Topotecan - Moligand™, 10mM in DMSO , DNA topoisomerase I, mitochondrial inhibitor, CAS No.123948-87-8, DNA topoisomerase I, mitochondrial inhibitor

CAS: 123948-87-8 Cat. No.: T421032 Molecular Weight: 421.45 EC Number: 687-471-1

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

(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 | (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 | BP-29353 | B

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Topotecan is an antineoplastic agent used to treat ovarian cancer that works by inhibitingDNA topoisomerases.

Targets

Topo I

Specifications

Synonyms

(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 | (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 | BP-29353 | B

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

Topotecan is an antineoplastic agent used to treat ovarian cancer that works by inhibiting DNA topoisomerases.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

DNA topoisomerase I, mitochondrial inhibitor

Product Properties

• ALogP: 0.5

Names and Identifiers

• Pubchem Sid: 528767519
• Canonical Smiles: CC[C@@]1(O)C(=O)OCc2c1cc1-c3nc4ccc(O)c(CN(C)C)c4cc3Cn1c2=O
• 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
• InChIKey: UCFGDBYHRUNTLO-QHCPKHFHSA-N
• INCHI: 1S/C23H23N3O5/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/t23-/m0/s1
• Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5CN(C)C)O)N=C4C3=C2)O
• Molecular Weight: 421.45

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Camptothecins

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Camptothecins
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Camptothecins
• Alternative Parents: Hydroxyquinolines Pyranopyridines Pyridinones 1-hydroxy-2-unsubstituted benzenoids Aralkylamines Tertiary alcohols Heteroaromatic compounds Trialkylamines Amino acids and derivatives Lactones Lactams Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Camptothecin - Hydroxyquinoline - Pyranopyridine - Quinoline - 1-hydroxy-2-unsubstituted benzenoid - Pyridinone - Aralkylamine - Benzenoid - Pyridine - Heteroaromatic compound - Tertiary alcohol - Carboxylic acid ester - Amino acid or derivatives - Lactam - Tertiary aliphatic amine - Tertiary amine - Lactone - Oxacycle - Carboxylic acid derivative - Azacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Organopnictogen compound - Alcohol - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
• External Descriptors: pyranoindolizinoquinoline

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

HIF1A Tchem Hypoxia-inducible factor 1-alpha (2 Activities)

Discover Target: HIF1A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TOP1 Tclin DNA topoisomerase 1 (7 Activities)

Discover Target: TOP1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Molecular Weight: 421.400 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 421.164 Da
• Monoisotopic Mass: 421.164 Da
• Topological Polar Surface Area: 103.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 867.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Tsz Cheung Chong, Iris L. K. Wong, Jiahua Cui, Man Chun Law, Xuezhen Zhu, Xuesen Hu, Jason W. Y. Kan, Clare S. W. Yan, Tak Hang Chan, Larry M. C. Chow.  (2022)  Characterization of a Potent, Selective, and Safe Inhibitor, Ac15(Az8)2, in Reversing Multidrug Resistance Mediated by Breast Cancer Resistance Protein (BCRP/ABCG2).  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  23  (21): (13261).  [PMID:36362047] [10.3390/ijms232113261]

2. Chen Biqing, Gao Jiayin, Sun Haizhu, Zhao Yinghan, Liu Yan, Lv Xinpeng, Qiu Xiaohong, Li Yang.  (2025)  Application of surface-enhanced Raman scattering combined with artificial intelligence for multiplex detection of chemotherapeutic agents used in solid tumors.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,      [PMID:41324706] [10.1007/s00216-025-06241-z]