| 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 users918 edits Change Category:Naphthoquinones to Category:1,4-Naphthoquinones |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| verifiedrevid = 401936553 |
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| verifiedrevid = 459985754 |
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| IUPAC_name = 2-((4-tert-butylcyclohexyl)methyl)-3-hydroxy-1,4-naphthoquinone |
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| IUPAC_name = 2-((4-''tert''-Butylcyclohexyl)methyl)-3-hydroxy-1,4-naphthoquinone |
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| image = Buparvaquone.svg |
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| image = Buparvaquone v2.svg |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| protein_bound = |
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| protein_bound = |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 88426-33-9 --> |
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| CAS_number = 88426-33-9 |
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| CAS_supplemental = |
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| CAS_supplemental = |
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| ATCvet = yes |
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| ATCvet = yes |
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| ATC_prefix = P51 |
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| ATC_prefix = P51 |
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| ATC_suffix = AX22 |
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| ATC_suffix = EX03 |
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| ATC_supplemental = |
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| ATC_supplemental = |
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| PubChem = |
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| PubChem = |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10807457 |
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| ChemSpiderID = 10807457 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 0354RT7LG4 |
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| UNII = 0354RT7LG4 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 292009 --> |
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| ChEMBL = 292009 |
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| ⚫ |
| chemical_formula = |
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<!--Chemical data--> |
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| C=21 | H=26 | O=3 |
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⚫ |
| chemical_formula = |
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| molecular_weight = 326.435 g/mol |
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| C=21 | H=26 | O=3 |
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| smiles = CC(C)(C)C3CCC(C\C2=C(/O)C(=O)c1ccccc1C2=O)CC3 |
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| smiles = CC(C)(C)C3CCC(C\C2=C(/O)C(=O)c1ccccc1C2=O)CC3 |
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| 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 |
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| InChIKey = KLLIVCPQDTYMLC-UHFFFAOYAS |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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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| 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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}} |
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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}} |
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'''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}} |
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It is the only really efficient commercial therapy product in bovine ], where it is used since the late 1980s.{{Citation needed|date=February 2010}} |
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== Industrial production == |
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== Industrial production == |
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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 ] |
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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}} |
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== Use in bovine theileriosis == |
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== Use in bovine theileriosis == |
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At unique dose of 2,5 mg/kg, recovery rate of curable cases is 90 to 98 %. |
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Using a single dose of 2.5 mg/kg, the recovery rate of curable cases is 90 to 98%. In ], a dosage of 2.0 mg/kg has the same efficacy. Body temperature returns to normal in two to five days. |
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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> |
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In ], a dosage of 2.0 mg/kg has the same efficiency. |
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Body temperature returns to normal in two days (but only after 5 days in some cases). |
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== Molecular target == |
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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> |
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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}} |
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== References == |
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== References == |
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{{antimicrobial-stub}} |
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