DORAVIRINE

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Search structure


Trade Names	PIFELTRO
Synonyms	Doravirine MK-1439 Mk-1439a Pifeltro
Status
Molecule Category	Free-form
ATC	J05AG06
UNII	913P6LK81M
EPA CompTox	DTXSID30158386


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	ZIAOVIPSKUPPQW-UHFFFAOYSA-N
Smiles	Cn1c(Cn2ccc(C(F)(F)F)c(Oc3cc(Cl)cc(C#N)c3)c2=O)n[nH]c1=O
InChI	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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C17H11ClF3N5O3
Molecular Weight	425.75
AlogP	2.65
Hydrogen Bond Acceptor	7.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	4.0
Polar Surface Area	105.7
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	29.0

Bioactivity

Mechanism of Action	Action	Reference
Reverse transcriptase negative allosteric modulator	NEGATIVE ALLOSTERIC MODULATOR	FDA PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Hydrolase	-	19	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of HIV wild-type reverse transcriptase by electrochemiluminescence assay	Human immunodeficiency virus	11.0 nM
Antiviral activity against wild type HIV1 3B infected in human MT4 cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay	Human immunodeficiency virus 1	13.0 nM
Antiviral activity against HIV1 RES056 containing reverse transcriptase K103N + Y181C mutant infected in human MT4 cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay	Human immunodeficiency virus 1	15.0 nM
Inhibition of recombinant wild type HIV1 reverse transcriptase assessed as reduction in biotin-dUTP incorporation using poly(A)/oligo(dT)15 as template/primer after 1 hr by ELISA	Human immunodeficiency virus 1	19.0 nM
Antiviral activity against HIV1 3B infected in human MT4 cells assessed as protection against virus-induced cytopathic effect incubated for 5 days by MTT assay	Human immunodeficiency virus 1	13.0 nM
Antiviral activity against HIV1 RES056 infected in human MT4 cells assessed as protection against virus-induced cytopathic effect incubated for 5 days by MTT assay	Human immunodeficiency virus 1	15.0 nM
Antiviral activity against HIV-1 IIIB	Human immunodeficiency virus 1	13.3 nM
Antiviral activity against HIV-1 IIIB harboring K103N/Y181C double mutant	Human immunodeficiency virus 1	14.5 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL2364608
DrugBank	DB12301
DrugCentral	5295
FDA SRS	913P6LK81M
PDB	2KW
PubChem	58460047
SureChEMBL	SCHEMBL2509885
ZINC	ZINC000072317283

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).