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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. Doravirine is a prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of HIV infection in adults who have never taken HIV medicines before. Doravirine is always used in combination with other HIV medicines.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
12.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PIFELTRO
PubMed

PubMed

TitleDatePubMed
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
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Recommended dosage: One tablet taken orally once daily with or without food in adult patients. (2.1) Dosage adjustment with rifabutin: One tablet taken twice daily (approximately 12 hours apart). (2.2) Tablets: 100 mg doravirine.
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