147221-93-0

Basic information

• Product Name: DELAVIRDINE, MESYLATE
• Synonyms: C08087;Delavirdine mesilate;MethanesulfonaMide, N-[2-[[4-[3-[(1-Methylethyl)aMino]-2-pyridinyl]-1-piperazinyl]carbonyl]-1H-indol-5-yl]-, Methanesulfonate;N-[2-[[4-[3-[(1-Methylethyl)aMino]-2-pyridinyl]-1-piperazinyl]carbonyl]-1H-indol-5-yl]MethanesulfonaMide Methanesulfonate;Delavirdine methane sulfonate;N-[2-[[4-[3-[(1-Methylethyl)amino]-2-pyridinyl]-1-piperazinyl]carbonyl]-1H-indol-5-yl]methanesulfonamide mesylate;U-90152S
• CAS NO: 147221-93-0
• Molecular Formula: C23H32N6O6S2
• Molecular Weight: 552.67
• Product Categories: Anti-viral Compounds;Anti-virals;Inhibitors;Intermediates & Fine Chemicals;Non-nucleoside Reverse Transcriptase;Pharmaceuticals
• Mol File: 147221-93-0.mol
• Article Data: 0

Chemical Properties

• Melting Point: 118-120°C
• Boiling Point: 732 °C at 760 mmHg
• Flash Point: 396.5 °C
• Appearance: white to tan/
• Vapor Pressure: 2.74E-21mmHg at 25°C
• Storage Temp.: -20°C Freezer
• Solubility: DMSO: >5mg/mL
• CAS DataBase Reference: DELAVIRDINE, MESYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DELAVIRDINE, MESYLATE(147221-93-0)
• EPA Substance Registry System: DELAVIRDINE, MESYLATE(147221-93-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 147221-93-0(Hazardous Substances Data)

Usage

Description

Delavirdine Mesylate, also known as Rescriptor, is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used for the treatment of HIV-1 infection. It belongs to the bis(heteroaryl)piperazine (BHAP) class and is a second-generation drug. Delavirdine Mesylate acts as an allosteric mixed inhibitor of both RNAand DNA-directed polymerase domains of reverse transcriptase (RT) with a higher binding affinity for the enzyme-substrate complex than for the free enzyme. It does not inhibit the RNase H activity of RT and has been shown to prevent the spread of HIV significantly longer than AZT. However, the development of resistance to Delavirdine Mesylate can occur, making it more vulnerable to other members of the NNRTIs. It is metabolized in the liver by CYP3A and is a light brown solid.

Uses

Used in Pharmaceutical Industry:
Delavirdine Mesylate is used as an antiretroviral agent for the treatment of HIV-1 infection. It is specifically used in combination therapy with other antiretrovirals to enhance the effectiveness of the treatment and reduce the emergence of viral resistance. The combination therapy helps in managing the HIV infection more effectively and prolonging the time it takes for the virus to develop resistance to the drugs.

Originator

Pharmacia ＆ Upjohn (US)

Manufacturing Process

5-Nitroindole-2-carboxylic acid (0.86 g), 1-[3-(N-isopropyl)amino-2- pyridinyl]piperazine (0.43 g), 1-(ethyl)-3-(dimethylaminopropyl)carbodiimide (0.45 g) and THF (4 ml), were stirred at 20-25°C for 3 hr; then the reaction mixture was dissolved in chloroform (50 ml) and extracted with saturated aqueous sodium bicarbonate, saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by flash column chromatography (200 g silica) eluting with ethyl acetate/hexane (50/50), the appropriate fractions were pooled and concentrated to give 1-[5-nitroindolyl2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine, mp 153°- 154°C.1-[5-Nitroindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2- pyridinyl]piperazine (1.0 g) was dissolved in ethanol (60 ml) and THF (60 ml) and palladium on carbon (10%, 0.15 g) was added. The reaction mixture was hydrogenated at 40 psi for 14 hr, then filtered through celite and concentrated under reduced pressure. Purification by flash chromatography, eluting with ethyl acetate/hexane (50/50) pooling and concentrating the appropriate fractions gave 1-[5-aminoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2- pyridinyl]piperazine, mp 212°-214°C.1-[5-Aminoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2- pyridinyl]piperazine (0.075 mg) was dissolved in methylene chloride (0.4 ml) and pyridine (0.016 g) was added and the reaction is cooled to 0°C. Then methanesulfonyl chloride (0.023 g) was added. After 2.5 hr of stirring, the reaction was diluted with chloroform and washed with saturated aqueous sodium bicarbonate, saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was dissolved in the minimum amount of chloroform and passed through a small plug of silica gel and then it is recrystallized with ethyl acetate/hexane to provide the 1-[5- methansulfoneamidolyl-2-carbonyl]-4-[3-(1-methylethylenamino)-2- pyridinyl]piperazine, mp 226°-228°C. The mesylate salt may be formed by dissolving the free base in methanol and methanesulfonic acid (1 eq) is added.

Therapeutic Function

Antiviral, Anti-HIV virus agent

InChI:InChI=1/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)