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1. (s)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2h-3,1-benzoxazin-2-one
2. Dmp 266
3. Dmp-266
4. Efavirenz, (r)-isomer
5. Efavirenz, (s)-isomer
6. L 743,726
7. L 743726
8. L-743,726
9. L-743726
10. Stocrin
11. Sustiva
1. 154598-52-4
2. Sustiva
3. Stocrin
4. Dmp-266
5. Dmp 266
6. Efv
7. (4s)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one
8. (4s)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1h-3,1-benzoxazin-2-one
9. Viraday
10. Efavirenz Teva
11. L-743726
12. (rac)-efavirenz
13. L-743,726
14. (s)-efavirenz
15. (4s)-6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one
16. (s)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one
17. Nsc-742403
18. (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2h-3,1-benzoxazin-2-one
19. (4s)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1h-3,1-benzoxazin-2-one
20. Je6h2o27p8
21. Chebi:119486
22. Nsc742403
23. (4s)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2h-3,1-benzoxazin-2-one
24. (s)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one
25. Dsstox_cid_26029
26. Dsstox_rid_81298
27. Dsstox_gsid_46029
28. (s)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2h-benzo[d][1,3]oxazin-2-one
29. (s)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1h-benzo[d][1,3]oxazin-2(4h)-one
30. 2h-3,1-benzoxazin-2-one, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4s)-
31. 6-chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4s)-1,4-dihydro-2h-benzo[d][1,3]oxazin-2-one
32. (-)-efavirenz
33. (rac)-dmp 266; (rac)-efv; (rac)-l-743726
34. Eravirenz
35. Smr000466351
36. Strocin (tm)
37. Sustiva (tm)
38. Sustiva (tn)
39. Cas-154598-52-4
40. L 743726
41. Hsdb 7163
42. Sr-01000759360
43. Efavirenz [usp:inn:ban]
44. Unii-je6h2o27p8
45. Efavirenzum
46. Met-sdf-1.beta. & Efavirenz
47. 1ikv
48. 1ikw
49. Efavirenz- Bio-x
50. Ncgc00159337-02
51. Efavirenz, (s)
52. Efavirenz & Plga
53. Mfcd05662344
54. Efavirenz & Ifnl1
55. Efavirenz & Ifnl2
56. Efavirenz & Ifnl3
57. Efavirenz & Il-29
58. Efavirenz [inn]
59. Efavirenz [jan]
60. Dmp-266; Efavirenz
61. Efavirenz & Il-28a
62. Efavirenz & Il-28b
63. Efavirenz [mi]
64. Efavirenz [hsdb]
65. Efavirenz [usan]
66. Efv & Interleukin 29
67. Efavirenz [vandf]
68. Efv & Interleukin 28a
69. Efv & Interleukin 28b
70. Efv & Plga
71. Efavirenz [mart.]
72. Efavirenz [usp-rs]
73. Efavirenz [who-dd]
74. Efavirenz [who-ip]
75. Efv & Ifnl1
76. Efv & Ifnl2
77. Efv & Ifnl3
78. Efavirenz (jan/usp/inn)
79. Efv & Interferon Lambda-1
80. Efv & Interferon Lambda-2
81. Efv & Interferon Lambda-3
82. Efavirenz & Interleukin 29
83. Schembl37762
84. Efavirenz [ema Epar]
85. Efavirenz & Interleukin 28a
86. Efavirenz & Interleukin 28b
87. Efavirenz Ready Made Solution
88. Mls000759465
89. Mls001424087
90. Bidd:gt0383
91. Amy229
92. Bdbm2483
93. Chembl223228
94. Dmp266
95. Efv & Il-28a
96. Efv & Il-28b
97. Efavirenz [orange Book]
98. Dtxsid9046029
99. Efavirenz, >=98% (hplc)
100. Efavirenz & Interferon Lambda-1
101. Efavirenz & Interferon Lambda-2
102. Efavirenz & Interferon Lambda-3
103. Efv & Il-29
104. Gtpl11287
105. Telura Component Efavirenz
106. Efavirenz [usp Monograph]
107. Atripla Component Efavirenz
108. Bcpp000245
109. Hms2051j08
110. Hms2090n16
111. Hms3393j08
112. Hms3713m14
113. Met-stromal Cell-derived Factor-1.beta. (human) & Efavirenz
114. Efavirenzum [who-ip Latin]
115. 2h-3,1-benzoxazin-2-one, 6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4s)-
116. Bcp27719
117. Zinc2020233
118. Tox21_111582
119. Dl-535
120. S4685
121. Efavirenz Component Of Atripla
122. Akos015894951
123. Efavirenz & Poly-lactide-co-glycolide
124. Tox21_111582_1
125. Ab21723
126. Bcp9000636
127. Ccg-101011
128. Db00625
129. Ks-5380
130. Nc00261
131. Nsc 742403
132. (s)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2h-3,1-benzoxazin-2-one
133. Efavirenz 100 Microg/ml In Acetonitrile
134. Ncgc00159337-04
135. Ncgc00159337-12
136. Ncgc00271713-05
137. Ncgc00271713-08
138. Ac-25006
139. Bc164402
140. Hy-10572
141. E0997
142. C08088
143. D00896
144. F17329
145. Ab00639956-06
146. Ab00639956-08
147. 598e524
148. A809555
149. Q422645
150. J-520431
151. Sr-01000759360-4
152. Sr-01000759360-5
153. Z2186909878
154. Efavirenz, United States Pharmacopeia (usp) Reference Standard
155. Efavirenz Solution, 1.0 Mg/ml In Acetonitrile, Certified Reference Material
156. (4s)-6-chloranyl-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1h-3,1-benzoxazin-2-one
157. 2h-3, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4s)-
158. (s)-6-chloro-4-(cyclopropyl-ethynyl)-1,4-dihydro-4-(trifluoromethyl)-2h-3,1-benzoxazine-2-one
159. (s)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-(s)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one
160. (s)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2h-3,1-ben Zoxazin-2-one
161. (s)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2h-3,1-benzoxazin-2-one
| Molecular Weight | 315.67 g/mol |
|---|---|
| Molecular Formula | C14H9ClF3NO2 |
| XLogP3 | 4 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 1 |
| Exact Mass | 315.0273907 g/mol |
| Monoisotopic Mass | 315.0273907 g/mol |
| Topological Polar Surface Area | 38.3 Ų |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Complexity | 519 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 4 | |
|---|---|
| Drug Name | Efavirenz |
| PubMed Health | Efavirenz (By mouth) |
| Drug Classes | Antiretroviral Agent |
| Drug Label | SUSTIVA (efavirenz) is an HIV-1 specific, non-nucleoside, reverse transcriptase inhibitor (NNRTI). Efavirenz is chemically described as (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one. Its empirical formu... |
| Active Ingredient | Efavirenz |
| Dosage Form | Tablet; Capsule |
| Route | oral |
| Strength | 200mg; 100mg; 50mg; 600mg |
| Market Status | Tentative Approval |
| Company | Matrix Labs; Macleods Pharms; Hetero Drugs; Strides; Aurobindo; Par Formulations Private; Emcure Pharma; Aurobindo Pharma; Cipla; Micro Labs |
| 2 of 4 | |
|---|---|
| Drug Name | Sustiva |
| PubMed Health | Efavirenz (By mouth) |
| Drug Classes | Antiretroviral Agent |
| Drug Label | SUSTIVA (efavirenz) is an HIV-1 specific, non-nucleoside, reverse transcriptase inhibitor (NNRTI). Efavirenz is chemically described as (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one. Its empirical formu... |
| Active Ingredient | Efavirenz |
| Dosage Form | Tablet; Capsule |
| Route | Oral |
| Strength | 200mg; 600mg; 50mg |
| Market Status | Prescription |
| Company | Bristol Myers Squibb |
| 3 of 4 | |
|---|---|
| Drug Name | Efavirenz |
| PubMed Health | Efavirenz (By mouth) |
| Drug Classes | Antiretroviral Agent |
| Drug Label | SUSTIVA (efavirenz) is an HIV-1 specific, non-nucleoside, reverse transcriptase inhibitor (NNRTI). Efavirenz is chemically described as (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one. Its empirical formu... |
| Active Ingredient | Efavirenz |
| Dosage Form | Tablet; Capsule |
| Route | oral |
| Strength | 200mg; 100mg; 50mg; 600mg |
| Market Status | Tentative Approval |
| Company | Matrix Labs; Macleods Pharms; Hetero Drugs; Strides; Aurobindo; Par Formulations Private; Emcure Pharma; Aurobindo Pharma; Cipla; Micro Labs |
| 4 of 4 | |
|---|---|
| Drug Name | Sustiva |
| PubMed Health | Efavirenz (By mouth) |
| Drug Classes | Antiretroviral Agent |
| Drug Label | SUSTIVA (efavirenz) is an HIV-1 specific, non-nucleoside, reverse transcriptase inhibitor (NNRTI). Efavirenz is chemically described as (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one. Its empirical formu... |
| Active Ingredient | Efavirenz |
| Dosage Form | Tablet; Capsule |
| Route | Oral |
| Strength | 200mg; 600mg; 50mg |
| Market Status | Prescription |
| Company | Bristol Myers Squibb |
Anti-HIV Agents; Reverse Transcriptase Inhibitors
National Library of Medicine's Medical Subject Headings. Efavirenz. Online file (MeSH, 2014). Available from, as of November 19, 2013: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html
Due to ongoing neuropsychiatric adverse events in some efavirenz (EFV)-treated patients, a switch to an alternative non-nucleoside reverse transcriptase inhibitor may be considered. Rilpivirine (RPV) has been coformulated as a single-tablet regimen (STR) with emtricitabine/tenofovir disoproxil fumarate (FTC/TDF), and the components have demonstrated noninferior efficacy to EFV+FTC/TDF, good tolerability profile, and high adherence. After discontinuation, EFV has an extended inductive effect on cytochrome P450 (CYP) 3A4 that, after switching, may reduce RPV exposures and adversely impact clinical outcomes. This study examines the clinical implications of reduced RPV exposures with concomitant FTC/TDF and declining EFV exposures when patients, intolerant to EFV, switch from EFV/FTC/TDF to RPV/FTC/TDF. This 48-week, phase 2b, open-label, multicenter study evaluated the efficacy and safety of switching from EFV/FTC/TDF (>/= 3 months duration) to RPV/FTC/TDF. Virologic suppression (HIV-1 RNA <50 copies/mL), safety, and EFV and RPV pharmacokinetics were assessed. At weeks 12 and 24, all 49 dosed subjects remained suppressed on RPV/FTC/TDF. At week 48, 46 (93.9%) subjects remained suppressed and virologic failure occurred in 2/49 (4.1%) subjects with no emergence of resistance. EFV concentrations were above the 90th percentile for inhibitory concentration (IC90) for several weeks after EFV discontinuation, and RPV exposures were in the range observed in phase 3 studies by approximately 2 weeks post switch. No subjects discontinued the study due to an adverse event. Switching from EFV/FTC/TDF to RPV/FTC/ TDF was a safe, efficacious option for virologically suppressed HIV-infected patients with EFV intolerance wishing to remain on an STR.
PMID:24144898 Mills AM et al; HIV Clin Trials 14 (5): 216-23 (2013)
Efavirenz is indicated in combination with other antiretroviral agents for the treatment of HIV-1 infection. /Included in US product labeling/
MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1184
To report a case of acquired long QT syndrome that, after exclusion of all other possible causes, was probably related to therapy with efavirenz, a novel nonnucleoside reverse transcriptase inhibitor.
PMID:12022902 Castillo R et al; Ann Pharmacother 36 (6): 1006-8 (2002)
About 53% of adults receiving efavirenz (600 mg once daily) in controlled clinical studies reported adverse CNS effects such as abnormal dreams, abnormal thinking, agitation, amnesia, confusion, depersonalization, dizziness, euphoria, hallucinations, impaired concentration, insomnia, somnolence, and stupor; these adverse effects were reported in 25% of adults in the control groups not receiving efavirenz. These effects were described as mild (do not interfere with daily activities) in 33.3%, moderate (may interfere with daily activities) in 17.4%, or severe (interrupt usual daily activities) in 2% of patients receiving efavirenz and required discontinuance of the drug in 2.1%. Dizziness was reported in 28.1% and insomnia was reported in 16.3% of patients receiving the drug. Impaired concentration, somnolence, or abnormal dreams were reported in 6.2-8.3% and hallucinations were reported in 1.2% of patients.
American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 660
Serious adverse psychiatric symptoms have been reported rarely in adults receiving efavirenz. Severe depression, suicidal ideation, nonfatal suicide attempts, aggressive behavior, paranoid reactions, or manic reactions have been reported in 0.4-1.6% of patients receiving efavirenz in controlled clinical studies; these psychiatric symptoms were reported in up to 0.6% of those in the control groups not receiving the drug. The incidence of each of these psychiatric symptoms ranges from 0.3% (for manic reactions) to 2% (for severe depression or suicidal ideation) in patients with a prior history of psychiatric disorders, and these individuals appear to be at greater risk of such symptoms than other individuals. Other psychiatric symptoms reported in controlled clinical studies in adults receiving efavirenz include depression (15.8%), anxiety (11.1%), and nervousness (6.3%); these symptoms were reported in 13.1, 7.6, or 2%, respectively, of those in the control groups not receiving the drug. Although a causal relationship with efavirenz has not been established, there have been occasional postmarketing reports of death by suicide, delusions, or psychosis-like behavior in patients receiving efavirenz. In addition, aggressive reactions, agitation, emotional lability, mania, neurosis,and paranoia have been reported during postmarketing surveillance. There is no evidence that patients who develop adverse CNS effects (e.g., dizziness, insomnia, impaired concentration, abnormal dreams) during efavirenz therapy are at greater risk of developing psychiatric symptoms.
American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 661
Fatigue has been reported in up to 7% of adults receiving efavirenz in clinical studies. Other adverse nervous system effects reported during postmarketing surveillance include abnormal coordination, ataxia, seizures, hypoesthesia, paresthesia, neuropathy, and tremor. Adverse CNS effects occurred in 18% of children receiving efavirenz in clinical studies.
American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 661
For more Drug Warnings (Complete) data for EFAVIRENZ (21 total), please visit the HSDB record page.
For use in combination treatment of HIV infection (AIDS)
FDA Label
Stocrin is indicated in antiviral combination treatment of human-immunodeficiency-virus-1 (HIV-1)-infected adults, adolescents and children three years of age and older.
Stocrin has not been adequately studied in patients with advanced HIV disease, namely in patients with CD4 counts < 50 cells/mm3, or after failure of protease-inhibitor (PI)-containing regimens. Although cross-resistance of efavirenz with PIs has not been documented, there are at present insufficient data on the efficacy of subsequent use of PI-based combination therapy after failure of regimens containing Stocrin.
Efavirenz is indicated in antiviral combination treatment of human-immunodeficiency-virus-1 (HIV-1)-infected adults, adolescents and children 3 years of age and older.
Efavirenz has not been adequately studied in patients with advanced HIV disease, namely in patients with CD4 counts < 50 cells/mm3, or after failure of protease inhibitor (PI)-containing regimens. Although cross-resistance of efavirenz with protease inhibitors (PIs) has not been documented, there are at present insufficient data on the efficacy of subsequent use of PI-based combination therapy after failure of regimens containing efavirenz.
Sustiva is indicated in antiviral combination treatment of human-immunodeficiency-virus-1 (HIV-1)-infected adults, adolescents and children three years of age and older.
Sustiva has not been adequately studied in patients with advanced HIV disease, namely in patients with CD4 counts < 50 cells/mm3, or after failure of protease-inhibitor (PI)-containing regimens. Although cross-resistance of efavirenz with PIs has not been documented, there are at present insufficient data on the efficacy of subsequent use of PI-based combination therapy after failure of regimens containing Sustiva.
