(9S)-2-carbamoyl-2-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaen-9-yl acetate

• ChemBase ID: 155793
• Molecular Formular: C17H16N2O3
• Molecular Mass: 296.32054
• Monoisotopic Mass: 296.11609238
• SMILES: CC(=O)O[C@H]1Cc2ccccc2N(c2c1cccc2)C(=O)N
• Canonical SMILES: CC(=O)O[C@H]1Cc2ccccc2N(c2c1cccc2)C(=O)N
• InChI: InChI=1S/C17H16N2O3/c1-11(20)22-16-10-12-6-2-4-8-14(12)19(17(18)21)15-9-5-3-7-13(15)16/h2-9,16H,10H2,1H3,(H2,18,21)/t16-/m0/s1
• InChIKey: QIALRBLEEWJACW-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9S)-2-carbamoyl-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3(8),4,6,11,13-hexaen-9-yl acetate; (9S)-2-carbamoyl-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-yl acetate
• IUPAC Traditional name: (9S)-2-carbamoyl-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3(8),4,6,11,13-hexaen-9-yl acetate; eslicarbazepine acetate
• Synonyms: S-(-)-10-Acetoxy-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide; BIA 2-093; (10S)-10-(Acetyloxy)-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide; (S)-(-)-10-Acetoxy-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide; BIA 2-093; Sep 0002093; Eslicarbazepine Acetate

Database IDs

• CAS Number: 236395-14-5
• MDL Number: MFCD06798333
• PubChem SID: 162249931; 24891837
• PubChem CID: 179344

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.1728663
• LogD (pH = 7.4): 2.1728663
• Log P: 2.1728663
• Molar Refractivity: 81.4384 cm^3
• Polarizability: 31.473017 Å^3
• Polar Surface Area: 72.63 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 15.959561

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: ~21 mg/mL; H2O: insoluble
• Apperance: white solid; White to Off-White Solid
• Melting Point: 183-185°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Scnn1g(24768)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H16N2O3

DETAILS

Sigma Aldrich - B5435

Biochem/physiol Actions
Blocker of voltage-gated sodium channels; significantly blocks excitatory amino acid (glutamate and aspartate) release.

Toronto Research Chemicals - E659000

Eslicarbazepine acetate, (BIA 2-093), is a promising antiepileptic drug structurally related to Carbamazepine and Oxcarbazepine.

REFERENCES

• Benes, J., et al.: J. Med. Chem., 42, 2582 (1999)
• Tong, X., et al.: Br. J. Pharmacol., 133, 867 (1999)
• Almeida, L., et al.: J. Clin. Pharmacol., 45, 1062 (1999)
• Elger, C., et al.: Epilepsia, 48, 497 (1999)