Efavirenz (BioDeep_00000003056)
Secondary id: BioDeep_00000406137
human metabolite blood metabolite Volatile Flavor Compounds
代谢物信息卡片
化学式: C14H9ClF3NO2 (315.027388)
中文名称: 依法韦仑
谱图信息:
最多检出来源 Homo sapiens(blood) 20%
分子结构信息
SMILES: C1CC1C#CC2(C3=C(C=CC(=C3)Cl)NC(=O)O2)C(F)(F)F
InChI: 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
描述信息
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.
J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AG - Non-nucleoside reverse transcriptase inhibitors
C471 - Enzyme Inhibitor > C1589 - Reverse Transcriptase Inhibitor > C97453 - Non-nucleoside Reverse Transcriptase Inhibitor
D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065689 - Cytochrome P-450 CYP2C19 Inhibitors
D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065688 - Cytochrome P-450 CYP2C9 Inhibitors
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D018894 - Reverse Transcriptase Inhibitors
D065693 - Cytochrome P-450 Enzyme Inducers > D065695 - Cytochrome P-450 CYP2B6 Inducers
D065693 - Cytochrome P-450 Enzyme Inducers > D065701 - Cytochrome P-450 CYP3A Inducers
D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors
C254 - Anti-Infective Agent > C281 - Antiviral Agent
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3292
CONFIDENCE standard compound; INTERNAL_ID 8518
同义名列表
19 个代谢物同义名
6-Chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[D][1,3]oxazin-2-one; (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-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; (S)-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; (-)-6-CHLORO-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; Merck sharp and dohme brand OF efavirenz; Bristol-myers squibb brand OF efavirenz; United drug brand OF efavirenz; Du pont brand OF efavirenz; Efavirenz, (S)-isomer; Efavirenz, (R)-isomer; Efavirenz; DMP-266; DMP 266; Stocrin; Sustiva; EFV; Efavirenz
数据库引用编号
31 个数据库交叉引用编号
- ChEBI: CHEBI:119486
- KEGG: C08088
- KEGGdrug: D00896
- PubChem: 64139
- HMDB: HMDB0014763
- Metlin: METLIN66808
- DrugBank: DB00625
- ChEMBL: CHEMBL223228
- Wikipedia: Efavirenz
- chemspider: 57715
- CAS: 154598-52-4
- MoNA: SM851803
- MoNA: EQ329252
- MoNA: EQ329256
- MoNA: EQ329251
- MoNA: EQ329255
- MoNA: EQ329202
- MoNA: SM851853
- MoNA: EQ329204
- MoNA: EQ329203
- MoNA: EQ329206
- MoNA: EQ329201
- MoNA: EQ329205
- MoNA: EQ329254
- MoNA: EQ329253
- PMhub: MS000007861
- PubChem: 10288
- PDB-CCD: EFZ
- NIKKAJI: J727.577C
- RefMet: Efavirenz
- KNApSAcK: 119486
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Chunmei Wang, Xiaoli Yu, Yingchun Ke, Yanhua Fu, Yanhe Luo, Ying Li, Yanmei Bi, Xingqiong Chen, Linghua Li, Xiuhong Zhao, Zhong Chen. Efficacy and effect on lipid profiles of switching to ainuovirine-based regimen versus continuing efavirenz-based regimen in people with HIV-1: 24-week results from a real-world, retrospective, multi-center cohort study.
Antimicrobial agents and chemotherapy.
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The lancet. HIV.
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BMJ open.
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Nutrition research (New York, N.Y.).
2023 Sep; 119(?):119-131. doi:
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Biochemical pharmacology.
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PLoS biology.
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International journal of molecular sciences.
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Annals of medicine.
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Chemico-biological interactions.
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AAPS PharmSciTech.
2022 Jun; 23(6):177. doi:
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Scientific reports.
2022 06; 12(1):9698. doi:
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Die Pharmazie.
2022 Jun; 77(6):191-195. doi:
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AIDS research and human retroviruses.
2022 06; 38(6):455-462. doi:
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AIDS research and human retroviruses.
2022 06; 38(6):441-450. doi:
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Medicine.
2022 Apr; 101(17):e29066. doi:
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International journal of infectious diseases : IJID : official publication of the International Society for Infectious Diseases.
2022 Apr; 117(?):48-55. doi:
10.1016/j.ijid.2022.01.051
. [PMID: 35108610] - David W Haas, Rosie Mngqibisa, Jose Francis, Helen McIlleron, Jennifer A Robinson, Michelle A Kendall, Paxton Baker, Sajeeda Mawlana, Sharlaa Badal-Faesen, Francis Angira, Ayotunde Omoz-Oarhe, Wadzanai P Samaneka, Paolo Denti, Susan E Cohn. Pharmacogenetics of interaction between depot medroxyprogesterone acetate and efavirenz, rifampicin, and isoniazid during treatment of HIV and tuberculosis.
Pharmacogenetics and genomics.
2022 01; 32(1):24-30. doi:
10.1097/fpc.0000000000000448
. [PMID: 34369424] - Wondmagegn Tamiru Tadesse, Birhanemeskel T Adankie, Workineh Shibeshi, Wondwossen Amogne, Eleni Aklillu, Ephrem Engidawork. Prevalence and predictors of glucose metabolism disorders among People Living with HIV on combination antiretroviral therapy.
PloS one.
2022; 17(1):e0262604. doi:
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. [PMID: 35045105] - Lisa M Frenkel, R Leavitt Morrison, Trevon L Fuller, Maria Isabel Gouvêa, Maria de Lourdes Benamor Teixeira, Robert W Coombs, David E Shapiro, Mark Mirochnick, Roslyn Hennessey, Kyle Whitson, Nahida Chakhtoura, Esaú C João. Brief Report: Vaginal Viral Shedding With Undetectable Plasma HIV Viral Load in Pregnant Women Receiving 2 Different Antiretroviral Regimens: A Randomized Clinical Trial.
Journal of acquired immune deficiency syndromes (1999).
2021 12; 88(4):361-365. doi:
10.1097/qai.0000000000002771
. [PMID: 34369908] - Xian-Min Meng, Zi-Ran Li, Xin-Yin Zheng, Yi-Xi Liu, Wan-Jie Niu, Xiao-Yan Qiu, Hong-Zhou Lu. Effect of albumin and CYP2B6 polymorphisms on exposure of efavirenz: A population pharmacokinetic analysis in Chinese HIV-infected adults.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2021 Dec; 167(?):105986. doi:
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Journal of clinical pharmacology.
2021 12; 61(12):1555-1566. doi:
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. [PMID: 34169526] - Musa Otieno Ngayo, Margaret Oluka, Wallace Dimbuson Bulimo, Faith Apolot Okalebo. Association between social psychological status and efavirenz and nevirapine plasma concentration among HIV patients in Kenya.
Scientific reports.
2021 11; 11(1):22071. doi:
10.1038/s41598-021-01345-9
. [PMID: 34764325] - Natália Bordin Andriguetti, Helena Katherina Van Schalkwyk, Daniel Thomas Barratt, Joseph Tucci, Paul Pumuye, Andrew Alexander Somogyi. Large variability in plasma efavirenz concentration in Papua New Guinea HIV/AIDS patients associated with high frequency of CYP2B6 516T allele.
Clinical and translational science.
2021 11; 14(6):2521-2531. doi:
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. [PMID: 34415664] - Huan Xia, Xiao-Jie Huang, Yue Hu, Li-Ying Gao, Yue Wu, Hao Wu, Zhong-Fang Yan, Ping Ma. Switching from efavirenz to elvitegravir/cobicistat/emtricitabine/tenofovir alafenamide reduces central nervous system symptoms in people living with HIV.
Chinese medical journal.
2021 Oct; 134(23):2850-2856. doi:
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. [PMID: 34653085] - Jessica Cusato, Massimo Tempestilli, Andrea Calcagno, Alessandra Vergori, Pierluca Piselli, Miriam Antonucci, Valeria Avataneo, Alice Palermiti, Stefania Notari, Andrea Antinori, Giovanni Di Perri, Chiara Agrati, Antonio D'Avolio. Vitamin D as Modulator of Drug Concentrations: A Study on Two Italian Cohorts of People Living with HIV Administered with Efavirenz.
Nutrients.
2021 Oct; 13(10):. doi:
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. [PMID: 34684572] - Jesper Sundell, Emile Bienvenu, Angela Äbelö, Michael Ashton. Effect of efavirenz-based ART on the pharmacokinetics of rifampicin and its primary metabolite in patients coinfected with TB and HIV.
The Journal of antimicrobial chemotherapy.
2021 10; 76(11):2950-2957. doi:
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. [PMID: 34337654] - Jacinta N Nwogu, Monica Gandhi, Andrew Owen, Saye H Khoo, Babafemi Taiwo, Adeniyi Olagunju, Baiba Berzins, Hideaki Okochi, Regina Tallerico, Kevin Robertson, Chinedum P Babalola. Associations between efavirenz concentrations, pharmacogenetics and neurocognitive performance in people living with HIV in Nigeria.
AIDS (London, England).
2021 10; 35(12):1919-1927. doi:
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. [PMID: 34115651] - Natália Bordin Andriguetti, Daniel T Barratt, Joseph Tucci, Paul Pumuye, Andrew A Somogyi. Instability of Efavirenz Metabolites Identified During Method Development and Validation.
Journal of pharmaceutical sciences.
2021 10; 110(10):3362-3366. doi:
10.1016/j.xphs.2021.06.028
. [PMID: 34175301] - Wangu Masenga, Giacomo Maria Paganotti, Kaelo Seatla, Simani Gaseitsiwe, Kwenga Sichilongo. A fast-screening dispersive liquid-liquid microextraction-gas chromatography-mass spectrometry method applied to the determination of efavirenz in human plasma samples.
Analytical and bioanalytical chemistry.
2021 Oct; 413(25):6401-6412. doi:
10.1007/s00216-021-03604-0
. [PMID: 34557941] - Wei-Chieh Huang, Chun-Kai Huang, Sung-Hsi Huang, Shu-Wen Lin, Shyh-Tyan Ou, Yi-Ting Chen, Ya-Wen Chen, Shu-Yuan Chang, Wen-Chun Liu, Hsin-Yun Sun, Chien-Ching Hung. Therapeutic drug monitoring study on the switch from coformulated 600-mg efavirenz, tenofovir disoproxil fumarate, and emtricitabine to coformulated 400-mg efavirenz, tenofovir disoproxil fumarate, and lamivudine among HIV-positive patients with viral suppression.
Journal of microbiology, immunology, and infection = Wei mian yu gan ran za zhi.
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. [PMID: 32675042] - Birgit E Watson, Kieran Atkinson, Kathleen Auyeung, Katherine A Baynes, Katherine J Lepik, Junine Toy, Paul Sereda, Rolando Barrios, Chanson J Brumme. Untimed Efavirenz Drug Levels After Switching From Brand to Generic Formulations: A Short Communication.
Therapeutic drug monitoring.
2021 10; 43(5):701-705. doi:
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. [PMID: 33560098] - Jose Francis, Rosie Mngqibisa, Helen McIlleron, Michelle A Kendall, Xingye Wu, Kelly E Dooley, Cynthia Firnhaber, Catherine Godfrey, Susan E Cohn, Paolo Denti. A Semimechanistic Pharmacokinetic Model for Depot Medroxyprogesterone Acetate and Drug-Drug Interactions With Antiretroviral and Antituberculosis Treatment.
Clinical pharmacology and therapeutics.
2021 10; 110(4):1057-1065. doi:
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. [PMID: 34151439] - Ngah Kuan Chow, Sabariah Noor Harun, E-Jinq Wong, Lee Lee Low, Siti Maisharah Sheikh Ghadzi, Amer Hayat Khan. The association between cigarette smoking and efavirenz plasma concentration using the population pharmacokinetic approach.
British journal of clinical pharmacology.
2021 10; 87(10):3756-3765. doi:
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. [PMID: 33608883] - Ken Ogasawara, Jeanelle Kam, Mark Thomas, Liangang Liu, Mary Liu, Yongjun Xue, Sekhar Surapaneni, Leonidas N Carayannopoulos, Simon Zhou, Maria Palmisano, Gopal Krishna. Effects of strong and moderate CYP3A4 inducers on the pharmacokinetics of fedratinib in healthy adult participants.
Cancer chemotherapy and pharmacology.
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. [PMID: 34019108] - Thalita Martins da Silva, Thiago da Silva Honorio, Marcelo Henrique da Cunha Chaves, Marcelo Dutra Duque, Lucio Mendes Cabral, Beatriz Ferreira de Carvalho Patricio, Helvécio Vinícius Antunes Rocha. In silico bioavailability for BCS class II efavirenz tablets using biorelevant dissolution media for IVIVR and simulation of formulation changes.
Drug development and industrial pharmacy.
2021 Aug; 47(8):1342-1352. doi:
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. [PMID: 34622730] - Eleni Aklillu, Alimuddin Zumla, Abiy Habtewold, Wondwossen Amogne, Eyasu Makonnen, Getnet Yimer, Jürgen Burhenne, Ulf Diczfalusy. Early or deferred initiation of efavirenz during rifampicin-based TB therapy has no significant effect on CYP3A induction in TB-HIV infected patients.
British journal of pharmacology.
2021 08; 178(16):3294-3308. doi:
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. [PMID: 33155675] - R E Akhigbe, M A Hamed, A O Aremu. HAART exacerbates testicular damage and impaired spermatogenesis in anti-Koch-treated rats via dysregulation of lactate transport and glutathione content.
Reproductive toxicology (Elmsford, N.Y.).
2021 08; 103(?):96-107. doi:
10.1016/j.reprotox.2021.06.007
. [PMID: 34118364] - Ketan Mahajan, Satish Rojekar, Dipen Desai, Smita Kulkarni, Gandhali Bapat, Smita Zinjarde, Pradeep Vavia. Layer-by-Layer Assembled Nanostructured Lipid Carriers for CD-44 Receptor-Based Targeting in HIV-Infected Macrophages for Efficient HIV-1 Inhibition.
AAPS PharmSciTech.
2021 Jun; 22(5):171. doi:
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. [PMID: 34100170] - Sung-Hsi Huang, Wei-Chieh Huang, Shu-Wen Lin, Yu-Chung Chuang, Hsin-Yun Sun, Sui-Yuan Chang, Po-Hsien Kuo, Pei-Ying Wu, Wen-Chun Liu, Chieh Chiang, Chien-Ching Hung, Shan-Chwen Chang. Impact of Efavirenz Mid-dose Plasma Concentration on Long-Term Weight Change Among Virologically Suppressed People Living With HIV.
Journal of acquired immune deficiency syndromes (1999).
2021 06; 87(2):834-841. doi:
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. [PMID: 33587507] - Danilo César Galindo Bedor, Noely Camila Tavares Cavalcanti Bedor, João Gomes Pontes Neto, Lucas José de Alencar Danda, Flávio Martins de Oliveira, Guilherme Henrique Onório de Oliveira, José Lamartine Soares Sobrinho, Eric Beyssac, Whocely Victor de Castro, Davi Pereira de Santana. Characterization, in vitro dissolution, and pharmacokinetics of different batches of efavirenz raw materials.
Drug development and industrial pharmacy.
2021 May; 47(5):725-734. doi:
10.1080/03639045.2021.1934860
. [PMID: 34038291] - Chenai Sheilla Mutiti, Nyasha Nicole Kapungu, Comfort Ropafadzo Kanji, Nadina Stadler, Julia Stingl, Charles Nhachi, James Hakim, Collen Masimirembwa, Roslyn Stella Thelingwani. Clinically relevant enantiomer specific R- and S-praziquantel pharmacokinetic drug-drug interactions with efavirenz and ritonavir.
Pharmacology research & perspectives.
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