Send us a Message



Submit Data |  Help |  Video Tutorials |  News |  Publications |  Download |  REST API |  Citing RGD |  Contact   

CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:efavirenz
go back to main search page
Accession:CHEBI:119486 term browser browse the term
Definition:1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.
Synonyms:exact_synonym: (4S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one
 related_synonym: (-)-6-CHLORO-4-CYCLOPROPYLETHYNYL-4-TRIFLUOROMETHYL-1,4-DIHYDRO-2H-3,1-BENZOXAZIN-2-ONE;   (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one;   (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one;   6-chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one;   Formula=C14H9ClF3NO2;   InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1;   InChIKey=XPOQHMRABVBWPR-ZDUSSCGKSA-N;   SMILES=FC(F)(F)[C@]1(OC(=O)Nc2ccc(Cl)cc12)C#CC1CC1
 alt_id: CHEBI:190461;   CHEBI:47396;   CHEBI:4760;   MESH:C098320
 xref: CAS:154598-52-4;   DrugBank:DB00625;   Drug_Central:989;   HMDB:HMDB0014763;   KEGG:C08088;   KEGG:D00896;   LINCS:LSM-5526
 xref_mesh: MESH:C098320
 xref: PDBeChem:EFZ;   PMID:10576692;   PMID:10673109;   PMID:25017682;   Patent:EP582455;   Patent:US5519021;   Reaxys:7387333;   Wikipedia:Efavirenz



show annotations for term's descendants           Sort by:
efavirenz term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb11 ATP binding cassette subfamily B member 11 multiple interactions
decreases activity
ISO efavirenz inhibits the reaction [ABCB11 protein results in increased transport of Taurocholic Acid]
efavirenz results in decreased activity of ABCB11 protein
CTD PMID:24014644 NCBI chr 3:74,424,620...74,520,646 JBrowse link
G Adipoq adiponectin, C1Q and collagen domain containing decreases expression
decreases secretion
ISO efavirenz results in decreased expression of ADIPOQ mRNA
efavirenz results in decreased secretion of ADIPOQ protein
CTD PMID:21619898 NCBI chr11:91,226,524...91,240,244 JBrowse link
G Alb albumin affects binding ISO efavirenz binds to ALB protein CTD PMID:15814459 PMID:16336266 NCBI chr14:17,891,564...17,907,043 JBrowse link
G Bcl2l11 Bcl2-like 11 increases response to substance
increases expression
ISO BCL2L11 protein results in increased susceptibility to efavirenz metabolite
efavirenz metabolite results in increased expression of BCL2L11 mRNA; efavirenz metabolite results in increased expression of BCL2L11 protein; efavirenz results in increased expression of BCL2L11 mRNA; efavirenz results in increased expression of BCL2L11 protein
CTD PMID:21958719 NCBI chr 3:135,820,042...135,857,330 JBrowse link
G Canx calnexin affects localization ISO efavirenz affects the localization of CANX protein CTD PMID:28940366 NCBI chr10:35,124,941...35,157,954 JBrowse link
G Casp3 caspase 3 multiple interactions ISO
EXP
efavirenz metabolite results in increased cleavage of and results in increased activity of CASP3 protein; efavirenz results in increased cleavage of and results in increased activity of CASP3 protein
[efavirenz co-treated with Lamivudine co-treated with Tenofovir] results in increased activity of CASP3 protein; Zinc inhibits the reaction [[efavirenz co-treated with Lamivudine co-treated with Tenofovir] results in increased activity of CASP3 protein]
CTD PMID:21958719 PMID:36309141 NCBI chr16:52,395,539...52,413,794 JBrowse link
G Cat catalase multiple interactions EXP [efavirenz co-treated with Lamivudine co-treated with Tenofovir] results in decreased activity of CAT protein CTD PMID:34118364 NCBI chr 3:110,297,340...110,329,526 JBrowse link
G Ccl2 C-C motif chemokine ligand 2 increases secretion ISO efavirenz results in increased secretion of CCL2 protein CTD PMID:21619898 NCBI chr10:67,503,077...67,504,875 JBrowse link
G Cebpa CCAAT/enhancer binding protein alpha decreases expression ISO efavirenz results in decreased expression of CEBPA mRNA CTD PMID:21619898 NCBI chr 1:87,759,631...87,762,303 JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 affects metabolic processing
increases metabolic processing
multiple interactions
decreases activity
ISO CYP2B6 gene polymorphism affects the metabolism of efavirenz; CYP2B6 protein affects the metabolism of efavirenz
CYP2B6 protein results in increased metabolism of efavirenz
[efavirenz results in decreased activity of CYP2B6 protein] which results in decreased metabolism of Bupropion; [efavirenz results in increased activity of NR1I3 protein alternative form] which results in increased expression of CYP2B6 mRNA; [efavirenz results in increased activity of NR1I3 protein] which results in increased expression of CYP2B6 mRNA
CTD PMID:15622315 PMID:15769884 PMID:17041008 PMID:17559344 PMID:26599973 NCBI chr 1:90,780,468...90,859,852 JBrowse link
G Cyp2c6 cytochrome P450, family 2, subfamily C, polypeptide 6 decreases activity ISO efavirenz results in decreased activity of CYP2C19 protein CTD PMID:11225565 NCBI chr 1:247,879,058...247,916,804 JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 decreases activity
increases activity
increases expression
ISO efavirenz results in decreased activity of CYP3A4 protein
efavirenz results in increased activity of CYP3A4 protein
efavirenz results in increased expression of CYP3A4 mRNA
CTD PMID:15980690 PMID:16837568 NCBI chr12:14,321,771...14,343,886 JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression ISO efavirenz results in increased expression of DDIT3 protein CTD PMID:28940366 NCBI chr 7:65,001,695...65,006,517 JBrowse link
G Dnm1l dynamin 1-like affects localization ISO efavirenz affects the localization of DNM1L protein modified form CTD PMID:28940366 NCBI chr11:98,084,049...98,135,663 JBrowse link
G Eif2ak3 eukaryotic translation initiation factor 2 alpha kinase 3 increases expression ISO efavirenz results in increased expression of EIF2AK3 protein modified form CTD PMID:28940366 NCBI chr 4:104,363,838...104,425,271 JBrowse link
G Fis1 fission, mitochondrial 1 increases expression ISO efavirenz results in increased expression of FIS1 mRNA CTD PMID:28940366 NCBI chr12:25,345,239...25,360,135 JBrowse link
G Hgf hepatocyte growth factor increases secretion ISO efavirenz results in increased secretion of HGF protein CTD PMID:21619898 NCBI chr 4:19,628,902...19,700,467 JBrowse link
G Hspa9 heat shock protein family A (Hsp70) member 9 multiple interactions ISO efavirenz promotes the reaction [VDAC1 protein binds to HSPA9 protein] CTD PMID:28940366 NCBI chr18:26,536,131...26,554,294 JBrowse link
G Il1b interleukin 1 beta multiple interactions EXP [efavirenz co-treated with Lamivudine co-treated with Tenofovir] results in increased expression of IL1B protein; Zinc inhibits the reaction [[efavirenz co-treated with Lamivudine co-treated with Tenofovir] results in increased expression of IL1B protein] CTD PMID:36309141 NCBI chr 3:137,030,200...137,036,581 JBrowse link
G Il6 interleukin 6 increases secretion ISO efavirenz results in increased secretion of IL6 protein CTD PMID:21619898 NCBI chr 4:5,889,999...5,894,575 JBrowse link
G Jun Jun proto-oncogene, AP-1 transcription factor subunit increases phosphorylation ISO efavirenz metabolite results in increased phosphorylation of JUN protein; efavirenz results in increased phosphorylation of JUN protein CTD PMID:21958719 NCBI chr 5:115,009,900...115,012,993 JBrowse link
G Lep leptin decreases expression ISO efavirenz results in decreased expression of LEP mRNA CTD PMID:21619898 NCBI chr 4:58,626,529...58,640,663 JBrowse link
G Lonp1 lon peptidase 1, mitochondrial multiple interactions
increases response to substance
increases expression
ISO efavirenz results in increased expression of and affects the localization of LONP1 protein; Mn(III) 5,10,15,20-tetrakis(N-methylpyridinium-2-yl)porphyrin inhibits the reaction [efavirenz results in increased expression of LONP1 mRNA]
LONP1 protein results in increased susceptibility to efavirenz
CTD PMID:28940366 NCBI chr 9:1,447,444...1,459,771 JBrowse link
G Lpl lipoprotein lipase decreases expression ISO efavirenz results in decreased expression of LPL mRNA CTD PMID:21619898 NCBI chr16:25,596,205...25,621,928 JBrowse link
G Map3k5 mitogen-activated protein kinase kinase kinase 5 increases phosphorylation ISO efavirenz metabolite results in increased phosphorylation of MAP3K5 protein; efavirenz results in increased phosphorylation of MAP3K5 protein CTD PMID:21958719 NCBI chr 1:16,505,387...16,723,899 JBrowse link
G Mapk8 mitogen-activated protein kinase 8 multiple interactions
increases phosphorylation
ISO Acetylcysteine inhibits the reaction [efavirenz metabolite results in increased phosphorylation of MAPK8 protein]; Acetylcysteine inhibits the reaction [efavirenz results in increased phosphorylation of MAPK8 protein]
efavirenz metabolite results in increased phosphorylation of MAPK8 protein; efavirenz results in increased phosphorylation of MAPK8 protein
CTD PMID:21958719 NCBI chr16:8,645,171...8,728,225 JBrowse link
G Mfn2 mitofusin 2 increases expression ISO efavirenz results in increased expression of MFN2 mRNA CTD PMID:28940366 NCBI chr 5:158,304,285...158,335,502 JBrowse link
G Mpo myeloperoxidase multiple interactions EXP [efavirenz co-treated with Lamivudine co-treated with Tenofovir] promotes the reaction [[isoniazid, pyrazinamide, rifampin drug combination co-treated with Ethambutol] results in increased activity of MPO protein]; [efavirenz co-treated with Lamivudine co-treated with Tenofovir] results in increased activity of MPO protein CTD PMID:34118364 NCBI chr10:73,092,124...73,102,057 JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 increases activity EXP efavirenz results in increased activity of NR1I2 protein CTD PMID:27732639 NCBI chr11:75,965,717...76,006,733 JBrowse link
G Nr1i3 nuclear receptor subfamily 1, group I, member 3 multiple interactions
increases activity
ISO
EXP
[efavirenz results in increased activity of NR1I3 protein alternative form] which results in increased expression of CYP2B6 mRNA; [efavirenz results in increased activity of NR1I3 protein] which results in increased expression of CYP2B6 mRNA CTD PMID:17041008 PMID:27732639 NCBI chr13:86,165,327...86,170,362 JBrowse link
G Opa1 OPA1, mitochondrial dynamin like GTPase increases expression ISO efavirenz results in increased expression of OPA1 mRNA CTD PMID:28940366 NCBI chr11:84,612,943...84,690,025 JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma decreases expression ISO efavirenz results in decreased expression of PPARG mRNA CTD PMID:21619898 NCBI chr 4:150,095,743...150,221,104 JBrowse link
G Rmdn3 regulator of microtubule dynamics 3 increases expression ISO efavirenz results in increased expression of RMDN3 protein CTD PMID:28940366 NCBI chr 3:126,579,811...126,601,016 JBrowse link
G Serpine1 serpin family E member 1 increases secretion ISO efavirenz results in increased secretion of SERPINE1 protein CTD PMID:21619898 NCBI chr12:25,237,977...25,248,356 JBrowse link
G Slc5a5 solute carrier family 5 member 5 multiple interactions ISO [efavirenz co-treated with TSHB protein] results in increased expression of SLC5A5 mRNA; [efavirenz co-treated with TSHB protein] results in increased expression of SLC5A5 protein CTD PMID:16030158 NCBI chr16:18,546,709...18,556,698 JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 decreases expression ISO efavirenz results in decreased expression of SREBF1 mRNA CTD PMID:21619898 NCBI chr10:45,507,152...45,529,164 JBrowse link
G Tg thyroglobulin increases expression ISO efavirenz results in increased expression of TG mRNA; efavirenz results in increased expression of TG protein CTD PMID:16030158 NCBI chr 7:98,418,293...98,603,210 JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP [efavirenz co-treated with Lamivudine co-treated with Tenofovir] results in increased expression of TNF protein; Zinc inhibits the reaction [[efavirenz co-treated with Lamivudine co-treated with Tenofovir] results in increased expression of TNF protein] CTD PMID:36309141 NCBI chr20:3,626,685...3,629,303 JBrowse link
G Tpo thyroid peroxidase increases expression ISO efavirenz results in increased expression of TPO mRNA; efavirenz results in increased expression of TPO protein CTD PMID:16030158 NCBI chr 6:52,425,998...52,495,793 JBrowse link
G Tshb thyroid stimulating hormone subunit beta multiple interactions ISO [efavirenz co-treated with TSHB protein] results in increased expression of SLC5A5 mRNA; [efavirenz co-treated with TSHB protein] results in increased expression of SLC5A5 protein; efavirenz promotes the reaction [TSHB protein affects the abundance of Iodine]; sodium perchlorate inhibits the reaction [efavirenz promotes the reaction [TSHB protein affects the abundance of Iodine]] CTD PMID:16030158 NCBI chr 2:190,224,676...190,229,559 JBrowse link
G Tshr thyroid stimulating hormone receptor increases expression ISO efavirenz results in increased expression of TSHR mRNA CTD PMID:16030158 NCBI chr 6:116,072,321...116,206,009 JBrowse link
G Vdac1 voltage-dependent anion channel 1 multiple interactions ISO efavirenz promotes the reaction [VDAC1 protein binds to HSPA9 protein] CTD PMID:28940366 NCBI chr10:37,029,377...37,060,542 JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19898
    role 19869
      biological role 19867
        antimicrobial agent 18275
          antiviral agent 11395
            antiviral drug 1997
              efavirenz 42
Path 2
Term Annotations click to browse term
  CHEBI ontology 19898
    subatomic particle 19896
      composite particle 19896
        hadron 19896
          baryon 19896
            nucleon 19896
              atomic nucleus 19896
                atom 19896
                  main group element atom 19835
                    p-block element atom 19835
                      carbon group element atom 19774
                        carbon atom 19770
                          organic molecular entity 19770
                            organic molecule 19724
                              organic cyclic compound 19516
                                organic heterocyclic compound 18896
                                  organic heteropolycyclic compound 18323
                                    organic heterobicyclic compound 17262
                                      benzoxazine 197
                                        efavirenz 42
paths to the root