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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H25NO9
Molecular Weight 483.4673
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMRUBICIN

SMILES

[H][C@@]1(C[C@H](O)[C@H](O)CO1)O[C@H]2C[C@@](N)(CC3=C(O)C4=C(C(=O)C5=CC=CC=C5C4=O)C(O)=C23)C(C)=O

InChI

InChIKey=VJZITPJGSQKZMX-XDPRQOKASA-N
InChI=1S/C25H25NO9/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31/h2-5,14-17,28-29,32-33H,6-9,26H2,1H3/t14-,15+,16-,17-,25-/m0/s1

HIDE SMILES / InChI
Molecular Formula C25H25NO9
Molecular Weight 483.4673
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Amrubicin is a totally synthetic 9-aminoanthracycline anticancer drug, which is approved in Japan for the treatment of small cell and non-small cell lung cancer. Upon administration amrubicin is reduced to its C-13 hydroxy metabolite, amrubicinol. The cytotoxicity of amrubicinol in vitro is 10 to 100 times greater than that of amrubicin. Thus, the anticancer activity of amrubicin is considered to derive from this active metabolite. The mechanism of action of the drug is related to the inhibition of topoisomerase II by stabilizing the cleavable complex.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
CALSED

Approved Use

Non small cell lung cancer, small cell lung cancer.

Launch Date

2002
Primary
Approved
8429
CALSED

Approved Use

Non small cell lung cancer, small cell lung cancer

Launch Date

2002
PubMed

PubMed

TitleDatePubMed
Progress in treatment of small-cell lung cancer: role of CPT-11.
2003 Dec 15
[Development of an individualized therapy for establishing the optimal dosage by the pharmacokinetics profiles of anticancer agents].
2005 Aug
Phase I/II study of amrubicin, a novel 9-aminoanthracycline, in patients with advanced non-small-cell lung cancer.
2005 Aug
Characterization of the enzymes involved in the in vitro metabolism of amrubicin hydrochloride.
2005 Dec
Small-cell lung cancer: current therapy and novel agents.
2005 Jan
[New anti-cancer agents--from cytotoxic systemic chemotherapy to target-based agents].
2005 Jun
[Treatment of small cell lung cancer].
2005 Jun
Phase I-II study of amrubicin and cisplatin in previously untreated patients with extensive-stage small-cell lung cancer.
2005 Mar
Phase I study of irinotecan and amrubicin in patients with advanced non-small-cell lung cancer.
2005 May-Jun
[A case of lung adenocarcinoma of the lung with disappearance of brain metastasis by re-treatment with gefitinib].
2005 Nov
Modification of thermosensitivity by amrubicin or amrubicinol in human lung adenocarcinoma A549 cells and the kinetics of apoptosis and necrosis induction.
2005 Sep
The combination effect of amrubicin with cisplatin or irinotecan for small-cell lung cancer cells.
2006 Apr
A phase I and pharmacological study of amrubicin and topotecan in patients of small-cell lung cancer with relapsed or extensive-disease small-cell lung cancer.
2006 Aug
Amrubicin induces apoptosis in human tumor cells mediated by the activation of caspase-3/7 preceding a loss of mitochondrial membrane potential.
2006 Dec
Pharmacokinetics of amrubicin and its active metabolite amrubicinol in lung cancer patients.
2006 Feb
Phase I and pharmacokinetic study of amrubicin, a synthetic 9-aminoanthracycline, in patients with refractory or relapsed lung cancer.
2006 Feb
Phase I study of amrubicin hydrochloride and cisplatin in patients previously treated for advanced non-small cell lung cancer.
2006 Jan
A phase I study of amrubicin combined with carboplatin for elderly patients with small-cell lung cancer.
2006 Jul
[A case of multiple pyomyositis after chemotherapy for lung cancer].
2006 Jun
[A case of small-cell lung cancer effectively treated by bi-weekly administration of amrubicin].
2006 Mar
Multicenter phase II study of amrubicin, 9-amino-anthracycline, in patients with advanced non-small-cell lung cancer (Study 1): West Japan Thoracic Oncology Group (WJTOG) trial.
2006 Mar
Amurubicinol-induced eotaxin-3 expression in human NCI-H69 small cell lung carcinoma cells.
2006 Mar
[Chemotherapy for lung cancer patients].
2006 Mar 1
Experimental designs for phase I and phase I/II dose-finding studies.
2006 Mar 13
A phase I study of irinotecan in combination with amrubicin for advanced lung cancer patients.
2006 May-Jun
Enhancement of radiosensitivity by topoisomerase II inhibitor, amrubicin and amrubicinol, in human lung adenocarcinoma A549 cells and kinetics of apoptosis and necrosis induction.
2006 Nov
Modern management of small-cell lung cancer.
2007
[A case of small cell lung cancer under hemodialysis with chronic renal failure treated with amrubicin while measuring blood concentration of the drug].
2007 Apr
Evaluation of the recommended dose and efficacy of amrubicin as second- and third-line chemotherapy for small cell lung cancer.
2007 Aug
Amrubicin for the treatment of small cell lung cancer: does effectiveness cross the Pacific?
2007 Feb
Small-cell lung cancer responds to amrubicin.
2007 Jan
Phase II study of amrubicin in previously untreated patients with extensive-disease small cell lung cancer: West Japan Thoracic Oncology Group (WJTOG) study.
2007 Jun
[Lung cancer].
2007 Mar
Phase I and pharmacologic study of irinotecan and amrubicin in advanced non-small cell lung cancer.
2007 Mar
Clinical benefit of readministration of gefitinib for initial gefitinib-responders with non-small cell lung cancer.
2007 Mar 20
Enhancement of death receptor 4 mediated apoptosis and cytotoxicity in renal cell carcinoma cells by subtoxic concentrations of doxorubicin.
2007 May
[Analysis of adverse events of amrubicin hydrochloride for pretreated lung cancer patients].
2007 Nov
Amrubicin for non-small-cell lung cancer and small-cell lung cancer.
2007 Oct
Dose escalation study of amrubicin in combination with fixed-dose irinotecan in patients with extensive small-cell lung cancer.
2008
Small cell carcinoma of the prostate treated with amrubicin.
2008 Apr
[Our clinical experiences of amrubicin hydrochloride monotherapy in extensive-disease small cell lung cancer].
2008 Feb
Novel systemic therapies for small cell lung cancer.
2008 Mar
Management of small-cell lung cancer: incremental changes but hope for the future.
2008 Nov 30
Effective monotherapy with amrubicin for a refractory extrapulmonary small-cell carcinoma of the liver.
2009
Retrospective analysis of efficacy and safety of amrubicin in refractory and relapsed small-cell lung cancer.
2009 Feb
Synergistic cell growth inhibition by the combination of amrubicin and Akt-suppressing tyrosine kinase inhibitors in small cell lung cancer cells: implication of c-Src and its inhibitor.
2009 Mar
[Second-line treatment and targeted therapy of advanced lung cancer].
2009 May
Multiple lung metastases presenting as ground-glass opacities in a pulmonary adenocarcinoma: a case report.
2009 May 29
Relationship of mRNA expressions of RanBP2 and topoisomerase II isoforms to cytotoxicity of amrubicin in human lung cancer cell lines.
2010 Jul
Salvage chemotherapy with amrubicin and platinum for relapsed thymic carcinoma: experience in six cases.
2010 Jun
Patents

Patents

06376469
2
JP2003201296A
2
JP2003201297A
2
JP2004323393A
2
JP2005120083A
2
JP2006519264A
58
JP2007506647A
5
JP2011168621A
2
JP2011511071A
2
JP2011525180A
180
JP2011528275A
455
JP4658037B2
37
JPH11222497A
2

Sample Use Guides

In Vivo Use Guide
The usual dose is 45 mg/m2 given intravenously once a day for 3 days.
Route of Administration: Intravenous
In Vitro Use Guide
In a cell viability assay, lung cancer cells DMS 114, NCI-H69, NCI-H82, NCI-H526 were incubated with amrubicin at concentrations from 18 nM to 16 uM for 72 h. IC50 values were 0.803, 1.54, 0.746 and 0.818 uM, respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:49 GMT 2023
Edited
by admin
on Fri Dec 15 15:54:49 GMT 2023
Record UNII
93N13LB4Z2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMRUBICIN
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
Amrubicin [WHO-DD]
Common Name English
AMRUBICIN [USAN]
Common Name English
AMRUBICIN [MI]
Common Name English
amrubicin [INN]
Common Name English
AMRUBICIN [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC L01DB10
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
FDA ORPHAN DRUG 255307
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
WHO-VATC QL01DB10
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
NCI_THESAURUS C1594
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C80089
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
MERCK INDEX
m1858
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY Merck Index
MESH
C055866
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
PUBCHEM
3035016
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
WIKIPEDIA
AMRUBICIN
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL1186894
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID30869526
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
CHEBI
135779
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
EVMPD
SUB05494MIG
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
DRUG CENTRAL
202
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
CAS
110267-81-7
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
FDA UNII
93N13LB4Z2
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
SMS_ID
100000086937
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
INN
6802
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
DRUG BANK
DB06263
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
USAN
TT-121
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
Related Record Type Details
Structure of AMRUBICIN HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of AMRUBICIN
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