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

• ChemBase编号: 586
• 分子式: C22H28N6O3S
• 平均质量: 456.56112
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: N-[2-(4-{3-[(propan-2-yl)amino]pyridin-2-yl}piperazine-1-carbonyl)-1H-indol-5-yl]methanesulfonamide
• IUPAC传统名: N-(2-{4-[3-(isopropylamino)pyridin-2-yl]piperazine-1-carbonyl}-1H-indol-5-yl)methanesulfonamide; delavirdine
• 商标名: Bhap Der; Rescriptor
• 别名: 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

登记号

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

理论计算性质

JChem

• Acid pKa: 9.392162
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): -0.08998388
• LogD (pH = 7.4): 0.9233841
• Log P: 1.0243266
• 摩尔折射率: 126.6434 cm^3
• 极化性: 48.65747 Å^3
• 极化表面积: 110.43 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.77
• LOG S: -3.73
• 溶解度: 8.60e-02 g/l

分子性质

理化性质

• 溶解度: Chloroform; Ethyl Acetate
• 外观: Pale Yellow Solid
• 熔点: 226-228°C
• 疏水性(logP): 2.8

安全信息

• 保存条件: -20°C Freezer

产品相关信息

• 纯度: 97%

详细说明

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.

参考文献

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