NAMITECAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H22N4O5
Molecular Weight	434.4446
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@@]1(O)C(=O)OCC2=C1C=C3N(CC4=C(\C=N\OCCN)C5=C(C=CC=C5)N=C34)C2=O

InChI

InChIKey=IBTISPLPBBHVSU-UVOOVGFISA-N

InChI=1S/C23H22N4O5/c1-2-23(30)17-9-19-20-15(11-27(19)21(28)16(17)12-31-22(23)29)14(10-25-32-8-7-24)13-5-3-4-6-18(13)26-20/h3-6,9-10,30H,2,7-8,11-12,24H2,1H3/b25-10+/t23-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H22N4O5
Molecular Weight	434.4446
Charge	0
Count

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

Description
Sources: https://adisinsight.springer.com/drugs/800025255 | https://www.ncbi.nlm.nih.gov/pubmed/22680917

Namitecan (ST1968) is a camptothecin analogue being developed by sigma-tau (a subsidiary of Alfasigma) in Switzerland for the treatment of cancer. Namitecan, a novel hydrophilic camptothecin analog of the 7-oxyiminomethyl series, was selected for clinical development on the basis of its promising preclinical efficacy. Namitecan is a topoisomerase I inhibitor. Namitecan exhibited an acceptable toxicity profile, with neutropenia being the dose-limiting toxic effect, and clinical benefit was appreciable in patients with different tumor types, particularly bladder and endometrium carcinomas.

Originator

Approval Year

PubMed

Title	Date	PubMed
Synergistic antitumor activity of cetuximab and namitecan in human squamous cell carcinoma models relies on cooperative inhibition of EGFR expression and depends on high EGFR gene copy number.	2014 Feb 15	24327272

Patents

Sample Use Guides

In Vivo Use Guide

Advanced solid tumours: With a target for haematological dose-limiting toxicity of <20%, the recommended dose was defined as 12.5 mg for the D1,8 regimen, 23 mg for the once every 3 week regimen and 7 mg for the D1-3 regimen.

Route of Administration: Intravenous

In Vitro Use Guide

The cellular response to Namitecan was heterogeneous with IC(50) (2 h) ranging between 0.14 and 13.26 uM, whereas SN38 (the active metabolite of Irinotecan) appeared more effective (IC(50): 0.03-11.7 uM). Interestingly, prolonged drug incubation times up to 72 h enhanced Namitecan cytotoxicity, with similar colony inhibition curves between the two analogues (IC(50), nM-SN38: 0.9 ± 0.2; Namitecan: 0.7 ± 0.4).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:38:12 UTC 2023` Edited by `admin` on `Sat Dec 16 17:38:12 UTC 2023`
Record UNII	X34Z8N66T3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NAMITECAN

Official Name

English

(4S)-11-((E)-((2-AMINOETHOXY)IMINO)METHYL)-4-ETHYL-4-HYDROXY-1,12-DIHYDRO-14H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H)-DIONE

Systematic Name

English

Namitecan [WHO-DD]

Common Name

English

namitecan [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2843