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

Stem definition	Drug id	CAS RN
antineoplastics, daunorubicin derivatives	1414	58957-92-9

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: idarubicin 4-Demethoxydaunomycin 4-Demethoxydaunorubicin demethoxydaunorubicin idarubicin hydrochloride idarubicin HCl	An orally administered anthracycline antineoplastic. The compound has shown activity against BREAST NEOPLASMS; LYMPHOMA; and LEUKEMIA. Molecular weight: 497.50 Formula: C26H27NO9 CLOGP: 0.84 LIPINSKI: 0 HAC: 10 HDO: 5 TPSA: 176.61 ALOGS: -2.81 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

idarubicin
4-Demethoxydaunomycin
4-Demethoxydaunorubicin
demethoxydaunorubicin
idarubicin hydrochloride
idarubicin HCl

An orally administered anthracycline antineoplastic. The compound has shown activity against BREAST NEOPLASMS; LYMPHOMA; and LEUKEMIA.

Molecular weight: 497.50
Formula: C26H27NO9
CLOGP: 0.84
LIPINSKI: 0
HAC: 10
HDO: 5
TPSA: 176.61
ALOGS: -2.81
ROTB: 3

Status: OFP

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

Drug dosage:

None

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	3 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	5.43 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	28 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	38 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	24 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.08 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	16 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Sept. 27, 1990	FDA

FDA Adverse Event Reporting System (Female)

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	550.44	37.38	239	4746	105306	56181776
Acute myeloid leukaemia	193.17	37.38	68	4917	16904	56270178
Differentiation syndrome	161.00	37.38	33	4952	1016	56286066
Acute myeloid leukaemia recurrent	159.70	37.38	35	4950	1493	56285589
Neutropenia	150.74	37.38	119	4866	158048	56129034
Neutropenic colitis	144.32	37.38	36	4949	2707	56284375
Fusarium infection	134.33	37.38	26	4959	593	56286489
Thrombocytopenia	132.96	37.38	104	4881	136120	56150962
Geotrichum infection	127.14	37.38	24	4961	477	56286605
Bone marrow failure	117.68	37.38	55	4930	28231	56258851
Mucosal inflammation	115.39	37.38	62	4923	42748	56244334
Septic shock	110.19	37.38	68	4917	60767	56226315
Neoplasm recurrence	108.22	37.38	28	4957	2436	56284646
Multiple organ dysfunction syndrome	95.58	37.38	59	4926	52711	56234371
Leukaemia recurrent	88.05	37.38	21	4964	1307	56285775
Pancytopenia	84.82	37.38	67	4918	88648	56198434
Second primary malignancy	81.64	37.38	29	4956	7373	56279709
Acute lymphocytic leukaemia recurrent	81.29	37.38	22	4963	2275	56284807
Sepsis	78.36	37.38	78	4907	139762	56147320
Myelodysplastic syndrome	62.37	37.38	30	4955	16376	56270706
Gene mutation	61.37	37.38	16	4969	1433	56285649
Bronchopulmonary aspergillosis	60.55	37.38	24	4961	8240	56278842
Neurotoxicity	60.40	37.38	29	4956	15766	56271316
Endophthalmitis	57.36	37.38	18	4967	3125	56283957
Haemophagocytic lymphohistiocytosis	57.14	37.38	24	4961	9548	56277534
Lower respiratory tract infection fungal	55.22	37.38	11	4974	292	56286790
Febrile bone marrow aplasia	54.93	37.38	21	4964	6551	56280531
Disseminated intravascular coagulation	54.08	37.38	28	4957	17857	56269225
Ejection fraction decreased	48.59	37.38	27	4958	19814	56267268
Ventricular hypokinesia	48.37	37.38	17	4968	4184	56282898
Chromosomal deletion	46.49	37.38	7	4978	31	56287051
Aspergillus infection	45.50	37.38	19	4966	7446	56279636
Neutropenic sepsis	43.70	37.38	23	4962	15162	56271920
Dedifferentiated liposarcoma	43.53	37.38	7	4978	51	56287031
Mucormycosis	42.87	37.38	14	4971	2760	56284322
Hyperbilirubinaemia	42.82	37.38	20	4965	10215	56276867
Fungaemia	42.27	37.38	13	4972	2111	56284971
Pneumonia fungal	42.20	37.38	16	4969	4877	56282205
Cytomegalovirus infection	41.17	37.38	24	4961	19272	56267810
Neutropenic infection	40.96	37.38	11	4974	1104	56285978
Product use in unapproved indication	40.77	37.38	56	4929	140766	56146316
Leukoerythroblastosis	39.51	37.38	8	4977	231	56286851
Haematopoietic neoplasm	38.18	37.38	6	4979	37	56287045

FDA Adverse Event Reporting System (Male)

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	466.69	31.72	290	5856	121559	31569639
Acute myeloid leukaemia	193.79	31.72	87	6059	18585	31672613
Acute myeloid leukaemia recurrent	165.30	31.72	44	6102	1930	31689268
Neutropenia	159.31	31.72	164	5982	140200	31550998
Bronchopulmonary aspergillosis	127.12	31.72	59	6087	13575	31677623
Fungal infection	126.52	31.72	60	6086	14491	31676707
Bone marrow failure	112.16	31.72	69	6077	27939	31663259
Mucormycosis	102.08	31.72	39	6107	5531	31685667
Differentiation syndrome	91.50	31.72	25	6121	1210	31689988
Septic shock	90.90	31.72	86	6060	66072	31625126
Myelodysplastic syndrome	83.65	31.72	50	6096	19201	31671997
Pancytopenia	81.12	31.72	92	6054	87224	31603974
Venoocclusive liver disease	75.09	31.72	34	6112	7378	31683820
Aspergillus infection	74.86	31.72	39	6107	11489	31679709
Fusarium infection	71.32	31.72	20	6126	1066	31690132
Neutropenic colitis	68.44	31.72	24	6122	2668	31688530
Thrombocytopenia	67.25	31.72	108	6038	142639	31548559
Febrile bone marrow aplasia	61.04	31.72	30	6116	7816	31683382
Aeromonas infection	58.15	31.72	13	6133	270	31690928
Pneumonia fungal	57.74	31.72	27	6119	6302	31684896
Sepsis	57.10	31.72	104	6042	151825	31539373
Cytomegalovirus infection reactivation	56.18	31.72	23	6123	3906	31687292
Stenotrophomonas infection	48.53	31.72	17	6129	1883	31689315
Second primary malignancy	46.24	31.72	24	6122	7008	31684190
Mucosal inflammation	45.76	31.72	44	6102	34383	31656815
Geotrichum infection	45.65	31.72	12	6134	500	31690698
Neoplasm progression	45.54	31.72	35	6111	20237	31670961
Product use in unapproved indication	45.20	31.72	74	6072	99097	31592101
Chronic graft versus host disease	40.88	31.72	19	6127	4373	31686825
T-cell type acute leukaemia	40.11	31.72	9	6137	190	31691008
Haematopoietic neoplasm	38.30	31.72	7	6139	49	31691149
Pyrexia	38.03	31.72	137	6009	303703	31387495
Adenomatous polyposis coli	36.51	31.72	8	6138	151	31691047
Poikiloderma	35.93	31.72	8	6138	163	31691035
Leukaemia recurrent	35.87	31.72	13	6133	1589	31689609
Premature ageing	35.22	31.72	7	6139	80	31691118
Drug resistance	33.11	31.72	31	6115	23422	31667776
Hyperbilirubinaemia	32.78	31.72	26	6120	15724	31675474
Neoplasm recurrence	32.36	31.72	13	6133	2101	31689097
Reticulocytosis	32.20	31.72	8	6138	265	31690933
Myelosuppression	31.85	31.72	25	6121	14895	31676303

FDA Adverse Event Reporting System (Geriatric)

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	942.32	27.28	507	10460	203811	70713666
Acute myeloid leukaemia	365.65	27.28	148	10819	30792	70886685
Neutropenia	272.12	27.28	261	10706	256895	70660582
Acute myeloid leukaemia recurrent	245.94	27.28	63	10904	2991	70914486
Differentiation syndrome	229.11	27.28	56	10911	2191	70915286
Fusarium infection	227.65	27.28	53	10914	1679	70915798
Bone marrow failure	216.86	27.28	119	10848	48891	70868586
Neutropenic colitis	213.78	27.28	63	10904	5051	70912426
Septic shock	191.66	27.28	150	10817	112108	70805369
Thrombocytopenia	170.74	27.28	197	10770	238913	70678564
Pancytopenia	170.12	27.28	159	10808	150948	70766529
Myelodysplastic syndrome transformation	169.32	27.28	35	10932	628	70916849
Geotrichum infection	159.89	27.28	36	10931	979	70916498
Bronchopulmonary aspergillosis	154.58	27.28	72	10895	20930	70896547
Myelodysplastic syndrome	139.10	27.28	75	10892	29710	70887767
Fungal infection	138.71	27.28	81	10886	37386	70880091
Second primary malignancy	135.59	27.28	57	10910	12994	70904483
Mucosal inflammation	116.38	27.28	91	10876	67759	70849718
Sepsis	113.70	27.28	163	10804	244382	70673095
Neoplasm recurrence	107.44	27.28	35	10932	3906	70913571
Mucormycosis	107.29	27.28	42	10925	7972	70909505
Aspergillus infection	103.49	27.28	52	10915	17816	70899661
Pneumonia fungal	98.49	27.28	42	10925	9911	70907566
Venoocclusive liver disease	95.65	27.28	42	10925	10636	70906841
Febrile bone marrow aplasia	81.72	27.28	39	10928	11952	70905525
Leukaemia recurrent	81.17	27.28	26	10941	2749	70914728
Multiple organ dysfunction syndrome	79.89	27.28	91	10876	108424	70809053
Acute lymphocytic leukaemia recurrent	77.47	27.28	29	10938	4875	70912602
Product use in unapproved indication	76.12	27.28	124	10843	207354	70710123
Haematopoietic neoplasm	75.37	27.28	13	10954	81	70917396
Hyperbilirubinaemia	73.63	27.28	45	10922	22523	70894954
Stenotrophomonas infection	68.61	27.28	24	10943	3325	70914152
Pain	67.17	27.28	9	10958	628807	70288670
Drug resistance	58.57	27.28	48	10919	38142	70879335
Aeromonas infection	57.60	27.28	13	10954	357	70917120
Myelosuppression	57.27	27.28	43	10924	30102	70887375
Fungaemia	56.78	27.28	22	10945	4060	70913417
Pyrexia	56.08	27.28	213	10754	606739	70310738
Bacteraemia	53.89	27.28	41	10926	29268	70888209
Haemophagocytic lymphohistiocytosis	53.69	27.28	35	10932	19577	70897900
Neoplasm progression	53.47	27.28	49	10918	45179	70872298
Pathogen resistance	52.54	27.28	30	10937	13249	70904228
Neutropenic infection	51.36	27.28	17	10950	1992	70915485
Arthralgia	49.64	27.28	9	10958	503381	70414096
Cytomegalovirus infection reactivation	49.10	27.28	23	10944	6758	70910719
Myocarditis	47.71	27.28	32	10935	18761	70898716
Dizziness	46.40	27.28	8	10959	464133	70453344
Dysplasia	46.19	27.28	14	10953	1233	70916244
Pneumonia	46.06	27.28	198	10769	596034	70321443
Fall	45.86	27.28	7	10960	444089	70473388
Respiratory failure	45.26	27.28	88	10879	168647	70748830
Cytomegalovirus infection	44.92	27.28	42	10925	39716	70877761
Fatigue	43.84	27.28	38	10929	824281	70093196
Disseminated intravascular coagulation	42.86	27.28	38	10929	33560	70883917
Ventricular hypokinesia	42.04	27.28	22	10945	8190	70909287
Lower respiratory tract infection fungal	41.92	27.28	12	10955	866	70916611
Rash maculo-papular	39.91	27.28	44	10923	50501	70866976
Acute respiratory distress syndrome	39.87	27.28	40	10927	41214	70876263
Ejection fraction decreased	39.65	27.28	35	10932	30727	70886750
Tumour lysis syndrome	39.53	27.28	30	10937	21330	70896147
T-cell type acute leukaemia	38.98	27.28	9	10958	274	70917203
Chloroma	38.93	27.28	11	10956	758	70916719
Acute lymphocytic leukaemia	37.67	27.28	18	10949	5527	70911950
Cytarabine syndrome	37.13	27.28	7	10960	76	70917401
Infective aneurysm	37.05	27.28	11	10956	903	70916574
Recurrent cancer	36.97	27.28	14	10953	2427	70915050
Pulmonary haemorrhage	36.44	27.28	24	10943	13649	70903828
Adenomatous polyposis coli	36.40	27.28	8	10959	194	70917283
Premature ageing	36.33	27.28	7	10960	86	70917391
Chromosomal deletion	36.33	27.28	7	10960	86	70917391
Cytopenia	35.80	27.28	26	10941	17297	70900180
Graft versus host disease	34.39	27.28	24	10943	14999	70902478
Chronic graft versus host disease	34.26	27.28	18	10949	6752	70910725
Leukoerythroblastosis	34.03	27.28	8	10959	264	70917213
Escherichia bacteraemia	33.74	27.28	17	10950	5852	70911625
Haemorrhagic pneumonia	33.53	27.28	7	10960	132	70917345
Streptococcal bacteraemia	33.50	27.28	14	10953	3139	70914338
Pain in extremity	32.01	27.28	6	10961	328076	70589401
Enterococcal bacteraemia	32.00	27.28	13	10954	2713	70914764
Cardiomyopathy	32.00	27.28	29	10938	26344	70891133
Weight decreased	31.78	27.28	5	10962	310483	70606994
Poikiloderma	31.69	27.28	8	10959	357	70917120
Hidradenitis	30.71	27.28	13	10954	3009	70914468
Acute graft versus host disease in skin	30.61	27.28	17	10950	7120	70910357
Pleural effusion	30.50	27.28	65	10902	132799	70784678
Aplasia	30.35	27.28	17	10950	7234	70910243
Gamma-glutamyltransferase increased	29.87	27.28	38	10929	50647	70866830
Malaise	29.63	27.28	15	10952	432917	70484560
Haematotoxicity	29.34	27.28	21	10946	13653	70903824
Leukaemia	29.24	27.28	15	10952	5360	70912117
Reticulocytosis	29.13	27.28	8	10959	496	70916981
Neurotoxicity	28.96	27.28	29	10938	29797	70887680
Colitis	28.75	27.28	42	10925	63772	70853705
Anti-platelet antibody positive	28.57	27.28	7	10960	276	70917201
Pharyngeal inflammation	27.99	27.28	9	10958	963	70916514
Posterior reversible encephalopathy syndrome	27.98	27.28	26	10941	24376	70893101

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	L01DB06	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES Anthracyclines and related substances
FDA CS	M0028312	Anthracyclines
FDA MoA	N0000000176	Topoisomerase Inhibitors
FDA EPC	N0000175414	Anthracycline Topoisomerase Inhibitor
MeSH PA	D000903	Antibiotics, Antineoplastic
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D059005	Topoisomerase II Inhibitors

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

Disease	Relation	SNOMED_ID	DOID
Acute myeloid leukemia, disease	indication	91861009
Acute promyelocytic leukemia, FAB M3	indication	110004001
Pericarditis	contraindication	3238004	DOID:1787
Enterocolitis	contraindication	43752006
Conduction disorder of the heart	contraindication	44808001
Chronic heart failure	contraindication	48447003
Myocarditis	contraindication	50920009	DOID:820
Gastrointestinal perforation	contraindication	51875005
Acute infectious disease	contraindication	63171007
Cardiomyopathy	contraindication	85898001	DOID:0050700
Kidney disease	contraindication	90708001	DOID:557
Disease of liver	contraindication	235856003	DOID:409
Anemia	contraindication	271737000	DOID:2355
Pregnancy, function	contraindication	289908002
Bone marrow depression	contraindication	307762000
Breastfeeding (mother)	contraindication	413712001

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.01	acidic
pKa2	9.88	acidic
pKa3	11.6	acidic
pKa4	8.73	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Bioact source	MoA source
DNA topoisomerase 2-alpha	Enzyme	P11388	TOP2A_HUMAN	INHIBITOR	WOMBAT-PK	CHEMBL
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN		WOMBAT-PK
Multidrug resistance-associated protein 1	Transporter	P33527	MRP1_HUMAN		WOMBAT-PK

External reference:

ID	Source
4019784	VUID
N0000147874	NUI
D01747	KEGG_DRUG
57852-57-0	SECONDARY_CAS_RN
4019569	VANDF
4019784	VANDF
C0020789	UMLSCUI
CHEBI:42068	CHEBI
DM5	PDB_CHEM_ID
CHEMBL1117	ChEMBL_ID
CHEMBL1200976	ChEMBL_ID
D015255	MESH_DESCRIPTOR_UI
DB01177	DRUGBANK_ID
7083	IUPHAR_LIGAND_ID
5174	INN_ID
ZRP63D75JW	UNII
42890	PUBCHEM_CID
5650	RXNORM
45101	MMSL
4865	MMSL
d00256	MMSL
003556	NDDF
004819	NDDF
108786002	SNOMEDCT_US
108788001	SNOMEDCT_US
372539000	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Idamycin PFS	HUMAN PRESCRIPTION DRUG LABEL	1	0013-2576	SOLUTION	1 mg	INTRAVENOUS	NDA	24 sections
Idamycin PFS	HUMAN PRESCRIPTION DRUG LABEL	1	0013-2576	SOLUTION	1 mg	INTRAVENOUS	NDA	24 sections
Idamycin PFS	HUMAN PRESCRIPTION DRUG LABEL	1	0013-2586	SOLUTION	1 mg	INTRAVENOUS	NDA	24 sections
Idamycin PFS	HUMAN PRESCRIPTION DRUG LABEL	1	0013-2586	SOLUTION	1 mg	INTRAVENOUS	NDA	24 sections
Idamycin PFS	HUMAN PRESCRIPTION DRUG LABEL	1	0013-2596	SOLUTION	1 mg	INTRAVENOUS	NDA	24 sections
Idamycin PFS	HUMAN PRESCRIPTION DRUG LABEL	1	0013-2596	SOLUTION	1 mg	INTRAVENOUS	NDA	24 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9217	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9218	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9219	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9306	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9307	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9308	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0703-4154	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0703-4154	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0703-4155	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0703-4155	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0703-4156	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections
Idarubicin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0703-4156	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	23 sections