VUN 37586
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 581367

CAS#: 21737-58-6

Description: VUN 37586, also known as De(5-carboxamide)oxcarbazepine is a compound useful in organic synthesis. This product has not formal name. For the convenience of scientific communication, we named it by combining its Inchi key (3 letters from the first letter of each section) with the last 5 digits of its CAS number or its molecule weight if its CAS number is not available (see MedKoo Chemical Nomenclature, https://www.medkoo.com/page/naming).


Chemical Structure

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VUN 37586
CAS# 21737-58-6

Theoretical Analysis

MedKoo Cat#: 581367
Name: VUN 37586
CAS#: 21737-58-6
Chemical Formula: C14H11NO
Exact Mass: 209.0841
Molecular Weight: 209.248
Elemental Analysis: C, 80.36; H, 5.30; N, 6.69; O, 7.65

Price and Availability

Size Price Availability Quantity
5.0mg USD 450.0 2 Weeks
10.0mg USD 800.0 2 Weeks
25.0mg USD 1570.0 2 Weeks
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Synonym: De(5-carboxamide)oxcarbazepine; Oxcarbazepine impurity C; Oxcarbazepine related compound E; VUN 37586; VUN-37586; VUN37586

IUPAC/Chemical Name: 10H-Dibenz(b,f)azepin-10-one, 5,11-dihydro-

InChi Key: VSZGCLXGCOECAY-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H11NO/c16-14-9-10-5-1-3-7-12(10)15-13-8-4-2-6-11(13)14/h1-8,15H,9H2

SMILES Code: O=C1CC2=CC=CC=C2NC3=CC=CC=C13

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

Shelf Life: >3 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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 209.248 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.

Recalculate based on batch purity %
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

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1: Bialer M, Soares-da-Silva P. Pharmacokinetics and drug interactions of eslicarbazepine acetate. Epilepsia. 2012 Jun;53(6):935-46. doi: 10.1111/j.1528-1167.2012.03519.x. Epub 2012 May 21. Review. PubMed PMID: 22612290.

2: Fortuna A, Alves G, Falcão A, Soares-da-Silva P. Evaluation of the permeability and P-glycoprotein efflux of carbamazepine and several derivatives across mouse small intestine by the Ussing chamber technique. Epilepsia. 2012 Mar;53(3):529-38. doi: 10.1111/j.1528-1167.2012.03409.x. PubMed PMID: 22372629.

3: Di Resta C, Ambrosi P, Curia G, Becchetti A. Effect of carbamazepine and oxcarbazepine on wild-type and mutant neuronal nicotinic acetylcholine receptors linked to nocturnal frontal lobe epilepsy. Eur J Pharmacol. 2010 Sep 15;643(1):13-20. doi: 10.1016/j.ejphar.2010.05.063. Epub 2010 Jun 16. PubMed PMID: 20561518.

4: Ayala-Guerrero F, Mexicano G, Campos-Sepúlveda E, Romero RM, Reynoso-Robles R, González-Maciel A. Effect of oxcarbazepine pretreatment on convulsive activity and brain damage induced by kainic acid administration in rats. Comp Biochem Physiol A Mol Integr Physiol. 2008 Nov;151(3):471-6. Epub 2007 Jun 23. PubMed PMID: 17669675.

5: Almeida L, Soares-da-Silva P. Eslicarbazepine acetate (BIA 2-093). Neurotherapeutics. 2007 Jan;4(1):88-96. Review. PubMed PMID: 17199020.

6: Lanckmans K, Van Eeckhaut A, Sarre S, Smolders I, Michotte Y. Capillary and nano-liquid chromatography-tandem mass spectrometry for the quantification of small molecules in microdialysis samples: comparison with microbore dimensions. J Chromatogr A. 2006 Oct 27;1131(1-2):166-75. Epub 2006 Aug 30. PubMed PMID: 16938304.

7: Sierra-Paredes G, Núñez-Rodriguez A, Vázquez-López A, Oreiro-García T, Sierra-Marcuño G. Anticonvulsant effect of eslicarbazepine acetate (BIA 2-093) on seizures induced by microperfusion of picrotoxin in the hippocampus of freely moving rats. Epilepsy Res. 2006 Dec;72(2-3):140-6. Epub 2006 Aug 21. PubMed PMID: 16920333.

8: Araújo IM, Ambrósio AF, Leal EC, Verdasca MJ, Malva JO, Soares-da-Silva P, Carvalho AP, Carvalho CM. Neurotoxicity induced by antiepileptic drugs in cultured hippocampal neurons: a comparative study between carbamazepine, oxcarbazepine, and two new putative antiepileptic drugs, BIA 2-024 and BIA 2-093. Epilepsia. 2004 Dec;45(12):1498-505. PubMed PMID: 15571507.

9: Almeida L, Soares-da-Silva P. Safety, tolerability, and pharmacokinetic profile of BIA 2-093, a novel putative antiepileptic, in a rising multiple-dose study in young healthy humans. J Clin Pharmacol. 2004 Aug;44(8):906-18. PubMed PMID: 15286095.

10: Almeida L, Soares-da-Silva P. Safety, tolerability and pharmacokinetic profile of BIA 2-093, a novel putative antiepileptic agent, during first administration to humans. Drugs R D. 2003;4(5):269-84. PubMed PMID: 12952496.

11: Ambrósio AF, Soares-Da-Silva P, Carvalho CM, Carvalho AP. Mechanisms of action of carbamazepine and its derivatives, oxcarbazepine, BIA 2-093, and BIA 2-024. Neurochem Res. 2002 Feb;27(1-2):121-30. Review. PubMed PMID: 11926264.

12: Parada A, Soares-da-Silva P. The novel anticonvulsant BIA 2-093 inhibits transmitter release during opening of voltage-gated sodium channels: a comparison with carbamazepine and oxcarbazepine. Neurochem Int. 2002 Apr;40(5):435-40. PubMed PMID: 11821151.

13: Learmonth DA, Benes J, Parada A, Hainzl D, Beliaev A, Bonifácio MJ, Matias PM, Carrondo MA, Garrett J, Soares-da-Silva P. Synthesis, anticonvulsant properties and pharmacokinetic profile of novel 10,11-dihydro-10-oxo-5H-dibenz/b,f/azepine-5-carboxamide derivatives. Eur J Med Chem. 2001 Mar;36(3):227-36. PubMed PMID: 11337101.

14: Ambrósio AF, Silva AP, Malva JO, Soares-da-Silva P, Carvalho AP, Carvalho CM. Inhibition of glutamate release by BIA 2-093 and BIA 2-024, two novel derivatives of carbamazepine, due to blockade of sodium but not calcium channels. Biochem Pharmacol. 2001 May 15;61(10):1271-5. PubMed PMID: 11322931.

15: Kiguchi S, Ichikawa K, Kojima M. Suppressive effects of oxcarbazepine on tooth pulp-evoked potentials recorded at the trigeminal spinal tract nucleus in cats. Clin Exp Pharmacol Physiol. 2001 Mar;28(3):169-75. PubMed PMID: 11207671.

16: Ambrósio AF, Silva AP, Araújo I, Malva JO, Soares-da-Silva P, Carvalho AP, Carvalho CM. Neurotoxic/neuroprotective profile of carbamazepine, oxcarbazepine and two new putative antiepileptic drugs, BIA 2-093 and BIA 2-024. Eur J Pharmacol. 2000 Oct 13;406(2):191-201. PubMed PMID: 11020481.

17: Benes J, Parada A, Figueiredo AA, Alves PC, Freitas AP, Learmonth DA, Cunha RA, Garrett J, Soares-da-Silva P. Anticonvulsant and sodium channel-blocking properties of novel 10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide derivatives. J Med Chem. 1999 Jul 15;42(14):2582-7. PubMed PMID: 10411478.