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Substance Name: Carminomycin
RN: 39472-31-6
InChIKey: XREUEWVEMYWFFA-CSKJXFQVSA-N

Note

  • A very toxic anthracycline-type antineoplastic related to DAUNORUBICIN, obtained from Actinomadura carminata.

Molecular Weight

  • 513.4963
 

Classification Codes

  • Antibiotics, Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Natural Product
  • Reproductive Effect
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Names and Synonyms

MeSH Heading

  • Carubicin

Synonyms

  • Carminomycin
  • CCRIS 961
  • O-Demethyldaunomycin

Systematic Names

  • Carminomycin
  • Karminomycin

Registry Numbers

CAS Registry Number

  • 39472-31-6

Related Registry Number

  • 52794-97-5 (hydrochloride)

System Generated Number

  • 0039472316

Structure Descriptors

InChI

1S/C26H27NO10/c1-9-21(30)13(27)6-16(36-9)37-15-8-26(35,10(2)28)7-12-18(15)25(34)20-19(23(12)32)22(31)11-4-3-5-14(29)17(11)24(20)33/h3-5,9,13,15-16,21,29-30,32,34-35H,6-8,27H2,1-2H3/t9-,13-,15-,16-,21+,26-/m0/s1

InChIKey

XREUEWVEMYWFFA-CSKJXFQVSA-N

Smiles

C[C@@H]1O[C@H](C[C@H](N)[C@@H]1O)O[C@H]2C[C@@](O)(Cc3c(O)c4C(=O)c5cccc(O)c5C(=O)c4c(O)c23)C(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 2700ug/kg (2.7mg/kg)   Cancer Treatment Reports. Vol. 63, Pg. 899, 1979.
dog LDLo intravenous 600ug/kg (0.6mg/kg)   Cancer Treatment Reports. Vol. 63, Pg. 899, 1979.
human TDLo intravenous 12mg/kg/5D (12mg/kg) BLOOD: LEUKOPENIA

BEHAVIORAL: ANOREXIA (HUMAN

GASTROINTESTINAL: NAUSEA OR VOMITING
Cancer Treatment Reports. Vol. 61, Pg. 1705, 1977.
mammal (species unspecified) LD50 intraperitoneal 1300ug/kg (1.3mg/kg)   Antibiotiki. Vol. 29, Pg. 748, 1984.
man TDLo intravenous 1071ug/kg/17D (1.071mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

VASCULAR: THROMBOSIS DISTANT FROM INJECTION SITE
Voprosy Onkologii. Problems of Oncology. For English translation, see PONCAU. Vol. 25(2), Pg. 63, 1979.
monkey LD50 oral 288mg/kg (288mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Drug and Chemical Toxicology. Vol. 4, Pg. 383, 1981.
mouse LD50 intraperitoneal 960ug/kg (0.96mg/kg)   Antibiotiki. Vol. 29, Pg. 437, 1984.
mouse LD50 intravenous 3200ug/kg (3.2mg/kg)   Antibiotiki. Vol. 23, Pg. 1005, 1978.
mouse LD50 oral 7300ug/kg (7.3mg/kg)   Cancer Treatment Reports. Vol. 61, Pg. 1705, 1977.
mouse LD50 subcutaneous 2500ug/kg (2.5mg/kg)   Antibiotiki. Vol. 21, Pg. 1030, 1976.
rat LD50 intraperitoneal 1550ug/kg (1.55mg/kg) ENDOCRINE: OTHER CHANGES

LIVER: FATTY LIVER DEGERATION

LIVER: LIVER FUNCTION TESTS IMPAIRED
Antibiotiki. Vol. 24, Pg. 218, 1979.
rat LD50 intravenous 1600ug/kg (1.6mg/kg)   Antibiotiki. Vol. 23, Pg. 1005, 1978.
rat LD50 oral 23mg/kg (23mg/kg)   Antibiotiki. Vol. 21, Pg. 904, 1976.
rat LD50 subcutaneous 4366ug/kg (4.366mg/kg)   Drug and Chemical Toxicology. Vol. 4, Pg. 383, 1981.