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Efavirenz

Athanor · official

C14H9ClF3NO2 · 315.67 g/mol

IUPAC name: (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one

Also called Sustiva, Stocrin, NNRTI, HIV

Drugs
Open in Athanor
The structure of Efavirenz
Drawn from its SMILES with RDKit
Harmful or irritantHealth hazardEnvironmental hazardDangerHarmful if swallowed · Causes serious eye irritation · May damage fertility or the unborn child · Causes damage to organs through prolonged or repeated exposure · Very toxic to aquatic life · Very toxic to aquatic life with long lasting effects

Names and identifiers

IUPAC name
(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
Synonyms
Sustiva, Stocrin, NNRTI
+ 37 more

HIV, DMP-266, (-)-Efavirenz, (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one, (4S)-6-Chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one, Viraday, Efavirenz teva, L-743726, Efavirenzum, DTXSID9046029, L-743,726, NSC-742403, JE6H2O27P8, (S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one, CHEBI:119486, DTXCID7026029, TELURA COMPONENT EFAVIRENZ, (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, (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-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, efavirenz, (S)-, Sustiva 600, RefChem:590606, J05AG03, EFAVIRENZ 200MG SCORED TABLETS, MK-0831, L743726, L 743,726, (4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one, EFV, (S)-Efavirenz, MFCD05662344, (S)-6-CHLORO-4-(CYCLOPROPYLETHYNYL)-4-(TRIFLUOROMETHYL)-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE, (-)-6-CHLORO-4-CYCLOPROPYLETHYNYL-4-TRIFLUOROMETHYL-1,4-DIHYDRO-2H-3,1-BENZOXAZIN-2-ONE, (4S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one

Molecular formula
C14H9ClF3NO2
Empirical formula
C14H9ClF3NO2
Molecular weight
315.67 g/mol
Exact mass
315.02739
CAS number
154598-52-4
PubChem CID
64139
Canonical SMILES
C1CC1C#CC2(C3=C(C=CC(=C3)Cl)NC(=O)O2)C(F)(F)F
Isomeric SMILES
C1CC1C#C[C@]2(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
InChIKey
XPOQHMRABVBWPR-ZDUSSCGKSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Physical properties

Appearance
White to slightly pink crystalline powder[1]
Solubility in water
Practically insoluble in water (less than 10 mg/L)[1]

Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.

Calculated

Heavy atoms
21
Rings
3
Aromatic rings
1
Fraction sp³ carbons (Fsp3)
0.36
H-bond donors
1
H-bond acceptors
2 computed here · PubChem 5
Rotatable bonds
0 computed here · PubChem 1
TPSA (Ų)
38.3
Formal charge
0
XLogP3
4 PubChem
Complexity
519 PubChem
Stereocenters
1 definedCIP: C5: S
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C53.27%
  • H2.87%
  • Cl11.23%
  • F18.05%
  • N4.44%
  • O10.14%

Isotope pattern

100%315.02716%316.03134%317.0255.1%318.028319.030

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
4.07 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-4.57 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.57 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 315.68
  • log P ≤ 5 (Crippen): 4.07
  • H-bond donors ≤ 5: 1
  • H-bond acceptors ≤ 10: 2

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Danger

Most widely reported: 88 company reports to ECHA. Source [2].

  • Harmful or irritant
  • Health hazard
  • Environmental hazard
  • H302Harmful if swallowed (52.3% of reports)
  • H319Causes serious eye irritation (47.7% of reports)
  • H360May damage fertility or the unborn child (48.9% of reports)
  • H372Causes damage to organs through prolonged or repeated exposure (43.2% of reports)
  • H400Very toxic to aquatic life (92% of reports)
  • H410Very toxic to aquatic life with long lasting effects (94.3% of reports)

Precautionary statements: P203, P260, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P318, P319, P330, P337+P317, P391, P405, P501

Storage

  • Commercially available efavirenz capsules and tablets should be stored at a controlled room temperature of 25 °C, but may be exposed to temperatures ranging from 15-30 °C.[1]

Safety data sheets on the supplier’s page: BOC Sciences, Protheragen, 10X CHEM.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
  2. [2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  3. [3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  5. [5]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  6. [6]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  7. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  8. ·Literature on PubChem

Data last updated 2026-10-14.