Oxcarbazepine

Base Information

• Chemical Name: Oxcarbazepine
• CAS No.: 28721-07-5
• Molecular Formula: C15H12N2O2
• Molecular Weight: 252.272
• Hs Code.: 29339900
• European Community (EC) Number: 249-188-8
• NSC Number: 758693
• UNII: VZI5B1W380
• DSSTox Substance ID: DTXSID0045703
• Nikkaji Number: J21.258J
• Wikipedia: Oxcarbazepine
• Wikidata: Q176301
• NCI Thesaurus Code: C47643
• RXCUI: 32624
• Pharos Ligand ID: VZRCU7JKKM9N
• Metabolomics Workbench ID: 43071
• ChEMBL ID: CHEMBL1068
• Mol file: 28721-07-5.mol

Synonyms:10,11-dihydro-10-oxo-5H-dibenz(b,f)azepine-5-carboxamide;GP 47680;oxcarbazepine;Timox;Trileptal

Chemical Property of Oxcarbazepine

Chemical Property:

• Appearance/Colour: Pale yellow powder
• Vapor Pressure: 1.52E-08mmHg at 25°C
• Melting Point: 215-216 °C
• Refractive Index: 1.661
• Boiling Point: 457.2 °C at 760 mmHg
• PKA: 13.73±0.20(Predicted)
• Flash Point: 230.3 °C
• PSA: 63.40000
• Density: 1.329 g/cm³
• LogP: 3.40750
• Storage Temp.: Store at RT
• Solubility.: DMSO: ~9 mg/mL
• Water Solubility.: Soluble in DMSO, methanol, water, ethanol and acetone.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 252.089877630
• Heavy Atom Count: 19
• Complexity: 382

Purity/Quality:

99% ^*data from raw suppliers

Oxcarbazepine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,F
• Hazard Codes: Xn,F
• Statements: 22-36-20/21/22-11
• Safety Statements: 16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anticonvulsants
• Canonical SMILES: C1C2=CC=CC=C2N(C3=CC=CC=C3C1=O)C(=O)N
• Recent ClinicalTrials: Gabapentin and Oxcarbazepine for Chronic Neuropathic Pain in Children and Adolescents: A Clinical Effectiveness Study
• Recent EU Clinical Trials: EFFICACY AND TOLERABILITY OF LOW VS. STANDARD DAILY DOSES OF ANTIEPILEPTIC DRUGS IN NEWLY DIAGNOSED, PREVIOUSLY UNTREATED EPILEPSY (STANDLOW). A MULTICENTER, RANDOMIZED, SINGLE-BLIND, PARALLEL GROUP TRIAL.
• Description: Oxcarbazepine is a new antiepileptic carbamazepine derivative, reportedly better tolerated than carbamazepine. It appears to be most effective in partial epilepsy with complex seizures.
• Uses: A metabolite of Eslicarbazepine acetate, (BIA 2-093), a novel central nervous system drug. beta-adrenergic blocker Oxcarbazepine is a sodium channel protein inhibitor. It is an anticonvulsant and mood-stab. The keto derivative of Carbamazepine. Used as an anticonvulsant
• Biological Functions: Oxcarbazepine is chemically and pharmacologically closely related to carbamazepine, but it has much less capacity to induce drug-metabolizing enzymes. This property decreases the problems associated with drug interactions when oxcarbazepine is used in combination with other drugs. The clinical uses and adverse effect profile of oxcarbazepine appear to be similar to those of carbamazepine.
• Clinical Use: Oxcarbazepine (Trileptal?) is the 10-keto analogue of carbamazepine. It is indicated as monotherapy or adjunctive therapy for partial seizures in adults with epilepsy, as monotherapy for the treatment of partial seizures in children 4 years of age or older, and as adjunct therapy in children 2 to 4 years of age.
• Drug interactions: Potentially hazardous interactions with other drugs Antidepressants: antagonism of anticonvulsant effect; avoid with St John’s wort. Antiepileptics: concentration of perampanel reduced, also increased oxcarbazepine concentration. Antimalarials: anticonvulsant effect antagonised by mefloquine. Antipsychotics: antagonism of anticonvulsant effect. Antivirals: concentration of rilpivirine and possibly daclatasvir and simeprevir reduced - avoid; possibly reduces dolutegravir concentration. Ciclosporin: metabolism accelerated (reduced ciclosporin concentration). Clopidogrel: possibly reduced antiplatelet effect. Cytotoxics: concentration of imatinib reduced - avoid. Guanfacine: possibly reduces guanfacine concentration - increase dose of guanfacine. Oestrogens and progestogens: metabolism accelerated (reduced contraceptive effect). Orlistat: possible increased risk of convulsions. Tacrolimus: metabolism accelerated (reduced tacrolimus concentration). Ulipristal: possibly reduces contraceptive effect.

Technology Process of Oxcarbazepine

There total 69 articles about Oxcarbazepine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.7%

10,11-dihydro-10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide (98253-74-8) → oxcarbazepine (28721-07-5)

Guidance literature:

With hydrogenchloride; In ethanol; water; for 1.3h; Solvent;

Reference yield: 93.0%

isocyanate de chlorosulfonyle (1189-71-5) + 10,11-dihydro-5H-dibenzo[b,f]azepin-10-one (21737-58-6) → oxcarbazepine (28721-07-5)

Guidance literature:

In dichloromethane; at 0 - 5 ℃; Inert atmosphere;

Reference yield: 90.0%

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide (29331-92-8) → oxcarbazepine (28721-07-5)

Guidance literature:

With peracetic acid; potassium dichromate; hydrogen; In 1,2-dichloro-ethane; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2013.12.035

upstream raw materials:

isocyanate de chlorosulfonyle

10,11-dihydro-5H-dibenzo[b,f]azepin-10-one

10-methoxy-5H-dibenzo[b,f]azepine

sodium isocyanate

Downstream raw materials:

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide

R-licarbazepine

S-licarbazepine

10-acetoxy-5H-dibenzo[b,f]azepine-5-carboxamide

Refernces

• 1、 Velugula, Siva Rama Kasibabu,Reddy, Aaramadaka Sunil Kumar,Misra, Nimesh Chandra,Reddy, Pindi Santhosh,Chavakula, Ramadas,Guduri, Anil Kumar,DouglasSanasi, Paul. "Synthesis and characterization of potential impurities of Oxcarbazepine drug substance: An antiepileptic agent". . p. 1581 - 1587. Retrieved 2021/05/06.
• 2、 -. "Intermediate compound, carbamazepine and derivative thereof as well as preparation method of oxcarbazepine and derivative thereof". . . Retrieved 2019/12/25.