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Substance Name: Natamycin [USAN:USP:INN:BAN]
RN: 7681-93-8
UNII: 8O0C852CPO
InChIKey: NCXMLFZGDNKEPB-FFPOYIOWSA-N

Note

  • Amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically.

Molecular Formula

  • C33-H47-N-O13

Molecular Weight

  • 665.7283
 

Classification Codes

  • Agricultural Chemical
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Anti-Infective Agents, Local
  • Antibacterial (Ophthalmic)
  • Antifungal Agents
  • Drug / Therapeutic Agent
  • Fungicide, Bactericide, Wood Preservative
  • Mutation Data
  • Natural Product
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Names and Synonyms

Name of Substance

  • Natamycin
  • Natamycin [USAN:USP:INN:BAN]

MeSH Heading

  • Natamycin

Synonyms

  • 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
  • Antibiotic A-5283
  • CL 12,625
  • CL 12625
  • Delvocid
  • Delvolan
  • Delvopos
  • EINECS 231-683-5
  • Mycophyt
  • Myprozine
  • Natacyn
  • Natafucin
  • Natamicina
  • Natamicina [INN-Spanish]
  • Natamycin
  • Natamycine
  • Natamycine [INN-French]
  • Natamycinum
  • Natamycinum [INN-Latin]
  • Pimafucin
  • Pimaricine
  • Pimarizin
  • Pimarizin [German]
  • 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
  • Synogil
  • Tennecetin
  • UNII-8O0C852CPO

Systematic Names

  • Natamycin
  • Pimaricin

Superlist Name

  • Natamycin

Registry Numbers

CAS Registry Number

  • 7681-93-8

FDA UNII

  • 8O0C852CPO

System Generated Number

  • 0007681938

Structure Descriptors

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

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intramuscular 90mg/kg (90mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
cat LD50 intraperitoneal 75mg/kg (75mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
cat LD50 oral > 300mg/kg (300mg/kg)   Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
dog LD50 intravenous 18mg/kg (18mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
dog LD50 oral > 300mg/kg (300mg/kg)   Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
guinea pig LD50 intramuscular 130mg/kg (130mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
guinea pig LD50 intraperitoneal 90mg/kg (90mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
guinea pig LD50 oral 450mg/kg (450mg/kg)   Antibiotics Annual. Vol. 5, Pg. 878, 1957/1958.
guinea pig LD50 subcutaneous 160mg/kg (160mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
mammal (species unspecified) LD30 intravenous 500mg/kg (500mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 954, 1978.
mouse LD50 intraperitoneal 40mg/kg (40mg/kg)   Quarterly Journal of Crude Drug Research. Vol. 8, Pg. 1274, 1968.
mouse LD50 intravenous > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 1461, 1985.
mouse LD50 oral 1500mg/kg (1500mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 517, 1967.
mouse LD50 subcutaneous 180mg/kg (180mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 639, 1967.
rabbit LD50 intramuscular 120mg/kg (120mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
rabbit LD50 intraperitoneal 68mg/kg (68mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
rabbit LD50 intravenous 20mg/kg (20mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
rabbit LD50 oral 1420mg/kg (1420mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Toxicology and Applied Pharmacology. Vol. 8, Pg. 97, 1966.
rabbit LD50 subcutaneous 180mg/kg (180mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
rat LD50 intramuscular 128mg/kg (128mg/kg) BEHAVIORAL: TOLERANCE Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
rat LD50 intraperitoneal 85mg/kg (85mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
rat LD50 intravenous 36mg/kg (36mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.
rat LD50 oral 2730mg/kg (2730mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 97, 1966.
rat LD50 subcutaneous 190mg/kg (190mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Antibiotics and Chemotherapy Vol. 9, Pg. 406, 1959.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 290 dec deg C   EXP
log P (octanol-water) -3.670 (none)   EST
Water Solubility 4100 mg/L 21 EXP
Atmospheric OH Rate Constant 4.18E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.