DELAVIRDINE, MESYLATE

ChemicalBook > CAS DataBase List > DELAVIRDINE, MESYLATE

DELAVIRDINE, MESYLATE

Product Name: DELAVIRDINE, MESYLATE
CAS No.: 147221-93-0
Chemical Name: DELAVIRDINE, MESYLATE
Synonyms: C08087;U-90152S;U 90152 (mesylate);elavirdinemesylate;Delavirdine Mesylat;Delavirdine mesilate;BHAP-U 90152 (mesylate);Delavirdine methane sulfonate;DELAVIRDINE (MESYLATE);U 90152;DELAVIRDINE MESYLATE (U 90152 MESYLATE)
CBNumber: CB1292152
Molecular Formula: C23H32N6O6S2
Formula Weight: 552.67
MOL File: 147221-93-0.mol

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DELAVIRDINE, MESYLATE Property

Melting point:: 118-120°C
storage temp.: Inert atmosphere,Room Temperature
solubility: DMSO: >5mg/mL
form: powder
color: white to tan
CAS DataBase Reference: 147221-93-0

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Safety

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PZ0180
Product name: Delavirdine mesylate
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $150
Updated: 2024/03/01

Sigma-Aldrich

Product number: PZ0180
Product name: Delavirdine mesylate
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $340.2
Updated: 2024/03/01

Cayman Chemical

Product number: 24026
Product name: Delavirdine (mesylate)
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 24026
Product name: Delavirdine (mesylate)
Purity: ≥98%
Packaging: 5mg
Price: $93
Updated: 2024/03/01

Cayman Chemical

Product number: 24026
Product name: Delavirdine (mesylate)
Purity: ≥98%
Packaging: 10mg
Price: $153
Updated: 2024/03/01

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DELAVIRDINE, MESYLATE Chemical Properties,Usage,Production

Description

Rescriptor was launched in the US for HIV positive individuals. It can be prepared in seven steps from 2-chloro-3-nitropyridine and piperazine. Rescriptor is a member of the bis(heteroaryl)piperazine (BHAP) class of non-nucleoside HIV-1 reverse transcriptase inhibitors (NNRTIs) of which it is a second generation drug. It acts exclusively as an allosteric mixed inhibitor of both RNA- and DNA-directed polymerase domains of RT and has a much higher binding affintiy for the enzymesubstrate complex than for the free enzyme. Rescriptor does not inhibit RNase H activity of RT. It prevented the spread of HIV significantly longer than AZT. Development of resistance to Rescriptor can occur, however the mutated strain becomes more vulnerable to other members of the NNRTIs. It is metabolized in the liver by CYP3A.

Chemical Properties

Light Brown Solid

Originator

Pharmacia ＆ Upjohn (US)

Uses

A bisheteroarylpiperazine (BHAP) reverse transcriptase inhibitor.

Definition

ChEBI: The monomethanesulfonic acid salt of delavirdine, a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection.

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.

brand name

Rescriptor (Agouron).

Therapeutic Function

Antiviral, Anti-HIV virus agent

DELAVIRDINE, MESYLATE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from DELAVIRDINE, MESYLATE manufacturers

Hebei Mojin Biotechnology Co., Ltd

Product: DELAVIRDINE, MESYLATE 147221-93-0
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-09-28

Career Henan Chemical Co

Product: DELAVIRDINE, MESYLATE 147221-93-0
Price: US $1.00/g
Min. Order: 1g
Purity: ≥98%
Supply Ability: g/kg/Ton
Release date: 2019-12-25

147221-93-0, DELAVIRDINE, MESYLATERelated Search:

DELAVIRDINE 2-(4-METHYLPIPERAZINO)-3-PYRIDINAMINE 3-PYRIDYLAMINE, N-(1-METHYLETHYL)-2-(1-PIPERAZINYL)-,DIHYDROCHLORIDE MONOHYDRATE 3-Pyridinamine,2-(1-piperazinyl)-(9CI) 3-(Ethylamino)-2-(1-piperazinyl)pyridine DELAVIRDINE, MESYLATE

DELAVIRDINE (MESYLATE);U 90152

1-[3-[(1-Methylethyl)amino]-2-pyridinyl]-4-[[5-[(methylsulfonyl)amino]-1H-indol-2-yl]carbonyl]-piperazine monomethanesulfonate

DELAVIRDINE MESYLATE (U 90152 MESYLATE)

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

BHAP-U 90152 (mesylate)

U 90152 (mesylate)

Delavirdine Mesylat

N-(2-(4-(3-(Isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)methanesulfonamide methanesulfonate

elavirdinemesylate

147221-93-0

C22H28N6O3SCH4SO3

C22H28N6O3SCH4O3S

C23H32N6O6S2

Anti-viral Compounds

Anti-virals

Inhibitors

Intermediates & Fine Chemicals

Non-nucleoside Reverse Transcriptase

Pharmaceuticals