U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H22N2O3
Molecular Weight 302.3682
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EMIVIRINE

SMILES

CCOCN1C(=O)NC(=O)C(C(C)C)=C1CC2=CC=CC=C2

InChI

InChIKey=MLILORUFDVLTSP-UHFFFAOYSA-N
InChI=1S/C17H22N2O3/c1-4-22-11-19-14(10-13-8-6-5-7-9-13)15(12(2)3)16(20)18-17(19)21/h5-9,12H,4,10-11H2,1-3H3,(H,18,20,21)

HIDE SMILES / InChI

Molecular Formula C17H22N2O3
Molecular Weight 302.3682
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

MKC-442 (6-benzyl-1-(ethoxymethyl)-5-isopropyl-uracil) is a highly potent and selective inhibitor of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT). Emivirine structurally is a nucleoside analog (NRTI) molecule, but it functions as a non-nucleoside reverse transcriptase inhibitor (NNRTI). Emivirine had reached phase 3 clinical trials for the treatment of HIV-1 infections before its further development was stopped.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Effect of human serum on the in vitro anti-HIV-1 activity of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) derivatives as related to their lipophilicity and serum protein binding.
1993 Jun 22
Selective and synergistic inhibition of human immunodeficiency virus type 1 reverse transcriptase by a non-nucleoside inhibitor, MKC-442.
1993 Oct
Preclinical evaluation of MKC-442, a highly potent and specific inhibitor of human immunodeficiency virus type 1 in vitro.
1994 Apr
Synthesis and antiviral activity of 6-benzyl analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents.
1995 Jul 21
The inhibition of human immunodeficiency virus type 1 in vitro by a non-nucleoside reverse transcriptase inhibitor MKC-442, alone and in combination with other anti-HIV compounds.
1995 Mar
Complexes of HIV-1 reverse transcriptase with inhibitors of the HEPT series reveal conformational changes relevant to the design of potent non-nucleoside inhibitors.
1996 Apr 12
Highly favorable antiviral activity and resistance profile of the novel thiocarboxanilide pentenyloxy ether derivatives UC-781 and UC-82 as inhibitors of human immunodeficiency virus type 1 replication.
1996 Aug
Preclinical studies on thiocarboxanilide UC-781 as a virucidal agent.
1998 Jul 9
5-Alkyl-2-[(methylthiomethyl)thio]-6-(benzyl)-pyrimidin-4-(1H)-ones as potent non-nucleoside reverse transcriptase inhibitors of S-DABO series.
1998 Jun 16
N'-[2-(2-thiophene)ethyl]-N'-[2-(5-bromopyridyl)] thiourea as a potent inhibitor of NNI-resistant and multidrug-resistant human immunodeficiency virus-1.
1999 Dec 20
Structure-based design of non-nucleoside reverse transcriptase inhibitors of drug-resistant human immunodeficiency virus.
1999 Sep
Mutational analysis of trp-229 of human immunodeficiency virus type 1 reverse transcriptase (RT) identifies this amino acid residue as a prime target for the rational design of new non-nucleoside RT inhibitors.
2000 May
Antiviral drugs: current state of the art.
2001 Aug
Structure-activity relationship studies on new DABOS: effect of substitutions at pyrimidine C-5 and C-6 positions on anti-HIV-1 activity.
2001 Jan
New developments in anti-HIV chemotherapy.
2001 Nov
Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants.
2002 Dec 19
New developments in anti-HIV chemotherapy.
2002 Jul 18
In vitro activity of potential anti-poxvirus agents.
2003 Jan
Synthesis of furoannelated analogues of Emivirine (MKC-442).
2004 Mar
Gateways to clinical trials.
2004 May
Chemo- and regioselective functionalization of uracil derivatives. Applications to the synthesis of oxypurinol and emivirine.
2006 Aug 17
Synthesis and antiviral evaluation of 6-(trifluoromethylbenzyl) and 6-(fluorobenzyl) analogues of HIV drugs emivirine and GCA-186.
2008 Jan
Synthesis of novel uracil non-nucleoside derivatives as potential reverse transcriptase inhibitors of HIV-1.
2009 Nov
Patents
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:08:24 UTC 2023
Edited
by admin
on Wed Jul 05 23:08:24 UTC 2023
Record UNII
X87G8IX72O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EMIVIRINE
INN   MART.   USAN   WHO-DD  
USAN   INN  
Official Name English
COACTINON
Brand Name English
Emivirine [WHO-DD]
Common Name English
EMIVIRINE [MART.]
Common Name English
2,4(1H,3H)-PYRIMIDINEDIONE, 1-(ETHOXYMETHYL)-5-(1-METHYLETHYL)-6-(PHENYLMETHYL)-
Systematic Name English
MKC-442
Code English
emivirine [INN]
Common Name English
EMIVIRINE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C97453
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
Code System Code Type Description
WIKIPEDIA
EMIVIRINE
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL35033
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
NCI_THESAURUS
C73147
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
CHEBI
44143
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID80164437
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
INN
7961
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
CAS
149950-60-7
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
DRUG BANK
DB08188
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
PUBCHEM
65013
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
FDA UNII
X87G8IX72O
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
SMS_ID
100000087260
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
MESH
C083858
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
EVMPD
SUB01880MIG
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
USAN
KK-34
Created by admin on Wed Jul 05 23:08:24 UTC 2023 , Edited by admin on Wed Jul 05 23:08:24 UTC 2023
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY