IDARUBICIN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H27NO9.ClH
Molecular Weight	533.955
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.C[C@@H]1O[C@H](C[C@H](N)[C@@H]1O)O[C@H]2C[C@@](O)(CC3=C2C(O)=C4C(=O)C5=CC=CC=C5C(=O)C4=C3O)C(C)=O

InChI

InChIKey=JVHPTYWUBOQMBP-RVFAQHLVSA-N

InChI=1S/C26H27NO9.ClH/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31;/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3;1H/t10-,15-,16-,17-,21+,26-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C26H27NO9
Molecular Weight	497.4939
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=0a5a6d93-cc1e-4d7f-8da1-446c134503b3&type=display | https://www.drugbank.ca/drugs/DB01177

Idarubicin is an antineoplastic in the anthracycline class.Idarubicin hydrochloride is a DNA-intercalating analog of daunorubicin which has an inhibitory effect on nucleic acid synthesis and interacts with the enzyme topoisomerase II. The absence of a methoxy group at position 4 of the anthracycline structure gives the compound a high lipophilicity which results in an increased rate of cellular uptake compared with other anthracyclines.Idarubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. Idarubicin in combination with other approved antileukemic drugs is indicated for the treatment of acute myeloid leukemia (AML) in adults.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II alpha 37 Target ID: CHEMBL1806 Sources: https://www.drugbank.ca/drugs/DB01177 \| https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=0a5a6d93-cc1e-4d7f-8da1-446c134503b3&type=display \| https://www.ncbi.nlm.nih.gov/pubmed/17616443 \| https://www.ncbi.nlm.nih.gov/pubmed/8036155	Inhibitor 8504
DNA 282 Target ID: CHEMBL2311221 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=0a5a6d93-cc1e-4d7f-8da1-446c134503b3&type=display \| https://www.drugbank.ca/drugs/DB01177 \| https://www.ncbi.nlm.nih.gov/pubmed/8036155	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute myeloid leukemia 141 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/050734s005lbl.pdf http://adisinsight.springer.com/drugs/800001995	Primary		Approved 8583	IDAMYCIN Approved Use IDAMYCIN PFS Injection in combination with other approved antileukemic drugs is indicated for the treatment of acute myeloid leukemia (AML) in adults. This includes French-American-British (FAB) classifications M1 through M7. Launch Date 1990

C_max

Value	Dose	Co-administered	Analyte	Population
7.7 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12621462	40 mg/m² single, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		IDARUBICIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
423.2 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12621462	40 mg/m² single, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		IDARUBICIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
38.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12621462	40 mg/m² single, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		IDARUBICIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
3% DRUG LABEL https://nctr-crs.fda.gov/fdalabel/services/spl/set-ids/7c20b574-285b-49eb-a98e-6752e4bb481d/spl-doc?hl=IDARUBICIN			IDARUBICIN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26750985/	unhealthy, 23-60 Health Status: unhealthy Age Group: 23-60 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/26750985/	Other AEs: Neutropenia, Thrombocytopenia... Other AEs: Neutropenia (all grades, 3 patients) Thrombocytopenia (all grades, 3 patients) Mucositis (all grades, 3 patients) Anorexia (all grades, 3 patients) Diarrhea (all grades, 3 patients) Vomiting (all grades, 2 patients) Left ventricular systolic dysfunction (all grades, 2 patients) Cardiac arrhythmia (all grades, 1 patient) Rash (all grades, 2 patients) Infection (all grades, 3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/26750985/
15 mg/m2 1 times / day multiple, oral Dose: 15 mg/m2, 1 times / day Route: oral Route: multiple Dose: 15 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2208149/	unhealthy, 66 years (range: 40-85 years) Health Status: unhealthy Age Group: 66 years (range: 40-85 years) Sources: https://pubmed.ncbi.nlm.nih.gov/2208149/	Other AEs: Nausea, Vomiting... Other AEs: Nausea (50%) Vomiting (50%) Mucositis (20%) Diarrhea (20%) Alopecia (15%) Anorexia (11%) Sepsis (2%) Hepatitis (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/2208149/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193 inhibitor 2438	substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 1057 CYP1A2 2153 MRP 9	CYP2C8 810 CYP1A2 1197

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/	no
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/	yes
MRP 9	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9188796/	yes
P-gp 1932	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/9063374/ \| https://pubmed.ncbi.nlm.nih.gov/15585622/	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/	yes
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:42068	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:42068
ChemicalBook	CB5283235	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5283235
eMolecules	539550	https://www.emolecules.com/cgi-bin/more?vid=539550
ZINC	ZINC000003920266	http://zinc15.docking.org/substances/ZINC000003920266

PubMed

Title	Date	PubMed
Comparison of idarubicin and daunorubicin regarding intracellular uptake, induction of apoptosis, and resistance.	2002-04-25	11867198
Automated differential counts in acute promyelocytic leukemia patients may be misleading.	2002-04	11920794
Phase I trial with escalating doses of idarubicin and multidrug resistance reversal by short-course cyclosporin A, sequential high-dose cytosine arabinoside, and granulocyte colony-stimulating factor for adult patients with refractory acute leukemia.	2002-03	11869937
Multiple interference of anthracyclines with mitochondrial creatine kinases: preferential damage of the cardiac isoenzyme and its implications for drug cardiotoxicity.	2002-03	11854431
Correlation between chromosome damage and apoptosis induced by fludarabine and idarubicin in normal human lymphocytes.	2002-02-28	11836027
Diversity of the apoptotic response to chemotherapy in childhood leukemia.	2002-02	11840289
AIDA treatment for high-risk acute promyelocytic leukemia in a pregnant woman at 21 weeks of gestation.	2002-02	11836189
Retinoic acid syndrome: a case of massive lung consolidation.	2002-02	11836180
P-glycoprotein inhibitors enhance saturable uptake of idarubicin in rat heart: pharmacokinetic/pharmacodynamic modeling.	2002-02	11805234
Evaluation of the clinical relevance of the expression and function of P-glycoprotein, multidrug resistance protein and lung resistance protein in patients with primary acute myelogenous leukemia.	2002-02	11755464
Pharmacokinetics and toxicity of idarubicin in the rat.	2002-01-26	11808862
Cell-based assays for identification of novel double-strand break-inducing agents.	2002-01-16	11792746
Effects of cytarabine and various anthracyclins on platelet activation: characterization of in vitro effects and their possible clinical relevance in acute myelogenous leukemia.	2002-01-01	11774251
[Acute myelogenous leukemia associated with severe esophageal stricture after chemotherapy].	2002-01	11868364
Secondary acute promyelocytic leukemia in a patient with non-Hodgkin's lymphoma treated with VP-16 and MST-16.	2002-01	11843282
Standard versus alternative myeloablative conditioning regimens in allogeneic hematopoietic stem cell transplantation for high-risk acute leukemia.	2002-01	11801465
A case of zygomycosis and invasive candidiasis involving the epiglottis and tongue in an immunocompromised patient.	2002	11928855
Differential antigenotoxic and cytoprotective effect of amifostine in idarubicin-treated mice.	2002	11813290
Comparison of idarubicin + ara-C-, fludarabine + ara-C-, and topotecan + ara-C-based regimens in treatment of newly diagnosed acute myeloid leukemia, refractory anemia with excess blasts in transformation, or refractory anemia with excess blasts.	2001-12-15	11739159
Histopathologic features of retinoblastoma and its relation with in vitro drug resistance measured by means of the MTT assay.	2001-12-01	11753969
Generation of reactive oxygen species is not involved in idarubicin-induced apoptosis in human leukaemic cells.	2001-12	11843815
Therapy-related myelodysplastic syndrome/acute myeloid leukemia M2 and translocation (8;21).	2001-12	11797121
Contribution of specific transport systems to anthracycline transport in tumor and normal cells.	2001-12	11766987
Idarubicin, cytarabine, and topotecan in patients with refractory or relapsed acute myelogenous leukemia and high-risk myelodysplastic syndrome.	2001-12	11754412
Treatment of relapse after allogeneic bone marrow transplantation with reduced intensity conditioning (FLAG +/- Ida) and second allogeneic stem cell transplant.	2001-12	11736947
An adjustment for a post-randomization variable in the comparison of two treatments for survival.	2001-11-30	11746330
Anthracyclines: recent developments in their separation and quantitation.	2001-11-25	11817026
Development of hepatic veno-occlusive disease after Mylotarg infusion for relapsed acute myeloid leukemia.	2001-11	11781652
Influence of P-glycoprotein modulators on cardiac uptake, metabolism, and effects of idarubicin.	2001-11	11758760
And the sun keeps shining.	2001-11	11713460
Inappropriate reporting and interpretation of subgroups in the AML-BFM 93 study.	2001-11	11681429
High-dose chemotherapy in high-risk myelodysplastic syndrome: covariate-adjusted comparison of five regimens.	2001-10-15	11596013
Intensive chemotherapy followed by allogeneic or autologous stem cell transplantation for patients with myelodysplastic syndromes (MDSs) and acute myeloid leukemia following MDS.	2001-10-15	11588026
FAB M4 and high CD14 surface expression is associated with high cellular resistance to Ara-C and daunorubicin: implications for clinical outcome in acute myeloid leukaemia.	2001-10	11860442
A pharmacokinetic study of idarubicin in Japanese patients with malignant lymphoma: relationship with leukocytopenia and neutropenia.	2001-10	11721966
LFA-1 and ICAM-1 antibody-idarubicin conjugates separately prolong murine cardiac allograft survival.	2001-10	11680574
High dose of idarubicin-based regimen for diffuse large cell AIDS-related non-Hodgkin's lymphoma patients: a pilot study.	2001-10	11602411
Long-term follow-up of the clinical efficacy of chemotherapy for acute myeloid leukemia at a single institute.	2001-09	11810577
[Comparison of the effectiveness of idarubicin (Zavedos) and mitoxantrone (Refador) in induction therapy of acute myeloid leukemia in elderly patients (55-75) (a prospective multicenter randomized study conducted 1998-2000].	2001-09	11693063
Drug-drug interactions arising from the use of liposomal vincristine in combination with other anticancer drugs.	2001-09	11683249
Granulomatous tubulointerstitial nephritis induced by all-trans retinoic acid.	2001-09	11604554
Acute basophilic leukemia.	2001-08	11722593
Amifostine does not inhibit the toxic effects of anthracycline derivates or mitoxantrone on MDR tumor cell lines.	2001-08	11697502
[CD7(+) acute myeloid leukemia (M0) associated with a mediastinal bulky mass lesion].	2001-08	11579505
Oligonucleotide enhanced cytotoxicity of Idarubicin for lymphoma cells.	2001-07	11699407
Cytosine arabinoside, idarubicin and divided dose etoposide for the treatment of acute myeloid leukemia in elderly patients.	2001-07	11699399
Treatment of newly-diagnosed acute promyelocytic leukemia with liposomal all-trans retinoic acid.	2001-07	11699395
High-dose idarubicin and busulphan as conditioning for autologous stem cell transplantation in acute myeloid leukemia: a feasibility study.	2001	11920252
Autologous hematopoietic stem cell transplantation in chronic myeloid leukemia with different clinical stages.	2001	11713374
Empirical therapy of febrile neutropenic patients with mucositis: challenge of risk-based therapy.	2001	11688534

Patents

Sample Use Guides

In Vivo Use Guide

For induction therapy in adult patients with AML the following dose schedule is recommended: Idarubicin 12 mg/m2 daily for 3 days by slow (10 to 15 min) intravenous injection in combination with cytarabine. The cytarabine may be given as 100 mg/m2 daily by continuous infusion for 7 days or as cytarabine 25 mg/m2 intravenous bolus followed by cytarabine 200 mg/m2 daily for 5 days continuous infusion. In patients with unequivocal evidence of leukemia after the first induction course, a second course may be administered. Administration of the second course should be delayed in patients who experience severe mucositis, until recovery from this toxicity has occurred, and a dose reduction of 25% is recommended. In patients with hepatic and/or renal impairment, a dose reduction of IDAMYCIN PFS should be considered. Idarubicin should not be administered if the bilirubin level exceeds 5 mg%

Route of Administration: Intravenous

In Vitro Use Guide

Treatment of HL-60 cells with 1 uM Idarubicin for 2 h could not induce internucleosomal DNA fragmentation, however, a ladder of DNA fragment, characteristic of apoptosis, was observed after incubation for 4 h. After 10-h, extensive DNA degradation was observed. When HL-60 cells were incubated with different doses of Idarubicin for 8 h, the degree of DNA fragmentation increased at the higher concentration.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:51:58 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:58 GMT 2025`
Record UNII	5VV3MDU5IE
Record Status	`Validated (UNII)`
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Name

Type

Language

IDAMYCIN

Preferred Name

English

IDARUBICIN HYDROCHLORIDE

Official Name

English

IDARUBICIN HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

IDARUBICIN HYDROCHLORIDE [JAN]

Common Name

English

IDARUBICIN HYDROCHLORIDE [VANDF]

Common Name

English

IDARUBICIN HYDROCHLORIDE [USAN]

Common Name

English

Idarubicin hydrochloride [WHO-DD]

Common Name

English

IMI-30

Code

English

1S,3S)-3-ACETYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSIDE, HYDROCHLORIDE

Common Name

English

5,12-NAPHTHACENEDIONE, 9-ACETYL-7-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,9,11-TRIHYDROXYHYDROCHLORIDE, (7S-CIS)-

Common Name

English

IDARUBICIN HYDROCHLORIDE [USP-RS]

Common Name

English

NSC-256439

Code

English

IDARUBICIN HYDROCHLORIDE [MI]

Common Name

English

IDARUBICIN HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

IDARUBICIN HCL

Common Name

English

IMI 30

Code

English

IDARUBICIN HYDROCHLORIDE [MART.]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

55890