Oxcarbazepine | CAS#28721-07-5

Oxcarbazepine
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318398

CAS#: 28721-07-5

Description: Oxcarbazepine is an anticonvulsant drug primarily used in the treatment of epilepsy. There is some evidence for oxcarbazepine as a mood-stabilizing agent and thus, it can be used as add-on therapy for bipolar disorder in patients that have failed or are unable to tolerate approved treatments.

Chemical Structure

Oxcarbazepine

CAS# 28721-07-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318398
Name: Oxcarbazepine
CAS#: 28721-07-5
Chemical Formula: C15H12N2O2
Exact Mass: 252.09
Molecular Weight: 252.268
Elemental Analysis: C, 71.42; H, 4.79; N, 11.10; O, 12.68

Price and Availability

Size	Price	Availability	Quantity
100g	USD -1
200g	USD -1
50mg	USD 200
100mg	USD 250
200mg	USD 280
500mg	USD 300
1g	USD 350
2g	USD 400
5g	USD 450
10g	USD 550
20g	USD 650
50g	USD 850
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Oxcarbazepine, GP 47680, Timox, Trileptal

IUPAC/Chemical Name: 5-oxo-6H-benzo[b][1]benzazepine-11-carboxamide

InChi Key: QZAQRPLWHYVQMM-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H12N2O2/c16-15(18)12-9-10-5-1-3-7-13(10)17(19)14-8-4-2-6-11(12)14/h1-6,8-9H,7H2,(H2,16,18)

SMILES Code: O=C(C1=CC2=CC=CCC2=[N+]([O-])C3=CC=CC=C13)N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:

Product Data

Instruction:

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Biological target:	Oxcarbazepine is a sodium channel blocker.
In vitro activity:	This study examined whether structural analogs of CBZ, oxcarbazepine (OXC), and its active metabolite, monohydroxy derivative (MHD), also potentiate GABA(A) receptor current and aggravate seizures. OXC, MHD, and CBZ were applied at or below therapeutically relevant concentrations, in the range of 1–100 μM (Clinckers et al., 2005). Reproducible GABAA receptor current potentiation by OXC was seen at all concentrations tested and was similar to that obtained with CBZ (Fig. 2). MHD had no effect on GABAA receptor current at 1 or 10 μM, and while there was some potentiation at 100 μM, this was significantly less than that induced by CBZ and OXC. Reference: Epilepsia. 2009 Jan;50(1):83-7. https://pubmed.ncbi.nlm.nih.gov/18717705/
In vivo activity:	Oxcarbazepine treatment after CA (cardiac arrest) significantly increased the survival rate and improved neurological deficit when compared with vehicle-treated rats with CA (survival rates ≥ 63.6 versus 6.5%), showing that oxcarbazepine treatment dramatically protected cerebellar Purkinje cells from ischemia and reperfusion injury induced by CA. The salvation of the Purkinje cells from ischemic injury by oxcarbazepine treatment paralleled a dramatic reduction in 4HNE (an end-product of lipid peroxidation) and increased or maintained the endogenous antioxidant enzymes (SOD1 and SOD2). In brief, this study shows that therapeutic treatment with oxcarbazepine after CA apparently saved cerebellar neurons (Purkinje cells) from CA-induced neuronal death by attenuating oxidative stress and suggests that oxcarbazepine can be utilized as a therapeutic medicine for ischemia and reperfusion brain (cerebellar) injury induced by CA. Reference: Antioxidants (Basel). 2022 Dec 12;11(12):2450. https://pubmed.ncbi.nlm.nih.gov/36552657/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	20.0	79.28
	DMF:PBS (pH 7.2) (1:1)	0.5	1.98
	DMSO	19.9	78.89

Preparing Stock Solutions

The following data is based on the product molecular weight 252.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Zheng T, Clarke AL, Morris MJ, Reid CA, Petrou S, O'Brien TJ. Oxcarbazepine, not its active metabolite, potentiates GABAA activation and aggravates absence seizures. Epilepsia. 2009 Jan;50(1):83-7. doi: 10.1111/j.1528-1167.2008.01759.x. Epub 2008 Aug 19. PMID: 18717705. 2. Schmutz M, Brugger F, Gentsch C, McLean MJ, Olpe HR. Oxcarbazepine: preclinical anticonvulsant profile and putative mechanisms of action. Epilepsia. 1994;35 Suppl 5:S47-50. doi: 10.1111/j.1528-1157.1994.tb05967.x. PMID: 8039471. 3. Kim YH, Lee TK, Lee JC, Kim DW, Hong S, Cho JH, Shin MC, Choi SY, Won MH, Kang IJ. Therapeutic Administration of Oxcarbazepine Saves Cerebellar Purkinje Cells from Ischemia and Reperfusion Injury Induced by Cardiac Arrest through Attenuation of Oxidative Stress. Antioxidants (Basel). 2022 Dec 12;11(12):2450. doi: 10.3390/antiox11122450. PMID: 36552657; PMCID: PMC9774942. 4. Kim HI, Lee JC, Kim DW, Shin MC, Cho JH, Ahn JH, Lim SS, Kang IJ, Park JH, Won MH, Lee TK. Hypothermia Induced by Oxcarbazepine after Transient Forebrain Ischemia Exerts Therapeutic Neuroprotection through Transient Receptor Potential Vanilloid Type 1 and 4 in Gerbils. Int J Mol Sci. 2021 Dec 27;23(1):237. doi: 10.3390/ijms23010237. PMID: 35008663; PMCID: PMC8745517.
In vitro protocol:	1. Zheng T, Clarke AL, Morris MJ, Reid CA, Petrou S, O'Brien TJ. Oxcarbazepine, not its active metabolite, potentiates GABAA activation and aggravates absence seizures. Epilepsia. 2009 Jan;50(1):83-7. doi: 10.1111/j.1528-1167.2008.01759.x. Epub 2008 Aug 19. PMID: 18717705. 2. Schmutz M, Brugger F, Gentsch C, McLean MJ, Olpe HR. Oxcarbazepine: preclinical anticonvulsant profile and putative mechanisms of action. Epilepsia. 1994;35 Suppl 5:S47-50. doi: 10.1111/j.1528-1157.1994.tb05967.x. PMID: 8039471.
In vivo protocol:	1. Kim YH, Lee TK, Lee JC, Kim DW, Hong S, Cho JH, Shin MC, Choi SY, Won MH, Kang IJ. Therapeutic Administration of Oxcarbazepine Saves Cerebellar Purkinje Cells from Ischemia and Reperfusion Injury Induced by Cardiac Arrest through Attenuation of Oxidative Stress. Antioxidants (Basel). 2022 Dec 12;11(12):2450. doi: 10.3390/antiox11122450. PMID: 36552657; PMCID: PMC9774942. 2. Kim HI, Lee JC, Kim DW, Shin MC, Cho JH, Ahn JH, Lim SS, Kang IJ, Park JH, Won MH, Lee TK. Hypothermia Induced by Oxcarbazepine after Transient Forebrain Ischemia Exerts Therapeutic Neuroprotection through Transient Receptor Potential Vanilloid Type 1 and 4 in Gerbils. Int J Mol Sci. 2021 Dec 27;23(1):237. doi: 10.3390/ijms23010237. PMID: 35008663; PMCID: PMC8745517.

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1: Yang Z, Xu X, Sun L, Zhao X, Wang H, Fawcett JP, Yang Y, Gu J. Development and validation of an enantioselective SFC-MS/MS method for simultaneous separation and quantification of oxcarbazepine and its chiral metabolites in beagle dog plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 May 1;1020:36-42. doi: 10.1016/j.jchromb.2016.03.013. Epub 2016 Mar 15. Review. PubMed PMID: 27003707.

2: Fang S, Gong ZC. [Adverse effects of oxcarbazepine]. Zhongguo Dang Dai Er Ke Za Zhi. 2015 Apr;17(4):414-9. Review. Chinese. PubMed PMID: 25919567.

3: Kaniwa N, Saito Y. The risk of cutaneous adverse reactions among patients with the HLA-A* 31:01 allele who are given carbamazepine, oxcarbazepine or eslicarbazepine: a perspective review. Ther Adv Drug Saf. 2013 Dec;4(6):246-53. doi: 10.1177/2042098613499791. Review. PubMed PMID: 25114785; PubMed Central PMCID: PMC4125310.

4: Zaccara G, Giovannelli F, Maratea D, Fadda V, Verrotti A. Neurological adverse events of new generation sodium blocker antiepileptic drugs. Meta-analysis of randomized, double-blinded studies with eslicarbazepine acetate, lacosamide and oxcarbazepine. Seizure. 2013 Sep;22(7):528-36. doi: 10.1016/j.seizure.2013.03.016. Epub 2013 Apr 25. Review. PubMed PMID: 23623245.

5: Fanella M, Egeo G, Fattouch J, Casciato S, Lapenta L, Morano A, Giallonardo AT, Di Bonaventura C. Oxcarbazepine-induced myoclonic status epilepticus in juvenile myoclonic epilepsy. Epileptic Disord. 2013 Jun;15(2):181-7. doi: 10.1684/epd.2013.0563. Review. PubMed PMID: 23774821.

6: Nolan SJ, Muller M, Tudur Smith C, Marson AG. Oxcarbazepine versus phenytoin monotherapy for epilepsy. Cochrane Database Syst Rev. 2013 May 31;(5):CD003615. doi: 10.1002/14651858.CD003615.pub3. Review. PubMed PMID: 23728645.

7: Zhou M, Chen N, He L, Yang M, Zhu C, Wu F. Oxcarbazepine for neuropathic pain. Cochrane Database Syst Rev. 2013 Mar 28;(3):CD007963. doi: 10.1002/14651858.CD007963.pub2. Review. PubMed PMID: 23543558.

8: Cárdenas-Rodríguez N, Coballase-Urrutia E, Rivera-Espinosa L, Romero-Toledo A, Sampieri A 3rd, Ortega-Cuellar D, Montesinos-Correa H, Floriano-Sánchez E, Carmona-Aparicio L. Modulation of antioxidant enzymatic activities by certain antiepileptic drugs (valproic acid, oxcarbazepine, and topiramate): evidence in humans and experimental models. Oxid Med Cell Longev. 2013;2013:598493. doi: 10.1155/2013/598493. Epub 2013 Dec 17. Review. PubMed PMID: 24454986; PubMed Central PMCID: PMC3877618.

9: Vasudev A, Macritchie K, Vasudev K, Watson S, Geddes J, Young AH. Oxcarbazepine for acute affective episodes in bipolar disorder. Cochrane Database Syst Rev. 2011 Dec 7;(12):CD004857. doi: 10.1002/14651858.CD004857.pub2. Review. PubMed PMID: 22161387.

10: Barrons R, Roberts N. The role of carbamazepine and oxcarbazepine in alcohol withdrawal syndrome. J Clin Pharm Ther. 2010 Apr;35(2):153-67. doi: 10.1111/j.1365-2710.2009.01098.x. Review. PubMed PMID: 20456734.

11: Bouquié R, Dailly E, Bentué-Ferrer D; le groupe Suivi Thérapeutique Pharmacologique de la Société Française de Pharmacologie et de Thérapeutique. [Therapeutic drug monitoring of oxcarbazepine]. Therapie. 2010 Jan-Feb;65(1):61-5. doi: 10.2515/therapie/2009070. Epub 2010 Mar 8. Review. French. PubMed PMID: 20205998.

12: Koch MW, Polman SK. Oxcarbazepine versus carbamazepine monotherapy for partial onset seizures. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD006453. doi: 10.1002/14651858.CD006453.pub2. Review. PubMed PMID: 19821367.

13: Bring P, Ensom MH. Does oxcarbazepine warrant therapeutic drug monitoring? A critical review. Clin Pharmacokinet. 2008;47(12):767-78. doi: 10.2165/0003088-200847120-00002. Review. PubMed PMID: 19026033.

14: Nasreddine W, Beydoun A. Oxcarbazepine in neuropathic pain. Expert Opin Investig Drugs. 2007 Oct;16(10):1615-25. Review. PubMed PMID: 17922625.

15: Knudsen JF, Flowers CM, Kortepeter C, Awaad Y. Clinical profile of oxcarbazepine-related angioneurotic edema: case report and review. Pediatr Neurol. 2007 Aug;37(2):134-7. Review. PubMed PMID: 17675030.

16: Popova E, Leighton C, Bernabarre A, Bernardo M, Vieta E. Oxcarbazepine in the treatment of bipolar and schizoaffective disorders. Expert Rev Neurother. 2007 Jun;7(6):617-26. Review. PubMed PMID: 17563245.

17: Muller M, Marson AG, Williamson PR. Oxcarbazepine versus phenytoin monotherapy for epilepsy. Cochrane Database Syst Rev. 2006 Apr 19;(2):CD003615. Review. Update in: Cochrane Database Syst Rev. 2013;5:CD003615. PubMed PMID: 16625587.

18: Horga de la Parte JF, Horga A. [Oxcarbazepine in the treatment of epilepsy. A review and update]. Rev Neurol. 2006 Jan 16-31;42(2):95-113. Review. Spanish. PubMed PMID: 16450324.

19: Hirschfeld RM, Kasper S. A review of the evidence for carbamazepine and oxcarbazepine in the treatment of bipolar disorder. Int J Neuropsychopharmacol. 2004 Dec;7(4):507-22. Epub 2004 Sep 30. Review. PubMed PMID: 15458610.

20: Centorrino F, Albert MJ, Berry JM, Kelleher JP, Fellman V, Line G, Koukopoulos AE, Kidwell JE, Fogarty KV, Baldessarini RJ. Oxcarbazepine: clinical experience with hospitalized psychiatric patients. Bipolar Disord. 2003 Oct;5(5):370-4. Review. PubMed PMID: 14525559.

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