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daunorubicin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antineoplastics, daunorubicin derivatives	786	20830-81-3

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: daunorubicin acetyladriamycin cerubidin daunoblastina daunomycine daunorubicine Leukaemomycin C rubidomycin daunorubicin hydrochloride daunorubicin citrate daunorubicin HCl	A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS. Molecular weight: 527.53 Formula: C27H29NO10 CLOGP: 0.78 LIPINSKI: 2 HAC: 11 HDO: 5 TPSA: 185.84 ALOGS: -2.93 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

daunorubicin
acetyladriamycin
cerubidin
daunoblastina
daunomycine
daunorubicine
Leukaemomycin C
rubidomycin
daunorubicin hydrochloride
daunorubicin citrate
daunorubicin HCl

A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.

Molecular weight: 527.53
Formula: C27H29NO10
CLOGP: 0.78
LIPINSKI: 2
HAC: 11
HDO: 5
TPSA: 185.84
ALOGS: -2.93
ROTB: 4

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

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Property	Value	Reference
CL (Clearance)	47.57 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	32.05 L/kg	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	2.05 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
t_half (Half-life)	14.24 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Bocci G, Oprea TI, Benet LZ
S (Water solubility)	0.63 mg/mL	Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine)	0.50 %	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.06 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Dec. 19, 1979	FDA
Feb. 24, 2021	PMDA	Meiji Seika Pharma Co., Ltd

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Febrile neutropenia	851.72	25.15	415	10828	118034	63359745
Hypofibrinogenaemia	367.33	25.15	75	11168	1095	63476684
Posterior reversible encephalopathy syndrome	203.94	25.15	86	11157	17259	63460520
Sepsis	202.36	25.15	187	11056	152936	63324843
Neutropenia	156.39	25.15	173	11070	174832	63302947
Hyperbilirubinaemia	152.96	25.15	62	11181	11252	63466527
Bone marrow failure	128.09	25.15	74	11169	29216	63448563
Pneumatosis intestinalis	124.10	25.15	36	11207	2377	63475402
Mucormycosis	117.92	25.15	36	11207	2835	63474944
Colitis	111.80	25.15	82	11161	48446	63429333

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Febrile neutropenia	590.64	20.27	458	13022	136391	34807060
Hypofibrinogenaemia	325.26	20.27	84	13396	1602	34941849
Posterior reversible encephalopathy syndrome	230.19	20.27	100	13380	9854	34933597
Bone marrow failure	173.08	20.27	119	13361	29134	34914317
Aspergillus infection	159.82	20.27	83	13397	12171	34931280
Septic shock	157.85	20.27	165	13315	71669	34871782
Neutropenia	149.78	20.27	238	13242	156540	34786911
Acute myeloid leukaemia recurrent	143.25	20.27	47	13433	2123	34941328
Hyperbilirubinaemia	127.58	20.27	80	13400	16763	34926688
Sepsis	126.08	20.27	228	13252	166333	34777118

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Febrile neutropenia	1314.25	20.91	838	23653	230161	79489736
Posterior reversible encephalopathy syndrome	409.43	20.91	187	24304	26094	79693803
Hypofibrinogenaemia	379.58	20.91	94	24397	1908	79717989
Secondary immunodeficiency	348.59	20.91	97	24394	3137	79716760
Bone marrow failure	320.28	20.91	198	24293	50909	79668988
Aspergillus infection	319.51	20.91	143	24348	19018	79700879
Sepsis	294.65	20.91	387	24104	269041	79450856
Neutropenia	285.28	20.91	394	24097	287316	79432581
Bacterial infection	269.49	20.91	149	24342	31131	79688766
Bronchopulmonary aspergillosis	251.03	20.91	127	24364	22167	79697730

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01DB02	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES Anthracyclines and related substances
ATC	L01XY01	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS OTHER ANTINEOPLASTIC AGENTS Combinations of antineoplastic agents
CHEBI has role	CHEBI:35610	antineoplastic agents
FDA CS	M0028312	Anthracyclines
FDA EPC	N0000175414	Anthracycline Topoisomerase Inhibitor
FDA MoA	N0000000176	Topoisomerase Inhibitors
MeSH PA	D000903	Antibiotics, Antineoplastic
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D059005	Topoisomerase II Inhibitors

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Acute lymphoid leukemia	indication	91857003	DOID:9952
Acute myeloid leukemia, disease	indication	91861009
Erythroleukemia, FAB M6	indication	93451002
Kaposi's sarcoma	indication	109385007
Acute promyelocytic leukemia, FAB M3	indication	110004001
Acute monocytic/monoblastic leukemia	indication	413442004
Blast crisis of chronic myeloidleukemia	indication	413656006
Nephroblastoma	off-label use	302849000	DOID:2154
Neuroblastoma	off-label use	432328008	DOID:769
Mycosis	contraindication	3218000	DOID:1564

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.85	acidic
pKa2	9.79	acidic
pKa3	11.6	acidic
pKa4	8.6	Basic

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Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	8431806	April 22, 2025	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
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	7850990	Jan. 23, 2027	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
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	8022279	Sept. 14, 2027	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
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	8092828	April 1, 2029	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
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	10028912	Oct. 15, 2032	METHOD OF ADMINISTERING A RECONSTITUTED LIPOSOMAL COMPOSITION CONTAINING CYTARABINE AND DAUNORUBICIN TO TREAT NEWLY-DIAGNOSED THERAPY-RELATED AML (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN PATIENTS 1 YEAR AND OLDER
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	10028912	Oct. 15, 2032	METHOD OF RECONSTITUTING A LYOPHILIZED LIPOSOMAL COMPOSITION FOR ADMINISTERING CYTARABINE AND DAUNORUBICIN TO TREAT NEWLY-DIAGNOSED THERAPY-RELATED AML (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN PATIENTS 1 YEAR AND OLDER
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	10166184	Oct. 15, 2032	METHOD OF RECONSTITUTING A LYOPHILIZED LIPOSOMAL COMPOSITION FOR ADMINISTERING CYTARABINE AND DAUNORUBICIN TO TREAT NEWLY-DIAGNOSED THERAPY-RELATED AML (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN PATIENTS 1 YEAR AND OLDER
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	10835492	Oct. 15, 2032	METHOD OF ADMINISTERING A RECONSTITUTED LIPOSOMAL COMPOSITION CONTAINING CYTARABINE AND DAUNORUBICIN TO TREAT NEWLY-DIAGNOSED THERAPY-RELATED AML (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN PATIENTS 1 YEAR AND OLDER

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	March 30, 2024	NEW PATIENT POPULATION
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	Aug. 3, 2024	TREATMENT OF ADULTS WITH NEWLY DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC)
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	March 30, 2028	TREATMENT OF NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN PEDIATRIC PATIENTS AGES 1 YEAR AND OLDER

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
DNA topoisomerase 2-alpha	Enzyme	P11388	TOP2A_HUMAN	INHIBITOR			WOMBAT-PK	CHEMBL
Multidrug resistance-associated protein 1	Transporter	P33527	MRP1_HUMAN				WOMBAT-PK
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN				WOMBAT-PK
Multidrug resistance-associated protein 6	Transporter	O95255	MRP6_HUMAN				WOMBAT-PK
72 kDa type IV collagenase	Enzyme	P08253	MMP2_HUMAN		IC50	5.72	CHEMBL
Histone deacetylase 1	Enzyme	Q13547	HDAC1_HUMAN		IC50	7.33	CHEMBL
Histone deacetylase 6	Enzyme	Q9UBN7	HDAC6_HUMAN		IC50	7.70	CHEMBL
Histone deacetylase 8	Enzyme	Q9BY41	HDAC8_HUMAN		IC50	6.66	CHEMBL
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN				WOMBAT-PK
ORF 73	Unclassified		O40947_HHV8		AC50	5.63	CHEMBL

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External reference:

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ID	Source
DM1	PDB_CHEM_ID
002662	NDDF
004821	NDDF
108790000	SNOMEDCT_US
11753	MMSL
1364321	RXNORM
2257	INN_ID
23541-50-6	SECONDARY_CAS_RN
30323	PUBCHEM_CID
35300007	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Daunorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9550	INJECTION	5 mg	INTRAVENOUS	NDA	21 sections
Daunorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9551	INJECTION	5 mg	INTRAVENOUS	NDA	21 sections
daunorubicin hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0703-5233	INJECTION, SOLUTION	5 mg	INTRAVENOUS	ANDA	26 sections
Daunorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	42658-019	INJECTION, SOLUTION	5 mg	INTRAVENOUS	ANDA	22 sections
Daunorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	42658-021	INJECTION, SOLUTION	5 mg	INTRAVENOUS	ANDA	22 sections
Daunorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	42658-021	INJECTION, SOLUTION	5 mg	INTRAVENOUS	ANDA	22 sections
VYXEOS	HUMAN PRESCRIPTION DRUG LABEL	2	68727-745	INJECTION, POWDER, LYOPHILIZED, FOR SUSPENSION	44 mg	INTRAVENOUS	NDA	28 sections
VYXEOS	HUMAN PRESCRIPTION DRUG LABEL	2	68727-745	INJECTION, POWDER, LYOPHILIZED, FOR SUSPENSION	44 mg	INTRAVENOUS	NDA	28 sections

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