Carbamazepine
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MedKoo CAT#: 317368

CAS#: 298-46-4

Description: Carbamazepine is a medication used primarily in the treatment of epilepsy and neuropathic pain. For seizures it works as well as phenytoin and valproate. It is not effective for absence seizures or myoclonic seizures. It may be used in schizophrenia along with other medications and as a second line agent in bipolar disorder. It is taken two to four times per day. A controlled release formulation is available for which there is tentative evidence showing less side effects.

Chemical Structure

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Carbamazepine
CAS# 298-46-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317368
Name: Carbamazepine
CAS#: 298-46-4
Chemical Formula: C15H12N2O
Exact Mass: 236.09
Molecular Weight: 236.270
Elemental Analysis: C, 76.25; H, 5.12; N, 11.86; O, 6.77

Price and Availability

Size Price Availability Quantity
10g USD 300 2 Weeks
25g USD 550 2 Weeks
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Synonym: Carbamazepine, Tegretol, Epitol

IUPAC/Chemical Name: benzo[b][1]benzazepine-11-carboxamide

InChi Key: RYLOOVOCHDAWIL-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H12N2O/c16-15(18)12-9-10-5-1-3-7-13(10)17-14-8-4-2-6-11(12)14/h1-9,17H,(H2,16,18)

SMILES Code: O=C(C1=CC2=CC=CC=C2NC3=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

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Carbamazepine (Carbatrol, NSC 169864) is a sodium channel blocker with IC50 of 131 μM in rat brain synaptosomes.
In vitro activity: Carbamazepine, an anticonvulsant known to inhibit voltage-gated sodium channels, has profound effects on K(ATP) channels. Like sulfonylureas, carbamazepine corrects trafficking defects in channels bearing mutations in the first transmembrane domain of SUR1. Moreover, carbamazepine inhibits the activity of K(ATP) channels such that rescued mutant channels are unable to open when the intracellular ATP/ADP ratio is lowered by metabolic inhibition. Here, we investigated the mechanism by which carbamazepine inhibits K(ATP) channel activity. We show that carbamazepine specifically blocks channel response to MgADP. This gating effect resembles that of sulfonylureas. Our results reveal striking similarities between carbamazepine and sulfonylureas in their effects on K(ATP) channel biogenesis and gating and suggest that the 2 classes of drugs may act via a converging mechanism. Reference: Channels (Austin). 2014;8(4):376-82. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/24849284/
In vivo activity: The effects of carbamazepine treatment was treated in female non-obese diabetic (NOD) mice by supplementing LabDiet 5053 with 0.5% w/w carbamazepine to achieve serum carbamazepine levels of 14.98 ± 3.19 µM. Remarkably, diabetes incidence over 25 weeks, as determined by fasting blood glucose, was ~50% lower in carbamazepine treated animals. Partial protection from diabetes in carbamazepine-fed NOD mice was also associated with improved glucose tolerance at 6 weeks of age, prior to the onset of diabetes in our colony. Less insulitis was detected in carbamazepine treated NOD mice at 6 weeks of age, but we did not observe differences in CD4+ and CD8+ T cell composition in the pancreatic lymph node, as well as circulating markers of inflammation. Taken together, our results demonstrate that carbamazepine reduces the development of type 1 diabetes in NOD mice by maintaining functional beta-cell mass. Reference: Sci Rep. 2018 Mar 15;8(1):4588. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/29545618/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Ethanol 18.0 76.18

Preparing Stock Solutions

The following data is based on the product molecular weight 236.27 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.

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
Formulation protocol:
In vitro protocol: 1. Ruiz CE, Manuguerra S, Curcuraci E, Santulli A, Messina CM. Carbamazepine, cadmium chloride and polybrominated diphenyl ether-47, synergistically modulate the expression of antioxidants and cell cycle biomarkers, in the marine fish cell line SAF-1. Mar Environ Res. 2020 Feb;154:104844. doi: 10.1016/j.marenvres.2019.104844. Epub 2019 Nov 21. PMID: 31784109. 2. Zhou Q, Chen PC, Devaraneni PK, Martin GM, Olson EM, Shyng SL. Carbamazepine inhibits ATP-sensitive potassium channel activity by disrupting channel response to MgADP. Channels (Austin). 2014;8(4):376-82. doi: 10.4161/chan.29117. PMID: 24849284; PMCID: PMC4203739.
In vivo protocol: 1. Lee JTC, Shanina I, Chu YN, Horwitz MS, Johnson JD. Carbamazepine, a beta-cell protecting drug, reduces type 1 diabetes incidence in NOD mice. Sci Rep. 2018 Mar 15;8(1):4588. doi: 10.1038/s41598-018-23026-w. PMID: 29545618; PMCID: PMC5854601. 2. Okada M, Hirano T, Mizuno K, Chiba T, Kawata Y, Kiryu K, Wada K, Tasaki H, Kaneko S. Biphasic effects of carbamazepine on the dopaminergic system in rat striatum and hippocampus. Epilepsy Res. 1997 Sep;28(2):143-53. doi: 10.1016/s0920-1211(97)00042-9. PMID: 9267779.

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1: Xiao Y, Gan L, Wang J, Luo M, Luo H. Vigabatrin versus carbamazepine
monotherapy for epilepsy. Cochrane Database Syst Rev. 2015 Nov 18;11:CD008781.
[Epub ahead of print] Review. PubMed PMID: 26580100.


2: Akyol L, Aslan K, Özgen M, Sayarlioglu M. A rare comorbidity: neurosarcoidosis
and cutaneous sarcoidosis. BMJ Case Rep. 2015 Nov 17;2015. pii: bcr2015211439.
doi: 10.1136/bcr-2015-211439. PubMed PMID: 26578505.


3: Ortiz ÓM. [Drug Abuse Comorbidity in Bipolar Disorder]. Rev Colomb Psiquiatr.
2012 Jun;41(2):371-383. doi: 10.1016/S0034-7450(14)60011-1. Epub 2014 May 10.
Review. Spanish. PubMed PMID: 26573500.


4: Gjestad C, Huynh DK, Haslemo T, Molden E. 4β-Hydroxycholesterol correlates
with dose but not steady-state concentration of carbamazepine: indication of
intestinal CYP3A in biomarker formation? Br J Clin Pharmacol. 2015 Nov 17. doi:
10.1111/bcp.12833. [Epub ahead of print] PubMed PMID: 26574235.