T2705

Topotecan hydrochloride hydrate

Name: Topotecan hydrochloride hydrate
Brand: SIGMA

≥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)

UNSPSC Code:

12352200

PubChem Substance ID:

329826724

NACRES:

NA.77

MDL number:

MFCD00870670

Product Name

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

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

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

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

GHS08

signalword

Danger

hcodes

H340,H361d

pcodes

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Muta. 1B - Repr. 2

Storage Class

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

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A systematic review on topoisomerase 1 inhibition in the treatment of metastatic breast cancer.

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

Novel ABCG2 Antagonists Reverse Topotecan-Mediated Chemotherapeutic Resistance in Ovarian Carcinoma Xenografts.

Jerec W Ricci et al.

Molecular cancer therapeutics, 15(12), 2853-2862 (2016-09-28)

Chemotherapeutic resistance remains a challenge in the treatment of ovarian carcinoma, especially in recurrent disease. Despite the fact that most patients with newly diagnosed tumors attain complete remission following cytoreductive surgery and chemotherapy, ovarian carcinoma has a recurrence rate that

Real-Time Positron Emission Tomography Evaluation of Topotecan Brain Kinetics after Ultrasound-Mediated Blood-Brain Barrier Permeability.

Andrei Molotkov et al.

Pharmaceutics, 13(3) (2021-04-04)

Glioblastoma (GBM) is the most common primary adult brain malignancy with an extremely poor prognosis and a median survival of fewer than two years. A key reason for this high mortality is that the blood-brain barrier (BBB) significantly restricts systemically

Multicenter phase II trial of topotecan, cisplatin and bevacizumab for recurrent or persistent cervical cancer.

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

Topoisomerases facilitate transcription of long genes linked to autism.

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

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