3-oxa-11-azatetracyclo[10.4.0.02,4.05,10]hexadeca-1(12),5(10),6,8,13,15-hexaene-11-carboxamide

• ChemBase ID: 130741
• Molecular Formular: C15H12N2O2
• Molecular Mass: 252.26798
• Monoisotopic Mass: 252.08987763
• SMILES: c1ccc2c(c1)C1C(O1)c1ccccc1N2C(=O)N
• Canonical SMILES: NC(=O)N1c2ccccc2C2C(c3c1cccc3)O2
• InChI: InChI=1S/C15H12N2O2/c16-15(18)17-11-7-3-1-5-9(11)13-14(19-13)10-6-2-4-8-12(10)17/h1-8,13-14H,(H2,16,18)
• InChIKey: ZRWWEEVEIOGMMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-oxa-11-azatetracyclo[10.4.0.0^2,^4.0^5,^1^0]hexadeca-1(12),5(10),6,8,13,15-hexaene-11-carboxamide; 3-oxa-11-azatetracyclo[10.4.0.0^2,^4.0^5,^1^0]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
• IUPAC Traditional name: 3-oxa-11-azatetracyclo[10.4.0.0^2,^4.0^5,^1^0]hexadeca-1(12),5(10),6,8,13,15-hexaene-11-carboxamide; 3-oxa-11-azatetracyclo[10.4.0.0^2,^4.0^5,^1^0]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
• Synonyms: 10,11-Epoxycarbamazepine; Carbamazepine 10,11-oxide; GP 49-023; Carbamazepine 10,11-Epoxide; 1a,10b-Dihdyro-6H-dibenzo[b,f]oxireno[d]azepine-6-carboxamide; 10,11-Dihydro-10,11-epoxycarbamazepine; 1a,10b-Dihydro-6H-dibenzo(b,f)oxireno[d]azepine-6-carboxamide; Carbamazepine 10,11-epoxide; 卡马西平 10,11-环氧化物

Database IDs

• CAS Number: 36507-30-9
• MDL Number: MFCD00467137
• PubChem SID: 162225019; 24892674
• PubChem CID: 2555

CALCULATED PROPERTIES

• Acid pKa: 15.959103
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.9744484
• LogD (pH = 7.4): 1.9744484
• Log P: 1.9744484
• Molar Refractivity: 69.9843 cm^3
• Polarizability: 26.979874 Å^3
• Polar Surface Area: 55.56 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Dimethyl Sulfoxide; Dimethylformamide; Ethanol; Water
• Apperance: White Solid
• Melting Point: 204-206°C

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Grade: analytical standard

DETAILS

Sigma Aldrich - C4206

Biochem/physiol Actions
First metabolite of carbamazepine

Toronto Research Chemicals - C175850

A metabolite of Carbamazepine (C175840).Representative lots contained 1-2% carbamazepine by HPLC.

REFERENCES

• Bellucci, G., et al.: J. Med. Chem., 30, 768 (1987)
• Johannessen, S., et al.: Ther. Drug. Monit., 27, 710 (1987)
• Bialer, M., et al.: Expert Opin. Invest. Drugs, 15, 637 (1987)
• Williams, J., et al.: J. Clin. Pharmacol., 46, 258 (1987)