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Namespace Prefixes

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Statements

Subject Item
n2:DB00625
rdf:type
n6:Drug
n6:description
Efavirenz (brand names Sustiva® and Stocrin®) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and is used as part of highly active antiretroviral therapy (HAART) for the treatment of a human immunodeficiency virus (HIV) type 1. For HIV infection that has not previously been treated, efavirenz and lamivudine in combination with zidovudine or tenofovir is the preferred NNRTI-based regimen. Efavirenz is also used in combination with other antiretroviral agents as part of an expanded postexposure prophylaxis regimen to prevent HIV transmission for those exposed to materials associated with a high risk for HIV transmission.
n6:dosage
n17:271B5A14-363D-11E5-9242-09173F13E4C5 n17:271B5A15-363D-11E5-9242-09173F13E4C5 n17:271B5A16-363D-11E5-9242-09173F13E4C5
n6:generalReferences
# Ren J, Bird LE, Chamberlain PP, Stewart-Jones GB, Stuart DI, Stammers DK: Structure of HIV-2 reverse transcriptase at 2.35-A resolution and the mechanism of resistance to non-nucleoside inhibitors. Proc Natl Acad Sci U S A. 2002 Oct 29;99(22):14410-5. Epub 2002 Oct 17. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12386343
n6:group
approved investigational
n6:halfLife
40-55 hours
n6:indication
For use in combination treatment of HIV infection (AIDS)
n6:manufacturer
n11:271B5A0E-363D-11E5-9242-09173F13E4C5 n11:271B5A0F-363D-11E5-9242-09173F13E4C5
owl:sameAs
n22:DB00625 n23:DB00625
dcterms:title
Efavirenz
adms:identifier
n4:64139 n5:46506827 n12:Efavirenz n25:2483 n26:119486 n27:EFZ n28:PA449441 n29:D00896 n30:0056-0474-92 n31:C08088 n32:57715 n33:DB00625
n6:mechanismOfAction
Similar to zidovudine, efavirenz inhibits the activity of viral RNA-directed DNA polymerase (i.e., reverse transcriptase). Antiviral activity of efavirenz is dependent on intracellular conversion to the active triphosphorylated form. The rate of efavirenz phosphorylation varies, depending on cell type. It is believed that inhibition of reverse transcriptase interferes with the generation of DNA copies of viral RNA, which, in turn, are necessary for synthesis of new virions. Intracellular enzymes subsequently eliminate the HIV particle that previously had been uncoated, and left unprotected, during entry into the host cell. Thus, reverse transcriptase inhibitors are virustatic and do not eliminate HIV from the body. Even though human DNA polymerase is less susceptible to the pharmacologic effects of triphosphorylated efavirenz, this action may nevertheless account for some of the drug's toxicity.
n6:packager
n11:271B5A09-363D-11E5-9242-09173F13E4C5 n11:271B5A0A-363D-11E5-9242-09173F13E4C5 n11:271B5A0D-363D-11E5-9242-09173F13E4C5 n11:271B5A0B-363D-11E5-9242-09173F13E4C5 n11:271B5A0C-363D-11E5-9242-09173F13E4C5
n6:patent
n10:5811423 n10:2101572 n10:2279198 n10:6238695
n6:routeOfElimination
Nearly all of the urinary excretion of the radiolabeled drug was in the form of metabolites.
n6:synonym
(-)-6-CHLORO-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (S)-6-chloro-4-Cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[D][1,3]oxazin-2-one Efavirenz Efavirenzum Éfavirenz 6-chloro-4-(2-Cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[D][1,3]oxazin-2-one (S)-6-chloro-4-(Cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one
n15:hasAHFSCode
n18:08-18-08-16
n6:foodInteraction
Avoid excessive or chronic alcohol consumption. Take without regard to meals.
n6:proteinBinding
99.5-99.75%
n6:synthesisReference
John Doney, "Amorphous efavirenz and the production thereof." U.S. Patent US20070026073, issued February 01, 2007.
n19:hasConcept
n20:M0258297
foaf:page
n14:efaviren.htm n24:efavirenz.html
n6:IUPAC-Name
n8:271B5A1B-363D-11E5-9242-09173F13E4C5
n6:InChI
n8:271B5A21-363D-11E5-9242-09173F13E4C5
n6:Molecular-Formula
n8:271B5A20-363D-11E5-9242-09173F13E4C5
n6:Molecular-Weight
n8:271B5A1D-363D-11E5-9242-09173F13E4C5
n6:Monoisotopic-Weight
n8:271B5A1E-363D-11E5-9242-09173F13E4C5
n6:SMILES
n8:271B5A1F-363D-11E5-9242-09173F13E4C5
n6:Water-Solubility
n8:271B5A19-363D-11E5-9242-09173F13E4C5
n6:logP
n8:271B5A32-363D-11E5-9242-09173F13E4C5 n8:271B5A17-363D-11E5-9242-09173F13E4C5 n8:271B5A1A-363D-11E5-9242-09173F13E4C5
n6:logS
n8:271B5A18-363D-11E5-9242-09173F13E4C5
n15:hasATCCode
n16:J05AG03
n6:H-Bond-Acceptor-Count
n8:271B5A27-363D-11E5-9242-09173F13E4C5
n6:H-Bond-Donor-Count
n8:271B5A28-363D-11E5-9242-09173F13E4C5
n6:InChIKey
n8:271B5A22-363D-11E5-9242-09173F13E4C5
n6:Polar-Surface-Area--PSA-
n8:271B5A23-363D-11E5-9242-09173F13E4C5
n6:Polarizability
n8:271B5A25-363D-11E5-9242-09173F13E4C5
n6:Refractivity
n8:271B5A24-363D-11E5-9242-09173F13E4C5
n6:Rotatable-Bond-Count
n8:271B5A26-363D-11E5-9242-09173F13E4C5
n6:affectedOrganism
Human Immunodeficiency Virus
n6:casRegistryNumber
154598-52-4
n6:category
n6:containedIn
n7:271B5A10-363D-11E5-9242-09173F13E4C5 n7:271B5A11-363D-11E5-9242-09173F13E4C5 n7:271B5A12-363D-11E5-9242-09173F13E4C5 n7:271B5A13-363D-11E5-9242-09173F13E4C5
n6:Bioavailability
n8:271B5A2D-363D-11E5-9242-09173F13E4C5
n6:Ghose-Filter
n8:271B5A2F-363D-11E5-9242-09173F13E4C5
n6:MDDR-Like-Rule
n8:271B5A30-363D-11E5-9242-09173F13E4C5
n6:Melting-Point
n8:271B5A31-363D-11E5-9242-09173F13E4C5
n6:Number-of-Rings
n8:271B5A2C-363D-11E5-9242-09173F13E4C5
n6:Physiological-Charge
n8:271B5A2B-363D-11E5-9242-09173F13E4C5
n6:Rule-of-Five
n8:271B5A2E-363D-11E5-9242-09173F13E4C5
n6:Traditional-IUPAC-Name
n8:271B5A1C-363D-11E5-9242-09173F13E4C5
n6:pKa--strongest-acidic-
n8:271B5A29-363D-11E5-9242-09173F13E4C5
n6:pKa--strongest-basic-
n8:271B5A2A-363D-11E5-9242-09173F13E4C5