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2D Structure
Also known as: 635728-49-3, Darunavir (ethanolate), Prezista, Rezolsta, Unii-33o78xf0bw, Tmc114 ethanolate
Molecular Formula
C29H43N3O8S
Molecular Weight
593.7  g/mol
InChI Key
QWSHKNICRJHQCY-VBTXLZOXSA-N
FDA UNII
33O78XF0BW

An HIV PROTEASE INHIBITOR that is used in the treatment of AIDS and HIV INFECTIONS. Due to the emergence of ANTIVIRAL DRUG RESISTANCE when used alone, it is administered in combination with other ANTI-HIV AGENTS.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate;ethanol
2.1.2 InChI
InChI=1S/C27H37N3O7S.C2H6O/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26;1-2-3/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32);3H,2H2,1H3/t22-,23-,24+,25-,26+;/m0./s1
2.1.3 InChI Key
QWSHKNICRJHQCY-VBTXLZOXSA-N
2.1.4 Canonical SMILES
CCO.CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2COC3C2CCO3)O)S(=O)(=O)C4=CC=C(C=C4)N
2.1.5 Isomeric SMILES
CCO.CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CO[C@@H]3[C@H]2CCO3)O)S(=O)(=O)C4=CC=C(C=C4)N
2.2 Other Identifiers
2.2.1 UNII
33O78XF0BW
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 114, Tmc

2. Darunavir

3. Ethanolate, Darunavir

4. Prezista

5. Tmc 114

6. Tmc-114

7. Tmc114

8. Uic 94017

9. Uic-94017

10. Uic94017

2.3.2 Depositor-Supplied Synonyms

1. 635728-49-3

2. Darunavir (ethanolate)

3. Prezista

4. Rezolsta

5. Unii-33o78xf0bw

6. Tmc114 Ethanolate

7. Darunavir Monoethanolate

8. Darunavir (as Ethanolate)

9. 33o78xf0bw

10. Darunavir Ethanolate (prezista)

11. [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2s,3r)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate;ethanol

12. Darunavir Ethanolate (jan)

13. Darunavir Ethanolate [jan]

14. Carbamic Acid, ((1s,2r)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-, (3r,3as,6ar)-hexahydrofuro(2,3-b)furan-3-yl Ester, Compd. With Ethanol (1:1)

15. Uic 94017

16. [14c]-darunavir Ethanolate

17. Prezista (tn)

18. Darunavir?ethanolate

19. Darunavir Ethanolate- Bio-x

20. Schembl562454

21. Chembl1201127

22. Dtxsid70979794

23. Symtuza Component Darunavir

24. Amy39006

25. Darunavir Ethanolate [vandf]

26. Darunavir Ethanolate [mart.]

27. Darunavir Monoethanolate [mi]

28. Mfcd18251642

29. Darunavir Component Of Symtuza

30. Darunavir Ethanolate [who-dd]

31. Akos025149225

32. Bcp9000588

33. Ccg-270170

34. Cs-0750

35. Ac-26777

36. As-35215

37. Bd164352

38. Darunavir Ethanolate [orange Book]

39. Hy-17041

40. S1620

41. Sw219052-1

42. D06478

43. Prezcobix Component Darunavir Ethanolate

44. A847955

45. Darunavir Ethanolate Component Of Prezcobix

46. Q27256287

47. ((1s,2r)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)- Carbamic Acid (3r,3as,6ar)-hexahydrofuro(2,3-b)furan-3-yl Ester Monoethanolate

48. (3r,3as,6ar)-hexahydrofuro(2,3-b)furan-3-yl ((1s,2r)-3-(((4-aminophenyl)sulfonyl)(isobutyl)amino)-1-benzyl-2-hydroxypropyl)carbamate - Ethanol (1:1)

49. (3r,3as,6ar)-hexahydrofuro[2,3-b]furan-3-yl ((2s,3r)-4-(4-amino-n-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate Ethanolate

50. (3r,3as,6ar)-hexahydrofuro[2,3-b]furan-3-yl((2s,3r)-4-((4-amino-n-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamatecompoundwithethanol(1:1)

51. [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2s,3r)-4-[(4-aminophenyl) Sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate; Ethanol; Tmc114

52. 635728-39-1

53. Hexahydrofuro[2,3-b]furan-3-yl Hydrogen {4-[(4-aminobenzene-1-sulfonyl)(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl}carbonimidate--ethanol (1/1)

54. N-[(1s,2r)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic Acid (3r,3as,6ar)-hexahydrofuro[2,3-b]furan-3-yl Ester Compd. With Ethanol

2.4 Create Date
2008-02-08
3 Chemical and Physical Properties
Molecular Weight 593.7 g/mol
Molecular Formula C29H43N3O8S
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count10
Rotatable Bond Count12
Exact Mass593.27708651 g/mol
Monoisotopic Mass593.27708651 g/mol
Topological Polar Surface Area169 Ų
Heavy Atom Count41
Formal Charge0
Complexity856
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameDarunavir ethanolate
Drug LabelPREZISTA (darunavir) is an inhibitor of the human immunodeficiency virus (HIV) protease.PREZISTA (darunavir), in the form of darunavir ethanolate, has the following chemical name: [(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-...
Active IngredientDarunavir ethanolate
Dosage FormTablet
RouteOral
Strength75mg; 150mg; 600mg; 400mg
Market StatusTentative Approval
CompanyTeva Pharms Usa; Hetero Labs Unit Iii

2 of 2  
Drug NameDarunavir ethanolate
Drug LabelPREZISTA (darunavir) is an inhibitor of the human immunodeficiency virus (HIV) protease.PREZISTA (darunavir), in the form of darunavir ethanolate, has the following chemical name: [(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-...
Active IngredientDarunavir ethanolate
Dosage FormTablet
RouteOral
Strength75mg; 150mg; 600mg; 400mg
Market StatusTentative Approval
CompanyTeva Pharms Usa; Hetero Labs Unit Iii

4.2 Drug Indication

Rezolsta, is indicated in combination with other antiretroviral medicinal products for the treatment of human immunodeficiency virus 1 (HIV 1) infection in adults aged 18 years or older.

Genotypic testing should guide the use of Rezolsta.


PREZISTA, co administered with low dose ritonavir is indicated in combination with other antiretroviral medicinal products for the treatment of human immunodeficiency virus (HIV 1) infection in adult and paediatric patients from the age of 3 years and at least 15 kg body weight.

PREZISTA, co administered with cobicistat is indicated in combination with other antiretroviral medicinal products for the treatment of human immunodeficiency virus (HIV 1) infection in adults and adolescents (aged 12 years and older, weighing at least 40 kg).

In deciding to initiate treatment with PREZISTA co administered with cobicistat or low dose ritonavir, careful consideration should be given to the treatment history of the individual patient and the patterns of mutations associated with different agents. Genotypic or phenotypic testing (when available) and treatment history should guide the use of PREZISTA.

PREZISTA, co administered with low dose ritonavir is indicated in combination with other antiretroviral medicinal products for the treatment of patients with human immunodeficiency virus (HIV 1) infection.

PREZISTA 75 mg, 150 mg, and 600 mg tablets may be used to provide suitable dose regimens:

- For the treatment of HIV 1 infection in antiretroviral treatment (ART) experienced adult patients, including those that have been highly pre treated.

- For the treatment of HIV 1 infection in paediatric patients from the age of 3 years and at least 15 kg body weight.

In deciding to initiate treatment with PREZISTA co administered with low dose ritonavir, careful consideration should be given to the treatment history of the individual patient and the patterns of mutations associated with different agents. Genotypic or phenotypic testing (when available) and treatment history should guide the use of PREZISTA.

PREZISTA, co administered with low dose ritonavir is indicated in combination with other antiretroviral medicinal products for the treatment of patients with human immunodeficiency virus (HIV 1) infection.

PREZISTA, co administered with cobicistat is indicated in combination with other antiretroviral medicinal products for the treatment of human immunodeficiency virus (HIV 1) infection in adults and adolescents (aged 12 years and older, weighing at least 40 kg).

PREZISTA 400 mg and 800 mg tablets may be used to provide suitable dose regimens for the treatment of HIV 1 infection in adult and paediatric patients from the age of 3 years and at least 40 kg body weight who are:

- antiretroviral therapy (ART) nave.

- ART experienced with no darunavir resistance associated mutations (DRV RAMs) and who have plasma HIV 1 RNA < 100,000 copies/ml and CD4+ cell count 100 cells x 106/L. In deciding to initiate treatment with PREZISTA in such ART experienced patients, genotypic testing should guide the use of PREZISTA.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

HIV Protease Inhibitors

Inhibitors of HIV PROTEASE, an enzyme required for production of proteins needed for viral assembly. (See all compounds classified as HIV Protease Inhibitors.)


5.2 ATC Code

J05


J05AE10