CAS Number154598-52-4
SynonymsStocrin; EFAVIRNEZ; (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; (4S)-6-Chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-4H-3,1-benzoxazin-2-ol; (4S)-6-Chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one; DMP 266; SUSTIVA; MDP-266; Efavirenz
Molecular FormulaC14H9ClF3NO2
Molecular Weight315.67
Purity≥98 (HPLC)%
Density1.5±0.1 g/cm3
Boiling Point422.7±55.0 °C at 760 mmHg
Melting Point139-141ºC
Appearancepowder
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 154598-52-4 |
| Catalog No. | 2A-9010286 |
| Chinese Name | 依法韦仑 |
| Synonyms | Stocrin; EFAVIRNEZ; (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; (4S)-6-Chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-4H-3,1-benzoxazin-2-ol; (4S)-6-Chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one; DMP 266; SUSTIVA; MDP-266; Efavirenz |
| Molecular Formula | C14H9ClF3NO2 |
| Molecular Weight | 315.67 |
| Purity | ≥98 (HPLC) |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 422.7±55.0 °C at 760 mmHg |
| Melting Point | 139-141ºC |
| Appearance | powder |
| Water Solubility | Water solubility: insoluble; easily soluble in: me |
| Storage Condition | <0°C; avoid heating |
| Application | Efavirenz is a potent inhibitor of wild-type HIV-1 RT with a Ki of 2.93 nM and inhibits HIV-1 replication with an IC95 of 1.5 nM. |
| HTC | 2942000000 |
| PubChem ID | 329825539 |
| MDL Number | MFCD05662344 |
| SMILES | ClC1=CC=C2C([C@@](C#CC3CC3)(C(F)(F)F)OC(N2)=O)=C1 |
| 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 |
| InChI Key | XPOQHMRABVBWPR-ZDUSSCGKSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| MSDS | msds/10286_1_154598_52_4.pdf |
| Use of | Efavirenz is a potent inhibitor of the wild-type HIV-1 reverse transcriptase with a Ki of 2.93 nM and exhibits an IC95 of 1.5 nM for the inhibition of HIV-1 replicative spread in cell culture. Properties Articles53 Name efavirenz Synonym More Synonyms Efavirenz Biological Activity Description Efavirenz is a potent inhibitor of the wild-type HIV-1 reverse transcriptase with a Ki of 2.93 nM and exhibits an IC95 of 1.5 nM for the inhibition of HIV-1 replicative spread in cell culture. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Anti-infection >> HIV Signaling Pathways >> Anti-infection >> Reverse Transcriptase Natural Products >> Alkaloid Research Areas >> Inflammation/Immunology Ki: 2.93 nM (HIV-1 RT)[1] In Vitro Efavirenz (L-743726) is found to be capable of inhibiting, with 95% inhibitory concentrations of ≤ 1.5μM, a panel of nonnucleoside reverse transcriptase (RT) inhibitors (NNRTIs)-resistant mutant viruses, each of which expresses a single RT amino acid substitution. Efavirenz is also tested for its activity against a variety of polymerase enzymes and is found to be inactive (IC50>300μM). Efavirenz effectively inhibits several wild-type T-lymphoid cell line-adapted variants. Identical activity (IC95, 1.5 to 3.0 nM) is seen with wild-type primary isolates of the virus in both primary lymphoid and monocytoid cell cultures. Efavirenz also effectively inhibits HIV-1 variants that expressed RT amino acid substitutions which confer the loss of susceptibility to other NNRTIs. For purposes of comparison[1]. Efavirenz is a non-nucleoside analog reverse transcriptase inhibitor (NNRTI) with IC50 of 60 nM[2]. Efavirenz inhibits synthesis using an RNA PPT-primed substrate with an IC50 of 17 nM[3]. Kinase Assay Recombinant RT enzymes are expressed, purified, and assessed for inhibition by Efavirenz (L-743726). Ki and Kii values are determined for each enzyme tested. The wild-type RT exhibited exclusively noncompetitive inhibition kinetics (data not shown), and, therefore, the Ki and Kii values are identical. Pure noncompetitive inhibition is not assumed for the mutant enzymes, and, hence, the values of both Ki and Kii are obtained from the linear mixed-type inhibition equation. The two- to threefold differences between the Ki and Kii values probably reflect a small contribution of competitive inhibition with the mutant RTs[1]. References [1]. Young SD, et al. L-743, 726 (DMP-266): a novel, highly potent nonnucleoside inhibitor of the human immunodeficiency virus type 1 reverse transcriptase. Antimicrob Agents Chemother. 1995 Dec;39(12):2602-5. [2]. Held DM, et al. Differential susceptibility of HIV-1 reverse transcriptase to inhibition by RNA aptamers in enzymatic reactions monitoring specific steps during genome replication. J Biol Chem. 2006 Sep 1;281(35):25712-22. [3]. Grobler JA, et al. HIV-1 reverse transcriptase plus-strand initiation exhibits preferential sensitivity to non-nucleoside reverse transcriptase inhibitors in vitro. J Biol Chem. 2007 Mar 16;282(11):8005-10. Chemical & Physical Properties Exact Mass 315.027405 PSA 38.33000 Index of Refraction 1.582 InChIKey XPOQHMRABVBWPR-ZDUSSCGKSA-N Safety Information Signal Word Warning Hazard Statements H410 Precautionary Statements P273 Hazard Codes N Risk Phrases 50 Safety Phrases 61 RIDADR UN3082 - class 9 - PG 3 - DOT NA1993 - Environmentally hazardous substances, liquid, n.o.s. HI: all (not BR) RTECS DM3440000 HS Code 2942000000 Synthetic Route (S)-carbamic ac... 1381993-90-3 154598-52-4 Triphosgene 32315-10-9 (S)-1-(2-Amino-... 209414-27-7 Diphosgene 154598-52-4 (S)-carbamic ac... 1381993-90-3 ENT Efavirenz 154801-74-8 154598-52-4 Precursor & DownStream Precursor 9 CAS#:1381993-90-3 (S)-carbamic ac... CAS#:32315-10-9 Triphosgene CAS#:209414-27-7 (S)-1-(2-Amino-... CAS#:503-38-8 Diphosgene DownStream 2 CAS#:205754-33-2 8-Hydroxy-efavirenz CAS#:110-89-4 Piperidine |
| Transport Info | Product Name: Efavirenz |
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