U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C33H46NO13.Na
Molecular Weight 687.707
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NATAMYCIN SODIUM

SMILES

[Na+].[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=CBRIFMNOKRNQEF-KTYYKLRQSA-M
InChI=1S/C33H47NO13.Na/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);/q;+1/p-1/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

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C33H46NO13
Molecular Weight 664.7172
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 14 / 14
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Originator

Curator's Comment: Natamycin was discovered in DSM laboratories in 1955

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2364028
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
NATACYN

Approved Use

NATACYN® (natamycin ophthalmic suspension) 5% is a sterile, antifungal drug for topical ophthalmic administration.

Launch Date

3.29702408E11
Curative
NATACYN

Approved Use

Natamycin

Launch Date

3.29702408E11
Curative
NATACYN

Approved Use

Natamycin

Launch Date

3.29702408E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
2.72 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2.78 h
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
Predictive genomic biomarkers for drug-induced nephrotoxicity in mice.
2012
Patents

Sample Use Guides

one drop of (natamycin ophthalmic suspension) 5% instilled in the conjunctival sac at hourly or two-hourly intervals. The frequency of application can usually be reduced to one drop 6 to 8 times daily after the first 3 to 4 days
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:38:22 UTC 2023
Edited
by admin
on Sat Dec 16 11:38:22 UTC 2023
Record UNII
E97SA84U57
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NATAMYCIN SODIUM
Common Name English
SODIUM PIMARICIN
Common Name English
Code System Code Type Description
PUBCHEM
137331870
Created by admin on Sat Dec 16 11:38:22 UTC 2023 , Edited by admin on Sat Dec 16 11:38:22 UTC 2023
PRIMARY
CAS
31634-95-4
Created by admin on Sat Dec 16 11:38:22 UTC 2023 , Edited by admin on Sat Dec 16 11:38:22 UTC 2023
PRIMARY
FDA UNII
E97SA84U57
Created by admin on Sat Dec 16 11:38:22 UTC 2023 , Edited by admin on Sat Dec 16 11:38:22 UTC 2023
PRIMARY