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

• ChemBase ID: 586
• Molecular Formular: C22H28N6O3S
• Molecular Mass: 456.56112
• Monoisotopic Mass: 456.19435979
• SMILES: S(=O)(=O)(Nc1cc2cc([nH]c2cc1)C(=O)N1CCN(CC1)c1ncccc1NC(C)C)C
• Canonical SMILES: CC(Nc1cccnc1N1CCN(CC1)C(=O)c1cc2c([nH]1)ccc(c2)NS(=O)(=O)C)C
• InChI: InChI=1S/C22H28N6O3S/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/h4-8,13-15,24-26H,9-12H2,1-3H3
• InChIKey: WHBIGIKBNXZKFE-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
• IUPAC Traditional name: N-(2-{4-[3-(isopropylamino)pyridin-2-yl]piperazine-1-carbonyl}-1H-indol-5-yl)methanesulfonamide; delavirdine
• Brand Name: Bhap Der; Rescriptor
• Synonyms: DLV; SPP; Delavirdine; (1-(5-METHANSULPHONAMIDO-1H-INDOL-2-YL-CARBONYL)4-[METHYLAMINO)PYRIDINYL]PIPERAZINE; N-[2-[[4-[3-[(1-Methylethyl)amino]-2-pyridinyl]-1-piperazinyl]carbonyl]-1H-indol-5-yl]methanesulfonamide; BHAP-U 90152; U-90152; 1-[3-(Isopropylamino)-2-pyridyl]-4-[(5-methanesulfonamidoindol-2-yl)carbonyl]piperazine; N-(2-(4-(3-(IsopropylaMino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)MethanesulfonaMide

Database IDs

• CAS Number: 136817-59-9
• PubChem SID: 160964049; 46508878
• PubChem CID: 5625

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.392162
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.08998388
• 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: true

ALOGPS 2.1

• Log P: 2.77
• LOG S: -3.73
• Solubility (Water): 8.60e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Pale Yellow Solid
• Melting Point: 226-228°C
• Hydrophobicity(logP): 2.8

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 97%

DETAILS

DrugBank - DB08563

Drug information: experimental

DrugBank - DB00705

• Drug Groups: approved
• Description: A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. [PubChem]
• Indication: For the treatment of HIV-1 infection in combination with appropriate antiretroviral agents when therapy is warranted
• Pharmacology: Delavirdine is a non-nucleoside reverse transcriptase inhibitor (nNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Delavirdine binds directly to reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by causing a disruption of the enzyme's catalytic site. The activity of Delavirdine does not compete with template or nucleoside triphosphates. HIV-2 RT and eukaryotic DNA polymerases (such as human DNA polymerases alpha, beta, or sigma) are not inhibited by Delavirdine.
• Toxicity: Major toxicity of delavirdine is rash and should be advised to promptly notify their physician should rash occur. The majority of rashes associated with delavirdine occur within 1 to 3 weeks after initiating treatment with delavirdine. The rash normally resolves in 3 to 14 days and may be treated symptomatically while therapy with delavirdine is continued. Any patient experiencing severe rash or rash accompanied by symptoms such as fever, blistering, oral lesions, conjunctivitis, swelling, muscle or joint aches should discontinue medication and consult a physician.
• Affected Organisms: Human Immunodeficiency Virus
• Biotransformation: Hepatic
• Absorption: Rapidly absorbed
• Half Life: 5.8 hours
• Protein Binding: 98%
• Elimination: Delavirdine is extensively converted to several inactive metabolites by cytochrome P450 3A (CYP3A). Delavirdine was excreted in the milk of lactating rats at a concentration three to five times that of rat plasma.
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - D230625

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)