natamycin

Trade name: natacyn

Small moleculeapproved

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

Phase 1
1
Phase 2
7
Phase 3
6
Phase 4
0

Earliest trial started Nov 1, 2007 (NCT00557362)

Timeline

1970s

  1. Oct 30, 1978

    Novartis — Earliest FDA Approval

  2. Oct 30, 1978

    Novartis — NDA Secondary Org

  3. Oct 30, 1978

    Novartis — NDA Organization

  4. Oct 30, 1978

    Novartis — Marketing Organization

  5. Oct 30, 1978

    Eyevance — Marketing Organization

  6. Oct 30, 1978

    Eyevance — NDA Secondary Org

  7. Oct 30, 1978

    Harrow Health — Marketing Organization

2000s

  1. Jan 1, 2007

    Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 2008

    Earliest Phase 3 Sponsor(trial)

2010s

  1. Jan 1, 2017

    Earliest Phase 2 Sponsor(trial)

Indications

Mechanism of action

  • ErgosterolSEQUESTERING AGENT

    Ergosterol sequestering agent

Approval history

  • approvedPriority reviewOct 30, 1978

Chemistry & pharmacology

Loading structure…

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

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 IDPhaseStart dateSponsor(s)
NCT06463678Phase 2Dec 1, 2024IVIEW Therapeutics Inc.
NCT06411314Phase 3Dec 29, 2022Avva Rus, JSC
NCT05110001Phase 3Jan 31, 2022Aravind Eye Hospital, National Eye Institute (NEI), Stanford University, University of California, San Francisco
NCT03230058Phase 2/Phase 3 (Phase 3)Jan 1, 2017L. V. Prasad Eye Institute
NCT02731638Phase 3Sep 1, 2016Aravind Eye Hospital, University of California, San Francisco
NCT02328053N/AFeb 1, 2014Aravind Eye Hospital
NCT00996736Phase 3Apr 1, 2010Aravind Eye Hospital, Dartmouth University, University of California, San Francisco
NCT00516399Phase 3Mar 1, 2008Los Angeles Biomedical Research Institute, University of California, Los Angeles
NCT00557362Phase 1/Phase 2 (Phase 2)Nov 1, 2007Aravind Eye Hospital, Dartmouth University, That Man May See, Inc., University of California, San Francisco
Showing 9 of 9 trials
Page 1 / 1

Organizations

Research & Development (11)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Aravind Eye HospitalAcademic/Hospital5132007
University of California, San FranciscoAcademic/Hospital4422007
Dartmouth UniversityAcademic/Hospital2022007
Avva Rus, JSCFor profit1112022
IVIEW Therapeutics Inc.For profit1112024
Los Angeles Biomedical Research InstituteAcademic/Hospital1012008
L. V. Prasad Eye InstituteAcademic/Hospital1112017
National Eye Institute (NEI)Government1012022
Stanford UniversityAcademic/Hospital1012022
That Man May See, Inc.Academic/Hospital1012007
University of California, Los AngelesAcademic/Hospital1112008
11 organizations
Page 1 / 1

Marketing (6)

OrganizationOrg typeRelationshipDate
EyevanceFor profitMKTGOct 30, 1978
EyevanceFor profitNDA2Oct 30, 1978
Harrow HealthFor profitMKTGOct 30, 1978
NovartisFor profitNDA2Oct 30, 1978
NovartisFor profitNDAOct 30, 1978
NovartisFor profitMKTGOct 30, 1978