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Substance Name: Carboquone [INN:JAN]
RN: 24279-91-2
UNII: 1CB0HBT12C
InChIKey: SHHKQEUPHAENFK-UHFFFAOYSA-N

Note

  • An alkylating agent structurally similar to MITOMYCIN and found to be effective in the treatment of leukemia and various other neoplasms in mice. It causes leukemia and thrombocytopenia in almost all human patients.

Molecular Formula

  • C15-H19-N3-O5

Molecular Weight

  • 321.3311
 

Classification Codes

  • Alkylating Agents
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Drug / Therapeutic Agent
  • Mutation Data
  • Noxae
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Names and Synonyms

Name of Substance

  • Carbazilquinone
  • Carboquone [INN:JAN]

MeSH Heading

  • Carbazilquinone

Synonyms

  • 2,5-Bis(1-aziridinyl)-3-(2-carbamoyloxy-1-methoxyethyl)-6-methyl-1,4-benzoquinone
  • 2,5-Bis(1-aziridinyl)-3-(2-hydroxy-1-methoxyethyl)-6-methyl-p-benzoquinone carbamate (ester)
  • 2-(2-((Aminocarbonyl)oxy)-1-methoxyethyl)-3,6-bis(1-aziridinyl)-5-methyl-2,5-cyclohexadiene-1,4-dione
  • 5-20-01-00076 (Beilstein Handbook Reference)
  • BRN 1400765
  • Carbazilequinone
  • Carbaziloquinone
  • Carbazilquinone
  • Carboquona
  • Carboquona [INN-Spanish]
  • Carboquone
  • Carboquonum
  • Carboquonum [INN-Latin]
  • CCRIS 2748
  • CS 310
  • Esquinon
  • NSC 134679
  • UNII-1CB0HBT12C

Systematic Names

  • 2,5-Bis(1-aziridinyl)-3-(2-hydroxy-1-methoxyethyl)-6-methyl-p-benzoquinone carbamate (ester)
  • 2,5-Cyclohexadiene-1,4-dione, 2-(2-((aminocarbonyl)oxy)-1-methoxyethyl)-3,6-bis(1-aziridinyl)-5-methyl-
  • Carbazilquinone
  • p-Benzoquinone, 2,5-bis(1-aziridinyl)-3-(2-hydroxy-1-methoxyethyl)-6-methyl-, carbamate (ester)

Registry Numbers

CAS Registry Number

  • 24279-91-2

FDA UNII

  • 1CB0HBT12C

System Generated Number

  • 0024279912

Structure Descriptors

InChI

1S/C15H19N3O5/c1-8-11(17-3-4-17)14(20)10(9(22-2)7-23-15(16)21)12(13(8)19)18-5-6-18/h9H,3-7H2,1-2H3,(H2,16,21)

InChIKey

SHHKQEUPHAENFK-UHFFFAOYSA-N

Smiles

C1(=C(C(C(N2CC2)=C(C1=O)C)=O)[C@@H](COC(N)=O)OC)N1CC1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 3440ug/kg (3.44mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 501, 1974.
mouse LD50 intraperitoneal 3440ug/kg (3.44mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 501, 1974.
mouse LD50 intravenous 5430ug/kg (5.43mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 501, 1974.
mouse LD50 oral 28600ug/kg (28.6mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 501, 1974.
mouse LD50 subcutaneous 4900ug/kg (4.9mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 501, 1974.
rat LD50 intraperitoneal 3070mg/kg (3070mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 501, 1974.
rat LD50 intravenous 3620ug/kg (3.62mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 501, 1974.
rat LD50 intravenous 3620ug/kg (3.62mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 501, 1974.
rat LD50 oral 27300ug/kg (27.3mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 501, 1974.
rat LD50 subcutaneous 3990ug/kg (3.99mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 501, 1974.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 202 dec deg C   EXP
log P (octanol-water) -0.15 (none)   EXP
Water Solubility 6160 mg/L 25 EST
Vapor Pressure 9.86E-09 mm Hg 25 EST
Henry's Law Constant 2.08E-21 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.28E-11 cm3/molecule-sec 25 EST

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