DM1

DAUNOMYCIN

Created:	1999-07-08
Last modified:	2020-06-05

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16 entries where DM1 is found as a standalone ligand3 entries where DM1 is covalently linked to polymer or other heterogen groups

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Chemical Details
Formal Charge	0
Atom Count	67
Chiral Atom Count	6
Bond Count	71
Aromatic Bond Count	12

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Chemical Component Summary
Name	DAUNOMYCIN
Synonyms	DAUNORUBICIN
Systematic Name (OpenEye OEToolkits)	(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
Formula	C₂₇ H₂₉ N O₁₀
Molecular Weight	527.52
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C2c1c(O)c5c(c(O)c1C(=O)c3cccc(OC)c23)CC(O)(C(=O)C)CC5OC4OC(C(O)C(N)C4)C
SMILES	CACTVS	3.341	COc1cccc2C(=O)c3c(O)c4C[C](O)(C[CH](O[CH]5C[CH](N)[CH](O)[CH](C)O5)c4c(O)c3C(=O)c12)C(C)=O
SMILES	OpenEye OEToolkits	1.5.0	CC1C(C(CC(O1)OC2CC(Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)O)(C(=O)C)O)N)O
Canonical SMILES	CACTVS	3.341	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(C)=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)O)(C(=O)C)O)N)O
InChI	InChI	1.03	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
InChIKey	InChI	1.03	STQGQHZAVUOBTE-VGBVRHCVSA-N

Drug Info: DrugBank

DrugBank ID	DB00694
Name	Daunorubicin
Groups	approved
Description	A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of leukemia and other neoplasms.
Synonyms	Rubidomycin (+)-Daunomycin Acetyladriamycin Daunorubicine Daunorubicin liposomal Daunorubicin citrate Leukaemomycin C Daunorubicin (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 Daunorubicina Daunorubicin hydrochloride Daunomycin Daunorubicinum
Brand Names	Vyxeos Liposomal Daunorubicin Hydrochloride Injection DaunoXome Daunoxome Liposomal - IV 2mg/ml, 50mg/vial Daunorubicin Injectable Solution Vyxeos Daunorubicin Hydrochloride Cerubidine Daunorubicin Hydrochloride for Injection
Indication	For remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults. Daunorubicin is indicated in combination with [cytarabine] for the treatment of newly-diagnosed therapy-related acute myeloid leukemia (t-AML) or AML with myelodysplasia-related changes (AML-MRC) in adults and pediatric patients 1 year and older.[L32843]
Categories	Anthracycline Topoisomerase Inhibitor Anthracyclines Anthracyclines and Related Substances Antibiotics, Antineoplastic Antineoplastic Agents Antineoplastic and Immunomodulating Agents BCRP/ABCG2 Substrates BSEP/ABCB11 Substrates BSEP/ABCB11 Substrates with a Narrow Therapeutic Index Cardiotoxic antineoplastic agents Cytochrome P-450 CYP3A Inducers Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A5 Inducers Cytochrome P-450 CYP3A5 Inducers (strength unknown) Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Cytotoxic Antibiotics and Related Substances Enzyme Inhibitors Glycosides Immunosuppressive Agents Myelosuppressive Agents Naphthacenes Narrow Therapeutic Index Drugs P-glycoprotein inducers P-glycoprotein inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Topoisomerase II Inhibitors Topoisomerase Inhibitors
ATC-Code	L01DB02 L01XY01
CAS number	20830-81-3

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
DNA	-	unknown	intercalation
DNA topoisomerase 2-alpha	MEVSPLQPVNENMQVNKIKKNEDAKKRLSVERIYQKKTQLEHILLRPDTY...	unknown	inhibitor
DNA topoisomerase 2-beta	MAKSGGCGAGAGVGGGNGALTWVTLFDQNNAAKKEESETANKNDSSKKLS...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	inducer
NADPH--cytochrome P450 reductase	MGDSHVDTSSTVSEAVAEEVSLFSMTDMILFSLIVGLLTYWFLFRKKKEE...	unknown	substrate,inducer
Cytochrome P450 1B1	MGTSLSPNDPWPLNPLSIQQTTLLLLLSVLATVHVGQRLLRQRRRQLRSA...	unknown	inhibitor
Aldose reductase	MASRLLLNNGAKMPILGLGTWKSPPGQVTEAVKVAIDVGYRHIDCAHVYQ...	unknown	substrate
Carbonyl reductase [NADPH] 1	MSSGIHVALVTGGNKGIGLAIVRDLCRLFSGDVVLTARDVTRGQAAVQQL...	unknown	substrate
Carbonyl reductase [NADPH] 3	MSSCSRVALVTGANRGIGLAIARELCRQFSGDVVLTARDVARGQAAVQQL...	unknown	substrate
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor,inducer
Multidrug resistance-associated protein 1	MALRGFCSADGSDPLWDWNVTWNTSNPDFTKCFQNTVLVWVPCFYLWACF...	unknown	substrate,inhibitor
Multidrug resistance-associated protein 7	MERLLAQLCGSSAAWPLPLWEGDTTGHCFTQLVLSALPHALLAVLSACYL...	unknown	substrate
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate
Multidrug resistance-associated protein 6	MAAPAEPCAGQGVWNQTEPEPAATSLLSLCFLRTAGVWVPPMYLWVLGPI...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682