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Chemistry

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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

Darunavir Ethanolate

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 Formula	C₂₉H₄₃N₃O₈S
Molecular Weight	593.7 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	12
Exact Mass	593.27708651 g/mol
Monoisotopic Mass	593.27708651 g/mol
Topological Polar Surface Area	169 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	856
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Darunavir ethanolate
Drug Label	PREZISTA (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 Ingredient	Darunavir ethanolate
Dosage Form	Tablet
Route	Oral
Strength	75mg; 150mg; 600mg; 400mg
Market Status	Tentative Approval
Company	Teva Pharms Usa; Hetero Labs Unit Iii

2 of 2
Drug Name	Darunavir ethanolate
Drug Label	PREZISTA (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 Ingredient	Darunavir ethanolate
Dosage Form	Tablet
Route	Oral
Strength	75mg; 150mg; 600mg; 400mg
Market Status	Tentative Approval
Company	Teva 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 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

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