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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
    Darunavir Ethanolate
    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 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

    API Reference Price

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    08-Jan-2021
    22-Oct-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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