eravacycline
Trade name: Xerava
Approved
Aug 27, 2018
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. — NCATS
Clinical trial activity
13 trials · 7 clinical orgs · 1 marketing orgs
Earliest trial started Jan 1, 2011 (NCT01265784)
Timeline
2010s
- Jan 1, 2011
Tetraphase Pharmaceuticals — Earliest Phase 2 Sponsor(trial)
- Jan 1, 2012
Tetraphase Pharmaceuticals — Earliest Phase 1 Sponsor(trial)
- Jan 1, 2013
Tetraphase Pharmaceuticals — Earliest Phase 3 Sponsor(trial)
- Aug 27, 2018
Tetraphase Pharmaceuticals — Earliest FDA Approval
- Aug 27, 2018
Tetraphase Pharmaceuticals — NDA Secondary Org
- Aug 27, 2018
Tetraphase Pharmaceuticals — NDA Organization
Indications
Approved for
Studied for
Mechanism of action
- 30S ribosomal protein S12ANTAGONIST
rpsL antagonist
- Bacterial 70S ribosomeINHIBITOR
Bacterial 70S ribosome inhibitor
- 30S ribosomal protein S2 (rpsB) ↗
- 50S ribosomal protein L4 (rplD) ↗
- 30S ribosomal protein S15 (rpsO) ↗
- 30S ribosomal protein S16 (rpsP) ↗
- 30S ribosomal protein S17 (rpsQ) ↗
- 30S ribosomal protein S18 (rpsR) ↗
- 30S ribosomal protein S19 (rpsS) ↗
- 30S ribosomal protein S20 (rpsT) ↗
- 30S ribosomal protein S21 (rpsU) ↗
- 30S ribosomal protein S3 (rpsC) ↗
- 30S ribosomal protein S4 (rpsD) ↗
- 30S ribosomal protein S5 (rpsE) ↗
- 30S ribosomal protein S6 (rpsF) ↗
- 30S ribosomal protein S7 (rpsG) ↗
- 30S ribosomal protein S8 (rpsH) ↗
- 30S ribosomal protein S9 (rpsI) ↗
- 50S ribosomal protein L35 (rpmI) ↗
- 50S ribosomal protein L36 2 (ykgO) ↗
- 50S ribosomal protein L36 (rpmJ) ↗
- 50S ribosomal protein L3 (rplC) ↗
- 50S ribosomal protein L5 (rplE) ↗
- 50S ribosomal protein L6 (rplF) ↗
- 50S ribosomal protein L7/L12 (rplL) ↗
- 30S ribosomal protein S1 (rpsA) ↗
- 30S ribosomal protein S10 (rpsJ) ↗
- 30S ribosomal protein S11 (rpsK) ↗
- 30S ribosomal protein S12 (rpsL) ↗
- 30S ribosomal protein S13 (rpsM) ↗
- 30S ribosomal protein S14 (rpsN) ↗
- 50S ribosomal protein L10 (rplJ) ↗
- 50S ribosomal protein L11 (rplK) ↗
- 50S ribosomal protein L13 (rplM) ↗
- 50S ribosomal protein L14 (rplN) ↗
- 50S ribosomal protein L15 (rplO) ↗
- 50S ribosomal protein L16 (rplP) ↗
- 50S ribosomal protein L17 (rplQ) ↗
- 50S ribosomal protein L18 (rplR) ↗
- 50S ribosomal protein L19 (rplS) ↗
- 50S ribosomal protein L1 (rplA) ↗
- 50S ribosomal protein L20 (rplT) ↗
- 50S ribosomal protein L21 (rplU) ↗
- 50S ribosomal protein L22 (rplV) ↗
- 50S ribosomal protein L23 (rplW) ↗
- 50S ribosomal protein L24 (rplX) ↗
- 50S ribosomal protein L25 (rplY) ↗
- 50S ribosomal protein L27 (rpmA) ↗
- 50S ribosomal protein L28 (rpmB) ↗
- 50S ribosomal protein L29 (rpmC) ↗
- 50S ribosomal protein L2 (rplB) ↗
- 50S ribosomal protein L30 (rpmD) ↗
- 50S ribosomal protein L31 type B (ykgM) ↗
- 50S ribosomal protein L31 (rpmE) ↗
- 50S ribosomal protein L32 (rpmF) ↗
- 50S ribosomal protein L33 (rpmG) ↗
- 50S ribosomal protein L34 (rpmH) ↗
Approval history
- approvedPriority reviewFast trackAug 27, 2018
Chemistry & pharmacology
SMILES
CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(F)C=C(NC(=O)CN5CCCC5)C(O)=C4C(=O)C3=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O- Mol. weight
- 558.5554 g/mol
- Lipinski Ro5
- 2 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Prescription Only
Oral
No
Parenteral
Yes
Topical
No
Sources
- WikipediaEravacycline ↗
- NCATS07896928ZC ↗
- ChEMBLCHEMBL2219414 ↗
- ChEMBLCHEMBL1951095 ↗
Also known as
- 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline
- eravacycline
- eravacycline
- eravacycline
- eravacycline
- eravacycline
- eravacycline dihydrochloride
- eravacyline
- tp-434
- tp-434
- tp-434
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06794541 | Phase 2 | Mar 31, 2025 | Innoviva, Tetraphase Pharmaceuticals |
| NCT06440304 | Phase 4 | Nov 30, 2024 | University of Zagreb |
| NCT05537896 | Phase 2 | Oct 31, 2022 | West Virginia University |
| NCT03696550 | Phase 1 | Dec 20, 2018 | Tetraphase Pharmaceuticals |
| NCT03032510 | Phase 3 | Jan 1, 2017 | Tetraphase Pharmaceuticals |
| NCT02784704 | Phase 3 | Oct 13, 2016 | Tetraphase Pharmaceuticals |
| NCT02135276 | Phase 1 | Dec 1, 2013 | Tetraphase Pharmaceuticals |
| NCT01978938 | Phase 3 | Dec 1, 2013 | Tetraphase Pharmaceuticals |
| NCT02135302 | Phase 1 | Oct 1, 2013 | New Orleans Center for Clinical Research, Orlando Clinical Research Center, Tetraphase Pharmaceuticals |
| NCT01844856 | Phase 3 | Aug 1, 2013 | Tetraphase Pharmaceuticals |
| NCT01941446 | Phase 1 | Mar 1, 2013 | Tetraphase Pharmaceuticals |
| NCT01989949 | Phase 1 | Nov 1, 2012 | Department of Health and Human Services, Tetraphase Pharmaceuticals |
| NCT01265784 | Phase 2 | Jan 1, 2011 | Tetraphase Pharmaceuticals |
Organizations
Research & Development (7)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Tetraphase Pharmaceuticals | For profit | 11 | 11 | 3 | 2011 |
| Department of Health and Human Services | Government | 1 | 0 | 1 | 2012 |
| Innoviva | For profit | 1 | 0 | 1 | 2025 |
| New Orleans Center for Clinical Research | For profit | 1 | 0 | 1 | 2013 |
| Orlando Clinical Research Center | For profit | 1 | 0 | 1 | 2013 |
| University of Zagreb | Academic/Hospital | 1 | 1 | 1 | 2024 |
| West Virginia University | Academic/Hospital | 1 | 1 | 1 | 2022 |
Marketing (2)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Tetraphase Pharmaceuticals | For profit | NDA2 | Aug 27, 2018 |
| Tetraphase Pharmaceuticals | For profit | NDA | Aug 27, 2018 |