U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CALSED

Approved Use

Non small cell lung cancer, small cell lung cancer.

Launch Date

2002
Primary
CALSED

Approved Use

Non small cell lung cancer, small cell lung cancer

Launch Date

2002
PubMed

PubMed

TitleDatePubMed
[Early phase II study of amrubicin (SM-5887) for superficial bladder cancer: a dose-finding study for intravesical chemotherapy].
2001 Apr
[Early phase II clinical trial of amrubicin hydrochloride in patients with malignant lymphoma].
2001 Nov
[Amrubicin].
2002 May
[Profile of the anti-tumor effects of amrubicin, a completely synthetic anthracycline].
2003 Aug
Transfer of IkappaBalpha gene increase the sensitivity of paclitaxel mediated with caspase 3 activation in human lung cancer cell.
2003 Mar
[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
[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
Phase II trial of amrubicin for treatment of refractory or relapsed small-cell lung cancer: Thoracic Oncology Research Group Study 0301.
2006 Dec 1
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 case of multiple pyomyositis after chemotherapy for lung cancer].
2006 Jun
Amurubicinol-induced eotaxin-3 expression in human NCI-H69 small cell lung carcinoma cells.
2006 Mar
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
Evaluation of the recommended dose and efficacy of amrubicin as second- and third-line chemotherapy for small cell lung cancer.
2007 Aug
Effective combination chemotherapy of carboplatin and paclitaxel in the treatment of a recurrent small-cell lung cancer patient.
2007 Feb
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
Amrubicin, a novel 9-aminoanthracycline, enhances the antitumor activity of chemotherapeutic agents against human cancer cells in vitro and in vivo.
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
Role of P-glycoprotein in accumulation and cytotoxicity of amrubicin and amrubicinol in MDR1 gene-transfected LLC-PK1 cells and human A549 lung adenocarcinoma cells.
2008 Feb 15
Current status of clinical trials for small cell lung cancer.
2008 Jan
Novel systemic therapies for small cell lung cancer.
2008 Mar
[A case of multidrug-resistant squamous cell lung carcinoma responding to S-1 plus CPT-11 combination chemotherapy].
2008 Mar
A case of intimal sarcoma of the pulmonary artery treated with chemoradiotherapy.
2009
Phase I study of amrubicin and vinorelbine in non-small cell lung cancer previously treated with platinum-based chemotherapy.
2009 Apr
Amrubicin for the treatment of advanced lung cancer.
2009 Feb
A phase I study of amrubicin and carboplatin for previously untreated patients with extensive-disease small cell lung cancer.
2009 Jun
Twenty-seven years of phase III trials for patients with extensive disease small-cell lung cancer: disappointing results.
2009 Nov 13
Long-term disease-free survivor of metastatic large-cell neuroendocrine carcinoma of the lung treated with amrubicin and irinotecan.
2009 Sep 21
Voreloxin is an anticancer quinolone derivative that intercalates DNA and poisons topoisomerase II.
2010 Apr 15
Treatment options for small cell lung cancer - do we have more choice?
2010 Feb 16
Imatinib mesylate (STI571) enhances amrubicin-induced cytotoxic activity through inhibition of the phosphatidylinositol 3-kinase/Akt pathway in small cell lung cancer cells.
2010 Jan
The clinical effectiveness and cost-effectiveness of topotecan for small cell lung cancer: a systematic review and economic evaluation.
2010 Mar
Patents

Sample Use Guides

The usual dose is 45 mg/m2 given intravenously once a day for 3 days.
Route of Administration: Intravenous
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
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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
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PRIMARY
MERCK INDEX
m1858
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PRIMARY Merck Index
MESH
C055866
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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
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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
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PRIMARY
EVMPD
SUB05494MIG
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PRIMARY
DRUG CENTRAL
202
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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
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