ATEVIRDINE

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

Structure Search

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

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10774589 | https://www.ncbi.nlm.nih.gov/pubmed/9763407 | https://www.ncbi.nlm.nih.gov/pubmed/9768622 |

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
Human immunodeficiency virus type 1 reverse transcriptase 67 Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7681060	Inhibitor 8297

PubMed

Title	Date	PubMed
5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase.	1993 Apr 30	7683725
U-90152, a potent inhibitor of human immunodeficiency virus type 1 replication.	1993 May	7685995
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	7684450
Human immunodeficiency virus type 1 drug-resistance patterns with different 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives.	1993 Oct	7694068
Knocking-out concentrations of HIV-1-specific inhibitors completely suppress HIV-1 infection and prevent the emergence of drug-resistant virus.	1993 Oct	7690501
Discovery, synthesis, and bioactivity of bis(heteroaryl)piperazines. 1. A novel class of non-nucleoside HIV-1 reverse transcriptase inhibitors.	1994 Apr 1	7512142
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	8809165
In-vitro selection of HIV-1 variants resistant to non-nucleoside reverse transcriptase inhibitors in monocyte-derived macrophages.	1997 Dec	9462437
Novel antiviral benzofuran-transition metal complexes.	2010 Jul	20398971

Patents

Name

Type

Language

ATEVIRDINE

Official Name

English

PIPERAZINE, 1-(3-(ETHYLAMINO)-2-PYRIDINYL)-4-((5-METHOXY-1H-INDOL-2-YL)CARBONYL)-, MONOMETHANESULFONATE

Systematic Name

English

ATEVIRDINE [MI]

Common Name

English

1-(3-(ETHYLAMINO)-2-PYRIDYL)-4-((5-METHOXYINDOL-2-YL)CARBONYL)PIPERAZINE MONOMETHANESULFONATE

Systematic Name

English

Atevirdine [WHO-DD]

Common Name

English

atevirdine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C97453