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    Chemistry

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    Also known as: 229975-97-7, Reyataz, Atazanavir sulphate, Bms-232632-05, Atazanavir (sulfate), Atazanavir sulfate [usan]
    Molecular Formula
    C38H54N6O11S
    Molecular Weight
    802.9  g/mol
    InChI Key
    DQSGVVGOPRWTKI-QVFAWCHISA-N
    FDA UNII
    4MT4VIE29P
    Atazanavir Sulfate
    An azapeptide and HIV-PROTEASE INHIBITOR that is used in the treatment of HIV INFECTIONS and AIDS in combination with other ANTI-HIV AGENTS.
    1 2D Structure

    Atazanavir Sulfate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl N-[(2S)-1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-4-phenylbutyl]-2-[(4-pyridin-2-ylphenyl)methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate;sulfuric acid
    2.1.2 InChI
    InChI=1S/C38H52N6O7.H2O4S/c1-37(2,3)31(41-35(48)50-7)33(46)40-29(22-25-14-10-9-11-15-25)30(45)24-44(43-34(47)32(38(4,5)6)42-36(49)51-8)23-26-17-19-27(20-18-26)28-16-12-13-21-39-28;1-5(2,3)4/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47);(H2,1,2,3,4)/t29-,30-,31+,32+;/m0./s1
    2.1.3 InChI Key
    DQSGVVGOPRWTKI-QVFAWCHISA-N
    2.1.4 Canonical SMILES
    CC(C)(C)C(C(=O)NC(CC1=CC=CC=C1)C(CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)C(C(C)(C)C)NC(=O)OC)O)NC(=O)OC.OS(=O)(=O)O
    2.1.5 Isomeric SMILES
    CC(C)(C)[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)[C@H](C(C)(C)C)NC(=O)OC)O)NC(=O)OC.OS(=O)(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    4MT4VIE29P
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 232632, Bms

    2. 3,12-bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-((4-(2-pyridinyl)phenyl)methyl)-2,5,6,10,13-pentaazatetradecanedioic Acid Dimethyl Ester

    3. Atazanavir

    4. Bms 232632

    5. Bms 232632 05

    6. Bms-232632

    7. Bms-232632-05

    8. Bms232632

    9. Bms23263205

    10. Cgp 73547

    11. Cgp 75136

    12. Cgp 75176

    13. Cgp 75355

    14. Cgp-73547

    15. Cgp-75136

    16. Cgp-75176

    17. Cgp-75355

    18. Cgp73547

    19. Cgp75136

    20. Cgp75176

    21. Cgp75355

    22. Reyataz

    2.3.2 Depositor-Supplied Synonyms

    1. 229975-97-7

    2. Reyataz

    3. Atazanavir Sulphate

    4. Bms-232632-05

    5. Atazanavir (sulfate)

    6. Atazanavir Sulfate [usan]

    7. Atazor

    8. Atazanavir So4

    9. 4mt4vie29p

    10. Atazanavir Sulfate (bms-232632-05)

    11. 229975-97-7 (sulfate)

    12. Nsc-742546

    13. 2,5,6,10,13-pentaazatetradecanedioic Acid, 3,12-bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-((4-(2-pyridinyl)phenyl)methyl)-, Dimethyl Ester, (3s,8s,9s,12s)-, Sulfate (1:1) (salt)

    14. Reyataz (tn)

    15. 2,5,6,10,13-pentaazatetradecanedioic Acid, 3-12-bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-((-4-(2-pyridinyl)phenyl)methyl)-, Dimethyl Ester, (3s,8s,9s,12s)-, Sulfate (1:1) (salt)

    16. Dimethyl (3s,8s,9s,12s)-9-benzyl-3,12,di-tert-butyl-8-hydroxy-4,11-dioxo-6-(p-2-pyridylbenzyl)-2,5,6,10,13-pentaazatetradecanedioate, Sulfate (1:1) (salt)

    17. Chebi:31243

    18. Smr002544693

    19. Atazanavir Bisulfate Salt

    20. Unii-4mt4vie29p

    21. Ulfuric Acid

    22. Atazanaviri Sulfas

    23. Mls003915641

    24. Mls006010199

    25. Schembl341700

    26. Atazanavir So4 [vandf]

    27. Atazanavir Sulfate [mi]

    28. Atazanavir Sulfate (jan/usan)

    29. Atazanavir Sulfate [jan]

    30. Chembl1200678

    31. Bms-232632-05, Reyataz

    32. Dtxsid401017206

    33. Atazanavir Sulfate [mart.]

    34. Amy36999

    35. Atazanavir Sulfate [usp-rs]

    36. Atazanavir Sulfate [who-dd]

    37. Atazanavir Sulfate [who-ip]

    38. Ex-a4010

    39. Methyl N-[(2s)-1-[2-[(2s,3s)-2-hydroxy-3-[[(2s)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-4-phenylbutyl]-2-[(4-pyridin-2-ylphenyl)methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate;sulfuric Acid

    40. Hy-17367a

    41. Mfcd08067748

    42. S1457

    43. Akos016000176

    44. Atazanavir Sulphate [ema Epar]

    45. Ccg-270493

    46. Cs-1890

    47. Nsc 742546

    48. Atazanavir Sulfate [orange Book]

    49. Atazanavir Sulfate [ep Monograph]

    50. As-14954

    51. Atazanaviri Sulfas [who-ip Latin]

    52. Evotaz Component Atazanavir Sulfate

    53. Methyl ((5s,10s,11s,14s)-11-benzyl-5-(tert-butyl)-10-hydroxy-15,15-dimethyl-3,6,13-trioxo-8-(4-(pyridin-2-yl)benzyl)-2-oxa-4,7,8,12-tetraazahexadecan-14-yl)carbamate Sulfate

    54. Atazanavir Sulfate Component Of Evotaz

    55. Sw220258-1

    56. D01276

    57. 975a977

    58. A816475

    59. J-014934

    60. 3-amino-3-(3-benzyloxy-phenyl)-propionicacid

    61. Q27114238

    62. 2,5,6,10,13-pentaazatetradecanedioic Acid, 3-12-bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-((-4-(2-pyridinyl)phenyl)methyl)-, Dimethyl Ester, (3s,8s,9s,12s)-, Sulphate (1:1) (salt)

    63. Dimethyl (3s,8s,9s,12s)-9-benzyl-3,12,di-tert-butyl-8-hydroxy-4,11-dioxo-6-(p-2-pyridylbenzyl)-2,5,6,10,13-pentaazatetradecanedioate, Sulphate (1:1) (salt)

    64. Dimethyl (3s,8s,9s,12s)-9-benzyl-3,12-di-tert-butyl-8-hydroxy-4,11-dioxo-6-((4-(pyridin-2-yl)phenyl)methyl)-2,5,6,10,13-pentaazatetradecanedioate Monosulfate

    65. Methyl N-[(1s)-1-[[(1s,2s)-1-benzyl-2-hydroxy-3-[[[(2s)-2-(methoxycarbonylamino)-3,3-dimethyl-butanoyl]amino]-[(4-phenylphenyl)methyl]amino]propyl]carbamoyl]-2,2-dimethyl-propyl]carbamate; Sulfuric Acid;atazanavir Sulfate

    66. Methyl N-[(2s)-1-[2-[(2s,3s)-2-hydroxy-3-[[(2s)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-4-phenylbutyl]-2-[(4-pyridin-2-ylphenyl)methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate;s

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 802.9 g/mol
    Molecular Formula C38H54N6O11S
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count18
    Exact Mass802.35712773 g/mol
    Monoisotopic Mass802.35712773 g/mol
    Topological Polar Surface Area254 Ų
    Heavy Atom Count56
    Formal Charge0
    Complexity1190
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    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 4  
    Drug NameAtazanavir sulfate
    Drug LabelREYATAZ (atazanavir sulfate) is an azapeptide inhibitor of HIV-1 protease.The chemical name for atazanavir sulfate is (3S,8S,9S,12S)-3,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-2,5,6,10,13-pen...
    Active IngredientAtazanavir sulfate
    Dosage FormCapsule
    Routeoral; Oral
    Strength300mg; eq 100mg base; 200mg; eq 200mg base; 100mg; eq 300mg base; 150mg; eq 150mg base
    Market StatusTentative Approval; Prescription
    CompanyMatrix Labs; Emcure Pharms; Aurobindo Pharma; Teva Pharms Usa; Emcure Pharma

    2 of 4  
    Drug NameReyataz
    PubMed HealthAtazanavir (By mouth)
    Drug ClassesAntiretroviral Agent, Antiviral
    Drug LabelREYATAZ (atazanavir sulfate) is an azapeptide inhibitor of HIV-1 protease.The chemical name for atazanavir sulfate is (3S,8S,9S,12S)-3,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-2,5,6,10,13-pen...
    Active IngredientAtazanavir sulfate
    Dosage FormCapsule; Powder
    RouteOral
    Strengtheq 50mg base/packet; eq 150mg base; eq 200mg base; eq 300mg base
    Market StatusPrescription
    CompanyBristol Myers Squibb

    3 of 4  
    Drug NameAtazanavir sulfate
    Drug LabelREYATAZ (atazanavir sulfate) is an azapeptide inhibitor of HIV-1 protease.The chemical name for atazanavir sulfate is (3S,8S,9S,12S)-3,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-2,5,6,10,13-pen...
    Active IngredientAtazanavir sulfate
    Dosage FormCapsule
    Routeoral; Oral
    Strength300mg; eq 100mg base; 200mg; eq 200mg base; 100mg; eq 300mg base; 150mg; eq 150mg base
    Market StatusTentative Approval; Prescription
    CompanyMatrix Labs; Emcure Pharms; Aurobindo Pharma; Teva Pharms Usa; Emcure Pharma

    4 of 4  
    Drug NameReyataz
    PubMed HealthAtazanavir (By mouth)
    Drug ClassesAntiretroviral Agent, Antiviral
    Drug LabelREYATAZ (atazanavir sulfate) is an azapeptide inhibitor of HIV-1 protease.The chemical name for atazanavir sulfate is (3S,8S,9S,12S)-3,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-2,5,6,10,13-pen...
    Active IngredientAtazanavir sulfate
    Dosage FormCapsule; Powder
    RouteOral
    Strengtheq 50mg base/packet; eq 150mg base; eq 200mg base; eq 300mg base
    Market StatusPrescription
    CompanyBristol Myers Squibb

    4.2 Drug Indication

    Reyataz capsules, co-administered with low dose ritonavir, are indicated for the treatment of HIV-1 infected adults and paediatric patients 6 years of age and older in combination with other antiretroviral medicinal products (see section 4. 2).

    Based on available virological and clinical data from adult patients, no benefit is expected in patients with strains resistant to multiple protease inhibitors ( 4 PI mutations).

    The choice of Reyataz in treatment experienced adult and paediatric patients should be based on individual viral resistance testing and the patients treatment history (see sections 4. 4 and 5. 1).

    Reyataz oral powder, co-administered with low dose ritonavir, is indicated in combination with other antiretroviral medicinal products for the treatment of HIV-1 infected paediatric patients at least 3 months of age and weighing at least 5 kg (see section 4. 2).

    Based on available virological and clinical data from adult patients, no benefit is expected in patients with strains resistant to multiple protease inhibitors ( 4 PI mutations). The choice of Reyataz in treatment experienced adult and paediatric patients should be based on individual viral resistance testing and the patients treatment history (see sections 4. 4 and 5. 1).

    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 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Cytochrome P450 3A Inhibitors [MoA]; Cytochrome P450 3A4 Inhibitors [MoA]; HIV Protease Inhibitors [MoA]; Protease Inhibitor [EPC]; UDP Glucuronosyltransferases Inhibitors [MoA]; UGT1A1 Inhibitors [MoA]; Cytochrome P450 2C8 Inhibitors [MoA]
    5.3 ATC Code

    J05AE08

    API Reference Price

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    16-Jan-2021
    15-Nov-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

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

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - TABLET;ORAL - EQ 300MG BASE;150MG

    USFDA APPLICATION NUMBER - 206353

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    DOSAGE - CAPSULE;ORAL - EQ 100MG BASE **Feder...DOSAGE - CAPSULE;ORAL - EQ 100MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 21567

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    DOSAGE - CAPSULE;ORAL - EQ 150MG BASE **Feder...DOSAGE - CAPSULE;ORAL - EQ 150MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 21567

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    DOSAGE - CAPSULE;ORAL - EQ 200MG BASE

    USFDA APPLICATION NUMBER - 21567

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    DOSAGE - CAPSULE;ORAL - EQ 300MG BASE

    USFDA APPLICATION NUMBER - 21567

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