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

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 67 Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7681060	Inhibitor 8297

PubMed

Title	Date	PubMed
Nonnucleoside reverse transcriptase inhibitors that potently and specifically block human immunodeficiency virus type 1 replication.	1991 Oct 1	1717988
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 Aug 20	7689109
U-90152, a potent inhibitor of human immunodeficiency virus type 1 replication.	1993 May	7685995
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
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 Feb	7531207
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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:43:45 GMT 2023` Edited by `admin` on `Sat Dec 16 17:43:45 GMT 2023`
Record UNII	N24015WC6D
Record Status	`Validated (UNII)`
Record Version

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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