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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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
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/s1InChIKey
AOJJSUZBOXZQNB-TZSSRYMLSA-NSmiles
COc1cccc2C(=O)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.