2-(2H5)cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one

• ChemBase ID: 175082
• Molecular Formular: C15H14N4O
• Molecular Mass: 266.29786
• Monoisotopic Mass: 266.11676109
• SMILES: [nH]1c(=O)c2c(n(c3c1c(ccn3)C)C1CC1)nccc2
• Canonical SMILES: Cc1ccnc2c1[nH]c(=O)c1c(n2C2CC2)nccc1
• InChI: InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)
• InChIKey: NQDJXKOVJZTUJA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(^2H₅)cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
• IUPAC Traditional name: 2-(^2H₅)cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
• Synonyms: 11-(Cyclopropyl-d5)-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2’,3’-e][1,4]diazepin-6-one; BI-RG 587-d5; NSC 641530-d5; Nevarapine-d5; Viramune-d5; Nevirapine-d5See N391278

Database IDs

• PubChem SID: 164230992
• PubChem CID: 45040009

CALCULATED PROPERTIES

• Acid pKa: 10.371185
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.3533716
• LogD (pH = 7.4): 2.480226
• Log P: 2.4880428
• Molar Refractivity: 77.482 cm^3
• Polarizability: 28.113253 Å^3
• Polar Surface Area: 58.12 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 246-248°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N391277

Labelled Nevirapine (N391275), a potent (IC50=84nM) and selective non-nucleoside inhibitor of HIV-1 reverse transcriptase. Antiviral.

REFERENCES

• Hargrave, K.D., et al.: J. Med. Chem., 34, 2231 (1991)
• Cheeseman, S.H., et al.: Antimicrob. Agents Chemother., 37, 178 (1991)
• Guay, L.A., et al.: Lancet, 354, 795 (1991)