LOSOXANTRONE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C22H27N5O4.4ClH.H2O
Molecular Weight	1014.821
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.Cl.Cl.Cl.Cl.OCCNCCNC1=CC=C2N(CCNCCO)N=C3C2=C1C(=O)C4=C3C=CC=C4O.OCCNCCNC5=CC=C6N(CCNCCO)N=C7C6=C5C(=O)C8=C7C=CC=C8O

InChI

InChIKey=CNQCTSLNJJVSAU-UHFFFAOYSA-N

InChI=1S/2C22H27N5O4.4ClH.H2O/c2*28-12-9-23-6-7-25-15-4-5-16-20-19(15)22(31)18-14(2-1-3-17(18)30)21(20)26-27(16)11-8-24-10-13-29;;;;;/h2*1-5,23-25,28-30H,6-13H2;4*1H;1H2

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
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
Phase I study of the combination of losoxantrone and cyclophosphamide in patients with refractory solid tumours.	2002 Feb 12	11870533

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 HYDROCHLORIDE

Official Name

English

LOSOXANTRONE DIHYDROCHLORIDE HEMIHYDRATE

Common 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, dihydrochloride, hemihydrate

Common Name

English

LOSOXANTRONE HYDROCHLORIDE [USAN]

Common Name

English

DUP-941

Code

English

DUP 941

Code

English

NSC-357885

Code

English

CI-941

Code

English

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

Common Name

English

PD-113785

Code

English

Losoxantrone hydrochloride hydrate [WHO-DD]

Common Name

English

LOSOXANTRONE HYDROCHLORIDE HYDRATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2107