LOSOXANTRONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H27N5O4
Molecular Weight	425.4809
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCCNCCNC1=CC=C2N(CCNCCO)N=C3C2=C1C(=O)C4=C3C=CC=C4O

InChI

InChIKey=YROQEQPFUCPDCP-UHFFFAOYSA-N

InChI=1S/C22H27N5O4/c28-12-9-23-6-7-25-15-4-5-16-20-19(15)22(31)18-14(2-1-3-17(18)30)21(20)26-27(16)11-8-24-10-13-29/h1-5,23-25,28-30H,6-13H2

HIDE SMILES / InChI

Description
Sources: https://adisinsight.springer.com/drugs/800000754 | DOI: 10.1016/0959-8049(93)91029-K | Weber, G.F. (2015) Molecular Therapies of Cancer, page 65, retrieved from: https://books.google.ru/books?id=dhs_CgAAQBAJ

Losoxantrone is an anthrapyrazole that induces both single and double strand breaks in DNA and is a potent inhibitor of DNA synthesis. The drug is in clinical trials for the treatment of breast cancer and of prostate cancer that is refractory to androgen ablation. Acute toxicity is negligible. Losoxantrone may be less cardiotoxic than doxorubicin. Up to 40% of patients encounter alopecia. 3% of patients develop congestive heart failure. Losoxantrone had been in phase II clinical trial for the treatment of breast and prostate cancer. However, this development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Monotherapy of metastatic breast cancer: a review of newer agents.	1999	10337368
The displacement of iron(III) from its complexes with the anticancer drugs piroxantrone and losoxantrone by the hydrolyzed form of the cardioprotective agent dexrazoxane.	1999 Nov-Dec	10643663
A multicenter phase II trial of losoxantrone (DuP-941) in hormone-refractory metastatic prostate cancer.	2000 Apr	10778959
A novel 9-aza-anthrapyrazole effective against human prostatic carcinoma xenografts.	2001	11574780
Elimination pathways of [14C]losoxantrone in four cancer patients.	2001 Feb	11159796
DNA-interactive anticancer aza-anthrapyrazoles: biophysical and biochemical studies relevant to the mechanism of action.	2001 Jan	11125029
The oxidative biotransformation of losoxantrone (CI-941).	2002 Apr	11901102
Phase I study of the combination of losoxantrone and cyclophosphamide in patients with refractory solid tumours.	2002 Feb 12	11870533
A structure-based 3D-QSAR study of anthrapyrazole analogues of the anticancer agents losoxantrone and piroxantrone.	2006 Jul-Aug	16859314
Structure-activity studies with cytotoxic anthrapyrazoles.	2006 Jun	16685398

Patents

Sample Use Guides

In Vivo Use Guide

Starting dose of 50 mg/m2 q3 weeks. Dose adjustments could be made anytime after the first dose

Route of Administration: Intravenous

Name

Type

Language

LOSOXANTRONE

Official Name

English

7-HYDROXY-2-(2-((2-HYDROXYETHYL)AMINO)ETHYL)-5-((2-((2-HYDROXYETHYL)AMINO)ETHYL)AMINO)ANTHRA(1,9-CD)PYRAZOL-6(2H)-ONE

Systematic Name

English

Losoxantrone [WHO-DD]

Common Name

English

BIANTRAZOLE

Common Name

English

C-1941

Code

English

losoxantrone [INN]

Common Name

English

ANTHRA(1,9-CD)PYRAZOL-6(2H)-ONE, 7-HYDROXY-2-(2-((2-HYDROXYETHYL)AMINO)ETHYL)-5-((2-((2-HYDROXYETHYL)AMINO)ETHYL)AMINO)

Common Name

English

BIANTHRAZOLE

Common Name

English

ANTHRAPYRAZOLONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2107