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Revision as of 16:13, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').← Previous edit Latest revision as of 05:30, 21 December 2024 edit undoPreimage (talk | contribs)Extended confirmed users988 edits Change Category:Naphthoquinones to Category:1,4-Naphthoquinones 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 401936553 | verifiedrevid = 459985754
| IUPAC_name = 2-((4-tert-butylcyclohexyl)methyl)-3-hydroxy-1,4-naphthoquinone | IUPAC_name = 2-((4-''tert''-Butylcyclohexyl)methyl)-3-hydroxy-1,4-naphthoquinone
| image = Buparvaquone.svg | image = Buparvaquone v2.svg


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 88426-33-9 --> | CAS_number = 88426-33-9
| CAS_supplemental = | CAS_supplemental =
| ATCvet = yes | ATCvet = yes
| ATC_prefix = P51 | ATC_prefix = P51
| ATC_suffix = AX22 | ATC_suffix = EX03
| ATC_supplemental = | ATC_supplemental =
| PubChem = | PubChem =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10807457 | ChemSpiderID = 10807457
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0354RT7LG4 | UNII = 0354RT7LG4
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 292009 --> | ChEMBL = 292009

⚫ | chemical_formula =
<!--Chemical data-->
⚫ | C=21 | H=26 | O=3
⚫ | chemical_formula =
| molecular_weight = 326.435 g/mol
⚫ | C=21 | H=26 | O=3
| smiles = CC(C)(C)C3CCC(C\C2=C(/O)C(=O)c1ccccc1C2=O)CC3 | smiles = CC(C)(C)C3CCC(C\C2=C(/O)C(=O)c1ccccc1C2=O)CC3
| InChI = 1/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
| InChIKey = KLLIVCPQDTYMLC-UHFFFAOYAS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
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}} }}


'''Buparvaquone''' is a hydroxynaphthoquinone ] drug related to ] and ]. It is a promising compound for the therapy and prophylaxis of all forms of ]. Buparvaquone has been shown to have anti-]l activity ''in vitro''. It can be used to treat bovine ] protozoal in-vitro, along with the only other substance known - ].{{Citation needed|date=February 2010}} '''Buparvaquone''' is a ] ] drug related to ]. It is a promising compound for the therapy and prophylaxis of all forms of ]<!--intentional link to DAB page-->. Buparvaquone has been shown to have anti-]l activity ''in vitro''. It can be used to treat bovine ] protozoa ''in vitro'', along with the only other substance known – '']''.{{Citation needed|date=February 2010}} It is the only really effective commercial therapeutic product against bovine ], where it has been used since the late 1980s.{{Citation needed|date=February 2010}}

It is the only really efficient commercial therapy product in bovine ], where it is used since the late 1980s.{{Citation needed|date=February 2010}}


== Industrial production == == Industrial production ==
It was first produced in ], then in ].{{Citation needed|date=February 2010}} It came out of license in the mid ], and was then produced in different countries, e.g. ] and of ] It was first produced in ], then in ].{{Citation needed|date=February 2010}} Its patent expired in the mid-2000s, and was then produced in different countries such as ] and ].{{cn|date=December 2022}}


== Use in bovine theileriosis == == Use in bovine theileriosis ==
At unique dose of 2,5&nbsp;mg/kg, recovery rate of curable cases is 90 to 98 %. Using a single dose of 2.5&nbsp;mg/kg, the recovery rate of curable cases is 90 to 98%. In ], a dosage of 2.0&nbsp;mg/kg has the same efficacy. Body temperature returns to normal in two to five days.
Parasitemia lowers from 12% on day 0 to 5% the next day, then to 1% by day 5 and none at day 7.<ref>{{cite journal | vauthors = Abdou TA, Abou-El-naga TR, Mahmoud MA | title = Clinicopathological Studies on Theileria Annulata Infection in Siwa Oasis in Egypt. | journal = BS. Vet. Med. J. | date = 2005 | volume = 15 | issue = 2 | pages = 40–6 | url = http://old.eaap.org/Previous_Annual_Meetings/2005Uppsala/Papers/M2.11_Abdou.pdf }}</ref>
In ], a dosage of 2.0&nbsp;mg/kg has the same efficiency.

Body temperature returns to normal in two days (but only after 5 days in some cases).
== Molecular target ==
Parasitemia lowers from 12 % (D0) to 5 % (D1), than to 1 % (D5) and is nul at D7.<ref>Abou-El-Naga ''at al'', Beni-Suef Vet. Med. J. 2005.</ref>
Buparvaquone resistance appears to be associated with parasite mutations in the Q<sub>o</sub> quinone-binding site of mitochondrial ].<ref>{{cite journal | vauthors = Sharifiyazdi H, Namazi F, Oryan A, Shahriari R, Razavi M | title = Point mutations in the Theileria annulata cytochrome b gene is associated with buparvaquone treatment failure | journal = Veterinary Parasitology | volume = 187 | issue = 3–4 | pages = 431–5 | date = July 2012 | pmid = 22305656 | doi = 10.1016/j.vetpar.2012.01.016 }}</ref> Its mode of action is thus likely to be similar to that of the antimalarial drug atovaquone, a similar 2-hydroxy-1,4-naphthoquinone that binds to the Q<sub>o</sub> site of cytochrome b thus inhibiting ].{{cn|date=December 2022}}


== References == == References ==
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] ]
]


{{antimicrobial-stub}}

Latest revision as of 05:30, 21 December 2024

Chemical compound Pharmaceutical compound
Buparvaquone
Clinical data
ATCvet code
Identifiers
IUPAC name
  • 2-((4-tert-Butylcyclohexyl)methyl)-3-hydroxy-1,4-naphthoquinone
CAS Number
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.115.556 Edit this at Wikidata
Chemical and physical data
FormulaC21H26O3
Molar mass326.436 g·mol
3D model (JSmol)
SMILES
  • CC(C)(C)C3CCC(C\C2=C(/O)C(=O)c1ccccc1C2=O)CC3
InChI
  • 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
  • Key:KLLIVCPQDTYMLC-UHFFFAOYSA-N
  (what is this?)  (verify)

Buparvaquone is a naphthoquinone antiprotozoal drug related to 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.

Industrial production

It was first produced in Great Britain, then in Germany. Its patent expired in the mid-2000s, and was then produced in different countries such as India and Iran.

Use in bovine theileriosis

Using a single dose of 2.5 mg/kg, the recovery rate of curable cases is 90 to 98%. In tropical theileriosis, a dosage of 2.0 mg/kg has the same efficacy. Body temperature returns to normal in two to five days. Parasitemia lowers from 12% on day 0 to 5% the next day, then to 1% by day 5 and none at day 7.

Molecular target

Buparvaquone resistance appears to be associated with parasite mutations in the Qo quinone-binding site of mitochondrial cytochrome b. Its mode of action is thus likely to be similar to that of the antimalarial drug atovaquone, a similar 2-hydroxy-1,4-naphthoquinone that binds to the Qo site of cytochrome b thus inhibiting Coenzyme Q – cytochrome c reductase.

References

  1. Abdou TA, Abou-El-naga TR, Mahmoud MA (2005). "Clinicopathological Studies on Theileria Annulata Infection in Siwa Oasis in Egypt" (PDF). BS. Vet. Med. J. 15 (2): 40–6.
  2. Sharifiyazdi H, Namazi F, Oryan A, Shahriari R, Razavi M (July 2012). "Point mutations in the Theileria annulata cytochrome b gene is associated with buparvaquone treatment failure". Veterinary Parasitology. 187 (3–4): 431–5. doi:10.1016/j.vetpar.2012.01.016. PMID 22305656.
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