MedKoo Cat#: 100870 Name: Topotecan HCl CAS#: 119413-54-6 (HCl salt); 123948-87-8 (free base) Chemical Formula: C23H24ClN3O5 Exact Mass: Molecular Weight: 457.91 Elemental Analysis: C, 60.33; H, 5.28; Cl, 7.74; N, 9.18; O, 17.47

Synonym: NSC 609699 NSC-609699 NSC609699; SKF S104864A. SKF 104864 A SKF-104864-A; SKF104864A; TOPO. Hycamtamine; Hycamtin Hydrochloride; Nogitecan Hydrochloride; Topotecan; Nogitecan Hydrochloride; US brand name: Hycamtin.

IUPAC/Chemical Name: (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 hydrochloride

InChi Key: DGHHQBMTXTWTJV-BQAIUKQQSA-N

InChi Code: InChI=1S/C23H23N3O5.ClH/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;1H/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.[H]Cl

Technical Data

Appearance: Yellow solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Certificate of Analysis: View CoA: current batch, Lot#EOS50323 View CoA: previous batch, Lot#YYP20130916

QC Data: View QC data: current batch, Lot#EOS50323 View QC Data: previous batch, Lot#YYP20130916.

Safety Data Sheet (MSDS): View Material Safety Data Sheet (MSDS)

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: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code: 293490

Additional Information

  HYCAMTIN (topotecan hydrochloride) is a semi-synthetic derivative of camptothecin and is an anti-tumor drug with topoisomerase I-inhibitory activity. HYCAMTIN for Injection is supplied as a sterile lyophilized, buffered, light yellow to greenish powder available in single-dose vials. Each vial contains topotecan hydrochloride equivalent to 4 mg of topotecan as free base. The reconstituted solution ranges in color from yellow to yellow-green and is intended for administration by intravenous infusion. Inactive ingredients are mannitol, 48 mg, and tartaric acid, 20 mg. Hydrochloric acid and sodium hydroxide may be used to adjust the pH. The solution pH ranges from 2.5 to 3.5. FDA approved for treating: ovarian cancer (FDA May 1996); cervical cancer (FDA June 2006); small cell lung cancer (SCLC) (FDA Oct 2007). FDA approved for treating: ovarian cancer (FDA May 1996); cervical cancer (FDA June 2006); small cell lung cancer (SCLC) (FDA Oct 2007).

References

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2: 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. Review. PubMed PMID: 20716361; PubMed Central PMCID: PMC2931489.

3: 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. Review. PubMed PMID: 20709456.

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7: 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. Review. PubMed PMID: 19766512.

8: 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 . Review. PubMed PMID: 19232038.

9: Peng LH, Chen XY, Wu TX. Topotecan for ovarian cancer. Cochrane Database Syst Rev. 2008 Apr 16;(2):CD005589. doi: 10.1002/14651858.CD005589.pub2. Review. PubMed PMID: 18425923.

10: Amini E, Roffidal T, Lee A, Fuller GN, Mahajan A, Ketonen L, Kobrinsky N, Cairo MS, Wells RJ, Wolff JE. Central neurocytoma responsive to topotecan, ifosfamide, carboplatin. Pediatr Blood Cancer. 2008 Jul;51(1):137-40. doi: 10.1002/pbc.21551. Review. PubMed PMID: 18338396.

11: Ackermann S, Beckmann MW, Thiel F, Bogenrieder T. Topotecan in cervical cancer. Int J Gynecol Cancer. 2007 Nov-Dec;17(6):1215-23. Review. PubMed PMID: 17997795.

12: O\'Brien M, Eckardt J, Ramlau R. Recent advances with topotecan in the treatment of lung cancer. Oncologist. 2007 Oct;12(10):1194-204. Review. PubMed PMID: 17962613.

13: Nicum SJ, O\'Brien ME. Topotecan for the treatment of small-cell lung cancer. Expert Rev Anticancer Ther. 2007 Jun;7(6):795-801. Review. PubMed PMID: 17555389.

14: Randall-Whitis LM, Monk BJ. Topotecan in the management of cervical cancer. Expert Opin Pharmacother. 2007 Feb;8(2):227-36. Review. PubMed PMID: 17257092.

15: Garst J. Safety of topotecan in the treatment of recurrent small-cell lung cancer and ovarian cancer. Expert Opin Drug Saf. 2007 Jan;6(1):53-62. Review. PubMed PMID: 17181452.

16: Pectasides D, Psyrri A, Pectasides M, Economopoulos T. Optimal therapy for platinum-resistant recurrent ovarian cancer: doxorubicin, gemcitabine or topotecan? Expert Opin Pharmacother. 2006 Jun;7(8):975-87. Review. PubMed PMID: 16722809.

17: Main C, Bojke L, Griffin S, Norman G, Barbieri M, Mather L, Stark D, Palmer S, Riemsma R. Topotecan, pegylated liposomal doxorubicin hydrochloride and paclitaxel for second-line or subsequent treatment of advanced ovarian cancer: a systematic review and economic evaluation. Health Technol Assess. 2006 Mar;10(9):1-132. iii-iv. Review. PubMed PMID: 16545208.

18: Armstrong DK, Spriggs D, Levin J, Poulin R, Lane S. Hematologic safety and tolerability of topotecan in recurrent ovarian cancer and small cell lung cancer: an integrated analysis. Oncologist. 2005 Oct;10(9):686-94. Review. PubMed PMID: 16249347.

19: McCluskey AG, Boyd M, Gaze MN, Mairs RJ. [131I]MIBG and topotecan: a rationale for combination therapy for neuroblastoma. Cancer Lett. 2005 Oct 18;228(1-2):221-7. Review. PubMed PMID: 15935554.

20: Stewart DJ. Update on the role of topotecan in the treatment of non-small cell lung cancer. Oncologist. 2004;9 Suppl 6:43-52. Review. PubMed PMID: 15616149.