Efavirenz

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Efavirenz are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Efavirenz?

The molecule Efavirenz presents a molecular formula of C14H9ClF3NO2 and its IUPAC name is (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one.

Efavirenz (also known as Sustiva) is a medication used to treat HIV/AIDS. It is a non-nucleoside reverse transcriptase inhibitor (NNRTI). Efavirenz was approved by the U.S. Food and Drug Administration (FDA) in 1998 and is manufactured by Bristol-Myers Squibb..

Efavirenz is generally well-tolerated, but can cause side effects such as rash, dizziness, and depression. It is recommended that people taking efavirenz start on a low dose and increase gradually to minimize side effects..

Efavirenz works by blocking the activity of reverse transcriptase, an enzyme that HIV uses to copy itself into the DNA of infected cells. By blocking this enzyme, efavirenz reduces the amount of HIV in the body and helps keep the virus from damaging the immune system..

Efavirenz is usually taken once a day, with or without food. It is important to take efavirenz exactly as prescribed and to continue taking it even if you feel well..

If you miss a dose of efavirenz, take it as soon as possible. If it is almost time for your next dose, skip the missed dose and continue with your regular dosing schedule. Do not take two doses of efavirenz at the same time..

Efavirenz is a powerful medication that can help people with HIV live longer, healthier lives. If you are taking efavirenz, be sure to follow your doctor's instructions and take all of your medications as prescribed..

3D structure

Cartesian coordinates

Geometry of Efavirenz in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Efavirenz XPOQHMRABVBWPR-ZDUSSCGKSA-N chemical compound 2D structure molecule svg
Efavirenz

 

Molecule descriptors

 
IUPAC name(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
InChI codeInChI=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 KeyXPOQHMRABVBWPR-ZDUSSCGKSA-N
SMILESO=C1Nc2ccc(Cl)cc2[C@@](C#CC2CC2)(C(F)(F)F)O1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-)-6-CHLORO-4-CYCLOPROPYLETHYNYL-4-TRIFLUOROMETHYL-1,4-DIHYDRO-2H-3,1-BENZOXAZIN-2-ONE
  • (-)-Efavirenz
  • (4S)-6-Chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one
  • (4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one
  • (4S)-6-chloranyl-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
  • (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
  • (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
  • (4S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one
  • (Rac)-DMP 266; (Rac)-EFV; (Rac)-L-743726
  • (Rac)-Efavirenz
  • (S)-6-CHLORO-4-(CYCLOPROPYLETHYNYL)-4-(TRIFLUOROMETHYL)-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE
  • (S)-6-Chloro-4-(cyclopropyl-ethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazine-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)-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
  • (S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-ben zoxazin-2-one
  • (S)-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-2H-benzo[d][1,3]oxazin-2-one
  • (S)-Efavirenz
  • (s)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one
  • 154598-52-4
  • 1ikv
  • 1ikw
  • 2H-3, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4S)-
  • 2H-3,1-Benzoxazin-2-one, 6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4S)-
  • 2H-3,1-Benzoxazin-2-one, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4S)-
  • 598E524
  • 6-chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one
  • A809555
  • AB00639956-06
  • AB00639956-08
  • AB21723
  • AC-25006
  • AMY229
  • ATRIPLA COMPONENT EFAVIRENZ
  • BC164402
  • BCP27719
  • BCP9000636
  • BCPP000245
  • BDBM2483
  • BIDD:GT0383
  • C08088
  • CCG-101011
  • D00896
  • DB00625
  • DL-535
  • DMP 266
  • DMP-266
  • DMP-266; Efavirenz
  • DMP266
  • DSSTox_CID_26029
  • DSSTox_GSID_46029
  • DSSTox_RID_81298
  • E0997
  • EFAVIRENZ COMPONENT OF ATRIPLA
  • EFV
  • EFV & IFNL1
  • EFV & IFNL2
  • EFV & IFNL3
  • EFV & IL-28A
  • EFV & IL-28B
  • EFV & IL-29
  • EFV & Interferon lambda-1
  • EFV & Interferon lambda-2
  • EFV & Interferon lambda-3
  • EFV & Interleukin 28A
  • EFV & Interleukin 28B
  • EFV & Interleukin 29
  • EFV & PLGA
  • Efavirenz
  • Efavirenz & IFNL1
  • Efavirenz & IFNL2
  • Efavirenz & IFNL3
  • Efavirenz & IL-28A
  • Efavirenz & IL-28B
  • Efavirenz & IL-29
  • Efavirenz & Interferon lambda-1
  • Efavirenz & Interferon lambda-2
  • Efavirenz & Interferon lambda-3
  • Efavirenz & Interleukin 28A
  • Efavirenz & Interleukin 28B
  • Efavirenz & Interleukin 29
  • Efavirenz & PLGA
  • Efavirenz & Poly-lactide-co-glycolide
  • Efavirenz (JAN/USP/INN)
  • Efavirenz Ready Made Solution
  • Efavirenz teva
  • Efavirenz, (S)
  • Efavirenz- Bio-X
  • Efavirenzum
  • Eravirenz
  • F17329
  • GTPL11287
  • HMS2051J08
  • HMS2090N16
  • HMS3393J08
  • HMS3713M14
  • HSDB 7163
  • HY-10572
  • J-520431
  • JE6H2O27P8
  • KS-5380
  • L 743726
  • L-743,726
  • L-743726
  • MFCD05662344
  • MLS000759465
  • MLS001424087
  • Met-SDF-1.beta. & Efavirenz
  • Met-Stromal Cell-derived Factor-1.beta. (Human) & Efavirenz
  • NC00261
  • NCGC00159337-02
  • NCGC00159337-04
  • NCGC00159337-12
  • NCGC00271713-05
  • NCGC00271713-08
  • NSC 742403
  • NSC-742403
  • NSC742403
  • Q422645
  • SMR000466351
  • SR-01000759360
  • SR-01000759360-4
  • SR-01000759360-5
  • Stocrin
  • Strocin (TM)
  • Sustiva
  • Sustiva (TM)
  • TELURA COMPONENT EFAVIRENZ
  • Viraday
  • Z2186909878
  • efavirenz
  • s4685

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2020233
  • CAS-154598-52-4
  • UNII-JE6H2O27P8
  • AKOS015894951
  • DTXSID9046029
  • CHEMBL223228
  • CHEBI:119486
  • Tox21_111582
  • Tox21_111582_1
  • SCHEMBL37762

Physico-Chemical properties

IUPAC name(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
Molecular formulaC14H9ClF3NO2
Molecular weight315.675
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity73.18
LogP4.2
Topological polar surface area38.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.