ATEVIRDINE MESYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H25N5O2.CH4O3S
Molecular Weight	475.561
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(O)(=O)=O.CCNC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(OC)=C4

InChI

InChIKey=HKPKBPALSLUFFM-UHFFFAOYSA-N

InChI=1S/C21H25N5O2.CH4O3S/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;1-5(2,3)4/h4-8,13-14,22,24H,3,9-12H2,1-2H3;1H3,(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

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

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
Human immunodeficiency virus type 1 drug-resistance patterns with different 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives.	1993 Oct	7694068
Anti-human immunodeficiency virus type 1 activities of novel non-nucleoside reverse transcriptase inhibitors.	1994 Feb	7514164
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
Novel antiviral benzofuran-transition metal complexes.	2010 Jul	20398971

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:37:09 UTC 2023` Edited by `admin` on `Fri Dec 15 16:37:09 UTC 2023`
Record UNII	A948D8673W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ATEVIRDINE MESYLATE

Official Name

English

ATEVIRDINE MESYLATE [USAN]

Common Name

English

U-87201E

Code

English

ATEVIRDINE MESILATE [MART.]

Common Name

English

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

Systematic Name

English

Atevirdine mesylate [WHO-DD]

Common Name

English

ATEVIRDINE METHANESULFONATE [MI]

Common Name

English

ATEVIRDINE MESILATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C97453