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Omadacycline Tosylate

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Chemistry

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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

Omadacycline

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 Formula	C₂₉H₄₀N₄O₇
Molecular Weight	556.6 g/mol
XLogP3	3
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	7
Exact Mass	556.28969963 g/mol
Monoisotopic Mass	556.28969963 g/mol
Topological Polar Surface Area	177 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	1140
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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API Reference Price

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