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Drug

D0036 | Daunorubicin

Molecular Formula C27H29NO10
Molecular Weight 527.5
Structure
State solid
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.
Protein binding 97% binding-albumin
Half life 18.5 hours
Description anthracycline aminoglycoside antineoplastic

L

L01XY01 Cytarabine and daunorubicin


[L01XY] Combinations of antineoplastic agents


[L01X] OTHER ANTINEOPLASTIC AGENTS


[L01] ANTINEOPLASTIC AGENTS


[L] Antineoplastic and immunomodulating agents

L01DB02 Daunorubicin


[L01DB] Anthracyclines and related substances


[L01D] CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES


[L01] ANTINEOPLASTIC AGENTS


[L] Antineoplastic and immunomodulating agents

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) Negative EC20 36
RESPIRATION 12.8 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. decrease EC20 36
RESPIRATION 10.9 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. decrease EC20 36
SWELLING < 6.25 µM 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) increase EC20 36

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 12.8 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. inhibit EC20 36
Succinate dehydrogenase 10.9 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. inhibit EC20 36
Cytochrome c 47.2 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 52 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]


H341 (100%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]


H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]


H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P264, P270, P281, P301+P310, P308+P313, P321, P330, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
mouse LD50 oral 205mg/kg (205mg/kg) Yakkyoku. Pharmacy. Vol. 25, Pg. 573, 1974.
rat LD50 oral 336mg/kg (336mg/kg) Yakkyoku. Pharmacy. Vol. 25, Pg. 573, 1974.
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.
child LDLo oral 10mg/kg/30D-I (10mg/kg) cardiac: cardiomyopathy including infarction British Journal of Clinical Practice. Vol. 44, Pg. 633, 1990.
mouse LD50 unreported 24900ug/kg (24.9mg/kg) Biochemical Pharmacology. Vol. 38, Pg. 167, 1989.
hamster LDLo intravenous 50mg/kg (50mg/kg) Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 15, Pg. 1614, 1973.
mouse LD50 intravenous 8600ug/kg (8.6mg/kg) Cancer Research. Vol. 49, Pg. 4098, 1989.
rat LD50 intravenous 13mg/kg (13mg/kg) National Cancer Institute Report. Vol. -, Pg. 304, 1967.
rat LD50 subcutaneous 33200ug/kg (33.2mg/kg) Yakkyoku. Pharmacy. Vol. 25, Pg. 573, 1974.
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.
rat LD50 intraperitoneal 20mg/kg (20mg/kg) Advances in Teratology. Vol. 3, Pg. 181, 1968.
mouse LD50 intraperitoneal 2500ug/kg (2.5mg/kg) gastrointestinal: other changes National Cancer Institute Report. Vol. -, Pg. 304, 1967.
rabbit LD50 intravenous 5mg/kg (5mg/kg) behavioral: somnolence (general depressed activity) Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 948, 1967.


  • (+)-Daunomycin (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranoside
    (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside (7S,9R)-9-Acetyl-7-[(2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione (7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-4-methoxy-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
    (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-quinone;hydrochloride (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
    (7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride (8S,10S)-8-acetyl-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione (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
    (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 (8S-cis)-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-5,12-naphthacenedione 1407-15-4
    15159-EP2270008A1 15159-EP2272827A1 15159-EP2277565A2
    15159-EP2277566A2 15159-EP2277567A1 15159-EP2277568A2
    15159-EP2277569A2 15159-EP2277570A2 15159-EP2289892A1
    15159-EP2292280A1 15159-EP2292617A1 15159-EP2295416A2
    15159-EP2295426A1 15159-EP2295427A1 15159-EP2298748A2
    15159-EP2298778A1 15159-EP2301928A1 15159-EP2305642A2
    15159-EP2305679A1 15159-EP2308833A2 15159-EP2308861A1
    15159-EP2311808A1 15159-EP2311829A1 15159-EP2311842A2
    15159-EP2316832A1 15159-EP2316833A1 16803-EP2272832A1
    16803-EP2277565A2 16803-EP2277566A2 16803-EP2277567A1
    16803-EP2277568A2 16803-EP2277569A2 16803-EP2277570A2
    16803-EP2280012A2 16803-EP2281815A1 16803-EP2286812A1
    16803-EP2292280A1 16803-EP2292615A1 16803-EP2298768A1
    16803-EP2301928A1 16803-EP2301933A1 16803-EP2305640A2
    16803-EP2305671A1 16803-EP2311825A1 16803-EP2311827A1
    16803-EP2311840A1 16803-EP2316937A1 20830-81-3
    30D813 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)- 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)-
    AB00514669 AB00514669-09 AB01644616_09
    AB01644616_10 AI3-52942 API0005415
    AX8123492 Acetyladriamycin Anthracyline
    BDBM32017 BDBM50368352 BPBio1_000389
    BRD-K43389675-001-01-3 BRD-K43389675-003-02-7 BRD-K43389675-003-03-5
    BRD-K43389675-003-20-9 BRN 1445583 BSPBio_000353
    C01907 C27H29NO10 CAS-20830-81-3
    CCG-212559 CCRIS 914 CHEBI:41977
    CHEMBL178 CS-2004 Cerubidin
    Cerubidine D07776 DB00694
    DSSTox_CID_2883 DSSTox_GSID_22883 DSSTox_RID_76773
    DTXSID7022883 Daunamycin Daunarubicinum
    Dauno-Rubidomycine DaunoXome DaunoXome (TN)
    Daunoblastin Daunoblastine Daunomycin
    Daunorrubicina Daunorubicin (INN) Daunorubicin (liposomal)
    Daunorubicin [INN:BAN] Daunorubicin(Daunomycin) Daunorubicina
    Daunorubicine Daunorubicinum Daunorubicinum [INN-Latin]
    EINECS 244-069-7 FI 6339 FI-6339
    FI6339 FT-0624457 GR-318
    GTPL7063 HMS2089H04 HMS2091K06
    HSDB 5095 HY-13062A LMPK13050002
    LS-187381 LS-997 Leukaemomycin C
    MLS000069508 NCGC00024246-05 NCGC00024246-06
    NCGC00024246-07 NCGC00024246-09 NCGC00024246-10
    NCGC00024246-15 NCGC00025173-01 NCI-C04693
    NDC 0082-4155 NDC-0082-4155 NSC 83142
    NSC-756717 NSC-82151 NSC756717
    NSC82151 Pharmakon1600-01500223 Prestwick3_000487
    Q411659 RCRA waste no. U059 RP 13057
    RP-13057 Rubidomycin Rubomycin
    Rubomycin C SBI-0206677.P002 SC-18793
    SCHEMBL3041 SMR000058559 SR-01000000033
    SR-01000000033-4 SR-05000001600 SR-05000001600-1
    SR-05000001600-2 STQGQHZAVUOBTE-VGBVRHCVSA-N Tocris-1467
    Tox21_110896 Tox21_110896_1 UNII-ZS7284E0ZP
    VS-103 ZINC3917708 ZS7284E0ZP
    cid_62770 daunorubicin

    DrugBank Name Daunorubicin
    DrugBank DB00694
    CAS Number 1407-15-4, 20830-81-3
    PubChem Compound 30323
    KEGG Compound ID C01907
    KEGG Drug D07776
    PubChem.Substance 46508433
    ChEBI 41977
    PharmGKB PA449212
    ChemSpider 28163
    BindingDB 32017.0
    TTD DNC000517
    Wikipedia Daunorubicin
    HET DM1
    DPD 68

    1. Dykens et al. (2007)