(18S)-18-{[bis(2H3)methylamino]methyl}-17-oxa-4,14,21-triazahexacyclo[19.6.1.17,14.02,6.08,13.022,27]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaene-3,5-dione hydrochloride

• ChemBase ID: 177652
• Molecular Formular: C28H29ClN4O3
• Molecular Mass: 505.00786
• Monoisotopic Mass: 504.19281849
• SMILES: C12=C(C(=O)NC1=O)c1c3c(cccc3)n(c1)CC[C@H](OCCn1c3ccccc3c2c1)CN(C)C.Cl
• Canonical SMILES: CN(C[C@H]1OCCn2cc(c3c2cccc3)C2=C(c3cn(CC1)c1ccccc31)C(=O)NC2=O)C.Cl
• InChI: InChI=1S/C28H28N4O3.ClH/c1-30(2)15-18-11-12-31-16-21(19-7-3-5-9-23(19)31)25-26(28(34)29-27(25)33)22-17-32(13-14-35-18)24-10-6-4-8-20(22)24;/h3-10,16-18H,11-15H2,1-2H3,(H,29,33,34);1H/t18-;/m0./s1
• InChIKey: NYQIEYDJYFVLPO-FERBBOLQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (18S)-18-{[bis(^2H₃)methylamino]methyl}-17-oxa-4,14,21-triazahexacyclo[19.6.1.1^7,^1^4.0^2,^6.0^8,^1^3.0^2^2,^2^7]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaene-3,5-dione hydrochloride
• IUPAC Traditional name: (18S)-18-{[bis(^2H₃)methylamino]methyl}-17-oxa-4,14,21-triazahexacyclo[19.6.1.1^7,^1^4.0^2,^6.0^8,^1^3.0^2^2,^2^7]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaene-3,5-dione hydrochloride
• Synonyms: 1-[(2,6-Difluorophenyl)methyl]-1H-1,2,3-triazole-4-carboxamide; CGP 33101; E 2080; Inovelon; RUF 331; Rufinamide

Database IDs

• CAS Number: 106308-44-5
• PubChem SID: 164233562
• PubChem CID: 71752139

CALCULATED PROPERTIES

• Acid pKa: 9.761606
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.17880318
• LogD (pH = 7.4): 1.8527069
• Log P: 2.9780278
• Molar Refractivity: 135.8512 cm^3
• Polarizability: 54.24105 Å^3
• Polar Surface Area: 68.5 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: White Solid
• Melting Point: 232-234°C

Safety Information

• Storage Condition: -20°C Freezer, store under inert atmosphere

DETAILS

Toronto Research Chemicals - R701550

Antiepileptic triazole derivative which decreases firing by neurons at sodium channels. Anticonvulsant.

REFERENCES

• Cheung, W.K., et al.: Pharm. Res., 12, 1878 (1995)
• Cardot, J.-M., et al.: Biopharm. Drug Dispos., 19, 259 (1995)
• Palhagen, S., et al.: Epilepsy Res., 43, 115 (1995)