ContaminantDB: Daunorubicin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:25 UTC

Update Date

2026-05-14 16:46:17 UTC

Accession Number

CHEM002249

Identification

Common Name

Daunorubicin

Class

Small Molecule

Description

Daunorubicin is only found in individuals that have used or taken this drug. It is a very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of leukemia and other neoplasms. [PubChem]Daunorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Daunorubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Urine
IARC Carcinogens Group 2B
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Antibiotic
Antibiotic, Antineoplastic
Antineoplastic Agent
Drug
Ester
Ether
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Daunomycin	ChEBI
(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	ChEBI
Acetyladriamycin	ChEBI
Daunomycin	ChEBI
Daunorubicinum	ChEBI
Leukaemomycin C	ChEBI
DM	Kegg
DaunoXome	Kegg
(8S-cis)-8-Acetyl-10-((3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione	Generator
(8S-cis)-8-Acetyl-10-((3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione	Generator
Dauno rubidomycine	HMDB
Daunoblastine	HMDB
Daunorubicin hydrochloride	HMDB
Cerubidine	HMDB
Rubidomycin	HMDB
Dauno-rubidomycine	HMDB
Daunoblastin	HMDB
Hydrochloride, daunorubicin	HMDB
Rubomycin	HMDB

Chemical Formula

C₂₇H₂₉NO₁₀

Average Molecular Mass

527.520 g/mol

Monoisotopic Mass

527.179 g/mol

CAS Registry Number

20830-81-3

IUPAC Name

(8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

Traditional Name

daunorubicin

SMILES

COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(C)=O)C(O)=C1C2=O

InChI Identifier

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

InChI Key

STQGQHZAVUOBTE-VGBVRHCVSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracycline
Anthracyclinone-skeleton
Aminoglycoside core
Tetracenequinone
9,10-anthraquinone
1,4-anthraquinone
Anthracene
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Aryl ketone
Anisole
Amino saccharide
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Tertiary alcohol
Alpha-hydroxy ketone
Secondary alcohol
1,2-aminoalcohol
Ketone
Organoheterocyclic compound
Acetal
Ether
Polyol
Oxacycle
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organooxygen compound
Carbonyl group
Alcohol
Primary aliphatic amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinone (CHEBI:41977 )
aminoglycoside antibiotic (CHEBI:41977 )
anthracycline (CHEBI:41977 )
Anthracyclinones (C01907 )
Anthracyclinones (LMPK13050002 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antineoplastic agent

Biological Roles

bacterial metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	208-209°C
Boiling Point	Not Available
Solubility	39.2 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	1.68	ALOGPS
logP	1.73	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.53	ChemAxon
pKa (Strongest Basic)	8.94	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	185.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.89 m³·mol⁻¹	ChemAxon
Polarizability	52.94 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200300000-b86566e84001e30da377	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-9200135000-1c14f3df000eec108899	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0229100000-35f2df54929348a28ee4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-0419110000-70d2a081fbad20bd67d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0219100000-b592d3a84cac9ef0b6cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01sj-0009280000-938bd3eaade51c04aafd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0319000000-543d7f990f443c45a59a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-5119000000-a692f22291ba5dcb0808	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1104190000-47330bcd3826d8820bc0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-2109420000-a7be1508cced736226fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-3109100000-13452a25c0c03df2d319	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-0409240000-c2e5b799e5c588ee6f3e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2709330000-ed3234db0e99dfed2fef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-4922200000-c1091039c837788e6ffc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-294a27e0915e38aa66fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fuj-0009000000-92a5bfac85109e9f056c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0301-0009010000-08c42b7b4f498ddf12ce	Spectrum

Toxicity Profile

Route of Exposure

Intravenous

Mechanism of Toxicity

Daunorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Daunorubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.

Metabolism

Hepatic Route of Elimination: Twenty-five percent of an administered dose of daunorubicin hydrochloride is eliminated in an active form by urinary excretion and an estimated 40% by biliary excretion. Half Life: 18.5 hours

Toxicity Values

LD50=20 mg/kg (mice, IV); LD50=13 mg/kg (rat, IV)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (3)

Uses/Sources

For remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults.

Minimum Risk Level

Not Available

Health Effects

Antibiotic resistance. Toxic manifestations of Daunorubicin include bone marrow depression, stomatitis, alopecia, gastrointestinal disturbances, and dermatological manifestations. Cardiac toxicity is a pecular effect. (2)

Symptoms

symptoms include gastrointestinal disturbances. (2)

Treatment

Infuse 10 to 20 mL/kg isotonic fluid. If hypotension persists, administer dopamine. (1)

Concentrations

Not Available

External Links

DrugBank ID

DB00694

HMDB ID

HMDB0014832

FooDB ID