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

Details

Stereochemistry ABSOLUTE
Molecular Formula C33H47NO13
Molecular Weight 665.7265
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NATAMYCIN

SMILES

C[C@]1([H])C/C(/[H])=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\[H])/[C@@]([H])(C[C@@]2([H])[C@@]([H])([C@]([H])(C[C@](C[C@]([H])(C[C@]3([H])[C@@]([H])(/C(/[H])=C(\[H])/C(=O)O1)O3)O)(O)O2)O)C(=O)O)O[C@@]4([H])[C@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C)O4)O)N)O

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

HIDE SMILES / InChI

Description
Curator's Comment:: 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

329702400000
Curative
NATACYN

Approved Use

Natamycin

Launch Date

329702400000
Curative
NATACYN

Approved Use

Natamycin

Launch Date

329702400000
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​
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
Name Type Language
NATAMYCIN
FCC   INCI   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INCI   INN   USAN  
Official Name English
NATAMYCIN [USP MONOGRAPH]
Common Name English
PIMARICIN [JAN]
Common Name English
NATAMYCIN [MI]
Common Name English
PIMAFUCIN
Brand Name English
PIMARICIN
Common Name English
CL 12,625
Code English
NATACYN
Brand Name English
NATAMYCIN [INCI]
Common Name English
INS-235
Code English
NATAMYCIN [USP-RS]
Common Name English
MYCOPHYT
Brand Name English
NATAMYCIN [INN]
Common Name English
E-235
Code English
PIMARACIN
Common Name English
DELVOCID
Brand Name English
NATAMYCIN [USAN]
Common Name English
NSC-759167
Code English
MYPROZINE
Brand Name English
ANTIBIOTIC A-5283
Code English
NATAMYCIN [MART.]
Common Name English
NATAMYCIN [FCC]
Common Name English
INS NO.235
Code English
CL-12625
Code English
SYNOGIL
Brand Name English
TENNECETIN
Common Name English
NATAMYCIN [WHO-DD]
Common Name English
NATAMYCIN [VANDF]
Common Name English
NATAMYCIN [ORANGE BOOK]
Common Name English
6,11,28-TRIOXATRICYCLO(22.3.1.05,7)OCTACOSA-8,14,16,18,20-PENTAENE-25-CARBOXYLIC ACID, 22-((3-AMINO-3,6-DIDEOXY-.BETA.-D-MANNOPYRANOSYL)OXY)-1,3,26-TRIHYDROXY-12-METHYL-10-OXO-, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-
Systematic Name English
Classification Tree Code System Code
JECFA EVALUATION INS-235
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
NDF-RT N0000007672
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
WHO-VATC QG01AA02
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
WHO-VATC QD01AA02
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
EPA PESTICIDE CODE 51102
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
WHO-VATC QA01AB10
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
WHO-ATC A01AB10
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
WHO-ATC S01AA10
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
WHO-VATC QA07AA03
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
NDF-RT N0000175936
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
WHO-VATC QS01AA10
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
WHO-ATC A07AA03
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
CODEX ALIMENTARIUS (GSFA) INS-235
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
CFR 21 CFR 172.155
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
WHO-ATC D01AA02
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
NCI_THESAURUS C514
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
WHO-ATC G01AA02
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
Code System Code Type Description
MERCK INDEX
M7779
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY Merck Index
FDA UNII
8O0C852CPO
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
JECFA MONOGRAPH
INS-235
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
RXCUI
7268
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
1885
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
EVMPD
SUB09169MIG
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200656
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
DRUG BANK
DB00826
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
EPA CompTox
7681-93-8
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
WIKIPEDIA
NATAMYCIN
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
MESH
D010866
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
CAS
7681-93-8
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
PUBCHEM
5284447
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
NCI_THESAURUS
C47634
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
INN
868
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY
USP_CATALOG
1457505
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
231-683-5
Created by admin on Fri Jun 25 21:04:09 UTC 2021 , Edited by admin on Fri Jun 25 21:04:09 UTC 2021
PRIMARY