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
Selective and synergistic inhibition of human immunodeficiency virus type 1 reverse transcriptase by a non-nucleoside inhibitor, MKC-442.
1993 Oct
Differential activities of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives against different human immunodeficiency virus type 1 mutant strains.
1995 Apr
Suppression of the breakthrough of human immunodeficiency virus type 1 (HIV-1) in cell culture by thiocarboxanilide derivatives when used individually or in combination with other HIV-1-specific inhibitors (i.e., TSAO derivatives).
1995 Jun 6
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
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
Synthesis and potent anti-HIV-1 activity of novel 6-benzyluracil analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine.
1996 Jun 7
Characteristics of the Pro225His mutation in human immunodeficiency virus type 1 (HIV-1) reverse transcriptase that appears under selective pressure of dose-escalating quinoxaline treatment of HIV-1.
1997 Nov
Structure-based design of novel dihydroalkoxybenzyloxopyrimidine derivatives as potent nonnucleoside inhibitors of the human immunodeficiency virus reverse transcriptase.
1998 Dec
A novel mutation (F227L) arises in the reverse transcriptase of human immunodeficiency virus type 1 on dose-escalating treatment of HIV type 1-infected cell cultures with the nonnucleoside reverse transcriptase inhibitor thiocarboxanilide UC-781.
1998 Feb 10
Synthesis and anti-HIV-1 activity of novel 2,3-dihydro-7H-thiazolo[3,2-a]pyrimidin-7-ones.
1998 Jan 15
Allosteric inhibitors against HIV-1 reverse transcriptase: design and synthesis of MKC-442 analogues having an omega-functionalized acyclic structure.
1998 Jul
Preclinical studies on thiocarboxanilide UC-781 as a virucidal agent.
1998 Jul 9
A proline-to-histidine substitution at position 225 of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) sensitizes HIV-1 RT to BHAP U-90152.
1998 Jun
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
Design of MKC-442 (emivirine) analogues with improved activity against drug-resistant HIV mutants.
1999 Nov 4
Inhibition of human immunodeficiency virus type 1 replication in acutely and chronically infected cells by EM2487, a novel substance produced by a Streptomyces species.
1999 Oct
Long-term exposure of HIV type 1-infected cell cultures to combinations of the novel quinoxaline GW420867X with lamivudine, abacavir, and a variety of nonnucleoside reverse transcriptase inhibitors.
2000 Apr 10
Structure-activity relationship studies on potential non-nucleoside DABO-like inhibitors of HIV-1 reverse transcriptase.
2000 Mar
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
Three-drug combinations of emivirine and nucleoside reverse transcriptase inhibitors in vitro: long-term culture of HIV-1-infected cells and breakthrough viruses.
2001 May
Dioxolane guanosine, the active form of the prodrug diaminopurine dioxolane, is a potent inhibitor of drug-resistant HIV-1 isolates from patients for whom standard nucleoside therapy fails.
2002 Jan 1
New developments in anti-HIV chemotherapy.
2002 Jul 18
New anti-HIV agents and targets.
2002 Nov
Multiple pathways in the synthesis of new annelated analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (emivirine).
2003 Aug 21
In vitro activity of potential anti-poxvirus agents.
2003 Jan
Gateways to clinical trials.
2003 Jan-Feb
Synthesis of novel MKC-442 analogues with potent activities against HIV-1.
2003 Jul
Gateways to clinical trials.
2003 Oct
Synthesis and evaluation of new potential HIV-1 non-nucleoside reverse transcriptase inhibitors. New analogues of MKC-442 containing Michael acceptors in the C-6 position.
2003 Oct 21
Synthesis of furoannelated analogues of Emivirine (MKC-442).
2004 Mar
Gateways to clinical trials.
2004 May
4-benzyl- and 4-benzoyl-3-dimethylaminopyridin-2(1H)-ones, a new family of potent anti-HIV agents: optimization and in vitro evaluation against clinically important HIV mutant strains.
2004 Oct 21
Synthesis and evaluation of double-prodrugs against HIV. Conjugation of D4T with 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine)-type reverse transcriptase inhibitors via the SATE prodrug approach.
2005 Feb 24
Synthesis of 2-(aminocarbonylmethylthio)-1H-imidazoles as novel Capravirine analogues.
2005 Jul 1
5-Alkyl-2-alkylamino-6-(2,6-difluorophenylalkyl)-3,4-dihydropyrimidin-4(3H)-ones, a new series of potent, broad-spectrum non-nucleoside reverse transcriptase inhibitors belonging to the DABO family.
2005 Mar 15
Chemo- and regioselective functionalization of uracil derivatives. Applications to the synthesis of oxypurinol and emivirine.
2006 Aug 17
The design and synthesis of 9-phenylcyclohepta[d]pyrimidine-2,4-dione derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase.
2006 Sep 7
Functionalization of unprotected uracil derivatives using the halogen-magnesium exchange.
2007 Apr 26
Synthesis and anti-HIV-1 activity of new MKC-442 analogues with an alkynyl-substituted 6-benzyl group.
2007 May
Synthesis and anti-HIV-1 activity of 1-substiuted 6-(3-cyanobenzoyl) and [(3-cyanophenyl)fluoromethyl]-5-ethyl-uracils.
2009 Sep
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:39:14 GMT 2023
Edited
by admin
on Fri Dec 15 15:39:14 GMT 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 Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
Code System Code Type Description
WIKIPEDIA
EMIVIRINE
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL35033
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
NCI_THESAURUS
C73147
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
CHEBI
44143
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID80164437
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
INN
7961
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
CAS
149950-60-7
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
DRUG BANK
DB08188
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
PUBCHEM
65013
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
FDA UNII
X87G8IX72O
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
SMS_ID
100000087260
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
MESH
C083858
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
EVMPD
SUB01880MIG
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
USAN
KK-34
Created by admin on Fri Dec 15 15:39:14 GMT 2023 , Edited by admin on Fri Dec 15 15:39:14 GMT 2023
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY