Delavirdine

Base Information

• Chemical Name: Delavirdine
• CAS No.: 136817-59-9
• Molecular Formula: C₂₂H₂₈N₆O₃S
• Molecular Weight: 456.569
• UNII: DOL5F9JD3E
• DSSTox Substance ID: DTXSID6022892
• Nikkaji Number: J571.558J
• Wikipedia: Delavirdine
• Wikidata: Q370244
• NCI Thesaurus Code: C65366
• Metabolomics Workbench ID: 43014
• ChEMBL ID: CHEMBL593
• Mol file: 136817-59-9.mol

Synonyms:Delavirdine;Delavirdine Mesylate;Mesylate, Delavirdine;Rescriptor;U 90152;U 90152S;U-90152;U-90152S;U90152;U90152S

Chemical Property of Delavirdine

Chemical Property:

• Vapor Pressure: 2.74E-21mmHg at 25°C
• Melting Point: 226-228 °C
• Refractive Index: 1.68
• Boiling Point: 732 °C at 760 mmHg
• PKA: pKa1 4.56; pKa2 8.9(at 25℃)
• Flash Point: 396.5 °C
• PSA: 118.81000
• Density: 1.388 g/cm³
• LogP: 3.94680
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 30g/L(temperature not stated)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 456.19435995
• Heavy Atom Count: 32
• Complexity: 749

Purity/Quality:

98%,99%, ^*data from raw suppliers

Delavirdine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(=C4)NS(=O)(=O)C
• Recent ClinicalTrials: Tipranavir Dose-response Study Using a Prototype Self-emulsifying Drug Delivery System (SEDDS) Formulation in Treatment-naive HIV-1 Infected Patients Report on the Post-study Option, a Treatment of Triple Therapy With Delavirdine, ZDV and 3TC Without Tipranavir
• Description: Delavirdine, a bisheteroarylpiperazine derivative, is a potent nonnucleoside RT inhibitor of activity specific for HIV-1. The U.S. FDA has approved this drug for use in combination with other anti-HIV agents. In Phase I/II study trials, it demonstrated sustained improvements in CD4 cell counts, p24 antigen levels, and RNA viral load. Promising results were obtained when the drug was used in two- or three-drug combinations with nucleoside drugs. Combination of delavirdine with ddI, ddC, or ZDV demonstrated additive or synergistic effects. Delavirdine with ZDV, however, was more beneficial in early HIV infection. Combinations of nevirapine and delavirdine had an antagonistic effect on HIV-1 RT inhibition.
• Uses: A bisheteroarylpiperazine (BHAP) reverse transcriptase inhibitor A bisheteroarylpiperazine (BHAP) reverse transcriptase inhibitor.
• Indications: Delavirdine (Rescriptor) is approved for the treatment of HIV-1 infection in adults and adolescents over age 16 as part of a combination therapy. Rash accompanied by pruritus is the most frequent adverse effect of this agent; however, it usually resolves within several weeks of treatment. Severe skin reactions are rare. Headache, nausea, vomiting, diarrhea, fatigue, and elevated hepatic enzymes also may be associated with delavirdine administration.
• Clinical Use: Treatment of HIV disease in adults and children over 12 years of age (in combination with other antiretroviral agents) Delavirdine has fallen out of favor with the increasing preference for antiretrovirals than can be dosed twice or once daily.

Technology Process of Delavirdine

There total 2 articles about Delavirdine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

methyl 5-methanesulfonylamino-1H-indole-2-carboxylate (1309923-85-0) + [3-(1-methylethylamino)-2-pyridinyl]piperazine (147539-21-7) → delavirdine (136817-59-9)

Guidance literature:

In ethanol; at 60 ℃;

DOI:10.1021/acs.joc.8b02180

Reference yield:

→ delavirdine (136817-59-9)

Guidance literature:

upstream raw materials:

methyl 5-methanesulfonylamino-1H-indole-2-carboxylate

[3-(1-methylethylamino)-2-pyridinyl]piperazine

Refernces

• 1、 -. "Methods for predicting the response to statins". . . Retrieved 2011/10/13.