2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione

• ChemBase编号: 232
• 分子式: C14H10F3NO5
• 平均质量: 329.2281096
• 单一同位素质量: 329.05110709
• SMILES: FC(F)(F)c1cc([N+](=O)[O-])c(C(=O)C2C(=O)CCCC2=O)cc1
• Canonical SMILES: O=C1CCCC(=O)C1C(=O)c1ccc(cc1[N+](=O)[O-])C(F)(F)F
• InChI: 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
• InChIKey: OUBCNLGXQFSTLU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione
• IUPAC传统名: 2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione; nitisone
• 商标名: Orfadin
• 别名: 2-(2-Nitro-4-(trifluoromethyl)benzoyl)cyclohexane-1,3-dione; nitisinone; Nitisinone; 2-[2-Nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione; NTBC; Nitisone; Orfadin; SC 0735

登记号

• CAS号: 104206-65-7
• PubChem SID: 160963695; 46507380
• PubChem CID: 115355

理论计算性质

JChem

• Acid pKa: 2.6103563
• 质子受体: 5
• 质子供体: 0
• LogD (pH = 5.5): 1.0931233
• LogD (pH = 7.4): 1.0293504
• Log P: 3.1276615
• 摩尔折射率: 71.3436 cm^3
• 极化性: 26.047016 Å^3
• 极化表面积: 94.35 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.06
• LOG S: -4.61
• 溶解度: 8.11e-03 g/l

分子性质

理化性质

• 溶解度: Chloroform; Ethyl Acetate
• 外观: Light Brown Solid
• 熔点: 129-131°C
• 疏水性(logP): 1.6

安全信息

• 保存条件: -20°C Freezer

产品相关信息

• 纯度: 95+%

详细说明

DrugBank - DB00348

• Drug Groups: approved; investigational
• Description: Nitisinone is a synthetic reversible inhibitor of 4-hydroxyphenylpyruvate dioxygenase. It is used in the treatment of hereditary tyrosinemia type 1. It is sold under the brand name Orfadin. [Wikipedia]
• Indication: Used as an adjunct to dietary restriction of tyrosine and phenylalanine in the treatment of hereditary tyrosinemia type 1.
• Pharmacology: Hereditary tyrosinemia type 1 occurs due to a deficiency in fumarylacetoacetase (FAH), the final enzyme in the tyrosine catabolic pathway. Nitisinone inhibits catabolism of tyrosine by preventing the catabolic intermediates. In patients with HT-1, these catabolic intermediates are converted to the toxic metabolites succinylacetone and succinylacetoacetate, which are responsible for the observed liver and kidney toxicity. Succinylacetone can also inhibit the porphyrin synthesis pathway leading to the accumulation of 5-aminolevulinate, a neurotoxin responsible for the porphyric crises characteristic of HT-1.
• Toxicity: Side effects include elevated plasma levels of this amino acid, hepatic and liver failure.
• Affected Organisms: Humans and other mammals
• Absorption: The capsule and liquid formulations are bioequivalent in both the plasma concentration-time curve and maximum plasma concentration (Cmax).
• Half Life: ~54 hours
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - N490135

Nitisinone is a herbicidal triketone that inhibits 4-hydroxyphenylpyruvate dioxygenase (HPPD), an enzyme involved in plastoquinone biosynthesis in plants and in tyrosine catabolism in mammals. It is used in treatment of inherited tyrosinemia type I.

参考文献

• Lindstedt, S., et al.: Lancet, 340, 813 (1992)
• Ellis, M.K., et al.: Toxicol. Appl. Pharmacol., 133, 12 (1992)
• Lock, E.A., et al.: J. Inherited Metab. Dis., 21, 498 (1992)