65B

4-({6-AMINO-5-BROMO-2-[(4-CYANOPHENYL)AMINO]PYRIMIDIN-4-YL}OXY)-3,5-DIMETHYLBENZONITRILE

Created:	2004-04-15
Last modified:	2020-06-05

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4 entries where 65B is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	43
Chiral Atom Count	0
Bond Count	45
Aromatic Bond Count	18

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Chemical Component Summary
Name	4-({6-AMINO-5-BROMO-2-[(4-CYANOPHENYL)AMINO]PYRIMIDIN-4-YL}OXY)-3,5-DIMETHYLBENZONITRILE
Synonyms	Etravine; Etravirine
Systematic Name (OpenEye OEToolkits)	4-[6-azanyl-5-bromanyl-2-[(4-cyanophenyl)amino]pyrimidin-4-yl]oxy-3,5-dimethyl-benzenecarbonitrile
Formula	C₂₀ H₁₅ Br N₆ O
Molecular Weight	435.277
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	N#Cc3cc(c(Oc1nc(nc(c1Br)N)Nc2ccc(C#N)cc2)c(c3)C)C
SMILES	CACTVS	3.370	Cc1cc(cc(C)c1Oc2nc(Nc3ccc(cc3)C#N)nc(N)c2Br)C#N
SMILES	OpenEye OEToolkits	1.7.6	Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N
Canonical SMILES	CACTVS	3.370	Cc1cc(cc(C)c1Oc2nc(Nc3ccc(cc3)C#N)nc(N)c2Br)C#N
Canonical SMILES	OpenEye OEToolkits	1.7.6	Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N
InChI	InChI	1.03	InChI=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)
InChIKey	InChI	1.03	PYGWGZALEOIKDF-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB06414
Name	Etravirine
Groups	approved
Description	Etravirine 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	Etravirina Etravirine
Brand Names	Intelence Etravirine
Indication	Etravirine 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 Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 inhibitors (strength unknown) Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP3A Inducers Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inducers Cytochrome P-450 CYP3A4 Inducers (moderate) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Direct Acting Antivirals Enzyme Inhibitors Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor Non-Nucleoside Reverse Transcriptase Inhibitors Nonnucleoside Reverse Transcriptase Inhibitors Nucleic Acid Synthesis Inhibitors P-glycoprotein inducers P-glycoprotein inhibitors Reverse Transcriptase Inhibitors
ATC-Code	J05AG04
CAS number	269055-15-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Gag-Pol polyprotein	MGARASVLSGGELDRWEKIRLRPGGKKKYKLKHIVWASRELERFAVNPGL...	unknown
Gag-Pol polyprotein	MGARASVLSGGELDRWEKIRLRPGGKKKYKLKHIVWASRELERFAVNPGL...	unknown
Reverse transcriptase/RNaseH	PISPIETVPVKLKPGMDGPKVKQWPLTEEKIKALVEICTEMEKEGKISKI...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inducer
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate,inhibitor
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	substrate,inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
Multidrug resistance protein 3	MDLEAAKNGTAWRPTSAEGDFELGISSKQKRKKTKTVKMIGVLTLFRYSD...	unknown	inhibitor
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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