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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H31FN4O8
Molecular Weight 558.5554
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERAVACYCLINE

SMILES

[H][C@@]12CC3=C(F)C=C(NC(=O)CN4CCCC4)C(O)=C3C(=O)C1=C(O)[C@]5(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]5([H])C2

InChI

InChIKey=HLFSMUUOKPBTSM-ISIOAQNYSA-N
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/h9,11,13,20,34,36-37,40H,3-8,10H2,1-2H3,(H2,29,39)(H,30,33)/t11-,13-,20-,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H31FN4O8
Molecular Weight 558.5554
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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, β-lactam/β-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 disrupts bacterial protein synthesis by binding to the 30S ribosomal subunit thus preventing the incorporation of amino acid residues into elongating peptide chains.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
XERAVA

Cmax

ValueDoseCo-administeredAnalytePopulation
2125 ng/mL
1 mg/kg single, intravenous
ERAVACYCLINE plasma
Homo sapiens
1825 ng/mL
1 mg/kg 2 times / day steady-state, intravenous
ERAVACYCLINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
4305 ng × h/mL
1 mg/kg single, intravenous
ERAVACYCLINE plasma
Homo sapiens
6309 ng × h/mL
1 mg/kg 2 times / day steady-state, intravenous
ERAVACYCLINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
20 h
1 mg/kg single, intravenous
ERAVACYCLINE plasma
Homo sapiens
20 h
1 mg/kg 2 times / day steady-state, intravenous
ERAVACYCLINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
15.5%
1 mg/kg single, intravenous
ERAVACYCLINE plasma
Homo sapiens
15.5%
1 mg/kg 2 times / day steady-state, intravenous
ERAVACYCLINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Administer XERAVA for injection 1 mg/kg by intravenous infusion over approximately 60 minutes every 12 hours for a total duration of 4 to 14 days. (2.1) • Severe Hepatic Impairment (Child Pugh C): 1 mg/kg XERAVA every 12 hours on Day 1, then 1 mg/kg every 24 hours starting on Day 2 for a total duration of 4 to 14 days. (2.2) • Concomitant Use of a Strong Cytochrome P450 Isoenzymes (CYP)3A Inducer: 1.5 mg/kg XERAVA every 12 hours for a total duration of 4 to 14 days. (2.3) For injection: 50 mg of eravacycline (equivalent to 63.5 mg eravacy cline dihydrochloride) as a lyophilized powder in a single-dose vial for reconstitution and further dilution.
Route of Administration: Intravenous
In Vitro Use Guide
In vitro activity data from Tetraphase Pharmaceuticals studies on the following groups of combined bacterial species: Enterobacteriaceae, 5975 isolates, MIC90 0.5 mcg/mL, ECOV 1 ug/mL All Enterococcus spp., 1403 isolates, MIC90 0.06 ug/mL, ECOV 0.25 ug/mL All Viridans Group Streptococcus, 414 isolates, MIC90 0.06 ug/mL, ECOV 0.12 ug/mL Anaerobes, 1190 isolates, MIC90 1 ug/mL, ECOV 1 ug/mL
Substance Class Chemical
Record UNII
07896928ZC
Record Status Validated (UNII)
Record Version