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]
Fungal keratitis	N.A.	Approved	[2]

• Therapeutic Class: Antifungal Agents
• Affected Organisms: Various Fungus Species
• ATC Code:
  A01AB10: Natamycin
  A01AB: Antiinfectives and antiseptics for local oral treatment
  A01A: STOMATOLOGICAL PREPARATIONS
  A01: STOMATOLOGICAL PREPARATIONS
  A: ALIMENTARY TRACT AND METABOLISM
  A07AA03: Natamycin
  A07AA: Antibiotics
  A07A: INTESTINAL ANTIINFECTIVES
  A07: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
  A: ALIMENTARY TRACT AND METABOLISM
  D01AA02: Natamycin
  D01AA: Antibiotics
  D01A: ANTIFUNGALS FOR TOPICAL USE
  D01: ANTIFUNGALS FOR DERMATOLOGICAL USE
  D: DERMATOLOGICALS
  G01AA02: Natamycin
  G01AA: Antibiotics
  G01A: ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
  G01: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
  G: GENITO URINARY SYSTEM AND SEX HORMONES
  S01AA10: Natamycin
  S01AA: Antibiotics
  S01A: ANTIINFECTIVES
  S01: OPHTHALMOLOGICALS
  S: SENSORY ORGANS
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 3:
  Molecular Weight (mw); 665.7
  Logarithm of the Partition Coefficient (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
  UNII: 8O0C852CPO
  DrugBank ID: DB00826
  TTD ID: D02FEM
  ACDINA ID: D01274
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

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]

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] Natamycin FDA Label
• [3] Natamycin blocks fungal growth by binding specifically to ergosterol without permeabilizing the membrane. J Biol Chem. 2008 Mar 7;283(10):6393-401.