ethionamide
Trade name: trecator
Approved
Apr 30, 1965
Ethionamide is a second-line agent, structurally similar to isoniazid, used as a second-line therapy for the treatment of multidrug-resistant tuberculosis or active tuberculosis in case of patient intolerance to other drugs. Depending on its the concentration at the infected site and the susceptibility of the infecting organism it may be bacteriostatic or bactericidal. When used alone rapidly develops bacterial resistance. Ethionamide was approved by FDA in 1965 as TRECATOR manufactured by Wyeth Pharmaceuticals Inc. (purchased by Pfizer in 2009). Ethionamide is specific for Mycobacteria and is thought to exert a toxic effect on mycolic acid components of the bacterial cell wall when activated through intermediate S-oxidation by EtaA. Mycolic acid synthesis was shown to be inhibited by ethionamide in the EthA protein-overexpressing mycobacteria, — NCATS
Clinical trial activity
7 trials · 12 clinical orgs · 2 marketing orgs
Earliest trial started Nov 2, 1999 (NCT00000796)
Timeline
1960s
- Apr 30, 1965
American Home Products — Earliest FDA Approval
- Apr 30, 1965
American Home Products — NDA Organization
- Apr 30, 1965
Wyeth — NDA Secondary Org
Indications
Approved for
Mechanism of action
inhA inhibitor
Prodrug enzyme: FAD-containing monooxygenase (EthA)
Approval history
- approvedPriority reviewApr 30, 1965
Chemistry & pharmacology
SMILES
CCC1=CC(=CC=N1)C(N)=S- Mol. weight
- 166.243 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- Yes
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Prescription Only
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaEthionamide ↗
- NCATSOAY8ORS3CQ ↗
- ChEMBLCHEMBL1441 ↗
Also known as
- 1314 th
- 1314 th
- 2-ethyl-4-thiopyridylamide
- 2-ethyl-4-thiopyridylamide
- 2-ethylthioisonicotinamide
- 2-ethylthioisonicotinamide
- amidazine
- ehionamide
- eth
- eth
- ethinamide
- ethinamide
- ethionamide
- ethionamide
- ethionamide
- ethionamide
- ethionamide
- ethionamide
- ethionamide
- ethionamide
- ethionamide
- ethionamidum
- ethionamidum
- ethioniamide
- ethioniamide
- ethioniamide
- ethioniamide
- ethioniamide
- ethioniamide
- ethylisothiamide
- ethylisothiamide
- ethyonomide
- ethyonomide
- etionamid
- etionamid
- etionamida
- etionamida
- etionamide
- etionamide
- etioniamid
- etioniamid
- etp
- etp
- trecator
- trecator
- trecator
- trecator-sc
- trecator-sc
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05473195 | Phase 2 | Oct 31, 2022 | TASK Applied Science |
| NCT02975570 | Phase 3 | Aug 1, 2017 | Boston University, University of Florida, Westat |
| NCT02354014 | Phase 2 | May 3, 2016 | Johnson and Johnson |
| NCT02454205 | Phase 2/Phase 3 (Phase 3) | Oct 1, 2015 | Stellenbosch University, University of Cape Town, University of Limpopo, Walter Sisulu University |
| NCT02365623 | Phase 2 | Feb 18, 2015 | Janssen Pharmaceutica NV, Johnson and Johnson |
| NCT00042289 | Phase 4 | Mar 1, 2003 | Boston University, National Institute of Allergy and Infectious Diseases (NIAID), National Institutes of Health (NIH) |
| NCT00000796 | N/A | Nov 2, 1999 | National Institute of Allergy and Infectious Diseases (NIAID) |
Organizations
Research & Development (12)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Boston University | Academic/Hospital | 2 | 1 | 2 | 2003 |
| Johnson and Johnson | For profit | 2 | 2 | 1 | 2015 |
| National Institute of Allergy and Infectious Diseases (NIAID) | Government | 2 | 2 | 2 | 1999 |
| Janssen Pharmaceutica NV | For profit | 1 | 0 | 1 | 2015 |
| National Institutes of Health (NIH) | Government | 1 | 0 | 1 | 2003 |
| Stellenbosch University | Academic/Hospital | 1 | 0 | 1 | 2015 |
| TASK Applied Science | For profit | 1 | 1 | 1 | 2022 |
| University of Cape Town | Academic/Hospital | 1 | 1 | 1 | 2015 |
| University of Florida | Academic/Hospital | 1 | 0 | 1 | 2017 |
| University of Limpopo | Academic/Hospital | 1 | 0 | 1 | 2015 |
| Walter Sisulu University | Academic/Hospital | 1 | 0 | 1 | 2015 |
| Westat | For profit | 1 | 0 | 1 | 2017 |
Marketing (2)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| American Home Products | For profit | NDA | Apr 30, 1965 |
| Wyeth | For profit | NDA2 | Apr 30, 1965 |