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Substance Name: Zinostatin [USAN:INN]
RN: 9014-02-2
UNII: PP082U6W1L
InChIKey: BLXZMHNVKCEIJX-LTZUVELHSA-N

Notes

  • An enediyne that alkylates DNA and RNA like MITOMYCIN does, so it is cytotoxic.
  • An enediyne that alkylates DNA and RNA like MITOMYCIN does, so it is cytotoxic.

    NCI: An enediyne antineoplastic antibiotic hybrid containing an aminoglycoside chromophore. Zinostatin is isolated from the bacterium Streptomyces carzinostaticus. The aminoglycoside component of zinostatin intercalates into DNA and the benzene diradical intermediate of the enediyne core binds to the minor groove of DNA, resulting in single- and double-strand breaks in DNA and apoptosis. (NCI Thesaurus)

Molecular Formula

  • Unspecified

Molecular Weight

  • 661.6565
 

Classification Codes

  • Antibiotics, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Cytotoxins
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Noxae
  • Nucleic Acid Synthesis Inhibitors
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Zinostatin
  • Zinostatin [USAN:INN]

MeSH Heading

  • Zinostatin

Synonyms

  • A 8544527G1
  • CCRIS 1177
  • Holoneocarzinostatin
  • NCS
  • Neocarcinostatin
  • Neocarzinostatin K
  • NSC 157365
  • NSC 69856
  • UNII-PP082U6W1L
  • Vinostatin
  • Zinostatin
  • Zinostatine
  • Zinostatine [INN-French]
  • Zinostatino
  • Zinostatino [INN-Spanish]
  • Zinostatinum
  • Zinostatinum [INN-Latin]

Systematic Name

  • Neocarzinostatin

Registry Numbers

CAS Registry Number

  • 9014-02-2

FDA UNII

  • PP082U6W1L

Other Registry Numbers

  • 11034-99-4
  • 56833-48-8

System Generated Number

  • 0009014022

Structure Descriptors

InChI

1S/C35H35NO12/c1-16-12-19(42-4)14-22-20(16)8-9-23(37)27(22)32(40)45-24-13-18-10-11-35(26-15-43-34(41)46-26)25(48-35)7-5-6-21(18)31(24)47-33-28(36-3)30(39)29(38)17(2)44-33/h8-9,12-14,17,21,24-26,28-31,33,36-39H,6,15H2,1-4H3/t17-,21?,24-,25?,26?,28-,29+,30-,31-,33-,35+/m1/s1

InChIKey

BLXZMHNVKCEIJX-LTZUVELHSA-N

Smiles

Cc1cc(cc2c1ccc(c2C(=O)O[C@@H]3C=C4C#C[C@]5(C(O5)C#CCC4[C@H]3O[C@@H]6[C@@H]([C@H]([C@H]([C@H](O6)C)O)O)NC)C7COC(=O)O7)O)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intraperitoneal 1mg/kg (1mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING
Kiso to Rinsho. Clinical Report. Vol. 10, Pg. 610, 1976.
dog LDLo intravenous 200ug/kg (0.2mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 10, Pg. 610, 1976.
dog LDLo intravenous 200ug/kg (0.2mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Kiso to Rinsho. Clinical Report. Vol. 10, Pg. 610, 1976.
mouse LD50 intraperitoneal 1720ug/kg (1.72mg/kg) BLOOD: CHANGES IN SPLEEN

GASTROINTESTINAL: ALTERATION IN GASTRIC SECRETION
Journal of Antibiotics. Vol. 31, Pg. 468, 1978.
mouse LD50 intravenous 960ug/kg (0.96mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Journal of Antibiotics. Vol. 28, Pg. 64, 1975.
mouse LD50 oral 1050mg/kg (1050mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Journal of Antibiotics. Vol. 28, Pg. 64, 1975.
mouse LD50 subcutaneous 7200ug/kg (7.2mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 309, 1976.
rabbit LD50 intravenous 900ug/kg (0.9mg/kg)   Journal of Antibiotics. Vol. 28, Pg. 64, 1975.
rabbit LD50 oral > 600mg/kg (600mg/kg)   Journal of Antibiotics. Vol. 28, Pg. 64, 1975.
rat LD50 intraperitoneal 940ug/kg (0.94mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

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

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 309, 1976.
rat LD50 intravenous 830ug/kg (0.83mg/kg)   Journal of Antibiotics. Vol. 28, Pg. 64, 1975.
rat LD50 subcutaneous 4980ug/kg (4.98mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

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

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 309, 1976.
rat LDLo oral 300mg/kg (300mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 309, 1976.