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Substance Name: Doxorubicin [USAN:INN:BAN]
RN: 23214-92-8
UNII: 80168379AG
InChIKey: AOJJSUZBOXZQNB-TZSSRYMLSA-N

Note

  • Antineoplastic antibiotic obtained from Streptomyces peucetius. It is a hydroxy derivative of DAUNORUBICIN.

Molecular Formula

  • C27-H29-N-O11

Molecular Weight

  • 543.5221
 

Classification Codes

Classification Codes

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

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 2A
  • Reasonably Anticipated to be a Carcinogen

Names and Synonyms

Name of Substance

  • Doxorubicin
  • Doxorubicin [USAN:INN:BAN]

MeSH Heading

  • Doxorubicin

Synonyms

  • (1S,3S)-3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl-(3-amino-2,3,6-tridesoxy-alpha-L-lyxo-hexopyranosid)
  • (8S,10S)-10-((3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
  • 1,2,3,4,6,11-Hexahydro-4beta,5,12-trihydroxy-4-(hydroxyacetyl)-10-methoxy-6,11-dioxonaphthacen-1beta-yl-3-amino-2,3,6-trideoxy-alpha-L-lyxohexopyranoside
  • 10-((3-Amino-2,3,6-trideoxy-D-lyxohexopyranosyl)oxy)-8-glycolcyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
  • 14-Hydroxydaunomycin
  • 14-Hydroxydaunorubicine
  • ADM
  • Adriablastin
  • Adriamycin semiquinone
  • Adriblastin
  • Adriblastina
  • Caelyx
  • CCRIS 739
  • Doxil
  • Doxorubicin
  • Doxorubicina
  • Doxorubicina [INN-Spanish]
  • Doxorubicine
  • Doxorubicine [INN-French]
  • Doxorubicinum
  • Doxorubicinum [INN-Latin]
  • EINECS 245-495-6
  • FI 106
  • HSDB 3070
  • NCI-C01514
  • NDC 38242-874
  • NSC 123127
  • UNII-80168379AG

Systematic Names

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

Superlist Names

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

Registry Numbers

CAS Registry Number

  • 23214-92-8

FDA UNII

  • 80168379AG

Other Registry Numbers

  • 23257-17-2
  • 24385-08-8
  • 25311-50-6
  • 29042-30-6

Related Registry Number

  • 25316-40-9 (hydrochloride)

System Generated Number

  • 0023214928

Structure Descriptors

InChI

1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1

InChIKey

AOJJSUZBOXZQNB-TZSSRYMLSA-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)CO

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 2400ug/kg (2.4mg/kg)   Drug and Chemical Toxicology. Vol. 6, Pg. 21, 1983.
hamster LD10 parenteral 3500ug/kg (3.5mg/kg)   Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980.
human LDLo intravenous 400ug/kg (0.4mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BLOOD: LEUKOPENIA

GASTROINTESTINAL: OTHER CHANGES
Cancer Chemotherapy Reports, Part 3. Vol. 3, Pg. 33, 1972.
human TDLo intravenous 15mg/kg/D (15mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Cancer Vol. 34, Pg. 518, 1974.
human TDLo intravenous 380mg/kg/31W (380mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

GASTROINTESTINAL: NAUSEA OR VOMITING

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Cancer Vol. 34, Pg. 518, 1974.
mammal (species unspecified) LD50 intraperitoneal 8500ug/kg (8.5mg/kg)   Antibiotiki. Vol. 29, Pg. 748, 1984.
man LDLo unreported 243ug/kg (0.243mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: OTHER CHANGES
Postgraduate Medical Journal. Vol. 68, Pg. 69, 1992.
mouse LD50 intraperitoneal 10700ug/kg (10.7mg/kg)   Huaxi Yike Daxue Xuebao. Journal of West China University of Medical Sciences. Vol. 20, Pg. 303, 1989.
mouse LD50 intravenous 10mg/kg (10mg/kg)   Journal of Antibiotics. Vol. 45, Pg. 1373, 1992.
mouse LD50 oral 570mg/kg (570mg/kg)   Antibiotiki. Vol. 28, Pg. 298, 1983.
mouse LD50 unreported 21900ug/kg (21.9mg/kg)   Biochemical Pharmacology. Vol. 38, Pg. 167, 1989.
mouse LDLo intratracheal 2400ug/kg (2.4mg/kg)   Toxicology Letters. Vol. 30, Pg. 63, 1986.
rabbit LD50 intravenous 5mg/kg (5mg/kg)   Yiyao Gongye. Pharmaceutical Industry. Vol. 17, Pg. 72, 1986.
rabbit LDLo intrapleural 400ug/kg (0.4mg/kg) LUNGS, THORAX, OR RESPIRATION: PLEURAL THICKENING

CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"
Pharmacology and Toxicology Vol. 62, Pg. 84, 1988.
rat LD50 intraperitoneal 16mg/kg (16mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1075, 1972.
rat LD50 intravenous 10510ug/kg (10.51mg/kg)   Toxicology and Applied Pharmacology. Vol. 79, Pg. 412, 1985.
rat LD50 unreported 7mg/kg (7mg/kg)   Antibiotiki i Khimioterapiya. Antibiotics and Chemotherapy. Vol. 34, Pg. 216, 1989.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 229-231 deg C   EXP
log P (octanol-water) 1.27 (none)   EXP
Water Solubility 92.8 mg/L 25 EST
Vapor Pressure 8.99E-25 mm Hg 25 EST
Henry's Law Constant 2.23E-23 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.45E-10 cm3/molecule-sec 25 EST

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