efavirenz (CHEBI:119486)

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CHEBI:119486 - efavirenz

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ChEBI Name	efavirenz

ChEBI ID	CHEBI:119486

Definition	1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:47396, CHEBI:4760, CHEBI:190461

Supplier Information	ChemicalBook:CB7181559, eMolecules:2735350, ZINC000002020233

Download	Molfile XML SDF

more structures >>

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Marvin 11090719313D

30 32 0 0 0 0 999 V2000

3.0000 -0.5310 -2.8740 Cl 0 0 0 0 0 0 0 0 0 0 0 0

-2.2340 -1.6270 1.6950 F 0 0 0 0 0 0 0 0 0 0 0 0

-0.0630 -1.5670 2.4010 F 0 0 0 0 0 0 0 0 0 0 0 0

-0.5680 -2.3850 0.3280 F 0 0 0 0 0 0 0 0 0 0 0 0

-0.6240 1.5250 3.8020 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.1080 0.9640 1.7060 O 0 0 0 0 0 0 0 0 0 0 0 0

1.0950 1.2280 2.4280 N 0 0 0 0 0 0 0 0 0 0 0 0

1.5570 0.8040 1.1770 C 0 0 0 0 0 0 0 0 0 0 0 0

2.8880 0.9740 0.8230 C 0 0 0 0 0 0 0 0 0 0 0 0

3.3270 0.5620 -0.4190 C 0 0 0 0 0 0 0 0 0 0 0 0

2.4450 -0.0260 -1.3080 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1210 -0.2140 -0.9500 C 0 0 0 0 0 0 0 0 0 0 0 0

0.6790 0.1910 0.2910 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7540 -0.0290 0.7030 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.6370 0.1130 -0.4650 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.3400 0.2270 -1.3980 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.2220 0.3690 -2.5680 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.2110 1.7120 -3.3020 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.5600 0.4850 -3.9420 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9080 -1.4320 1.2950 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.2270 1.2500 2.6880 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7270 1.5060 3.1090 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5780 1.4290 1.5180 H 0 0 0 0 0 0 0 0 0 0 0 0

4.3610 0.7000 -0.6980 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4340 -0.6790 -1.6430 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.1710 -0.1630 -2.5090 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.1520 2.0620 -3.7260 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5500 2.4900 -2.9180 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4710 0.4550 -3.9800 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0730 0.0270 -4.7880 H 0 0 0 0 0 0 0 0 0 0 0 0

1 11 1 0 0 0 0

2 20 1 0 0 0 0

3 20 1 0 0 0 0

4 20 1 0 0 0 0

5 21 2 0 0 0 0

6 14 1 0 0 0 0

6 21 1 0 0 0 0

7 8 1 0 0 0 0

7 21 1 0 0 0 0

7 22 1 0 0 0 0

8 9 4 0 0 0 0

8 13 4 0 0 0 0

9 10 4 0 0 0 0

9 23 1 0 0 0 0

10 11 4 0 0 0 0

10 24 1 0 0 0 0

11 12 4 0 0 0 0

12 13 4 0 0 0 0

12 25 1 0 0 0 0

13 14 1 0 0 0 0

14 15 1 0 0 0 0

14 20 1 0 0 0 0

15 16 3 0 0 0 0

16 17 1 0 0 0 0

17 18 1 0 0 0 0

17 19 1 0 0 0 0

17 26 1 0 0 0 0

18 19 1 0 0 0 0

18 27 1 0 0 0 0

18 28 1 0 0 0 0

19 29 1 0 0 0 0

19 30 1 0 0 0 0

M END): 41 ms

reading 30 atoms

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Wikipedia	License
Efavirenz (EFV), sold under the brand names Sustiva among others, is an antiretroviral medication used to treat and prevent HIV/AIDS. It is generally recommended for use with other antiretrovirals. It may be used for prevention after a needlestick injury or other potential exposure. It is sold both by itself and in combination as efavirenz/emtricitabine/tenofovir. It is taken by mouth. Common side effects include rash, nausea, headache, feeling tired, and trouble sleeping. Some of the rashes may be serious such as Stevens–Johnson syndrome. Other serious side effects include depression, thoughts of suicide, liver problems, and seizures. It is not safe for use during pregnancy. It is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and works by blocking the function of reverse transcriptase. Efavirenz was approved for medical use in the United States in 1998, and in the European Union in 1999. It is on the World Health Organization's List of Essential Medicines. As of 2016, it is available as a generic medication.
Read full article at Wikipedia

Formula

C14H9ClF3NO2

Net Charge

Average Mass

315.67500

Monoisotopic Mass

315.02739

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

SMILES

FC(F)(F)[C@]1(OC(=O)Nc2ccc(Cl)cc12)C#CC1CC1

Roles Classification
Biological Role(s):	HIV-1 reverse transcriptase inhibitor An entity which inhibits the activity of HIV-1 reverse transcriptase. antiviral drug A substance used in the prophylaxis or therapy of virus diseases.

Application(s):	antiviral drug A substance used in the prophylaxis or therapy of virus diseases.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	efavirenz (CHEBI:119486) has role antiviral drug (CHEBI:36044) efavirenz (CHEBI:119486) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756) efavirenz (CHEBI:119486) is a acetylenic compound (CHEBI:73474) efavirenz (CHEBI:119486) is a benzoxazine (CHEBI:46969) efavirenz (CHEBI:119486) is a cyclopropanes (CHEBI:51454) efavirenz (CHEBI:119486) is a organochlorine compound (CHEBI:36683) efavirenz (CHEBI:119486) is a organofluorine compound (CHEBI:37143)

IUPAC Name

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

Synonyms	Sources
(-)-6-CHLORO-4-CYCLOPROPYLETHYNYL-4-TRIFLUOROMETHYL-1,4-DIHYDRO-2H-3,1-BENZOXAZIN-2-ONE	PDBeChem
(S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one	ChemIDplus
(S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one	ChEMBL
6-chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one	ChEMBL
Efavirenz	KEGG COMPOUND

Manual Xrefs	Databases
989	DrugCentral
C08088	KEGG COMPOUND
D00896	KEGG DRUG
DB00625	DrugBank
Efavirenz	Wikipedia
EFZ	PDBeChem
EP582455	Patent
HMDB0014763	HMDB
LSM-5526	LINCS
US5519021	Patent
View more database links

Registry Numbers	Types	Sources
154598-52-4	CAS Registry Number	KEGG COMPOUND
154598-52-4	CAS Registry Number	ChemIDplus
7387333	Reaxys Registry Number	Reaxys

Citations

Milpied-Homsi B, Moran EM, Phillips EJ (2014)
Antiviral drug allergy.
Immunology and allergy clinics of North America 34, 645-62, ix [PubMed:25017682]
[show Abstract]

Corbett JW, Gearhart LA, Ko SS, Rodgers JD, Cordova BC, Klabe RM, Erickson-Viitanen SK (2000)
Novel 2,2-dioxide-4,4-disubstituted-1,3-H-2,1,3-benzothiadiazines as non-nucleoside reverse transcriptase inhibitors.
Bioorganic & medicinal chemistry letters 10, 193-195 (Source: ChEMBL) [PubMed:10673109]
[show Abstract]

Patel M, McHugh RJ, Cordova BC, Klabe RM, Erickson-Viitanen S, Trainor GL, Ko SS (1999)
Synthesis and evaluation of benzoxazinones as HIV-1 reverse transcriptase inhibitors. Analogs of Efavirenz (SUSTIVA).
Bioorganic & medicinal chemistry letters 9, 3221-3224 (Source: ChEMBL) [PubMed:10576692]
[show Abstract]

Last Modified

22 February 2017

CHEBI:119486 - efavirenz

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