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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H25NO9.ClH
Molecular Weight 519.928
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMRUBICIN HYDROCHLORIDE

SMILES

Cl.[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=BHMLHEQFWVQAJS-IITOGVPQSA-N
InChI=1S/C25H25NO9.ClH/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;1H/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
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

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
[Recent progress in the treatment of ED small cell lung cancer].
2002 May
Progress in treatment of small-cell lung cancer: role of CPT-11.
2003 Dec 15
Mechanism of apoptosis induced by doxorubicin through the generation of hydrogen peroxide.
2005 Feb 11
The combination effect of amrubicin with cisplatin or irinotecan for small-cell lung cancer cells.
2006 Apr
Pharmacokinetics of amrubicin and its active metabolite amrubicinol in lung cancer patients.
2006 Feb
Phase I study of amrubicin hydrochloride and cisplatin in patients previously treated for advanced non-small cell lung cancer.
2006 Jan
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
Experimental designs for phase I and phase I/II dose-finding studies.
2006 Mar 13
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
[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
Phase II study of amrubicin, 9-amino-anthracycline, in patients with advanced non-small-cell lung cancer: a West Japan Thoracic Oncology Group (WJTOG) study.
2007 Aug
Sequential treatment with SN-38 followed by 5-fluorouracil shows synergistic cytotoxic activity in small cell lung cancer cells.
2008 Apr
Current status of clinical trials for small cell lung cancer.
2008 Jan
Pulse gradient, large-volume injection, high-throughput ultra-performance liquid chromatographic/tandem mass spectrometry bioanalysis for measurement of plasma amrubicin and its metabolite amrubicinol.
2008 Jun 6
Novel systemic therapies for small cell lung cancer.
2008 Mar
Phase I study of amrubicin and vinorelbine in non-small cell lung cancer previously treated with platinum-based chemotherapy.
2009 Apr
Next-generation anthracycline for the management of small cell lung cancer: focus on amrubicin.
2009 Feb 6
A phase I study of amrubicin and carboplatin for previously untreated patients with extensive-disease small cell lung cancer.
2009 Jun
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
Co-administration of irinotecan decreases the plasma concentration of an active metabolite of amrubicin, amrubicinol in rats.
2010 Apr
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
The clinical effectiveness and cost-effectiveness of topotecan for small cell lung cancer: a systematic review and economic evaluation.
2010 Mar
Phase II study of amrubicin as second-line therapy in patients with platinum-refractory small-cell lung cancer.
2010 May 20
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 16:25:42 GMT 2023
Edited
by admin
on Fri Dec 15 16:25:42 GMT 2023
Record UNII
EUL6MP8FZW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMRUBICIN HYDROCHLORIDE
JAN   MI   USAN   WHO-DD  
USAN  
Official Name English
SM-5887
Code English
CALSED
Brand Name English
Amrubicin hydrochloride [WHO-DD]
Common Name English
AMRUBICIN HYDROCHLORIDE [MI]
Common Name English
(+)-(7S,9S)-9-ACETYL-9-AMINO-7-((2-DEOXY-.BETA.-D-ERYTHRO-PENTOPYRANOSYL)OXY)-6,11-DIHYDROXY-7,8,9,10-TETRAHYDROTETRACENE-5,12-DIONE HYDROCHLORIDE
Common Name English
AMRUBICIN HYDROCHLORIDE [JAN]
Common Name English
SM 5887
Code English
AMRUBICIN HYDROCHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
EU-Orphan Drug EU/3/08/538
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
Code System Code Type Description
FDA UNII
EUL6MP8FZW
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY
CHEBI
135779
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY
MERCK INDEX
m1858
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY Merck Index
DRUG BANK
DBSALT001934
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY
PUBCHEM
114897
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY
EVMPD
SUB20586
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY
NCI_THESAURUS
C47948
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY
CAS
110311-30-3
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY
ChEMBL
CHEMBL1186894
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID10911577
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY
SMS_ID
100000085964
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY
USAN
TT-122
Created by admin on Fri Dec 15 16:25:42 GMT 2023 , Edited by admin on Fri Dec 15 16:25:42 GMT 2023
PRIMARY
Related Record Type Details
Structure of AMRUBICIN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of AMRUBICIN
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