rifamycin
Trade name: aemcolo
Approved
Nov 16, 2018
Rifamycin SV is a derivative of antibiotic rifamycin B (the natural fermentation product of S. mediterranei broths). The primary target of rifampicin on whole bacteria is the synthesis of RNA. Rifamycin belongs to the ansamycin class of antibacterial drugs and acts by inhibiting the beta subunit of the bacterial DNA-dependent RNA polymerase, blocking one of the steps in DNA transcription. This results in inhibition of bacterial synthesis and consequently growth of bacteria. Rifampicin exhibits bactericidal activity on Gram-positive and Gram-negative bacteria and on mycobacteria. Rifamycin SV MMX® (AEMCOLO), a non-absorbable rifamycin antibiotic formulated using the multi-matrix system, was designed to exhibit its pharmacological action on the distal small intestine and colon. AEMCOLO is indicated for the treatment of travelers’ diarrhea (TD) caused by non-invasive strains of Escherichia coli in adults. — NCATS
Clinical trial activity
13 trials · 14 clinical orgs · 2 marketing orgs
Earliest trial started Feb 29, 2008 (NCT03447821)
Timeline
2000s
- Jan 1, 2008
Cosmo Technologies Ltd — Earliest Phase 2 Sponsor(trial)
2010s
- Jan 1, 2010
Earliest Phase 3 Sponsor(trial)
- Jan 1, 2015
Earliest Phase 1 Sponsor(trial)
- Nov 16, 2018
Cosmo Technologies Ltd — Earliest FDA Approval
- Nov 16, 2018
RedHill Biopharma — Marketing Organization
- Nov 16, 2018
Cosmo Technologies Ltd — NDA Secondary Org
- Nov 16, 2018
Cosmo Technologies Ltd — NDA Organization
- Nov 16, 2018
RedHill Biopharma — NDA Secondary Org
Indications
Approved for
Studied for
- Diarrhea · Phase 3
- Diverticulitis · Phase 2
- Gastrointestinal Diseases · Phase 2
- Healthy Volunteers · Phase 1
- Hepatic Encephalopathy · Phase 2
- HIV · Phase 3
- Intestinal Neoplasms · Phase 2
- Irritable Bowel Syndrome · Phase 2
- Liver Cirrhosis · Phase 2
- Pulmonary Medicine · Phase 4
- Tooth Abnormalities · Phase 4
- Tuberculosis · Phase 3
Mechanism of action
- Bacterial DNA-directed RNA polymeraseANTAGONIST
Bacterial DNA-directed RNA polymerase antagonist
- DNA-directed RNA polymeraseINHIBITOR
DNA-directed RNA polymerase inhibitor
Binds to the beta subunit of RNA polymerase inhibiting bacterial RNA synthesis.
Active against enterotoxigenic and enteroaggregative E coli involved in traveller's diarrhea.
Beta subunit RpoB
Approval history
- approvedPriority reviewFast trackNov 16, 2018
Chemistry & pharmacology
SMILES
CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C- Mol. weight
- 697.78 g/mol
- Lipinski Ro5
- 3 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Prescription Only
Oral
Yes
Parenteral
No
Topical
No
Sources
- ChEMBLCHEMBL437765 ↗
- WikipediaRifamycin ↗
- NCATSDU69T8ZZPA ↗
- ChEMBLCHEMBL2105680 ↗
Also known as
- 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2-h)-dione, 21-acetate
- cb-01-11
- cb-01-11
- cb-01-11
- otafa
- r-75-1
- rifacin
- rifacin
- rifacin
- rifacin
- rifacin
- rifacin
- rifamicina colirio
- rifamicine sv
- rifamicine sv
- rifamycin
- rifamycin
- rifamycin
- rifamycin
- rifamycin
- rifamycin
- rifamycin
- rifamycin
- rifamycine chibret
- rifamycin sodium
- rifamycin sv
- rifamycin sv
- rifamycin sv
- rifamycin sv
- rifamycin sv
- rifamycin sv, monosodium salt
- rifamycin sv, sodium salt
- rifocina
- rifocyna
- rifomycin
- rifomycin
- rifomycin sv
- rifomycin sv
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05575518 | Phase 3 | Jan 30, 2023 | Kibong'oto Infectious Diseases Hospital, Radboud University, University of St Andrews |
| NCT05588492 | Phase 4 | Jan 1, 2022 | National Taiwan University |
| NCT04501380 | Phase 2 | Jun 30, 2020 | The New York Center for Travel and Tropical Medicine |
| NCT04026984 | Phase 2 | Mar 31, 2020 | Cosmo Technologies Ltd |
| NCT04027894 | Phase 2 | Mar 31, 2020 | Cosmo Technologies Ltd |
| NCT04082780 | Phase 2 | Sep 1, 2019 | Department of Veteran Affairs |
| NCT04349579 | Phase 4 | Oct 15, 2018 | Cairo University, Yuzuncu Yıl University |
| NCT03099785 | Phase 2 | Jun 1, 2017 | Cosmo Pharmaceuticals |
| NCT02969252 | Phase 1 | Jul 1, 2015 | Cosmo Pharmaceuticals |
| NCT01847664 | Phase 2 | Aug 1, 2013 | Dr. Falk Pharma GmbH |
| NCT01208922 | Phase 3 | Oct 1, 2010 | Dr. Falk Pharma GmbH, University of Zurich |
| NCT01142089 | Phase 3 | May 1, 2010 | Bausch Health Companies |
| NCT03447821 | Phase 2 | Feb 29, 2008 | Cosmo Technologies Ltd, Saglik Bilimleri Universitesi |
Organizations
Research & Development (14)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Cosmo Technologies Ltd | For profit | 3 | 3 | 1 | 2008 |
| Cosmo Pharmaceuticals | For profit | 2 | 2 | 2 | 2015 |
| Dr. Falk Pharma GmbH | For profit | 2 | 2 | 2 | 2010 |
| Bausch Health Companies | For profit | 1 | 1 | 1 | 2010 |
| Cairo University | Academic/Hospital | 1 | 0 | 1 | 2018 |
| Department of Veteran Affairs | Government | 1 | 1 | 1 | 2019 |
| Kibong'oto Infectious Diseases Hospital | Academic/Hospital | 1 | 1 | 1 | 2023 |
| National Taiwan University | Academic/Hospital | 1 | 1 | 1 | 2022 |
| Radboud University | Academic/Hospital | 1 | 0 | 1 | 2023 |
| Saglik Bilimleri Universitesi | Academic/Hospital | 1 | 0 | 1 | 2008 |
| The New York Center for Travel and Tropical Medicine | Academic/Hospital | 1 | 0 | 1 | 2020 |
| University of St Andrews | Academic/Hospital | 1 | 0 | 1 | 2023 |
| University of Zurich | Academic/Hospital | 1 | 0 | 1 | 2010 |
| Yuzuncu Yıl University | Academic/Hospital | 1 | 1 | 1 | 2018 |
Marketing (4)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Cosmo Technologies Ltd | For profit | NDA2 | Nov 16, 2018 |
| Cosmo Technologies Ltd | For profit | NDA | Nov 16, 2018 |
| RedHill Biopharma | For profit | MKTG | Nov 16, 2018 |
| RedHill Biopharma | For profit | NDA2 | Nov 16, 2018 |