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    Eravacycline

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    2D Structure
    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

    2D Structure

    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 Weight 558.6 g/mol
    Molecular Formula C27H31FN4O8
    XLogP31
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count5
    Exact Mass558.21259212 g/mol
    Monoisotopic Mass558.21259212 g/mol
    Topological Polar Surface Area194 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity1200
    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

    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.