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Substance Name: Daunorubicin [INN:BAN]
RN: 20830-81-3
UNII: ZS7284E0ZP
InChIKey: STQGQHZAVUOBTE-VGBVRHCVSA-N

Note

  • A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.

Molecular Formula

  • C27-H29-N-O10

Molecular Weight

  • 527.5231
 

Classification Codes

Classification Codes

  • Antibiotics, Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Natural Product
  • Reproductive Effect
  • Topoisomerase II Inhibitors
  • Topoisomerase Inhibitors
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 2B
  • Reportable Quantity (RQ) = 10 lb

Names and Synonyms

Name of Substance

  • Daunorubicin
  • Daunorubicin [INN:BAN]

MeSH Heading

  • Daunorubicin

Synonyms

  • (+)-Daunomycin
  • (8S-cis)-8-Acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione
  • Acetyladriamycin
  • AI3-52942
  • BRN 1445583
  • CCRIS 914
  • Cerubidin
  • Daunamycin
  • Daunarubicinum
  • Daunomycin
  • Daunorrubicina
  • Daunorubicin
  • Daunorubicine
  • Daunorubicinum
  • Daunorubicinum [INN-Latin]
  • Daunoxome
  • EINECS 244-069-7
  • FI6339
  • HSDB 5095
  • Leukaemomycin C
  • NCI-C04693
  • NSC 82151
  • NSC 83142
  • RP 13057
  • Rubidomycin
  • Rubomycin C
  • UNII-ZS7284E0ZP

Systematic Names

  • 5,12-Naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-
  • Daunomycin
  • Daunorubicin

Superlist Names

  • 5,12-Naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S-cis)-
  • Daunomycin
  • RCRA waste no. U059

Registry Numbers

CAS Registry Number

  • 20830-81-3

FDA UNII

  • ZS7284E0ZP

Other Registry Numbers

  • 11006-54-5
  • 11048-29-6
  • 1407-15-4
  • 149541-57-1
  • 182250-71-1
  • 23942-76-9
  • 27576-81-4
  • 28020-80-6

System Generated Number

  • 0020830813

Structure Descriptors

InChI

1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1

InChIKey

STQGQHZAVUOBTE-VGBVRHCVSA-N

Smiles

COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 10mg/kg/30D-I (10mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION British Journal of Clinical Practice. Vol. 44, Pg. 633, 1990.
dog LD50 intravenous 4mg/kg (4mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 948, 1967.
guinea pig LD50 intravenous 6mg/kg (6mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 948, 1967.
hamster LDLo intravenous 50mg/kg (50mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 15, Pg. 1614, 1973.
human LDLo oral 6mg/kg (6mg/kg) CARDIAC: OTHER CHANGES "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 521, 1969.
mouse LD50 intraperitoneal 2500ug/kg (2.5mg/kg) GASTROINTESTINAL: OTHER CHANGES National Cancer Institute Report. Vol. -, Pg. 304, 1967.
mouse LD50 intravenous 8600ug/kg (8.6mg/kg)   Cancer Research. Vol. 49, Pg. 4098, 1989.
mouse LD50 oral 205mg/kg (205mg/kg)   Yakkyoku. Pharmacy. Vol. 25, Pg. 573, 1974.
mouse LD50 unreported 24900ug/kg (24.9mg/kg)   Biochemical Pharmacology. Vol. 38, Pg. 167, 1989.
rabbit LD50 intravenous 5mg/kg (5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 948, 1967.
rat LD50 intraperitoneal 20mg/kg (20mg/kg)   Advances in Teratology. Vol. 3, Pg. 181, 1968.
rat LD50 intravenous 13mg/kg (13mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BLOOD: OTHER CHANGES
National Cancer Institute Report. Vol. -, Pg. 304, 1967.
rat LD50 oral 336mg/kg (336mg/kg)   Yakkyoku. Pharmacy. Vol. 25, Pg. 573, 1974.
rat LD50 subcutaneous 33200ug/kg (33.2mg/kg)   Yakkyoku. Pharmacy. Vol. 25, Pg. 573, 1974.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 208-209 deg C   EXP
log P (octanol-water) 1.83 (none)   EXP
Water Solubility 39.2 mg/L 25 EST
Vapor Pressure 3.46E-22 mm Hg 25 EST
Henry's Law Constant 1.43E-25 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.42E-10 cm3/molecule-sec 25 EST

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