natamycin
Trade name: natacyn
Approved
Oct 30, 1978
Natamycin (Pimaricin, Pimafucin, Natadrops, Natacyn) is a polyene antifungal agent originally isolated from Streptomyces natalensis found in a soil sample from Natal, South Africa. Natamycin was discovered in DSM laboratories in 1955. Similar to other polyenes, natamycin binds to ergosterol in the fungal cell membrane. Natamycin blocks fungal growth by binding specifically to ergosterol with¬out permeabilizing the membrane where it inhibits vacuole fusion at the priming phase and interferes with membrane protein functions. Natamycin is also used in the food industry as an effective preservative. Natamycin is active against most Candida spp. Aspergillus spp., Fusarium spp. and other rarer fungi that cause keratitis. Secondary or acquired resistance is probably rare, but not extensively studied. Natamycin is not effective in vitro against gram-positive or gram-negative bacteria. Topical administration appears to produce effective concentrations of natamycin within the corneal stroma but not in intraocular fluid. Natamycin is poorly soluble in water and not absorbed through the skin or mucous membranes, including the vagina. Very little is absorbed through the gastrointestinal tract. After ocular application, therapeutic concentrations are present within the infected cornea, but not in intra-ocular fluid Natamycin may cause some irritation on skin or mucous membranes — NCATS
Clinical trial activity
9 trials · 11 clinical orgs · 3 marketing orgs
Earliest trial started Nov 1, 2007 (NCT00557362)
Timeline
1970s
- Oct 30, 1978
Novartis — Earliest FDA Approval
- Oct 30, 1978
Novartis — NDA Secondary Org
- Oct 30, 1978
Novartis — NDA Organization
- Oct 30, 1978
Novartis — Marketing Organization
- Oct 30, 1978
Eyevance — Marketing Organization
- Oct 30, 1978
Eyevance — NDA Secondary Org
- Oct 30, 1978
Harrow Health — Marketing Organization
2010s
- Jan 1, 2017
Earliest Phase 2 Sponsor(trial)
Indications
Approved for
Mechanism of action
- ErgosterolSEQUESTERING AGENT
Ergosterol sequestering agent
Approval history
- approvedPriority reviewOct 30, 1978
Chemistry & pharmacology
SMILES
C[C@H]1O[C@@H](O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]4O[C@@H]4\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)[C@@H](O)[C@@H](N)[C@@H]1O- Mol. weight
- 665.7252 g/mol
- Lipinski Ro5
- 3 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Topical
- Availability
- Prescription Only
Oral
No
Parenteral
No
Topical
Yes
Sources
- WikipediaNatamycin ↗
- NCATS8O0C852CPO ↗
- ChEMBLCHEMBL1200656 ↗
Also known as
- antibiotic a-5283
- antibiotic a-5283
- cl-12625
- cl-12625
- e235
- e235
- myprozine
- myprozine
- myuprozine
- natacyn
- natacyn
- natacyn
- natamicina
- natamicina
- natamycin
- natamycin
- natamycin
- natamycin
- natamycin
- natamycin
- natamycin
- natamycin
- natamycin
- natamycine
- natamycine
- natamycinum
- natamycinum
- pimafucin
- pimafucin
- pimafucin
- pimaracin
- pimaracin
- pimaricin
- pimaricin
- pimaricin
- pimaricin
- pimaricin
- pimaricin
- tennecetin
- tennecetin
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06463678 | Phase 2 | Dec 1, 2024 | IVIEW Therapeutics Inc. |
| NCT06411314 | Phase 3 | Dec 29, 2022 | Avva Rus, JSC |
| NCT05110001 | Phase 3 | Jan 31, 2022 | Aravind Eye Hospital, National Eye Institute (NEI), Stanford University, University of California, San Francisco |
| NCT03230058 | Phase 2/Phase 3 (Phase 3) | Jan 1, 2017 | L. V. Prasad Eye Institute |
| NCT02731638 | Phase 3 | Sep 1, 2016 | Aravind Eye Hospital, University of California, San Francisco |
| NCT02328053 | N/A | Feb 1, 2014 | Aravind Eye Hospital |
| NCT00996736 | Phase 3 | Apr 1, 2010 | Aravind Eye Hospital, Dartmouth University, University of California, San Francisco |
| NCT00516399 | Phase 3 | Mar 1, 2008 | Los Angeles Biomedical Research Institute, University of California, Los Angeles |
| NCT00557362 | Phase 1/Phase 2 (Phase 2) | Nov 1, 2007 | Aravind Eye Hospital, Dartmouth University, That Man May See, Inc., University of California, San Francisco |
Organizations
Research & Development (11)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Aravind Eye Hospital | Academic/Hospital | 5 | 1 | 3 | 2007 |
| University of California, San Francisco | Academic/Hospital | 4 | 4 | 2 | 2007 |
| Dartmouth University | Academic/Hospital | 2 | 0 | 2 | 2007 |
| Avva Rus, JSC | For profit | 1 | 1 | 1 | 2022 |
| IVIEW Therapeutics Inc. | For profit | 1 | 1 | 1 | 2024 |
| Los Angeles Biomedical Research Institute | Academic/Hospital | 1 | 0 | 1 | 2008 |
| L. V. Prasad Eye Institute | Academic/Hospital | 1 | 1 | 1 | 2017 |
| National Eye Institute (NEI) | Government | 1 | 0 | 1 | 2022 |
| Stanford University | Academic/Hospital | 1 | 0 | 1 | 2022 |
| That Man May See, Inc. | Academic/Hospital | 1 | 0 | 1 | 2007 |
| University of California, Los Angeles | Academic/Hospital | 1 | 1 | 1 | 2008 |