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{{drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 394798751
| verifiedrevid = 394798751
|IUPAC_name=2-[2-nitro-4-(trifluoromethyl)benzoyl]<br>cyclohexane-1,3-dione
| IUPAC_name = 2-[2-nitro-4-(trifluoromethyl)benzoyl]<br>cyclohexane-1,3-dione
|image=Nitisinone.svg
| image = Nitisinone.svg

⚫
|CASNo_Ref = {{cascite|correct|CAS}}
<!--Clinical data-->
| tradename =
| Drugs.com = {{drugs.com|CDI|nitisinone}}
⚫
| licence_EU = Orfadin
⚫
| licence_US = Nitisinone
⚫
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
⚫
| legal_UK = <!-- GSL / P / POM / CD -->
⚫
| legal_US = Rx-only
⚫
| routes_of_administration = Oral

<!--Pharmacokinetic data-->
⚫
| elimination_half-life = Approximately 54 h

<!--Identifiers-->
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
⚫
| CAS_number = 104206-65-7
⚫
| ATC_prefix = A16
⚫
| ATC_suffix = AX04
⚫
| PubChem = 115355
⚫
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫
| DrugBank = APRD01141
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 103195
| ChemSpiderID = 103195
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = K5BN214699
| UNII = K5BN214699
⚫
| KEGG_Ref = {{keggcite|changed|kegg}}
⚫
| KEGG = D05177
⚫
| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫
| ChEBI = 50378
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1337
| ChEMBL = 1337

| InChI1 = 1/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,12H,1-3H2
<!--Chemical data-->
| InChIKey1 = OUBCNLGXQFSTLU-UHFFFAOYAM
⚫
| C=14 | H=10 | F=3 | N=1 | O=5
⚫
| molecular_weight = 329.228 g/mol
| smiles = O=C(c1ccc(cc1[N+]([O-])=O)C(F)(F)F)C2C(=O)CCCC2=O
| smiles = O=C(c1ccc(cc1[N+]([O-])=O)C(F)(F)F)C2C(=O)CCCC2=O
⚫
| CAS_number=104206-65-7
⚫
|ATC_prefix=A16
⚫
|ATC_suffix=AX04
|ATC_supplemental=
⚫
| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫
| ChEBI = 50378
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,12H,1-3H2
| StdInChI = 1S/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,12H,1-3H2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = OUBCNLGXQFSTLU-UHFFFAOYSA-N
| StdInChIKey = OUBCNLGXQFSTLU-UHFFFAOYSA-N
⚫
| PubChem=115355
⚫
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫
| DrugBank=APRD01141
⚫
| KEGG_Ref = {{keggcite|changed|kegg}}
⚫
| KEGG = D05177
⚫
|C=14|H=10|F=3|N=1|O=5
⚫
|molecular_weight=329.228 g/mol
|bioavailability=
|protein_bound=
|metabolism=
⚫
|elimination_half-life=Approximately 54 h
|excretion=
⚫
|pregnancy_AU=<!-- A / B1 / B2 / B3 / C / D / X -->
⚫
|pregnancy_US=<!-- A / B / C / D / X -->
|pregnancy_category=
⚫
| licence_EU = Orfadin
⚫
| licence_US = Nitisinone
⚫
|legal_AU=<!-- Unscheduled / S2 / S4 / S8 -->
⚫
|legal_UK=<!-- GSL / P / POM / CD -->
⚫
|legal_US=Rx-only
|legal_status=
⚫
|routes_of_administration=Oral
}}
}}
'''Nitisinone''' (also known as '''NTBC''', an abbreviation of its full chemical name) is a drug originally developed as an [[herbicide]] now used in the treatment of [[Tyrosinemia#Types|hereditary tyrosinemia type 1]]. Since its first use for this indication in 1991, it has replaced [[liver transplantation]] as the first-line treatment for this rare condition.<ref name="pmid16706549">{{cite journal |author=McKiernan PJ |title=Nitisinone in the treatment of hereditary tyrosinaemia type 1 |journal=Drugs |volume=66 |issue=6 |pages=743–50 |year=2006 |pmid=16706549 |doi=10.2165/00003495-200666060-00002}}</ref> It is also being studied in the less severe but related condition [[alkaptonuria]].<ref name=Phornphutkul>{{cite journal |author=Phornphutkul C, Introne WJ, Perry MB, ''et al.'' |title=Natural history of alkaptonuria |journal=New England Journal Medicine |volume=347 |issue=26 |pages=2111–21 |year=2002 |pmid=12501223 |doi=10.1056/NEJMoa021736| url=http://content.nejm.org/cgi/content/full/347/26/2111}}</ref> It is marketed under the brand name '''Orfadin'''.
'''Nitisinone''' (also known as '''NTBC''', an abbreviation of its full chemical name) is a drug originally developed as an [[herbicide]] now used in the treatment of [[Tyrosinemia#Types|hereditary tyrosinemia type 1]]. Since its first use for this indication in 1991, it has replaced [[liver transplantation]] as the first-line treatment for this rare condition.<ref name="pmid16706549">{{cite journal |author=McKiernan PJ |title=Nitisinone in the treatment of hereditary tyrosinaemia type 1 |journal=Drugs |volume=66 |issue=6 |pages=743–50 |year=2006 |pmid=16706549 |doi=10.2165/00003495-200666060-00002}}</ref> It is also being studied in the less severe but related condition [[alkaptonuria]].<ref name=Phornphutkul>{{cite journal |author=Phornphutkul C, Introne WJ, Perry MB, ''et al.'' |title=Natural history of alkaptonuria |journal=New England Journal Medicine |volume=347 |issue=26 |pages=2111–21 |year=2002 |pmid=12501223 |doi=10.1056/NEJMoa021736| url=http://content.nejm.org/cgi/content/full/347/26/2111}}</ref> It is marketed under the brand name '''Orfadin'''.

Revision as of 07:09, 31 August 2011

Nitisinone
Clinical data
AHFS/Drugs.comConsumer Drug Information
License data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-lifeApproximately 54 h
Identifiers
  • 2-[2-nitro-4-(trifluoromethyl)benzoyl]
    cyclohexane-1,3-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.218.521 Edit this at Wikidata
Chemical and physical data
FormulaC14H10F3NO5
Molar mass329.228 g/mol g·mol−1
3D model (JSmol)
  • O=C(c1ccc(cc1[N+]([O-])=O)C(F)(F)F)C2C(=O)CCCC2=O
  • InChI=1S/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,12H,1-3H2 ☒N
  • Key:OUBCNLGXQFSTLU-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Nitisinone (also known as NTBC, an abbreviation of its full chemical name) is a drug originally developed as an herbicide now used in the treatment of hereditary tyrosinemia type 1. Since its first use for this indication in 1991, it has replaced liver transplantation as the first-line treatment for this rare condition.[1] It is also being studied in the less severe but related condition alkaptonuria.[2] It is marketed under the brand name Orfadin.

The mechanism of action of nitrisinone involves reversibile inhibition of 4-hydroxyphenylpyruvate oxidase,[3] [4] thus preventing the formation of maleylacetoacetic acid and fumarylacetoacetic acid, which have the potential to be converted to succinyl acetone, a toxin that damages the liver and kidneys.[1]

Chem

Anon US application 19,920,903,691 .

References

  1. ^ a b McKiernan PJ (2006). "Nitisinone in the treatment of hereditary tyrosinaemia type 1". Drugs. 66 (6): 743–50. doi:10.2165/00003495-200666060-00002. PMID 16706549.
  2. ^ Phornphutkul C, Introne WJ, Perry MB; et al. (2002). "Natural history of alkaptonuria". New England Journal Medicine. 347 (26): 2111–21. doi:10.1056/NEJMoa021736. PMID 12501223. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  3. ^ Lock EA, Ellis MK, Gaskin P, Robinson M, Auton TR, Provan WM, Smith LL, Prisbylla MP, Mutter LC, Lee DL (1998). "From toxicological problem to therapeutic use: The discovery of the mode of action of 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione (NTBC), its toxicology and development as a drug". Journal of Inherited Metabolic Disease. 42 (21): 498–506. doi:10.1023/A:1005458703363. PMID 9728330.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ Kavana M, Moran GR (2003). "Interaction of (4-hydroxyphenyl)pyruvate dioxygenase with the specific inhibitor 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione". Biochemistry. 42 (34): 10238–45. doi:10.1021/bi034658b. PMID 12939152.
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