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
| 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 |
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Nonnucleoside reverse transcriptase inhibitors that potently and specifically block human immunodeficiency virus type 1 replication. | 1991 Oct 1 |
|
| Prevention of the spread of HIV-1 infection with nonnucleoside reverse transcriptase inhibitors. | 1992 Sep |
|
| 5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase. | 1993 Apr 30 |
|
| U-90152, a potent inhibitor of human immunodeficiency virus type 1 replication. | 1993 May |
|
| 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 |
|
| Human immunodeficiency virus type 1 drug-resistance patterns with different 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives. | 1993 Oct |
|
| Anti-human immunodeficiency virus type 1 activities of novel non-nucleoside reverse transcriptase inhibitors. | 1994 Feb |
|
| 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 |
|
| 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 |
|
| In-vitro selection of HIV-1 variants resistant to non-nucleoside reverse transcriptase inhibitors in monocyte-derived macrophages. | 1997 Dec |
|
| Factors in AIDS dementia complex trial design: results and lessons from the abacavir trial. | 2007 Mar 30 |
|
| Synthesis of potent antitumor and antiviral benzofuran derivatives. | 2009 May 1 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:43:45 UTC 2023
by
admin
on
Sat Dec 16 17:43:45 UTC 2023
|
| Record UNII |
N24015WC6D
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C97453
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
7082
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | |||
|
m573
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | Merck Index | ||
|
60848
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | |||
|
N24015WC6D
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | |||
|
DB12264
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | |||
|
100000086631
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | |||
|
C076632
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | |||
|
C73840
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | |||
|
ATEVIRDINE
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | |||
|
SUB05591MIG
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | |||
|
DTXSID40159940
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | |||
|
CHEMBL280527
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY | |||
|
136816-75-6
Created by
admin on Sat Dec 16 17:43:46 UTC 2023 , Edited by admin on Sat Dec 16 17:43:46 UTC 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
SALT/SOLVATE -> PARENT |
|
||
|
|
TARGET ORGANISM->INHIBITOR |
|
||
|
|
TARGET -> INHIBITOR |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
|
