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    Omadacycline

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

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    2D Structure
    Also known as: Amadacycline, 389139-89-3, Nuzyra, Ptk 0796, Omadacycline [usan], Ptk-0796
    Molecular Formula
    C29H40N4O7
    Molecular Weight
    556.6  g/mol
    InChI Key
    VJYKVCURWJGLPG-IQZGDKDPSA-N
    FDA UNII
    090IP5RV8F
    Omadacycline has been used in trials studying the treatment of Bacterial Pneumonia, Bacterial Infections, Community-Acquired Infections, and Skin Structures and Soft Tissue Infections. Omadacycline represents a significant advance over the well-known tetracycline family, and has been shown to be highly effective in animal models at treating increasingly problematic, clinically prevalent infections caused by gram-positive bacteria, such as methicillin-resistant Staphylococcus aureus (MRSA), and by gram-negative, atypical and anaerobic bacteria, including those resistant to currently available classes of antibiotics and known to cause diseases such as pneumonias, urinary tract infections, skin diseases and blood-borne infections in both the hospital and community settings.
    Omadacycline is a Tetracycline-class Antibacterial.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4S,4aS,5aR,12aR)-4,7-bis(dimethylamino)-9-[(2,2-dimethylpropylamino)methyl]-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
    2.1.2 InChI
    InChI=1S/C29H40N4O7/c1-28(2,3)12-31-11-14-10-17(32(4)5)15-8-13-9-16-21(33(6)7)24(36)20(27(30)39)26(38)29(16,40)25(37)18(13)23(35)19(15)22(14)34/h10,13,16,21,31,34-35,38,40H,8-9,11-12H2,1-7H3,(H2,30,39)/t13-,16-,21-,29-/m0/s1
    2.1.3 InChI Key
    VJYKVCURWJGLPG-IQZGDKDPSA-N
    2.1.4 Canonical SMILES
    CC(C)(C)CNCC1=CC(=C2CC3CC4C(C(=O)C(=C(C4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N(C)C)N(C)C
    2.1.5 Isomeric SMILES
    CC(C)(C)CNCC1=CC(=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N(C)C)N(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    090IP5RV8F
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Nuzyra

    2.3.2 Depositor-Supplied Synonyms

    1. Amadacycline

    2. 389139-89-3

    3. Nuzyra

    4. Ptk 0796

    5. Omadacycline [usan]

    6. Ptk-0796

    7. Bay 73-6944

    8. 090ip5rv8f

    9. 389139-89-3 (free Base)

    10. (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-9-[(2,2-dimethylpropylamino)methyl]-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide

    11. Omadacycline (usan)

    12. (4s,4as,5ar,12as)-4,7-bis(dimethylamino)-9-(((2,2-dimethylpropyl)amino)methyl)- 3,10,12,12a- Tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2- Carboxamide

    13. Amadacycline Methanesulfonate

    14. Omadacycline [usan:inn]

    15. Unii-090ip5rv8f

    16. (4s,4as,5ar,12as)-4,7-bis(dimethylamino)-9-[(2,2-dimethylpropylamino)methyl]-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide

    17. 2-naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-(((2,2-dimethylpropyl)amino)methyl)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4s,4as,5ar,12as)-

    18. 2-naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-[[(2,2-dimethylpropyl)amino]methyl]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4s,4as,5ar,12as)-

    19. Mk-2764

    20. Omadacycline [mi]

    21. Omadacycline [inn]

    22. Omadacycline [who-dd]

    23. Schembl1525961

    24. 9-neopentylaminomethylminocycline

    25. Chembl1689772

    26. Schembl17150976

    27. Schembl20952297

    28. Gtpl10839

    29. Ptk-796

    30. Ptk0796

    31. Chebi:177758

    32. Dtxsid201027687

    33. Bcp12946

    34. Ex-a4252

    35. Zinc4836283

    36. Compound 6 [pmid: 21302930]

    37. Cs-1338

    38. Db12455

    39. Bay-73-6944

    40. Bay-73-7388

    41. Ncgc00378946-03

    42. Ac-33245

    43. Hy-14865

    44. Ptk 0796, Bay 73-6944

    45. D09647

    46. E80520

    47. Q15426992

    48. (4s,4as,5ar,12as)-4,7-bis(dimethylamino)-9-(((2,2-dimethylpropyl)amino)methyl)-3,10,12,12a- Tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

    49. 2-naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-(((2,2- Dimethylpropyl)amino)methyl)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a- Tetrahydroxy-1,11-dioxo-, (4s,4as,5ar,12as)-

    2.4 Create Date
    2011-12-26
    3 Chemical and Physical Properties
    Molecular Weight 556.6 g/mol
    Molecular Formula C29H40N4O7
    XLogP33
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count7
    Exact Mass556.28969963 g/mol
    Monoisotopic Mass556.28969963 g/mol
    Topological Polar Surface Area177 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity1140
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Omadacycline is indicated for the treatment of community acquired bacterial pneumonia and acute bacterial skin and skin structure infections caused by omadacycline-susceptible organisms in adults.

    FDA Label

    Treatment of bacterial pneumonia

    Treatment of acute bacterial skin and skin structure infections

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Omadacycline can be either bacteriostatic or bacteriocidal depending on the organism involved. It disrupts bacterial protein synthesis without affecting DNA, RNA, or peptidoglycan synthesis. Omadacycline represents an improvement over existing tetracycline agents as it has not been found to be subject to tetracycline resistance mediated by tetracycline efflux pumps encoded by the tet(K), tet(L), and tet(B) or to ribosomal protection proteins encoded by tet(O) and tet(M). Omadacycline is susceptible to RNA mutations which confer resistance to tetracyclines.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    OMADACYCLINE
    5.2.2 FDA UNII
    090IP5RV8F
    5.2.3 Pharmacological Classes
    Tetracyclines [CS]; Tetracycline-class Antibacterial [EPC]
    5.3 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01A - Tetracyclines

    J01AA - Tetracyclines

    J01AA15 - Omadacycline

    5.4 Absorption, Distribution and Excretion

    Absorption

    Omadacycline has an mean absolute oral bioavailability of 34.5% and a mean Tmax of2.5 h with oral dosing. With multiple dosing, Omadacycline displays an accumulation factor of 1.5. Official labeling states that food does not significantly impact rate or extent of absorption, however, conflicting data exists suggesting food may lower the bioavailability of omadacycline taken after eating. The exposure in alveolar cells and epithelial lining fluid is 25.8 and 1.5 fold higher than plasma exposure after IV administration, suggesting Omadacycline penetrates the lungs to a significant degree.

    Route of Elimination

    After IV dosing 27% of Omadacycline was eliminated by the kidneys. In oral dosing 14.4% was found to be eliminated by the kidneys and 81.1% in the feces. Neither renal nor hepatic impairment appears to produce a clinically relevant effect elimination.

    Volume of Distribution

    Omadacycline has a mean Vd of 256 L after a single dose and a Vss of 190 L.

    Clearance

    Omadacycline has a mean systemic clearance of 11.24 L/h and a renal clearance of 2.4-3.3 L/h.

    5.5 Metabolism/Metabolites

    Omadacycline is not known to be metabolized in humans.

    5.6 Biological Half-Life

    Omadacycline has a mean half life of elimination of 16.2 h.

    5.7 Mechanism of Action

    Omadacycline binds to the primary tetracycline binding site on the bacterial 30s ribosomal subunit with high specificity. There it acts to block protein synthesis, disrupting many facets of cellular function and resulting in either cell death or stasis.