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Substance Name: Anisomycin
RN: 22862-76-6
UNII: 6C74YM2NGI
InChIKey: YKJYKKNCCRKFSL-RDBSUJKOSA-N

Note

  • An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.

Molecular Formula

  • C14-H19-N-O4

Molecular Weight

  • 265.3071
 

Classification Codes

  • Agricultural Chemical
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Fungicide, Bactericide, Wood Preservative
  • Natural Product
  • Nucleic Acid Synthesis Inhibitors
  • Protein Synthesis Inhibitors
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Names and Synonyms

Name of Substance

  • Anisomycin

MeSH Heading

  • Anisomycin

Synonyms

  • (-)-Anisomycin
  • (2R,3S,4S)-2-((4-Methoxyphenyl)methyl)-3,4-pyrrolidinediol 3-acetate
  • (2R,3S,4S)-2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate
  • (2R,3S,4S)-2-(p-Methoxyphenylmethyl)-3-acetoxy-4-hydroxypyrrolidine
  • 2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate
  • 2-p-Methoxyphenylmethyl-3-acetoxy-4-hydroxypyrrolidine
  • 3,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, 3-acetate, (2R,3S,4S)-
  • 3,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, 3-acetate, (2R-(2-alpha,3-alpha,4-beta))-
  • 3,4-Pyrrolidinediol, 2-(p-methoxybenzyl)-, 3-acetate, (2S,3R,4R)-
  • 5-21-05-00523 (Beilstein Handbook Reference)
  • AI3-50846
  • Antibiotic PA-106
  • BRN 0020705
  • EINECS 245-269-7
  • Flagecidin
  • NSC 147340
  • NSC 76712
  • NSC-76712
  • UNII-6C74YM2NGI
  • Upjohn 204t3

Systematic Names

  • 1,4,5-Trideoxy-1,4-imino-5-(p-methoxyphenyl)-D-xylo-pentitol 3-acetate
  • 3,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, 3-acetate, (2R-(2alpha,3alpha,4beta))-
  • 3,4-Pyrrolidinediol, 2-(p-methoxybenzyl)-, 3-acetate, (2S,3R,4R)- (8CI)
  • Anisomycin

Registry Numbers

CAS Registry Number

  • 22862-76-6

FDA UNII

  • 6C74YM2NGI

Other Registry Numbers

  • 11023-48-6
  • 2322-08-9

System Generated Number

  • 0022862766

Structure Descriptors

InChI

1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m1/s1

InChIKey

YKJYKKNCCRKFSL-RDBSUJKOSA-N

Smiles

[C@H]1([C@@H]([C@H](CN1)O)OC(=O)C)Cc1ccc(cc1)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD oral > 200mg/kg (200mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
dog LD intramuscular > 100mg/kg (100mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
dog LD intravenous > 100mg/kg (100mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
dog LD oral > 300mg/kg (300mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
guinea pig LDLo oral 300mg/kg (300mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
monkey LD intramuscular > 50mg/kg (50mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
monkey LD oral > 300mg/kg (300mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
monkey LDLo intravenous 200mg/kg (200mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
mouse LD50 intraperitoneal 400mg/kg (400mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
mouse LD50 intravenous 10mg/kg (10mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 77, 1981.
mouse LD50 oral 148mg/kg (148mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
mouse LD50 subcutaneous 600mg/kg (600mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rabbit LD oral > 200mg/kg (200mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat LD50 intraperitoneal 345mg/kg (345mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat LD50 intravenous 167mg/kg (167mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat LD50 oral 72mg/kg (72mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat LD50 subcutaneous 230mg/kg (230mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 140.5 deg C   EXP
log P (octanol-water) 0.610 (none)   EST
Water Solubility 6550 mg/L 28 EXP
Atmospheric OH Rate Constant 1.25E-10 cm3/molecule-sec 25 EST

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