Eravacycline dihydrochlorideProduct ingredient for Eravacycline

Name
Eravacycline dihydrochloride
Drug Entry
Eravacycline

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 1. It was first approved by the FDA on August 27, 2018 4. Eravacycline has demonstrated superior potency to that of antibiotics that are currently being marketed for intraabdominal infections 3.

Accession Number
DBSALT002787
Structure
Thumb
Synonyms
Eravacycline dihydrochloride / Eravacycline HCl / Eravacycline hydrochloride
External IDs
TP-434-046 / TP434046
UNII
WK1NMH89VJ
CAS Number
1334714-66-7
Weight
Average: 631.48
Monoisotopic: 630.1659476
Chemical Formula
C27H33Cl2FN4O8
InChI Key
JYCNMRVZELJVAW-RZVFYPHASA-N
InChI
InChI=1S/C27H31FN4O8.2ClH/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);2*1H/t11-,13-,20-,27-;;/m0../s1
IUPAC Name
(4S,4aS,5aR,12aS)-4-(dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[2-(pyrrolidin-1-yl)acetamido]-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide dihydrochloride
SMILES
Cl.Cl.[H][C@@]12CC3=C(F)C=C(NC(=O)CN4CCCC4)C(O)=C3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2
ChemSpider
28651527
ChEMBL
CHEMBL2219414
Predicted Properties
PropertyValueSource
Water Solubility0.838 mg/mLALOGPS
logP0.24ALOGPS
logP-3.5ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area193.73 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity144.16 m3·mol-1ChemAxon
Polarizability54.35 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon