LURTOTECAN DIHYDROCHLORIDE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H30N4O6.2ClH
Molecular Weight	591.483
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.CC[C@@]1(O)C(=O)OCC2=C1C=C3N(CC4=C3N=C5C=C6OCCOC6=CC5=C4CN7CCN(C)CC7)C2=O

InChI

InChIKey=ORIWMYRMOGIXGG-ZXVJYWQYSA-N

InChI=1S/C28H30N4O6.2ClH/c1-3-28(35)20-11-22-25-18(14-32(22)26(33)19(20)15-38-27(28)34)17(13-31-6-4-30(2)5-7-31)16-10-23-24(12-21(16)29-25)37-9-8-36-23;;/h10-12,35H,3-9,13-15H2,1-2H3;2*1H/t28-;;/m0../s1

HIDE SMILES / InChI

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

Molecular Formula	C28H30N4O6
Molecular Weight	518.561
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800004939 | https://www.cancer.gov/publications/dictionaries/cancer-drug/def/lurtotecan

Lurtotecan is a semisynthetic analog of camptothecin with antineoplastic activity. It is an inhibitor of DNA topoisomerase I. Liposomal formulation of lurtotecan was being studied in the treatment of cancer. Lurtotecan development has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase I 60 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9632354 \| https://www.ncbi.nlm.nih.gov/pubmed/9328158	Inhibitor 8504

PubMed

Title	Date	PubMed
Organic anion-transporting polypeptide 1B1 mediates transport of Gimatecan and BNP1350 and can be inhibited by several classic ATP-binding cassette (ABC) B1 and/or ABCG2 inhibitors.	2009-04	19139163
Tumour-targeted nanomedicines: principles and practice.	2008-08-05	18648371
Experimental designs for phase I and phase I/II dose-finding studies.	2006-03-13	16434987
Stealth liposomes: review of the basic science, rationale, and clinical applications, existing and potential.	2006	17717971
Gateways to clinical trials.	2005-12	16395422
Gateways to clinical trials.	2005-09-24	16179960
Randomized trial of two intravenous schedules of the topoisomerase I inhibitor liposomal lurtotecan in women with relapsed epithelial ovarian cancer: a trial of the national cancer institute of Canada clinical trials group.	2005-03-20	15699482
Alternative administration of camptothecin analogues.	2005-03	16296757
Phase II study of OSI-211 (liposomal lurtotecan) in patients with metastatic or loco-regional recurrent squamous cell carcinoma of the head and neck. An EORTC New Drug Development Group study.	2004-12	15571957
Gateways to clinical trials.	2004-09	15538546
Topoisomerase I inhibitors in the treatment of gastrointestinal cancer: from intravenous to oral administration.	2004-09	15377400
A phase 1 study of OSI-211 given as an intravenous infusion days 1, 2, and 3 every three weeks in patients with solid cancers.	2004-08	15122073
Gateways to clinical trials.	2004-06	15319815
Phase I and pharmacokinetic study of a low-clearance, unilamellar liposomal formulation of lurtotecan, a topoisomerase 1 inhibitor, in patients with advanced leukemia.	2004-04-01	15042679
A phase II study of liposomal lurtotecan (OSI-211) in patients with topotecan resistant ovarian cancer.	2004-04	15047241
A phase I study of OSI-211 and cisplatin as intravenous infusions given on days 1, 2 and 3 every 3 weeks in patients with solid cancers.	2004-04	15033677
OSI-211, a novel liposomal topoisomerase I inhibitor, is active in SCID mouse models of human AML and ALL.	2003-11	12859997
Are there any better camptothecins than the ones we have?	2003-10	16258452
Gateways to clinical trials.	2003-09-02	12949633
[A symphony for the camptothecins].	2003-03	12801826
Phase I and pharmacologic study of liposomal lurtotecan, NX 211: urinary excretion predicts hematologic toxicity.	2002-03-01	11870164
Structural identification and biological activity of 7-methyl-10,11-ethylenedioxy-20(S)-camptothecin, a photodegradant of lurtotecan.	2002-03	11895919
Population pharmacokinetic and dynamic analysis of the topoisomerase I inhibitor lurtotecan in phase II studies.	2002-02	12003197
Camptothecins: a review of their chemotherapeutic potential.	2002	12269849
Quantitation of camptothecin and related compounds.	2001-11-25	11817024
Biodistribution of NX211, liposomal lurtotecan, in tumor-bearing mice.	2001-03	11290871
Modulation of camptothecin analogs in the treatment of cancer: a review.	2001-02	11261892

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:26:27 GMT 2025` Edited by `admin` on `Mon Mar 31 21:26:27 GMT 2025`
Record UNII	S31P37BX03
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GI-147211C

Preferred Name

English

LURTOTECAN DIHYDROCHLORIDE

Official Name

English

(8S)-8-ETHYL-2,3-DIHYDRO-8-HYDROXY-15-((4-METHYL-1-PIPERAZINYL)METHYL)-11H-P-DIOXINO(2,3-G)PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-9,12(8H,14H)-DIONE DIHYDROCHLORIDE

Common Name

English

LURTOTECAN DIHYDROCHLORIDE [USAN]

Common Name

English

GI147211C

Code

English

11H-1,4-DIOXINO(2,3-G)PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-9,12(8H,14H)-DIONE, 8-ETHYL-2,3-DIHYDRO-8-HYDROXY-15-((4-METHYL-1-PIPERAZINYL)METHYL)-, DIHYDROCHLORIDE, (S)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2843