Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H25N5O2 |
Molecular Weight | 379.4555 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCNC1=CC=CN=C1N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(OC)=C4
InChI
InChIKey=UCPOMLWZWRTIAA-UHFFFAOYSA-N
InChI=1S/C21H25N5O2/c1-3-22-18-5-4-8-23-20(18)25-9-11-26(12-10-25)21(27)19-14-15-13-16(28-2)6-7-17(15)24-19/h4-8,13-14,22,24H,3,9-12H2,1-2H3
Atevirdine (U-87201E) is a nonnucleoside inhibitor of HIV-1 reverse transcriptase, that has been studied for the treatment of HIV infection. Atevirdine mesylate is the first-generation member of the bisheteroarylpiperazine class of nonnucleoside inhibitors, which inhibits reverse transcriptase noncompetitively by binding near the catalytic site. The safety, tolerability, and antiviral activity of atevirdine were studied in phase I/II clinical trial. Rash was the most common adverse event, with a grade 3 or 4 rash. No significant change from baseline in HIV-1 plasma RNA mean copy number was detected.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7681060 |
PubMed
Title | Date | PubMed |
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5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase. | 1993 Apr 30 |
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U-90152, a potent inhibitor of human immunodeficiency virus type 1 replication. | 1993 May |
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Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-carbonyl]-4-[3- [(1-methylethyl)amino]-pyridinyl]piperazine monomethanesulfonate (U-90152S), a second-generation clinical candidate. | 1993 May 14 |
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Human immunodeficiency virus type 1 drug-resistance patterns with different 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives. | 1993 Oct |
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Knocking-out concentrations of HIV-1-specific inhibitors completely suppress HIV-1 infection and prevent the emergence of drug-resistant virus. | 1993 Oct |
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Discovery, synthesis, and bioactivity of bis(heteroaryl)piperazines. 1. A novel class of non-nucleoside HIV-1 reverse transcriptase inhibitors. | 1994 Apr 1 |
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Targeting delavirdine/atevirdine resistant HIV-1: identification of (alkylamino)piperidine-containing bis(heteroaryl)piperazines as broad spectrum HIV-1 reverse transcriptase inhibitors. | 1996 Sep 13 |
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In-vitro selection of HIV-1 variants resistant to non-nucleoside reverse transcriptase inhibitors in monocyte-derived macrophages. | 1997 Dec |
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Novel antiviral benzofuran-transition metal complexes. | 2010 Jul |
Patents
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C97453
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m573
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C076632
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C73840
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ATEVIRDINE
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SUB05591MIG
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CHEMBL280527
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136816-75-6
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)