104746-04-5

Basic information

• Product Name: S-10-MONOHYDROXY-DIHYDRO-CARBAMAZEPIN
• Synonyms: S-10-MONOHYDROXY-DIHYDRO-CARBAMAZEPIN;(10S)-10,11-DIHYDRO-10-HYDROXY CARBAMAZEPINE;S-(+)-10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide,S-MHD;(S)-10-Monohydroxy-dihydro-carbamazepine (Eslicarbazepine);(S)-10-Hydroxy-10,11-dihydro-5H-dibenzo[b,f]azepin-5-carboxamide;(S)-10-Monohydroxydihydrocarbamazepine;(S)-Licarbazepine;(10S)-
• CAS NO: 104746-04-5
• Molecular Formula: C₁₅H₁₄N₂O₂
• Molecular Weight: 254.288
• Product Categories: Chiral Reagents;Metabolites;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 104746-04-5.mol
• Article Data: 32

Chemical Properties

• Melting Point: 188-190°C
• Boiling Point: 431.275 °C at 760 mmHg
• Flash Point: 214.628 °C
• Appearance: off-white solid
• Density: 1.336
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly), Pyridine (Slightly)
• PKA: 13.75±0.20(Predicted)
• CAS DataBase Reference: S-10-MONOHYDROXY-DIHYDRO-CARBAMAZEPIN(CAS DataBase Reference)
• NIST Chemistry Reference: S-10-MONOHYDROXY-DIHYDRO-CARBAMAZEPIN(104746-04-5)
• EPA Substance Registry System: S-10-MONOHYDROXY-DIHYDRO-CARBAMAZEPIN(104746-04-5)

Safety Data

• Hazardous Substances Data: 104746-04-5(Hazardous Substances Data)

Usage

Description

S-10-MONOHYDROXY-DIHYDRO-CARBAMAZEPIN, also known as (S)-10-Monohydroxy-10,11-dihydro Carbamazepine, is an optically active metabolite of carbamazepine. It is an off-white solid and is derived from Eslicarbazepine acetate, which is a novel central nervous system drug. S-10-MONOHYDROXY-DIHYDRO-CARBAMAZEPIN plays a significant role in the pharmaceutical industry due to its unique properties and applications.

Uses

Used in Pharmaceutical Industry:
S-10-MONOHYDROXY-DIHYDRO-CARBAMAZEPIN is used as an active metabolite for the treatment of various central nervous system disorders. As a metabolite of carbamazepine, it contributes to the therapeutic effects of the parent drug, enhancing its efficacy in managing conditions such as epilepsy and neuropathic pain.
Used in Research and Development:
In the field of pharmaceutical research and development, S-10-MONOHYDROXY-DIHYDRO-CARBAMAZEPIN serves as a valuable compound for studying the mechanisms of action, pharmacokinetics, and potential drug interactions of carbamazepine and its derivatives. This helps in the development of new drugs with improved safety and efficacy profiles.
Used in Quality Control and Standardization:
S-10-MONOHYDROXY-DIHYDRO-CARBAMAZEPIN is utilized as a reference compound in the quality control and standardization of carbamazepine-containing pharmaceutical products. Its presence in these products ensures that they meet the required specifications and maintain a consistent level of therapeutic activity.
Used in Drug Metabolism Studies:
S-10-MONOHYDROXY-DIHYDRO-CARBAMAZEPIN is also used in drug metabolism studies to understand how carbamazepine is metabolized in the body and how its metabolites contribute to its overall pharmacological effects. This knowledge is crucial for optimizing drug dosages and minimizing potential side effects.

InChI:InChI=1/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)/t14-/m0/s1

Upstream product

• 28721-07-5 oxcarbazepine 
• 356760-08-2 5-Carbamoyl-5H-dibenz[b,f]azepinEN₅-Cyano-10-hydroxy-10,11-dihydro-5H-dibenz[b,f]azepine 
• 29331-92-8 10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide 
• 1296102-94-7 C₁₈H₁₈N₂O₄ 
• 1296102-92-5 licarbazepine methoxyacetate 
• 1346462-62-1 (R)-((S)-5-carbamoyl-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl) 1-benzylpyrrolidine-2-carboxylate 
• 186694-45-1 Licarbazepine acetate 
• 123-20-6 vinyl n-butyrate 
• 105-38-4 vinyl propionate 
• 108-05-4 vinyl acetate 
• 769-78-8 vinyl benzoate 
• 21737-58-6 10,11-dihydro-5H-dibenzo[b,f]azepin-10-one 
• 186694-45-1 eslicarbazepine acetate 
• 36507-30-9 carbamazepine 10,11-epoxide 

Downstream Products

• 186694-45-1 (+)-Licarbazepine acetate 
• 186694-45-1 eslicarbazepine acetate 

Relevant articles and documents

Synthesis of S-licarbazepine by asymmetric reduction of oxcarbazepine with Saccharomyces cerevisiae CGMCC No. 2266

S-licarbazepine was synthesized by asymmetric reduction of oxcarbazepine with CGMCC No. 2266. The optimum batch reduction conditions were found to consist of a reaction time of 36 h, temperature of 30 °C, and initial pH value of 7.0. The optimum concentration of the glucose co-substrate was found to be 0.3 mol L-1. The addition of glucose contributed to in situ regeneration of NADPH in cells and improved conversion. Conversion increased with the addition of more biomass and with a decrease in the initial concentration of substrate. Within the membrane reactor, a continuous reduction process was used to improve production efficiency and reduce the inhibition of high-concentration substrate upon reduction. The optimum flux was found to be 20 ml h-1. S-licarbazepine yield was 3.7678 mmol L-1 d -1 in continuous reduction over four days. The enantiometric excess of S-licarbazepine was 100% for both batch and continuous reduction processes.

Preparation method of eslicarbazepine

The invention relates to the field of preparation of chemical substances and medicines, in particular to a preparation method of eslicarbazepine. The method is characterized in that oxcarbazepine is subjected to a reaction in the presence of a chiral catalyst and a hydrogen source to obtain eslicarbazepine, and the reaction equation is disclosed in the invention, wherein the chiral catalyst can be R1, R2, R3, R4, R5 and R6 which can be hydrogen or methyl respectively; M is Ru, Rh or Ir.

Chiral amino-pyridine-phosphine tridentate ligand, manganese complex, and preparation method and application thereof

The invention discloses a chiral amino-pyridine-phosphine tridentate ligand, a manganese complex, and a preparation method and application thereof. The chiral amino-pyridine-phosphine tridentate ligand is shown as a formula II, and the manganese complex of the chiral amino-pyridine-phosphine tridentate ligand can be used for efficiently catalyzing and hydrogenating ketone compounds to prepare chiral alcohol compounds in a high enantioselectivity mode. The chiral amino-pyridine-phosphine tridentate ligand and the manganese complex are simple in synthesis process, good in stability, high in catalytic activity and mild in reaction conditions.

Brain-targeting eslicarbazepine ester prodrug and application thereof

The invention relates to an eslicarbazepine ester prodrug and an application thereof, wherein the prodrug is a compound represented by the formula (I) or optical isomers or physiologically acceptable salts of the compound represented by the formula (I), wherein R represents a lipophilic substituent. The compound represented by the formula (I) is the eslicarbazepine ester prodrug containing the lipophilic substituent, is converted into eslicarbazepine through metabolism in vivo to play pharmacological effects, and can be applied in preparation of drugs for treatment, prevention or adjuvant treatment of central nervous system diseases, such as epilepsy and the like.