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Eravacycline

Synopsis, Chemistry

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Also known as: 1207283-85-9, Tp-434, Xerava, Eravacycline [usan], Tp434, (4s,4as,5ar,12ar)-4-(dimethylamino)-7-fluoro-1,10,11,12a-tetrahydroxy-3,12-dioxo-9-[(2-pyrrolidin-1-ylacetyl)amino]-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide

Molecular Formula

C₂₇H₃₁FN₄O₈

Molecular Weight

558.6 g/mol

InChI Key

AKLMFDDQCHURPW-ISIOAQNYSA-N

FDA UNII

07896928ZC

Eravacycline, known as Xerava by Tetraphase Pharmaceuticals, is a fully synthetic fluorocycline antibiotic of the tetracycline class with activity against clinically significant gram-negative, gram-positive aerobic, and facultative bacteria. This includes most of those bacteria resistant to cephalosporins, fluoroquinolones, -lactam/-lactamase inhibitors, multidrug-resistant strains, and carbapenem-resistant Enterobacteriaceae, and the majority of anaerobic pathogens. It was first approved by the FDA on August 27, 2018. Eravacycline has demonstrated superior potency to that of antibiotics that are currently being marketed for intraabdominal infections.

Eravacycline is a Tetracycline-class Antibacterial.

1 2D Structure

Eravacycline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4S,4aS,5aR,12aR)-4-(dimethylamino)-7-fluoro-1,10,11,12a-tetrahydroxy-3,12-dioxo-9-[(2-pyrrolidin-1-ylacetyl)amino]-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide

2.1.2 InChI

InChI=1S/C27H31FN4O8/c1-31(2)20-13-8-11-7-12-14(28)9-15(30-16(33)10-32-5-3-4-6-32)21(34)18(12)22(35)17(11)24(37)27(13,40)25(38)19(23(20)36)26(29)39/h9,11,13,20,34-35,38,40H,3-8,10H2,1-2H3,(H2,29,39)(H,30,33)/t11-,13-,20-,27-/m0/s1

2.1.3 InChI Key

AKLMFDDQCHURPW-ISIOAQNYSA-N

2.1.4 Canonical SMILES

CN(C)C1C2CC3CC4=C(C=C(C(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)NC(=O)CN5CCCC5)F

2.1.5 Isomeric SMILES

CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=C(C(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)NC(=O)CN5CCCC5)F

2.2 Other Identifiers

2.2.1 UNII

07896928ZC

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (4s,4as,5ar,12as)-4-(dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-((pyrrolidin-1-ylacetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

2. (4s,4as,5ar,12as)-4-(dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-((pyrrolidin-1-ylacetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide Dihydrochloride

3. 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline

4. Eravacycline Dihydrochloride

5. Tp-434

6. Tp-434-046

7. Tp-434046

8. Tp434

9. Xerava

2.3.2 Depositor-Supplied Synonyms

1. 1207283-85-9

2. Tp-434

3. Xerava

4. Eravacycline [usan]

5. Tp434

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

7. Eravacycline (usan)

8. 07896928zc

9. 1-pyrrolidineacetamide, N-((5ar,6as,7s,10as)-9-(aminocarbonyl)-7-(dimethylamino)-4-fluoro-5,5a,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl)-

10. Eravacycline [usan:inn]

11. Unii-07896928zc

12. Yqm

13. Tp434;eravacycline

14. Eravacycline [mi]

15. Eravacycline [inn]

16. Eravacycline [who-dd]

17. Chembl1951095

18. Chembl4597183

19. Schembl10040430

20. Gtpl10805

21. Ex-a751

22. Chebi:177804

23. Dtxsid401026285

24. Mfcd31010183

25. Zinc200151468

26. Cs-7564

27. Db12329

28. Compound 17j [pmid: 2148514]

29. Hy-16980

30. D10369

31. J-690064

32. Q15410941

33. 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline

34. (4s,4as,5ar,12ar)-4-(dimethylamino)-7-fluoro-1,10,11,12a-tetrahydroxy-3,12-dioxo-9-[2-(pyrrolidin-1-yl)acetamido]-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboxamide

35. (4s,4as,5ar,12ar)-4-(dimethylamino)-7-luoro-1,10,11,12a-tetrahydroxy-3,12-dioxo-9-[(2-pyrrolidin-1-ylacetyl)amino]-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide

36. (4s,4as,5ar,12as)-4-(dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-((pyrrolidin-1-ylacetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

37. (4s,4as,5ar,12as)-4-(dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[(2-pyrrolidin-1-ylacetyl)amino]-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide

38. (4s,4as,5ar,12as)-4-(dimethylamino)-7-fluoro-3,10,12,12atetrahydroxy-1,11-dioxo-9-(2-(pyrrolidin-1-yl)acetamido)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

39. 4s,4as,5ar,12as)-4-(dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-((pyrrolidin-1-ylacetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

40. 7-[6-(2-hydroxy-2-propanyl)-3-pyridinyl]-1-(4-methoxycyclohexyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1h)-one

41. N-[(5ar,6as,7s,10as)-9-(aminocarbonyl)-7-(dimethylamino)-4-fluoro-5,5a,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl]-1-pyrrolidineacetamide

2.4 Create Date

2011-12-26

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₁FN₄O₈
Molecular Weight	558.6 g/mol
XLogP3	1
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	5
Exact Mass	558.21259212 g/mol
Monoisotopic Mass	558.21259212 g/mol
Topological Polar Surface Area	194 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	1200
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

Eravacycline is a tetracycline class antibacterial indicated for the treatment of complicated intra-abdominal infections in patients 18 years of age and older.

FDA Label

Xerava is indicated for the treatment of complicated intra-abdominal infections (cIAI) in adults.

Consideration should be given to official guidance on the appropriate use of antibacterial agents.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Eravacycline is an antibiotic that disrupts bacterial protein synthesis, treating complicated intraabdominal infections.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

ERAVACYCLINE

5.2.2 FDA UNII

07896928ZC

5.2.3 Pharmacological Classes

Tetracyclines [CS]; Tetracycline-class Antibacterial [EPC]

5.3 ATC Code

J01AA

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01A - Tetracyclines

J01AA - Tetracyclines

J01AA13 - Eravacycline

5.4 Absorption, Distribution and Excretion

Absorption

Following single-dose intravenous administration, eravacycline AUC (area under the curve) and Cmax (maximum concentration) increase dose-proportionally for doses from 1 mg/kg - 3 mg/kg (3 times the approved dose). There is approximately 45% accumulation following intravenous dosing of 1 mg/kg every 12 hours.

Route of Elimination

Following a single intravenous dose of radiolabeled eravacycline 60 mg, approximately 34% of the dose is excreted in urine and 47% in feces as unchanged eravacycline (20% in urine and 17% in feces) and metabolites.

Volume of Distribution

The volume of distribution at steady-state is approximately 321 L.

Clearance

17.82 L/min (standard deviation of 3.4).

5.5 Metabolism/Metabolites

Eravacycline is metabolized primarily by CYP3A4- and FMO-mediated oxidation.

5.6 Biological Half-Life

The mean elimination half-life is 20 hours.

5.7 Mechanism of Action

Eravacycline is a fluorocycline antibacterial of the tetracycline class of antibacterial drugs. Eravacycline disrupts bacterial protein synthesis by binding to the 30S ribosomal subunit, preventing the incorporation of amino acid residues into elongating peptide chains. In general, eravacycline is bacteriostatic against gram-positive bacteria (e.g., Staphylococcus aureus and Enterococcus faecalis); however, in vitro bactericidal activity has been shown against certain strains of Escherichia coli and Klebsiella pneumoniae.