Eravacycline
Eravacycline
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Eravacycline

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Catalog Number PR1207283859
CAS 1207283-85-9
Synonyms Xerava; Eravacycline [USAN]; TP434
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
Molecular Weight 558.6
Molecular Formula C27H31FN4O8
InChI AKLMFDDQCHURPW-ISIOAQNYSA-N
InChI Key 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
Drug Categories Anti-Bacterial Agents; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; Cytochrome P-450 CYP3A Substrates; Cytochrome P-450 CYP3A4 Substrates; Cytochrome P-450 Substrates; Monoamine Oxidase A Substrates; Naphthacenes; Tetracyclines
Drug Interactions Abametapir-The serum concentration of Eravacycline can be increased when it is combined with Abametapir.
Acenocoumarol-Eravacycline may increase the anticoagulant activities of Acenocoumarol.
Acitretin-The risk or severity of pseudotumor cerebri can be increased when Acitretin is combined with Eravacycline.
Alitretinoin-The risk or severity of pseudotumor cerebri can be increased when Alitretinoin is combined with Eravacycline.
Ambroxol-The risk or severity of methemoglobinemia can be increased when Eravacycline is combined with Ambroxol.
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
Type Small Molecule
Pharmacology

Indications

Eravacycline is an antibacterial agent belonging to the tetracycline class. It is specifically indicated for the treatment of complicated intra-abdominal infections in adults aged 18 and over.

Pharmacodynamics

Eravacycline operates by disrupting bacterial protein synthesis, thereby effectively targeting and treating complicated intra-abdominal infections. This mechanism enables it to combat a wide range of bacteria responsible for such infections.

Absorption

Following a single-dose intravenous administration, eravacycline exhibits dose-proportional increases in both the area under the curve (AUC) and maximum concentration (Cmax) for doses ranging from 1 mg/kg to 3 mg/kg, which is three times the approved dose. Furthermore, after intravenous administration of 1 mg/kg every 12 hours, there is approximately a 45% accumulation of the drug.

Metabolism

Eravacycline is primarily metabolized through oxidation, a process mediated by cytochrome P450 3A4 (CYP3A4) and flavin-containing monooxygenase (FMO) enzymes.

Mechanism of Action

Eravacycline is classified as a fluorocycline antibacterial agent within the tetracycline class of antimicrobial drugs. It functions by interfering with bacterial protein synthesis. Specifically, eravacycline binds to the 30S ribosomal subunit, thereby obstructing the addition of amino acid residues into the elongating peptide chains. Generally, eravacycline exhibits a bacteriostatic effect on gram-positive bacteria, such as Staphylococcus aureus and Enterococcus faecalis. Notably, it has demonstrated bactericidal activity in vitro against particular strains of Escherichia coli and Klebsiella pneumoniae.

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