MedKoo Cat#: 414450 | Name: Topotecan acetate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Topotecan is a topoisomerase inhibitor. It is a synthetic, water-soluble analog of the natural chemical compound camptothecin. In physiological environments, topotecan is in equilibrium with its inactive carboxylate form. Topotecan's active lactone form intercalates between DNA bases in the topoisomerase-I cleavage complex. The binding of topotecan in the cleavage complex prevents topoisomerase-I from religating the nicked DNA strand after relieving the strain. This intercalation therefore traps the topoisomerase-I in the cleavage complex bound to the DNA. When the replication-fork collides with the trapped topoisomerase-I, DNA damage occurs. This disruption prevents DNA replication and ultimately leads to cell death.

Chemical Structure

Topotecan acetate
Topotecan acetate
CAS#123948-88-9 (acetate)

Theoretical Analysis

MedKoo Cat#: 414450

Name: Topotecan acetate

CAS#: 123948-88-9 (acetate)

Chemical Formula: C25H27N3O7

Exact Mass: 421.1638

Molecular Weight: 481.51

Elemental Analysis: C, 62.36; H, 5.65; N, 8.73; O, 23.26

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 850.00 2 Weeks
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Synonym
Topotecan acetate; NSC 609699 NSC-609699 NSC609699; SKF S104864A. SKF 104864 A SKF-104864-A; SKF104864A; TOPO. Hycamtamine; Nogitecan; Topotecan; Topocecan free base
IUPAC/Chemical Name
1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 10-((dimethylamino)methyl)-4-ethyl-4,9-dihydroxy-, (S)-, acetic acid
InChi Key
LYUVKGDSGUQAAH-BQAIUKQQSA-N
InChi Code
InChI=1S/C23H23N3O5.C2H4O2/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;1-2(3)4/h5-8,27,30H,4,9-11H2,1-3H3;1H3,(H,3,4)/t23-;/m0./s1
SMILES Code
O=C1[C@](O)(CC)C2=C(CO1)C(N3CC4=CC5=C(CN(C)C)C(O)=CC=C5N=C4C3=C2)=O.CC(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 481.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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Topotecan. 2021 Aug 16. PMID: 30372006. 4: Upadhyayula PS, Spinazzi EF, Argenziano MG, Canoll P, Bruce JN. Convection Enhanced Delivery of Topotecan for Gliomas: A Single-Center Experience. Pharmaceutics. 2020 Dec 30;13(1):39. doi: 10.3390/pharmaceutics13010039. PMID: 33396668; PMCID: PMC7823846. 5: Rosen VM, Guerra I, McCormack M, Nogueira-Rodrigues A, Sasse A, Munk VC, Shang A. Systematic Review and Network Meta-Analysis of Bevacizumab Plus First- Line Topotecan-Paclitaxel or Cisplatin-Paclitaxel Versus Non-Bevacizumab- Containing Therapies in Persistent, Recurrent, or Metastatic Cervical Cancer. Int J Gynecol Cancer. 2017 Jul;27(6):1237-1246. doi: 10.1097/IGC.0000000000001000. PMID: 28448304; PMCID: PMC5499964. 6: Saraf S, Jain A, Hurkat P, Jain SK. Topotecan Liposomes: A Visit from a Molecular to a Therapeutic Platform. Crit Rev Ther Drug Carrier Syst. 2016;33(5):401-432. doi: 10.1615/CritRevTherDrugCarrierSyst.2016015926. PMID: 27910741. 7: Bracher F, Tremmel T. From Lead to Drug Utilizing a Mannich Reaction: The Topotecan Story. Arch Pharm (Weinheim). 2017 Jul;350(7). doi: 10.1002/ardp.201600236. Epub 2016 Nov 2. PMID: 27805723. 8: Rao V, Bauer F, Vredenburgh JJ. Refractory Small Cell Carcinoma of the Ovary - Hypercalcemic Type (SCCOHT) Treated with Romidepsin and Topotecan: A Case Report and Review of the Literature. Conn Med. 2016 Oct;80(9):529-532. PMID: 29772136. 9: Vennepureddy A, Atallah JP, Terjanian T. Role of Topotecan in Non-Small Cell Lung Cancer: A Review of Literature. World J Oncol. 2015 Oct;6(5):429-436. doi: 10.14740/wjon950e. Epub 2015 Oct 26. PMID: 28983343; PMCID: PMC5624667. 10: Francis JH, Marr BP, Schaiquevich P, Kellick MG, Abramson DH. Properties and clinical utility of topotecan fluorescence: uses for retinoblastoma. Br J Ophthalmol. 2015 Oct;99(10):1320-2. doi: 10.1136/bjophthalmol-2015-306633. Epub 2015 Apr 29. PMID: 25926516. 11: Edwards SJ, Barton S, Thurgar E, Trevor N. Topotecan, pegylated liposomal doxorubicin hydrochloride, paclitaxel, trabectedin and gemcitabine for advanced recurrent or refractory ovarian cancer: a systematic review and economic evaluation. Health Technol Assess. 2015 Jan;19(7):1-480. doi: 10.3310/hta19070. PMID: 25626481; PMCID: PMC4781035. 12: Schaiquevich P, Carcaboso AM, Buitrago E, Taich P, Opezzo J, Bramuglia G, Chantada GL. Ocular pharmacology of topotecan and its activity in retinoblastoma. Retina. 2014 Sep;34(9):1719-27. doi: 10.1097/IAE.0000000000000253. PMID: 25099219. 13: Musa F, Blank S, Muggia F. A pharmacokinetic evaluation of topotecan as a cervical cancer therapy. Expert Opin Drug Metab Toxicol. 2013 Feb;9(2):215-24. doi: 10.1517/17425255.2013.758249. PMID: 23320990. 14: Riemsma R, Simons JP, Bashir Z, Gooch CL, Kleijnen J. Systematic Review of topotecan (Hycamtin) in relapsed small cell lung cancer. BMC Cancer. 2010 Aug 17;10:436. doi: 10.1186/1471-2407-10-436. PMID: 20716361; PMCID: PMC2931489. 15: Hartwell D, Jones J, Loveman E, Harris P, Clegg A, Bird A. Topotecan for relapsed small cell lung cancer: a systematic review and economic evaluation. Cancer Treat Rev. 2011 May;37(3):242-9. doi: 10.1016/j.ctrv.2010.07.005. Epub 2010 Aug 14. PMID: 20709456. 16: Pirker R, Berzinec P, Brincat S, Kasan P, Ostoros G, Pesek M, Plāte S, Purkalne G, Rooneem R, Skricková J, Stanculeanu D, Timcheva C, Tzekova V, Zakotnik B, Zielinski CC, Zwitter M. Therapy of small cell lung cancer with emphasis on oral topotecan. Lung Cancer. 2010 Oct;70(1):7-13. doi: 10.1016/j.lungcan.2010.05.020. Epub 2010 Jun 23. PMID: 20576312. 17: Paton F, Paulden M, Saramago P, Manca A, Misso K, Palmer S, Eastwood A. Topotecan for the treatment of recurrent and stage IVB carcinoma of the cervix. Health Technol Assess. 2010 May;14 Suppl 1:55-62. doi: 10.3310/hta14Suppl1/08. PMID: 20507804. 18: Loveman E, Jones J, Hartwell D, Bird A, Harris P, Welch K, Clegg A. The clinical effectiveness and cost-effectiveness of topotecan for small cell lung cancer: a systematic review and economic evaluation. Health Technol Assess. 2010 Mar;14(19):1-204. doi: 10.3310/hta14190. PMID: 20356561. 19: Lorusso D, Pietragalla A, Mainenti S, Masciullo V, Di Vagno G, Scambia G. Review role of topotecan in gynaecological cancers: current indications and perspectives. Crit Rev Oncol Hematol. 2010 Jun;74(3):163-74. doi: 10.1016/j.critrevonc.2009.08.001. Epub 2009 Sep 18. PMID: 19766512. 20: Sehouli J, Oskay-Ozcelik G. Current role and future aspects of topotecan in relapsed ovarian cancer. Curr Med Res Opin. 2009 Mar;25(3):639-51. doi: 10.1185/03007990802707139. PMID: 19232038.