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=C(N=CC=C1)N2CCN(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

HIDE SMILES / InChI

Molecular Formula	C21H25N5O2
Molecular Weight	379.4555
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 70 Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7681060	Inhibitor 8504

PubMed

Title	Date	PubMed
Novel antiviral benzofuran-transition metal complexes.	2010-07	20398971
Synthesis of potent antitumor and antiviral benzofuran derivatives.	2009-05-01	19345581
Factors in AIDS dementia complex trial design: results and lessons from the abacavir trial.	2007-03-30	17401456
In-vitro selection of HIV-1 variants resistant to non-nucleoside reverse transcriptase inhibitors in monocyte-derived macrophages.	1997-12	9462437
Targeting delavirdine/atevirdine resistant HIV-1: identification of (alkylamino)piperidine-containing bis(heteroaryl)piperazines as broad spectrum HIV-1 reverse transcriptase inhibitors.	1996-09-13	8809165
Phase I study of atevirdine, a nonnucleoside reverse transcriptase inhibitor, in combination with zidovudine for human immunodeficiency virus type 1 infection. ACTG 199 Study Team.	1995-02	7531207
Discovery, synthesis, and bioactivity of bis(heteroaryl)piperazines. 1. A novel class of non-nucleoside HIV-1 reverse transcriptase inhibitors.	1994-04-01	7512142
Anti-human immunodeficiency virus type 1 activities of novel non-nucleoside reverse transcriptase inhibitors.	1994-02	7514164
Human immunodeficiency virus type 1 drug-resistance patterns with different 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives.	1993-10	7694068
Knocking-out concentrations of HIV-1-specific inhibitors completely suppress HIV-1 infection and prevent the emergence of drug-resistant virus.	1993-10	7690501
Selective non-nucleoside HIV-1 reverse transcriptase inhibitors. New 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones and related compounds with anti-HIV-1 activity.	1993-08-20	7689109
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.	1993-05-14	7684450
U-90152, a potent inhibitor of human immunodeficiency virus type 1 replication.	1993-05	7685995
5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase.	1993-04-30	7683725
Synthesis and evaluation of 2-pyridinone derivatives as specific HIV-1 reverse transcriptase inhibitors. 3. Pyridyl and phenyl analogs of 3-aminopyridin-2(1H)-one.	1993-01-22	7678654
Prevention of the spread of HIV-1 infection with nonnucleoside reverse transcriptase inhibitors.	1992-09	1382341
Nonnucleoside reverse transcriptase inhibitors that potently and specifically block human immunodeficiency virus type 1 replication.	1991-10-01	1717988

Patents

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:29:27 GMT 2025` Edited by `admin` on `Wed Apr 02 09:29:27 GMT 2025`
Record UNII	N24015WC6D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ATEVIRDINE

Official Name

English

ATEVIRDINE [MI]

Preferred Name

English

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

Systematic 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