EMIVIRINE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7694070 | https://www.ncbi.nlm.nih.gov/pubmed/11367264 | https://adisinsight.springer.com/drugs/800002827

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 reverse transcriptase 70 Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7694070	Inhibitor 8504		8.0 nM [IC50]

PubMed

Title	Date	PubMed
Synthesis of novel uracil non-nucleoside derivatives as potential reverse transcriptase inhibitors of HIV-1.	2009-11	19856332
Synthesis and anti-HIV-1 activity of 1-substiuted 6-(3-cyanobenzoyl) and [(3-cyanophenyl)fluoromethyl]-5-ethyl-uracils.	2009-09	19637180
Synthesis and antiviral activity of new dimeric inhibitors against HIV-1.	2008-01-01	17904371
Synthesis and antiviral evaluation of 6-(trifluoromethylbenzyl) and 6-(fluorobenzyl) analogues of HIV drugs emivirine and GCA-186.	2008-01	18161905
Synthesis and anti-HIV-1 activity of new MKC-442 analogues with an alkynyl-substituted 6-benzyl group.	2007-05	17464964
Functionalization of unprotected uracil derivatives using the halogen-magnesium exchange.	2007-04-26	17388601
The design and synthesis of 9-phenylcyclohepta[d]pyrimidine-2,4-dione derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase.	2006-09-07	17036113
Chemo- and regioselective functionalization of uracil derivatives. Applications to the synthesis of oxypurinol and emivirine.	2006-08-17	16898805
Synthesis of 2-(aminocarbonylmethylthio)-1H-imidazoles as novel Capravirine analogues.	2005-07-01	15896963
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.	2005-03-15	15727860
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.	2005-02-24	15715487
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.	2004-10-21	15481987
Gateways to clinical trials.	2004-05	15319808
Synthesis of 6-arylvinyl analogues of the HIV drugs SJ-3366 and Emivirine.	2004-03-01	14980626
Synthesis of furoannelated analogues of Emivirine (MKC-442).	2004-03	15038059
Computer-aided design, synthesis, and anti-HIV-1 activity in vitro of 2-alkylamino-6-[1-(2,6-difluorophenyl)alkyl]-3,4-dihydro-5-alkylpyrimidin-4(3H)-ones as novel potent non-nucleoside reverse transcriptase inhibitors, also active against the Y181C variant.	2004-02-12	14761194
3-iodo-4-phenoxypyridinones (IOPY's), a new family of highly potent non-nucleoside inhibitors of HIV-1 reverse transcriptase.	2003-12-15	14643315
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.	2003-10-21	14599015
Gateways to clinical trials.	2003-10	14671684
Multiple pathways in the synthesis of new annelated analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (emivirine).	2003-08-21	12968341
Synthesis of novel MKC-442 analogues with potent activities against HIV-1.	2003-07	12916058
Gateways to clinical trials.	2003-04-15	12690708
In vitro activity of potential anti-poxvirus agents.	2003-01	12615301
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.	2002-12-19	12477355
New anti-HIV agents and targets.	2002-11	12369088
New developments in anti-HIV chemotherapy.	2002-07-18	12084468
Prediction of activity for nonnucleoside inhibitors with HIV-1 reverse transcriptase based on Monte Carlo simulations.	2002-07-04	12086483
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.	2002-01-01	11782585
Three-drug combinations of emivirine and nucleoside reverse transcriptase inhibitors in vitro: long-term culture of HIV-1-infected cells and breakthrough viruses.	2001-05	12959324
Structure-based design of novel dihydroalkoxybenzyloxopyrimidine derivatives as potent nonnucleoside inhibitors of the human immunodeficiency virus reverse transcriptase.	1998-12	9835518
Preclinical studies on thiocarboxanilide UC-781 as a virucidal agent.	1998-07-09	9677161
Allosteric inhibitors against HIV-1 reverse transcriptase: design and synthesis of MKC-442 analogues having an omega-functionalized acyclic structure.	1998-07	9875411
5-Alkyl-2-[(methylthiomethyl)thio]-6-(benzyl)-pyrimidin-4-(1H)-ones as potent non-nucleoside reverse transcriptase inhibitors of S-DABO series.	1998-06-16	9873370
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.	1998-06	9634074
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.	1998-02-10	9491916
Synthesis and anti-HIV-1 activity of novel 2,3-dihydro-7H-thiazolo[3,2-a]pyrimidin-7-ones.	1998-01-15	9457243
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.	1997-11	9343170
Anti-HIV active naphthyl analogues of HEPT and DABO.	1997-03	9210288
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.	1996-08	8700148
Synthesis and potent anti-HIV-1 activity of novel 6-benzyluracil analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine.	1996-06-07	8691437
Complete inhibition of viral breakthrough by combination of MKC-442 with AZT during a long-term culture of HIV-1 infected cells.	1996-06	8793010
Marked inhibitory activity of non-nucleoside reverse transcriptase inhibitors against human immunodeficiency virus type 1 when combined with (-)2',3'-dideoxy-3'-thiacytidine.	1996-05	8622638
Complexes of HIV-1 reverse transcriptase with inhibitors of the HEPT series reveal conformational changes relevant to the design of potent non-nucleoside inhibitors.	1996-04-12	8648598
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.	1995-07-21	7636846
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).	1995-06-06	7539917
Differential activities of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives against different human immunodeficiency virus type 1 mutant strains.	1995-04	7540384
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.	1995-03	7541619
Preclinical evaluation of MKC-442, a highly potent and specific inhibitor of human immunodeficiency virus type 1 in vitro.	1994-04	7518216
Selective and synergistic inhibition of human immunodeficiency virus type 1 reverse transcriptase by a non-nucleoside inhibitor, MKC-442.	1993-10	7694070
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.	1993-06-22	8328988

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:04:21 GMT 2025` Edited by `admin` on `Mon Mar 31 18:04:21 GMT 2025`
Record UNII	X87G8IX72O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

COACTINON

Preferred Name

English

EMIVIRINE

Official 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