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T2705

Sigma-Aldrich

Topotecan hydrochloride hydrate

≥98% (HPLC and enzymatic), powder, topoisomerase I inhibitor

Synonym(s):

9-[(dimethylamino)methyl]-10-hydroxy-(20S)-camptothecin hydrochloride hydrate, NSC-609669 hydrochloride hydrate, SKF-104864A hydrochloride hydrate, hycamptamine hydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):
C23H23N3O5 · xHCl · yH2O
CAS Number:
123948-87-8
Molecular Weight:
421.45 (anhydrous free base basis)
MDL number:
MFCD00870670
UNSPSC Code:
12352200
PubChem Substance ID:
329826724
NACRES:
NA.77

Product Name

Topotecan hydrochloride hydrate, ≥98% (HPLC and enzymatic)

Quality Level

100

Assay

≥98% (HPLC and enzymatic)

form

powder

storage condition

desiccated
protect from light

color

yellow

solubility

DMSO: ≥20 mg/mL

originator

GlaxoSmithKline

storage temp.

−20°C

SMILES string

[n]21c(cc5c([c]2=O)COC(=O)[C@]5(O)CC)c3nc4c(cc3C1)c(c(cc4)O)CN(C)C

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

InChI key

UCFGDBYHRUNTLO-QHCPKHFHSA-N

Gene Information

human ... TOP1MT(116447)

Application

Topotecan has been used as a positive control for the identification and analysis of HIF-1α and VEGF inhibitors in human glioma cells under hypoxic conditions1. It has also been used for in vitro apoptosis assays in PA317 cells2.

Biochem/physiol Actions

Topotecan is a topoisomerase I inhibitor and an apoptosis inducer. It is a potent antineoplastic agent.

Features and Benefits

This compound is a featured product for ADME Tox and Apoptosis research. Discover more featured ADME Tox and Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

This product is soluble in water, however, the concentration has not been determined. Various sources state this chemical can be solubilized in water at greater than 1 mg/mL.
Topotecan hydrochloride hydrate is soluble in DMSO at a concentration that is greater than or equal to 20 mg/ml.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H340,H361d

Hazard Classifications

Muta. 1B - Repr. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

监管及禁止进口产品

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Certificates of Analysis (COA)

Lot/Batch Number
0000314301
0000314301
0000239575
0000218334
0000239575

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Ian F King et al.
Nature, 501(7465), 58-62 (2013-09-03)
Topoisomerases are expressed throughout the developing and adult brain and are mutated in some individuals with autism spectrum disorder (ASD). However, how topoisomerases are mechanistically connected to ASD is unknown. Here we find that topotecan, a topoisomerase 1 (TOP1) inhibitor
Ya-Lin Lu et al.
Proceedings of the National Academy of Sciences of the United States of America, 118(22) (2021-05-26)
Neuron-enriched microRNAs (miRNAs), miR-9/9* and miR-124 (miR-9/9*-124), direct cell fate switching of human fibroblasts to neurons when ectopically expressed by repressing antineurogenic genes. How these miRNAs function after the repression of fibroblast genes for neuronal fate remains unclear. Here, we
Kaleem Ashraf et al.
Pediatric blood & cancer, 60(10), 1636-1641 (2013-05-08)
Reports of responses and toxicities of salvage therapies for relapsed neuroblastoma are rare and often confounded by effects of additional treatments. Our objective was to describe the outcomes and toxicities for a topotecan and cyclophosphamide (TOPO/CTX) regimen for first relapse
Israel Zighelboim et al.
Gynecologic oncology, 130(1), 64-68 (2013-04-18)
We evaluated the activity and safety of the combination of topotecan, cisplatin and bevacizumab in patients with recurrent or persistent carcinoma of the cervix. Eligible patients had persistent or recurrent cervical cancer not amenable to curative intent treatment. No prior
Iben Kümler et al.
Breast cancer research and treatment, 138(2), 347-358 (2013-03-21)
Following treatment with anthracyclines and taxanes, few established options exist for the treatment of metastatic breast cancer (MBC). Although the topoisomerase 1 inhibitors irinotecan, etirinotecan, and topotecan have been used in clinical trials on MBC, the drugs have never been
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