9-oxo-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide

• ChemBase编号: 656
• 分子式: C15H12N2O2
• 平均质量: 252.26798
• 单一同位素质量: 252.08987763
• SMILES: O=C1Cc2c(N(c3c1cccc3)C(=O)N)cccc2
• Canonical SMILES: O=C1Cc2ccccc2N(c2c1cccc2)C(=O)N
• InChI: InChI=1S/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)
• InChIKey: CTRLABGOLIVAIY-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 9-oxo-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide; 9-oxo-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide; 9-oxo-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide
• IUPAC传统名: 9-oxo-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide; oxcarbazepine; 9-oxo-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide
• 商标名: Trileptal
• 别名: Oxcarbamazepine; Oxcarbazepine; 10,11-Dihydro-10-oxo-5h-dibenz[b,f]azepine-5-carboxamide; Oxacarbazepine; Oxcarbazepine; 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide; 10,11-Dihdyro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide; Aurene; GP 47680; Oxecarb; Oxetol; Trileptal; Oxcarb; 9-oxo-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide

登记号

• CAS号: 28721-07-5
• EC号: 249-188-8
• MDL号: MFCD00865307
• PubChem SID: 46507580; 24724563; 160964119
• PubChem CID: 34312

理论计算性质

JChem

• Acid pKa: 12.921005
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 1.8181766
• LogD (pH = 7.4): 1.8181754
• Log P: 1.8181767
• 摩尔折射率: 71.5579 cm^3
• 极化性: 27.078526 Å^3
• 极化表面积: 63.4 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.76
• LOG S: -3.2
• 溶解度: 1.60e-01 g/l

分子性质

理化性质

• 溶解度: 308 mg/L at 25 oC (SRC PhysProp estimated -- MEYLAN,WM et al. (1996)); DMSO: ~9 mg/mL; Methanol
• 外观: white solid; Yellow Solid
• 熔点: 215-216°C
• 疏水性(logP): 1.206; 1.5

安全信息

• 保存条件: -20°C Freezer, Under Inert Atmosphere
• RTECS编号: HN8445000
• 德国WGK号: 3
• TSCA收录: 否
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 作用靶点: Sodium Channel
• 相关基因信息: rat ... Scnn1g(24768)
• 生物活性机理: Adenosine-Agonist-A1; Gabaminergic-A; Sodium channel inhibitor; Sympathomimetic-Alpha-2

产品相关信息

• 纯度: ≥98% (HPLC); 95%; 98%
• 成盐信息: Free Base
• 应用领域: Analgesic; Anticonvulsant; Neuroleptic agent
• Empirical Formula (Hill Notation): C15H12N2O2

详细说明

DrugBank - DB00776

• Drug Groups: approved
• Description: Oxcarbazepine is structurally a derivative of carbamazepine, adding an extra oxygen atom to the benzylcarboxamide group. This difference helps reduce the impact on the liver of metabolizing the drug, and also prevents the serious forms of anemia occasionally associated with carbamazepine. Aside from this reduction in side effects, it is thought to have the same mechanism as carbamazepine - sodium channel inhibition - and is generally used to treat partial seizures in epileptic children and adults.
• Indication: For use as monotherapy or adjunctive therapy in the treatment of partial seizures in adults with epilepsy and as adjunctive therapy in the treatment of partial seizures in children ages 4-16 with epilepsy.
• Pharmacology: Oxcarbazepine is structurally a derivative of carbamazepine, adding an extra oxygen atom to the benzylcarboxamide group. This difference helps reduce the impact on the liver of metabolizing the drug, and also prevents the serious forms of anemia occasionally associated with carbamazepine. Aside from this reduction in side effects, it is thought to have the same mechanism as carbamazepine - sodium channel inhibition - and is generally used to treat the same conditions.
• Toxicity: Isolated cases of overdose with oxcarbazepine have been reported. The maximum dose taken was approximately 24,000 mg. All patients recovered with symptomatic treatment.
• Affected Organisms: Humans and other mammals
• Biotransformation: Oxcarbazepine is completely absorbed and extensively metabolized to its pharmacologically active 10-monohydroxy metabolite (MHD). MHD is metabolized further by conjugation with glucuronic acid.
• Absorption: Completely absorbed following oral administration. Food has no effect on the rate and extent of absorption of oxcarbazepine.
• Half Life: The half-life of the parent is about 2 hours, while the half-life of MHD is about 9 hours, so that MHD is responsible for most anti-epileptic activity.
• Protein Binding: Approximately 40% of the active 10-monohydroxy metabolite (MHD) is bound to serum proteins, predominantly to albumin. Neither oxcarbazepine nor its MHD binds with alpha-1–acid blycoprotein.
• Elimination: Oxcarbazepine is cleared from the body mostly in the form of metabolites which are predominantly excreted by the kidneys. Fecal excretion accounts for less than 4% of the administered dose.
• Distribution: * 49 L
• References: Mazza M, Della Marca G, Di Nicola M, Martinotti G, Pozzi G, Janiri L, Bria P, Mazza S: Oxcarbazepine improves mood in patients with epilepsy. Epilepsy Behav. 2007 May;10(3):397-401. Epub 2007 Feb 14. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - O3764

Biochem/physiol Actions
Anticonvulsant, antineuralgic. Inhibits veratrine-induced transmitter release.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. O3764.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - O869250

A metabolite of Eslicarbazepine acetate, (BIA 2-093), a novel central nervous system drug. A keto derivative of Carbamazepine. Used as an anticonvulsant.

参考文献

• Mazza M, Della Marca G, Di Nicola M, Martinotti G, Pozzi G, Janiri L, Bria P, Mazza S: Oxcarbazepine improves mood in patients with epilepsy. Epilepsy Behav. 2007 May;10(3):397-401. Epub 2007 Feb 14. Pubmed
• Dam., M., et al.: Epilepsy Res., 3, 70 (1989)
• Beydoun, A., et al.: Expert Opin. Pharmacother., 3, 59 (1989)
• U.K. Pat., 1963, 943 277; CA, 61, 1815f, (synth)
• Ger. Pat., 1970, 2 011 087; CA, 73, 109711r, (deriv, synth, pharmacol)
• Feldmann, K.F. et al., Adv. Epileptol., 1981, 12, 89, (metab)
• Theisohn, M. et al., Eur. J. Clin. Pharmacol., 1982, 22, 545, (metab)
• Kumps, A., J. Liq. Chromatogr., 1984, 7, 1235, (hplc)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 301
• Schachter, S.C. et al., Expert Opin. Invest. Drugs, 1999, 8, 1103-1112
• Lohse, O. et al., Tet. Lett., 2001, 42, 385-389, (deriv, synth)