Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H47NO13 |
Molecular Weight | 665.7252 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 14 / 14 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@H](O)C[C@]3(O)C[C@H](O)[C@@H](C(O)=O)[C@]([H])(C[C@@]([H])(O[C@@H]4O[C@H](C)[C@@H](O)[C@H](N)[C@@H]4O)\C=C\C=C\C=C\C=C\C[C@@H](C)OC(=O)\C=C\[C@@]1([H])O2)O3
InChI
InChIKey=NCXMLFZGDNKEPB-FFPOYIOWSA-N
InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1
DescriptionCurator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Natamycin
http://www.life-worldwide.org/fungal-diseases/natamycin
http://www.drugbank.ca/drugs/DB00826
Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Natamycin
http://www.life-worldwide.org/fungal-diseases/natamycin
http://www.drugbank.ca/drugs/DB00826
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364028 Sources: http://www.drugbank.ca/drugs/DB00826 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | NATACYN Approved UseNATACYN® (natamycin ophthalmic suspension) 5% is a sterile, antifungal drug for topical ophthalmic administration. Launch Date3.29702408E11 |
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Curative | NATACYN Approved UseNatamycin Launch Date3.29702408E11 |
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Curative | NATACYN Approved UseNatamycin Launch Date3.29702408E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32315560/ |
2.5 μL single, ocular dose: 2.5 μL route of administration: Ocular experiment type: SINGLE co-administered: |
NATAMYCIN plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.72 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32315560/ |
2.5 μL single, ocular dose: 2.5 μL route of administration: Ocular experiment type: SINGLE co-administered: |
NATAMYCIN plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.78 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32315560/ |
2.5 μL single, ocular dose: 2.5 μL route of administration: Ocular experiment type: SINGLE co-administered: |
NATAMYCIN plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
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JECFA EVALUATION |
INS-235
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NDF-RT |
N0000007672
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WHO-VATC |
QG01AA02
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QD01AA02
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EPA PESTICIDE CODE |
51102
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WHO-VATC |
QA01AB10
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WHO-ATC |
A01AB10
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WHO-ATC |
S01AA10
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WHO-VATC |
QA07AA03
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NDF-RT |
N0000175936
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WHO-VATC |
QS01AA10
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WHO-ATC |
A07AA03
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CODEX ALIMENTARIUS (GSFA) |
INS-235
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CFR |
21 CFR 172.155
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WHO-ATC |
D01AA02
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NCI_THESAURUS |
C514
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WHO-ATC |
G01AA02
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M7779
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578
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INS-235
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7268
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natamycin
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CHEMBL1200656
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DB00826
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DTXSID6021163
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NATAMYCIN
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759167
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5284447
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C47634
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231-683-5
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ACTIVE MOIETY