N-[2-(4-{3-[(propan-2-yl)amino]pyridin-2-yl}piperazine-1-carbonyl)-1H-indol-5-yl]methanesulfonamide; methanesulfonic acid

• ChemBase ID: 154903
• Molecular Formular: C23H32N6O6S2
• Molecular Mass: 552.66678
• Monoisotopic Mass: 552.18247477
• SMILES: CC(C)Nc1cccnc1N1CCN(CC1)C(=O)c1cc2cc(ccc2[nH]1)NS(=O)(=O)C.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.CC(Nc1cccnc1N1CCN(CC1)C(=O)c1cc2c([nH]1)ccc(c2)NS(=O)(=O)C)C
• InChI: InChI=1S/C22H28N6O3S.CH4O3S/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20;1-5(2,3)4/h4-8,13-15,24-26H,9-12H2,1-3H3;1H3,(H,2,3,4)
• InChIKey: MEPNHSOMXMALDZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(4-{3-[(propan-2-yl)amino]pyridin-2-yl}piperazine-1-carbonyl)-1H-indol-5-yl]methanesulfonamide; methanesulfonic acid
• IUPAC Traditional name: delavirdine; methanesulfonic acid
• Synonyms: N-[2-[[4-[3-[(1-Methylethyl)amino]-2-pyridinyl]-1-piperazinyl]carbonyl]-1H-indol-5-yl]methanesulfonamide mesylate; Delavirdine mesylate; N-[2-[[4-[3-[(1-Methylethyl)amino]-2-pyridinyl]-1-piperazinyl]carbonyl]-1H-indol-5-yl]methanesulfonamide Methanesulfonate; U-90152S; Delavirdine Mesylate

Database IDs

• CAS Number: 147221-93-0
• MDL Number: MFCD00866948
• PubChem SID: 162249041
• PubChem CID: 441386

CALCULATED PROPERTIES

• Acid pKa: 9.392162
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.08998393
• LogD (pH = 7.4): 0.9233841
• Log P: 1.0243266
• Molar Refractivity: 126.6434 cm^3
• Polarizability: 48.65747 Å^3
• Polar Surface Area: 110.43 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL; Methanol
• Apperance: Light Brown Solid; white to tan powder
• Melting Point: 118-120°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H28N6O3S · CH3SO3H

DETAILS

Sigma Aldrich - PZ0180

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Delavirdine is a non-nucleoside reverse transcriptase inhibitor (NNRTI). It is used as part of highly active antiretroviral therapy (HAART) for the treatment of human immunodeficiency virus (HIV) type 1.

Toronto Research Chemicals - D230630

A bisheteroarylpiperazine (BHAP) reverse transcriptase inhibitor.

REFERENCES

• Dueweke, T.J., et al.: Antimicrob. Ag. Chemother., 37, 1127 (1993)
• Althaus, I.W., et al.: Biochem. Pharmacol., 47, 2017 (1994)