119413-54-6 Topotecan HCl AKSci H030
 
 
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  H030    AKSci Reference Standard
Topotecan HCl
, >98% (HPLC)
 
Hycamtin
NSC 609699




IDENTITY
CAS Number:119413-54-6
MDL Number:MFCD00866235
MF:C23H24ClN3O5
MW:457.91
SPECIFICATIONS & PROPERTIES
Purity:>98% (HPLC)
Spectra:LCMS, HPLC
Physical Form:Light yellow to orange to green crystalline powder
Melting Point:213-218°C
Long-Term Storage:Store long-term at 2-8°C

BIOLOGICAL INFO
Solubility:DMSO: 92mg/mL; H2O: 92mg/mL; EtOH: <1mg/mL
Application(s):DNA Topoisomerase I Inhibitor
Form:HCl salt

REVIEW

 Topotecan has the same mechanism of action as irinotecan and is believed to exert its cytotoxic effects during the S-phase of DNA synthesis. Topoisomerase I relieves torsional strain in DNA by inducing reversible single strand breaks. Topotecan binds to the topoisomerase I-DNA complex and prevents religation of these single strand breaks. This ternary complex interferes with the moving replication fork, which leads to the induction of replication arrest and lethal double-stranded breaks in DNA. As mammalian cells cannot efficiently repair these double strand breaks, the formation of this ternary complex eventually leads to apoptosis (programmed cell death). Topotecan mimics a DNA base pair and binds at the site of DNA cleavage by intercalating between the upstream (-1) and downstream (+1) base pairs. Intercalation displaces the downstream DNA, thus preventing religation of the cleaved strand. By specifically binding to the enzyme-substrate complex, Topotecan acts as an uncompetitive inhibitor.

REFERENCES
[1]Kollmannsberger C, Mross K, Jakob A, Kanz L, Bokemeyer C: Topotecan - A novel topoisomerase I inhibitor: pharmacology and clinical experience. Oncology. 1999;56(1):1-12.
[2] Herben VM, ten Bokkel Huinink WW, Beijnen JH: Clinical pharmacokinetics of topotecan. Clin Pharmacokinet. 1996 Aug;31(2):85-102.
[3] Dennis MJ, Beijnen JH, Grochow LB, van Warmerdam LJ: An overview of the clinical pharmacology of topotecan. Semin Oncol. 1997 Feb;24(1 Suppl 5):S5-12-S5-18.
[4] Puri, S. C.; Synthetic Communications 2004, V34(15), P2857-2862

GHS

Pictograms

Signal Word
Warning

Hazard Statements
H315; H319; H335

Precautionary Statements
P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501


Current as of February 17, 2020

AKSci Reference Standards are high-purity, low-impurity compounds suitable for use as standards.


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For research use only. Not for diagnostic or therapeutic use.
Not for human use.


CATEGORIES

 APIs and Bioactives > Chemotherapeutics


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