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Substance Name: Phleomycin
RN: 11006-33-0
InChIKey: QRBLKGHRWFGINE-UGWAGOLRSA-N

Note

  • Water-soluble, copper-containing low molecular weight polypeptides obtained from the culture medium of Streptomyces verticillus. They are specific inhibitors of DNA synthesis in bacteria and have been found to act as antitumor agents. They have also been used against rust fungi of plants.

Molecular Formula

  • C13-H28-N3-O12

Molecular Weight

  • 1326.38
 

Classification Codes

  • Agricultural Chemical
  • Antibiotics, Antineoplastic
  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Germicide, Bactericide, Disinfectant
  • Mutation Data
  • Natural Product
  • Nucleic Acid Synthesis Inhibitors
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Names and Synonyms

MeSH Heading

  • Phleomycins

Synonyms

  • NSC 61586
  • NSC 616586
  • Phleomycin
  • Phleomycin complex
  • RTECS SY1148000

Systematic Name

  • Phleomycin

Registry Numbers

CAS Registry Number

  • 11006-33-0

System Generated Number

  • 0011006330

Structure Descriptors

InChI

1S/C51H75N17O21S2/c1-16-29(65-41(68-38(16)54)21(8-27(53)72)60-9-20(52)39(55)78)44(82)67-31(34(22-10-58-15-61-22)88-49-50(5,36(76)33(74)25(11-69)87-49)89-47-37(77)51(85,48(57)84)35(75)26(12-70)86-47)45(83)62-18(3)32(73)17(2)42(80)66-30(19(4)71)43(81)59-7-6-28-63-24(14-90-28)46-64-23(13-91-46)40(56)79/h10,13,15,17-18,20-21,24-26,30-37,47,49,60,69-70,73-77,85H,6-9,11-12,14,52H2,1-5H3,(H2,53,72)(H2,55,78)(H2,56,79)(H2,57,84)(H,58,61)(H,59,81)(H,62,83)(H,66,80)(H,67,82)(H2,54,65,68)/t17?,18?,20?,21?,24?,25-,26?,30?,31?,32?,33+,34?,35-,36-,37-,47-,49-,50-,51+/m0/s1

InChIKey

QRBLKGHRWFGINE-UGWAGOLRSA-N

Smiles

O([C@]1([C@H]([C@@H]([C@H](CO)O[C@H]1O[C@@H]([C@@H](C(N[C@@H]([C@@H]([C@@H](C(N[C@@H](C(=O)NCCC1=N[C@@H](c2nc(C(=O)N)cs2)CS1)C(=O)C)=O)C)O)C)=O)NC(c1nc([C@@H](CC(=O)N)NC[C@@H](C(=O)N)N)nc(c1C)N)=O)c1nc[nH]c1)O)O)C)[C@H]1[C@H](O)[C@](C(=O)N)(O)[C@H]([C@@H](O1)CO)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 2500ug/kg (2.5mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 14, Pg. 590, 1969.
guinea pig LDLo intravenous 13mg/kg (13mg/kg)   Journal of Antibiotics, Series A. Vol. 19, Pg. 260, 1966.
mouse LD50 intraperitoneal 13mg/kg (13mg/kg)   Journal of Antibiotics, Series A. Vol. 19, Pg. 260, 1966.
mouse LD50 intravenous 21mg/kg (21mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Toxicology and Applied Pharmacology. Vol. 14, Pg. 590, 1969.
mouse LD50 oral 371mg/kg (371mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 14, Pg. 590, 1969.
mouse LD50 subcutaneous 25mg/kg (25mg/kg)   Journal of Antibiotics, Series A. Vol. 19, Pg. 260, 1966.
rat LD50 intravenous 4mg/kg (4mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Toxicology and Applied Pharmacology. Vol. 14, Pg. 590, 1969.
rat LD50 oral 649mg/kg (649mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 14, Pg. 590, 1969.