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=C2C3=C(C=C1)N(CCNCCO)N=C3C4=CC=CC(O)=C4C2=O.OCCNCCNC5=C6C7=C(C=C5)N(CCNCCO)N=C7C8=CC=CC(O)=C8C6=O

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

Molecular Formula	C22H27N5O4
Molecular Weight	425.4809
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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
A structure-based 3D-QSAR study of anthrapyrazole analogues of the anticancer agents losoxantrone and piroxantrone.	2006-07-25	16859314
Structure-activity studies with cytotoxic anthrapyrazoles.	2006-06	16685398
The oxidative biotransformation of losoxantrone (CI-941).	2002-04	11901102
Phase I study of the combination of losoxantrone and cyclophosphamide in patients with refractory solid tumours.	2002-02-12	11870533
Separation methods for anthraquinone related anti-cancer drugs.	2001-11-25	11817028
Elimination pathways of [14C]losoxantrone in four cancer patients.	2001-02	11159796
DNA-interactive anticancer aza-anthrapyrazoles: biophysical and biochemical studies relevant to the mechanism of action.	2001-01	11125029
A novel 9-aza-anthrapyrazole effective against human prostatic carcinoma xenografts.	2001	11574780
A multicenter phase II trial of losoxantrone (DuP-941) in hormone-refractory metastatic prostate cancer.	2000-04	10778959
The displacement of iron(III) from its complexes with the anticancer drugs piroxantrone and losoxantrone by the hydrolyzed form of the cardioprotective agent dexrazoxane.	2000-01-22	10643663
Monotherapy of metastatic breast cancer: a review of newer agents.	1999	10337368

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:15:45 GMT 2025` Edited by `admin` on `Mon Mar 31 18:15:45 GMT 2025`
Record UNII	W6E275IURX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOSOXANTRONE HYDROCHLORIDE

Official Name

English

LOSOXANTRONE HYDROCHLORIDE HYDRATE

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C2107