Details of the Drug

General Information of Drug (ID: DMAE6LK)

Drug Name

Topetecan

Synonyms

TOPOTECAN HYDROCHLORIDE; 119413-54-6; Topotecan Hcl; Hycamptamine hydrochloride; Topotecan (Hydrochloride); Topotecan monohydrochloride; UNII-956S425ZCY; Topotecan hydrochloride [USAN]; Nogitecan hydrochloride; DRG-0288; F S-104864-A; NSC-609699; NSC 609699; NSC609699; 956S425ZCY; (S)-10-((Dimethylamino)methyl)-4-ethyl-4,9-dihydroxy-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione monohydrochloride; NCGC00095189-01; AK-48920; DSSTox_RID_81248; DSSTox_CID_25952

Indication

Disease Entry	ICD 11	Status	REF
Small-cell lung cancer	2C25.Y	Approved	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski):
0

Molecular Weight

457.9

Topological Polar Surface Area

Not Available

Rotatable Bond Count

3

Hydrogen Bond Donor Count

3

Hydrogen Bond Acceptor Count

7

Chemical Identifiers

Formula: C23H24ClN3O5
IUPAC Name: (19S)-8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione;hydrochloride
Canonical SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5CN(C)C)O)N=C4C3=C2)O.Cl
InChI: InChI=1S/C23H23N3O5.ClH/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20;/h5-8,27,30H,4,9-11H2,1-3H3;1H/t23-;/m0./s1
InChIKey: DGHHQBMTXTWTJV-BQAIUKQQSA-N

Cross-matching ID

PubChem CID: 60699
CAS Number: 119413-54-6
TTD ID: D0Z4XW

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
DNA topoisomerase I (TOP1)	TTGTQHC	TOP1_HUMAN	Inhibitor	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Small-cell lung cancer

ICD Disease Classification

2C25.Y

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
DNA topoisomerase I (TOP1)	DTT	TOP1	6.65E-01	0.2	0.39

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 020671.
2	Clinical pipeline report, company report or official report of GlaxoSmithKline (2009).
3	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
4	Luteolin, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase I. Biochem J. 2002 Sep 1;366(Pt 2):653-61.
5	Impact of natural products on developing new anti-cancer agents. Chem Rev. 2009 Jul;109(7):3012-43.
6	Characterization of protein kinase chk1 essential for the cell cycle checkpoint after exposure of human head and neck carcinoma A253 cells to a novel topoisomerase I inhibitor BNP1350. Mol Pharmacol.2000 Mar;57(3):453-9.
7	Topoisomerase I inhibitors: camptothecins and beyond. Nat Rev Cancer. 2006 Oct;6(10):789-802.
8	Phase I study of topoisomerase I inhibitor exatecan mesylate (DX-8951f) given as weekly 24-hour infusions three of every four weeks. Clin Cancer Res. 2001 Dec;7(12):3963-70.
9	Edotecarin: a novel topoisomerase I inhibitor. Clin Colorectal Cancer. 2005 May;5(1):27-36.
10	Rubitecan. Expert Opin Investig Drugs. 2006 Jan;15(1):71-9.
11	Nonclinical pharmacokinetics and activity of etirinotecan pegol (NKTR-102), a long-acting topoisomerase 1 inhibitor, in multiple cancer models. Cancer Chemother Pharmacol. 2014 Dec;74(6):1125-37.