Scroll

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

Stem definition	Drug id	CAS RN
antineoplastics, daunorubicin derivatives	960	23214-92-8

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: doxorubicin hydroxydaunomycin hydroxydaunorubicin rubidox doxorubicin hydrochloride liposomal doxorubicin hydroxydaunorubicin hydrochloride adriamycin doxorubicin HCl hydroxydaunorubicin HCl adriacin	Antineoplastic antibiotic obtained from Streptomyces peucetius. It is a hydroxy derivative of DAUNORUBICIN. Molecular weight: 543.53 Formula: C27H29NO11 CLOGP: 0.26 LIPINSKI: 3 HAC: 12 HDO: 6 TPSA: 206.07 ALOGS: -2.67 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

doxorubicin
hydroxydaunomycin
hydroxydaunorubicin
rubidox
doxorubicin hydrochloride
liposomal doxorubicin
hydroxydaunorubicin hydrochloride
adriamycin
doxorubicin HCl
hydroxydaunorubicin HCl
adriacin

Antineoplastic antibiotic obtained from Streptomyces peucetius. It is a hydroxy derivative of DAUNORUBICIN.

Molecular weight: 543.53
Formula: C27H29NO11
CLOGP: 0.26
LIPINSKI: 3
HAC: 12
HDO: 6
TPSA: 206.07
ALOGS: -2.67
ROTB: 5

Status: OFP

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

Drug dosage:

None

ADMET properties:

Show entries

Search:

Property	Value	Reference
S (Water solubility)	50 mg/mL	Bocci G, Oprea TI, Benet LZ
BA (Bioavailability)	5 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
MRTD (Maximum Recommended Therapeutic Daily Dose)	4.47 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
t_half (Half-life)	32 hours	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	3.50 %	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	22 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	15 mL/min/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.28 %	Lombardo F, Berellini G, Obach RS

Showing 1 to 9 of 9 entries

Previous1Next

Approvals:

Show entries

Search:

Date	Agency	Company
Aug. 7, 1974	FDA
June 20, 1996	EMA	BAXTER HOLDING B.V.
March 1, 1975	PMDA	SANDOZ PHARMA K.K.

Showing 1 to 3 of 3 entries

Previous1Next

FDA Adverse Event Reporting System (Female)

Show entries

Search:

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	5745.12	12.78	3151	105228	115298	63265345
Neutropenia	2913.74	12.78	2397	105982	172608	63208035
Disease progression	1930.56	12.78	1629	106750	121129	63259514
Acute myeloid leukaemia	1221.84	12.78	593	107786	16554	63364089
Cardiotoxicity	1103.73	12.78	447	107932	7991	63372652
Mucosal inflammation	1018.69	12.78	754	107625	46174	63334469
Thrombocytopenia	988.04	12.78	1252	107127	149905	63230738
Myelodysplastic syndrome	945.93	12.78	495	107884	16259	63364384
Haematotoxicity	897.67	12.78	398	107981	8978	63371665
Second primary malignancy	870.39	12.78	371	108008	7582	63373061

Showing 1 to 10 of 842 entries

Previous1 2 3 4 5…85Next

FDA Adverse Event Reporting System (Male)

Show entries

Search:

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	3905.61	14.22	2963	81537	133886	34738545
Disease progression	1427.40	14.22	1520	82980	106557	34765874
Neutropenia	1342.36	14.22	1766	82734	155012	34717419
Off label use	976.22	14.22	2701	81799	416823	34455608
Product use in unapproved indication	840.11	14.22	1215	83285	116284	34756147
Diffuse large B-cell lymphoma recurrent	719.99	14.22	277	84223	2951	34869480
Mucosal inflammation	708.48	14.22	651	83849	37971	34834460
Haematotoxicity	621.50	14.22	331	84169	7863	34864568
Second primary malignancy	596.55	14.22	318	84182	7568	34864863
Hepatitis B	570.53	14.22	282	84218	5701	34866730

Showing 1 to 10 of 583 entries

Previous1 2 3 4 5…59Next

FDA Adverse Event Reporting System (Geriatric)

Show entries

Search:

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	8548.78	12.33	5536	160497	225463	79352892
Neutropenia	3428.35	12.33	3570	162463	284140	79294215
Disease progression	2303.56	12.33	2350	163683	182012	79396343
Acute myeloid leukaemia	1522.82	12.33	893	165140	29992	79548363
Mucosal inflammation	1445.57	12.33	1223	164810	74357	79503998
Myelodysplastic syndrome	1337.66	12.33	816	165217	29485	79548870
Second primary malignancy	1315.49	12.33	628	165405	13722	79564633
Haematotoxicity	1301.50	12.33	639	165394	14880	79563475
Off label use	1216.88	12.33	4386	161647	902829	78675526
Product use in unapproved indication	1199.63	12.33	1987	164046	248372	79329983

Showing 1 to 10 of 1,073 entries

Previous1 2 3 4 5…108Next

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Show entries

Search:

Source	Code	Description
ATC	L01DB01	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES Anthracyclines and related substances
CHEBI has role	CHEBI:76971	Escherichia coli metabolites
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
MeSH PA	D059003	Topoisomerase Inhibitors

Showing 1 to 10 of 10 entries

Previous1Next

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

Show entries

Search:

Disease	Relation	SNOMED_ID	DOID
Acute lymphoid leukemia	indication	91857003	DOID:9952
Acute myeloid leukemia, disease	indication	91861009
Kaposi's sarcoma	indication	109385007
Diffuse non-Hodgkin's lymphoma, large cell	indication	109969005
Multiple myeloma	indication	109989006	DOID:9538
Hodgkin's disease	indication	118599009
Non-Hodgkin's lymphoma	indication	118601006
Burkitt's lymphoma	indication	118617000
Small cell carcinoma of lung	indication	254632001	DOID:5409
Carcinoma of breast	indication	254838004	DOID:3459

Showing 1 to 10 of 60 entries

Previous1 2 3 4 5 6Next

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Show entries

Search:

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.85	acidic
pKa2	9.21	acidic
pKa3	9.92	acidic
pKa4	11.11	acidic
pKa5	8.6	Basic

Showing 1 to 5 of 5 entries

Previous1Next

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Show entries

Search:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
DNA topoisomerase 2-alpha	Enzyme	P11388	TOP2A_HUMAN	INHIBITOR	IC50	6	CHEMBL	CHEMBL
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN		IC50	4.01	CHEMBL
Muscarinic acetylcholine receptor M1	GPCR	P11229	ACM1_HUMAN		Ki	5.43	DRUG MATRIX
Canalicular multispecific organic anion transporter 1	Transporter	Q92887	MRP2_HUMAN				WOMBAT-PK
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
Caspase-1	Enzyme	P29466	CASP1_HUMAN		IC50	4.91	DRUG MATRIX
Tyrosine-protein kinase Lck	Kinase	P06239	LCK_HUMAN		IC50	4.50	DRUG MATRIX
Tyrosine-protein kinase Fyn	Kinase	P06241	FYN_HUMAN		IC50	5.29	DRUG MATRIX

Showing 1 to 10 of 29 entries

Previous1 2 3Next

External reference:

Show entries

Search:

ID	Source
DM2	PDB_CHEM_ID
002659	NDDF
004818	NDDF
142433	RXNORM
25316-40-9	SECONDARY_CAS_RN
3005	INN_ID
31703	PUBCHEM_CID
3368	MMSL
372817009	SNOMEDCT_US
4018106	VANDF

Showing 1 to 10 of 31 entries

Previous1 2 3 4Next

Pharmaceutical products:

Show entries

Search:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Doxorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3030	INJECTION, SOLUTION	2 mg	INTRAVENOUS	NDA	34 sections
Doxorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3030	INJECTION, SOLUTION	2 mg	INTRAVENOUS	NDA	34 sections
Doxorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3031	INJECTION, SOLUTION	2 mg	INTRAVENOUS	NDA	34 sections
Doxorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3031	INJECTION, SOLUTION	2 mg	INTRAVENOUS	NDA	34 sections
Doxorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3032	INJECTION, SOLUTION	2 mg	INTRAVENOUS	NDA	34 sections
Doxorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3032	INJECTION, SOLUTION	2 mg	INTRAVENOUS	NDA	34 sections
Doxorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3033	INJECTION, SOLUTION	2 mg	INTRAVENOUS	NDA	34 sections
Doxorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3033	INJECTION, SOLUTION	2 mg	INTRAVENOUS	NDA	34 sections
Doxorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3034	INJECTION, SOLUTION	2 mg	INTRAVENOUS	NDA	34 sections
Doxorubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3034	INJECTION, SOLUTION	2 mg	INTRAVENOUS	NDA	34 sections

Showing 1 to 10 of 30 entries

Previous1 2 3Next