Details of the Drug

General Information of Drug (ID: DMFEHXD)

Drug Name
Natamycin
Synonyms
Delvocid; Delvolan; Delvopos; Mycophyt; Myprozine; Natacyn; Natafucin; Natamicina; Natamycine; Natamycinum; Pimafucin; Pimaricin; Pimaricine; Pimarizin; Synogil; Tennecetin; Natamycin preparation; Pimaricin preparation; Pimarizin [German]; CL 12625; Antibiotic A-5283; CL 12,625; CL-12625; Natacyn (TN); Natamicina [INN-Spanish]; Natamycine [INN-French]; Natamycinum [INN-Latin]; Pimaricin (JP15); Natamycin (USP/INN); Natamycin [USAN:INN:BAN]; Stereoisomer of 22-((3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo(22.3.1.0(sup 5,7))octacosa-8,14,16,18,20-pentaene-25-carboxylic acid; (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0~5,7~]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid; 16-(3-Amino-3,6-didesoxy-beta-D-mannopyranosyloxy)-5,6-epoxy-8,12,14-trihydroxy-26-methyl-2,10-dioxo-1-oxacyclohexacosa-3,17,19,21,23-pentaen-13-carbonsaeure; 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,14
Indication
Disease Entry ICD 11 Status REF
Conjunctivitis 9A60 Approved [1], [2]
Therapeutic Class
Antifungal Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 665.7
Topological Polar Surface Area (xlogp) -1.3
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 7
Hydrogen Bond Acceptor Count (hbondacc) 14
Chemical Identifiers
Formula
C33H47NO13
IUPAC Name
(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
Canonical SMILES
C[C@@H]1C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@@H]3[C@H](O3)/C=C/C(=O)O1)O)O)O)C(=O)O)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)O)N)O
InChI
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
InChIKey
NCXMLFZGDNKEPB-FFPOYIOWSA-N
Cross-matching ID
PubChem CID
5284447
CAS Number
7681-93-8
DrugBank ID
DB00826
TTD ID
D02FEM
ACDINA ID
D01274

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Fungal Cell membrane (Fung CM) TTAH0B3 NOUNIPROTAC Binder [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Hydrochloric acid E00015 313 Acidulant
Benzalkonium chloride E00536 21988052 Antimicrobial preservative; Penetration agent; Solubilizing agent; Surfactant
Sodium hydroxide E00234 14798 Alkalizing agent
Water E00035 962 Solvent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Natamycin 5% suspension 5% Suspension Ophthalmic
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 050514.
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 Natamycin blocks fungal growth by binding specifically to ergosterol without permeabilizing the membrane. J Biol Chem. 2008 Mar 7;283(10):6393-401.
4 Haloprogin: mode of action studies in Candida albicans. Can J Microbiol. 1974 Sep;20(9):1241-5.