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Substance Name: Doxorubicin hydrochloride [USP:JAN]
RN: 25316-40-9
UNII: 82F2G7BL4E
InChIKey: MWWSFMDVAYGXBV-RUELKSSGSA-N

Note

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

Molecular Formula

  • C27-H29-N-O11.Cl-H

Molecular Weight

  • 579.983
 

Classification Codes

  • Antineoplastic
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Doxorubicin hydrochloride [USP:JAN]

Synonyms

  • (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 hydrochloride
  • ADM hydrochloride
  • Adriacin
  • Adriamycin
  • Adriamycin PFS
  • Adriamycin RDF
  • Adriblastin
  • Adriblastina
  • Adrosal
  • Caelyx
  • CCRIS 740
  • Doxil
  • Doxorubicin HCl
  • Doxorubicin hydrochloride
  • Duxocin
  • EINECS 246-818-3
  • FI 6804
  • Hydroxydaunorubicin hydrochloride
  • KW-125
  • Lipo-Dox
  • Lipodox
  • NSC 123127
  • Rubex
  • UNII-82F2G7BL4E

Systematic Names

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

Superlist Name

  • 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-, hydrochloride, (8S-cis)-

Registry Numbers

CAS Registry Number

  • 25316-40-9

FDA UNII

  • 82F2G7BL4E

Related Registry Number

  • 23214-92-8 (Parent)

System Generated Number

  • 0025316409

Molecular Formulas

Molecular Formula

  • C27-H29-N-O11.Cl-H

Molecular Formula Fragments

  • C27-H29-N-O11
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C27H29NO11.ClH/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;1H/t10-,13-,15-,17-,22+,27-;/m0./s1

InChIKey

MWWSFMDVAYGXBV-RUELKSSGSA-N

Smiles

Cl.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
man LDLo intravenous 2571ug/kg/3W- (2.571mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Archives of Internal Medicine. Vol. 137, Pg. 385, 1977.
man TDLo intravenous 12mg/kg/26W-I (12mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Annals of Internal Medicine. Vol. 106, Pg. 814, 1987.
mouse LD50 intramuscular 13700ug/kg (13.7mg/kg)   Drugs in Japan Vol. 6, Pg. 506, 1982.
mouse LD50 intraperitoneal 11160ug/kg (11.16mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 1245ug/kg (1.245mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 oral 698mg/kg (698mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: MUSCLE WEAKNESS
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973.
mouse LD50 subcutaneous 7678ug/kg (7.678mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
rabbit LD50 intravenous 5980ug/kg (5.98mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973.
rat LD50 intramuscular 16mg/kg (16mg/kg)   Drugs in Japan Vol. 6, Pg. 506, 1982.
rat LD50 intraperitoneal 16030ug/kg (16.03mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER TOPICAL EXPOSURE"
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973.
rat LD50 intravenous 12510ug/kg (12.51mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973.
rat LD50 intravenous 12510ug/kg (12.51mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER TOPICAL EXPOSURE"
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973.
rat LD50 subcutaneous 21840ug/kg (21.84mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER TOPICAL EXPOSURE"

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1052, 1973.