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Details

Stereochemistry ACHIRAL
Molecular Formula C17H11ClF3N5O3
Molecular Weight 425.749
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DORAVIRINE

SMILES

CN1C(=O)NN=C1CN2C=CC(=C(OC3=CC(Cl)=CC(=C3)C#N)C2=O)C(F)(F)F

InChI

InChIKey=ZIAOVIPSKUPPQW-UHFFFAOYSA-N
InChI=1S/C17H11ClF3N5O3/c1-25-13(23-24-16(25)28)8-26-3-2-12(17(19,20)21)14(15(26)27)29-11-5-9(7-22)4-10(18)6-11/h2-6H,8H2,1H3,(H,24,28)

HIDE SMILES / InChI

Molecular Formula C17H11ClF3N5O3
Molecular Weight 425.749
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Doravirine (MK-1439) is a nonnucleoside inhibitor of HIV reverse transcriptase (NNRTI). It displays excellent activities against not only WT viruses but also a broader panel of NNRTI-resistant viruses. Merck is developing doravirine for the treatment of HIV-1 infections.

CNS Activity

Originator

Approval Year

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
12.0 nM [IC50]
Condition Info

Condition Info

PMID

PMID

TitleDatePMID
In vitro characterization of MK-1439, a novel HIV-1 nonnucleoside reverse transcriptase inhibitor.
2014
Discovery of MK-1439, an orally bioavailable non-nucleoside reverse transcriptase inhibitor potent against a wide range of resistant mutant HIV viruses.
2014 Feb 1
Patent

Patent

Sample Use Guides

In Vivo Use Guide
Doravirine is generally well tolerated in single doses up to 1,200 mg and multiple doses up to 750 mg once daily for up to 10 days, with a pharmacokinetic profile supportive of once-daily dosing. The safety and efficacy of Doravirine (MK-1439) 100 mg once daily is planning to evaluate in a Phase 3 clinical trial.
Route of Administration: Oral
In Vitro Use Guide
In the presence of 50% normal human serum (NHS), Doravirine (MK-1439) showed excellent potency in suppressing the replication of WT HIV-1 virus, with a 95% effective concentration (EC95) of 20 nM, as well as K103N, Y181C, and K103N/Y181C mutant viruses with EC95 of 43, 27, and 55 nM, respectively. MK-1439 exhibited similar antiviral activities against 10 different HIV-1 subtype viruses (a total of 93 viruses).
Substance Class Chemical
Created
by admin
on Tue Mar 06 11:45:42 UTC 2018
Edited
by admin
on Tue Mar 06 11:45:42 UTC 2018
Record UNII
913P6LK81M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DORAVIRINE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
DORAVIRINE [USAN]
Common Name English
DORAVIRINE [WHO-DD]
Common Name English
3-CHLORO-5-((1-((4-METHYL-5-OXO-4,5-DIHYDRO-1H-1,2,4-TRIAZOL-3-YL)METHYL)-2-OXO-4-(TRIFLUOROMETHYL)-1,2-DIHYDROPYRIDIN-3-YL)OXY)BENZONITRILE
Systematic Name English
BENZONITRILE, 3-CHLORO-5-((1-((4,5-DIHYDRO-4-METHYL-5-OXO-1H-1,2,4-TRIAZOL-3-YL)METHYL)-1,2-DIHYDRO-2-OXO-4-(TRIFLUOROMETHYL)-3-PYRIDINYL)OXY)-
Systematic Name English
MK-1439
Code English
DORAVIRINE [INN]
Common Name English
Code System Code Type Description
EVMPD
SUB177834
Created by admin on Tue Mar 06 11:45:42 UTC 2018 , Edited by admin on Tue Mar 06 11:45:42 UTC 2018
PRIMARY
EPA CompTox
1338225-97-0
Created by admin on Tue Mar 06 11:45:42 UTC 2018 , Edited by admin on Tue Mar 06 11:45:42 UTC 2018
PRIMARY
CAS
1338225-97-0
Created by admin on Tue Mar 06 11:45:42 UTC 2018 , Edited by admin on Tue Mar 06 11:45:42 UTC 2018
PRIMARY
PUBCHEM
58460047
Created by admin on Tue Mar 06 11:45:42 UTC 2018 , Edited by admin on Tue Mar 06 11:45:42 UTC 2018
PRIMARY SWITZERF
WIKIPEDIA
DORAVIRINE
Created by admin on Tue Mar 06 11:45:42 UTC 2018 , Edited by admin on Tue Mar 06 11:45:42 UTC 2018
PRIMARY
ChEMBL
CHEMBL2364608
Created by admin on Tue Mar 06 11:45:42 UTC 2018 , Edited by admin on Tue Mar 06 11:45:42 UTC 2018
PRIMARY
INN
9797
Created by admin on Tue Mar 06 11:45:42 UTC 2018 , Edited by admin on Tue Mar 06 11:45:42 UTC 2018
PRIMARY
Related Record Type Details
ACTIVE MOIETY