LURTOTECAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H30N4O6
Molecular Weight	518.561
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=RVFGKBWWUQOIOU-NDEPHWFRSA-N

InChI=1S/C28H30N4O6/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/t28-/m0/s1

HIDE SMILES / InChI

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 59 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9632354 \| https://www.ncbi.nlm.nih.gov/pubmed/9328158	Inhibitor 8297

PubMed

Title	Date	PubMed
Modulation of camptothecin analogs in the treatment of cancer: a review.	2001 Feb	11261892
Biodistribution of NX211, liposomal lurtotecan, in tumor-bearing mice.	2001 Mar	11290871
Quantitation of camptothecin and related compounds.	2001 Nov 25	11817024
Camptothecins: a review of their chemotherapeutic potential.	2002	12269849
Population pharmacokinetic and dynamic analysis of the topoisomerase I inhibitor lurtotecan in phase II studies.	2002 Feb	12003197
Structural identification and biological activity of 7-methyl-10,11-ethylenedioxy-20(S)-camptothecin, a photodegradant of lurtotecan.	2002 Mar	11895919
Phase I and pharmacologic study of liposomal lurtotecan, NX 211: urinary excretion predicts hematologic toxicity.	2002 Mar 1	11870164
Gateways to clinical trials.	2003 Jul-Aug	12949633
[A symphony for the camptothecins].	2003 Mar	12801826
OSI-211, a novel liposomal topoisomerase I inhibitor, is active in SCID mouse models of human AML and ALL.	2003 Nov	12859997
Are there any better camptothecins than the ones we have?	2003 Oct	16258452
A phase II study of liposomal lurtotecan (OSI-211) in patients with topotecan resistant ovarian cancer.	2004 Apr	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 Apr	15033677
Phase I and pharmacokinetic study of a low-clearance, unilamellar liposomal formulation of lurtotecan, a topoisomerase 1 inhibitor, in patients with advanced leukemia.	2004 Apr 1	15042679
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 Aug	15122073
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 Dec	15571957
Gateways to clinical trials.	2004 Jun	15319815
Gateways to clinical trials.	2004 Sep	15538546
Topoisomerase I inhibitors in the treatment of gastrointestinal cancer: from intravenous to oral administration.	2004 Sep	15377400
Gateways to clinical trials.	2005 Dec	16395422
Gateways to clinical trials.	2005 Jul-Aug	16179960
Alternative administration of camptothecin analogues.	2005 Mar	16296757
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 Mar 20	15699482
Stealth liposomes: review of the basic science, rationale, and clinical applications, existing and potential.	2006	17717971
Experimental designs for phase I and phase I/II dose-finding studies.	2006 Mar 13	16434987
Tumour-targeted nanomedicines: principles and practice.	2008 Aug 5	18648371
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 Apr	19139163

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:14:55 UTC 2023` Edited by `admin` on `Sat Dec 16 17:14:55 UTC 2023`
Record UNII	4J1L80T08I
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LURTOTECAN

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

Common Name

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)-, (S)

Common Name

English

lurtotecan [INN]

Common Name

English

Lurtotecan [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2843