Chemical Component Summary

Name4-({6-AMINO-5-BROMO-2-[(4-CYANOPHENYL)AMINO]PYRIMIDIN-4-YL}OXY)-3,5-DIMETHYLBENZONITRILE
SynonymsEtravine; Etravirine
Identifiers4-[6-azanyl-5-bromanyl-2-[(4-cyanophenyl)amino]pyrimidin-4-yl]oxy-3,5-dimethyl-benzenecarbonitrile
FormulaC20 H15 Br N6 O
Molecular Weight435.277
TypeNON-POLYMER
Isomeric SMILESCc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N
InChIInChI=1S/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)
InChIKeyPYGWGZALEOIKDF-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count43
Chiral Atom Count0
Bond Count45
Aromatic Bond Count18

Drug Info: DrugBank

DrugBank IDDB06414 
NameEtravirine
Groups approved
DescriptionEtravirine is an antiretroviral agent more specifically classified as a Non-Nucleoside Reverse Transcriptase Inhibitor (NNRTI). Etraverine is used clinically for the treatment of human immunodeficiency virus type 1 (HIV-1) infection. On January 18, 2007, the FDA granted accelerated approved for the use of etravirine 100mg tablets in the treatment of adult HIV-1 infection documented to be resistant to therapy with other NNRTIs and antiretroviral agents. On March 26, 2012, approval was extended for use in treatment-experienced pediatric patients 6 to 18 years of age, weighing at least 16 kg. Etravarine must always be used in combination with other antiretroviral drugs. Etravirine exerts its effects via direct inhibition of the reverse transcriptase enzyme of human immunodeficiency virus type 1 (HIV-1), and consequently blocks DNA-dependent and RNA-dependent polymerase activity. Etravirine does not inhibit human DNA polymerase alpha, beta or gamma. Common side effects of use include mild to moderate rash within the first 6 weeks of therapy, nausea, diarrhea and peripheral neuropathy. Patients are advised to immediately contact their healthcare provider if a rash develops. In 2009, postmarketing case reports of Stevens-Johnson Syndrome, toxic epidermal necrolysis, erythema multiforme, and other hypersensitivity reactions lead to a revision of etravirine's "Warnings and Precautions," as well as notification of health care providers. In 2013, reports of Autoimmune disorders (such as Graves’ disease, polymyositis, and Guillain-Barré syndrome) in the setting of immune reconstitution, as well as more in depth information about the development of rashes in patients taking etravirine, lead to a modification of etravirine's monograph.
Synonyms
  • Etravirine
  • Etravirina
Brand Names
  • Etravirine
  • Intelence
IndicationEtravirine is indicated, in combination with other antiretroviral agents, for the treatment of HIV-1 infection in treatment-experienced patients ≥2 years of age.[L9320]
Categories
  • Anti-Infective Agents
  • Anti-Retroviral Agents
  • Antiinfectives for Systemic Use
  • Antiviral Agents
  • Antivirals for Systemic Use
ATC-CodeJ05AG04
CAS number269055-15-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Gag-Pol polyproteinMGARASVLSGGELDRWEKIRLRPGGKKKYKLKHIVWASRELERFAVNPGL...unknown
Gag-Pol polyproteinMGARASVLSGGELDRWEKIRLRPGGKKKYKLKHIVWASRELERFAVNPGL...unknown
Reverse transcriptase/RNaseHPISPIETVPVKLKPGMDGPKVKQWPLTEEKIKALVEICTEMEKEGKISKI...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inducer
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate,inhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 193962
ChEMBL CHEMBL308954
ChEBI CHEBI:63589
CCDC/CSD LIKTIK, LIKWIN, LIKTUW, LIKWUZ, LIKTOQ, LIKWOT, LIKVAE, RANTIN, RANTOT, RANTAF, RANTAF01