Basic information
- CAS
136817-59-9- Standard SMILES
CC(C)Nc1cccnc1N1CCN(C(=O)c2cc3cc(NS(C)(=O)=O)ccc3[nH]2)CC1- InChIKey
WHBIGIKBNXZKFE-UHFFFAOYSA-N- Molecular formula
- C22H28N6O3S
- Average molar mass
- 456.6 g/mol
- Monoisotopic mass
- 456.19435995
Overview
Delavirdine is the amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavirdine is 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. It has a role as an antiviral drug and a HIV-1 reverse transcriptase inhibitor. It is a sulfonamide, an aminopyridine, a N-acylpiperazine and an indolecarboxamide.
Names & identifiers
- Preferred name
- Delavirdine
- IUPAC
- N-[2-[4-[3-(propan-2-ylamino)-2-pyridinyl]piperazine-1-carbonyl]-1H-indol-5-yl]methanesulfonamide
- English name
- DELAVIRDINE
- Molecular formula
- C22H28N6O3S
- Molecular weight
- 456.56
Names & synonyms
Delavirdine136817-59-9U 90152DelavirdinaDTXSID6022892DOL5F9JD3E2-(4-(5-Methanesulfonamido-1H-indol-2-ylcarbonyl)-1-piperazinyl)-N-(1-methylethyl)-3-pyridinamineN-[2-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazine-1-carbonyl]-1H-indol-5-yl]methanesulfonamide1-(3-((1-Methylethyl)amino)-2-pyridinyl)-4-((5-((methylsulfonyl)amino)-1H-indol-2-yl)carbonyl)piperazineDTXCID302892CHEBI:119573N-(2-(1-(3-(isopropylamino)pyridin-2-yl)piperazine-4-carbonyl)-1H-indol-5-yl)methanesulfonamide
Show more names
N-(2-(4-(3-(IsopropylaMino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)MethanesulfonaMideU-90152Bhap-U 90152Delavirdine D8Unii-dol5F9jd3eDELAVIRDINE USP/EP/BP$2200/10G,$5700/50G,96% ,IN STOCKDelavirdine & Delavirdine MesylateDelavirdine - U 90152 | Rescriptor
U90152(N-[2-[4-[3-(1-methylethylamino)pyridin-2-yl]piperazin-1-yl]carbonyl-1H-indol-5-yl] methanesulfonamide)N-{2-[4-(3-Isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yl}-methanesulfonamideN-{2-[(4-{3-[(propan-2-yl)amino]pyridin-2-yl}piperazin-1-yl)carbonyl]-1H-indol-5-yl}methanesulfonamideDelavirdinum(N-(2-(4-(3-(1-methylethylamino)pyridin-2-yl)piperazin-1-yl)carbonyl-1H-indol-5-yl) methanesulfonamide)N-(2-((4-(3-((propan-2-yl)amino)pyridin-2-yl)piperazin-1-yl)carbonyl)-1H-indol-5-yl)methanesulfonamideN-(2-(4-(3-(propan-2-ylamino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)methanesulfonamide
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 119 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 6
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 749
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.8
Solubility8.60e-02 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antiviral Agents; Anti-HIV Agents; Anti-Retroviral Agents; Reverse Transcriptase Inhibitors
Melting Point
226-228 °C
226 - 228 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 226 · 226-228°C
- Boiling point
- 732 · 732.0±70.0 °C(Predicted)
- Density
- 1.388 · 1.388
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Hepatotoxicity
Serum aminotransferase elevations occur in 25% or more of patients on delavirdine therapy, but rise above 5 times the upper limit of normal in 4% or less; this rate is higher in patients who have chronic hepatitis C coinfection. Clinically apparent hepatotoxicity due to delavirdine must be rare, as individual case reports of hepatitis or jaundice have not been published. Nevertheless, cases of hepatitis, jaundice and hepatic failure have been reported to the sponsor and are mentioned in the product label. The liver injury may be immunoallergic and similar in pattern to that attributed to nevirapine and efavirenz. In immunoallergic hepatitis due to nonnucleoside reverse transcriptase inhibitors, injury usually arises within 1 to 8 weeks of starting therapy. Signs of hypersensitivity are common including rash, fever, and eosinophilia and sometimes facial edema, lymphadenoapthy and lymphocytosis. The serum enzyme pattern can be cholestatic, hepatocellular or mixed. Recovery is rapid upon stopping therapy.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
delavirdine
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Binding98%
Pharmacodynamics
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.
Mechanism of ActionDelavirdine binds directly to viral reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by disrupting the enzyme's catalytic site.
Biological Half-Life5.8 hours
Metabolism/Metabolites
Hepatic
Delavirdine has known human metabolites that include N-Desisopropyl delavirdine and N-[2-[4-[6-oxo-3-(propan-2-ylamino)-1H-pyridin-2-yl]piperazine-1-carbonyl]-1H-indol-5-yl]methanesulfonamide.
FDA Pharmacological Classification
DOL5F9JD3E
DELAVIRDINE
Established Pharmacologic Class [EPC] - Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor
Non-Nucleoside Analog [EXT]
Mechanisms of Action [MoA] - Non-Nucleoside Reverse Transcriptase Inhibitors
Delavirdine is a Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of delavirdine is as a Non-Nucleoside Reverse Transcriptase Inhibitor.
MeSH Pharmacological Classification
Related reactions
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Compound notes
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