;126:116-122. doi: 10.1016/j.micpath.2018.10.033. Epub 2018 Oct 30. PMID: 30385396.