Topotecan HCl
featured

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

MedKoo CAT#: 100870

CAS#: 119413-54-6 (HCl)

Description: Topocecan is a semisynthetic derivative of camptothecin with antineoplastic activity. During the S phase of the cell cycle, topotecan selectively stabilizes topoisomerase I-DNA covalent complexes, inhibiting religation of topoisomerase I-mediated single-strand DNA breaks and producing potentially lethal double-strand DNA breaks when complexes are encountered by the DNA replication machinery. Camptothecin is a cytotoxic quinoline-based alkaloid extracted from the Asian tree Camptotheca acuminata.


Chemical Structure

img
Topotecan HCl
CAS# 119413-54-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 100870
Name: Topotecan HCl
CAS#: 119413-54-6 (HCl)
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

Price and Availability

Size Price Availability Quantity
500.0mg USD 150.0 Same day
1.0g USD 250.0 Same day
2.0g USD 450.0 Same day
5.0g USD 750.0 Same day
10.0g USD 1250.0 Same day
20.0g USD 1950.0 Same day
50.0g USD 4450.0 2 Weeks
100.0g USD 7450.0 2 Weeks
Click to view more sizes and prices
Bulk inquiry

Related CAS #: 119413-54-6 (HCl)   123948-87-8 (free base)    

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

Appearance: Yellow 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: 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).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 457.91 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Yu XW, Wei D, Gao YS, Du HZ, Yu BY, Li RM, Qian CM, Luo XJ, Yuan ST, Wang JS, Sun L. Synergistic combination of DT-13 and Topotecan inhibits aerobic glycolysis in human gastric carcinoma BGC-823 cells via NM IIA/EGFR/HK II axis. J Cell Mol Med. 2019 Aug 9. doi: 10.1111/jcmm.14523. [Epub ahead of print] PubMed PMID: 31397978.

2: D'Amico RS, Neira JA, Yun J, Alexiades NG, Banu M, Englander ZK, Kennedy BC, Ung TH, Rothrock RJ, Romanov A, Guo X, Zhao B, Sonabend AM, Canoll P, Bruce JN. Validation of an effective implantable pump-infusion system for chronic convection-enhanced delivery of intracerebral topotecan in a large animal model. J Neurosurg. 2019 Aug 2:1-10. doi: 10.3171/2019.3.JNS1963. [Epub ahead of print] PubMed PMID: 31374547.

3: Choi JY, Kang HJ, Hong KT, Hong CR, Lee YJ, Park JD, Phi JH, Kim SK, Wang KC, Kim IH, Park SH, Choi YH, Cheon JE, Park KD, Shin HY. Tandem high-dose chemotherapy with topotecan-thiotepa-carboplatin and melphalan-etoposide-carboplatin regimens for pediatric high-risk brain tumors. Int J Clin Oncol. 2019 Jul 27. doi: 10.1007/s10147-019-01517-8. [Epub ahead of print] PubMed PMID: 31352632.

4: Menyhárt O, Fekete JT, Győrffy B. Gene Expression Indicates Altered Immune Modulation and Signaling Pathway Activation in Ovarian Cancer Patients Resistant to Topotecan. Int J Mol Sci. 2019 Jun 5;20(11). pii: E2750. doi: 10.3390/ijms20112750. PubMed PMID: 31195594; PubMed Central PMCID: PMC6600443.

5: Parmakhtiar B, Burger RA, Kim JH, Fruehauf JP. HIF Inactivation of p53 in Ovarian Cancer Can Be Reversed by Topotecan, Restoring Cisplatin and Paclitaxel Sensitivity. Mol Cancer Res. 2019 Aug;17(8):1675-1686. doi: 10.1158/1541-7786.MCR-18-1109. Epub 2019 May 14. PubMed PMID: 31088908.

6: Prasad C, Banerjee R. Ultrasound Triggered Spatiotemporal Delivery of Topotecan and Curcumin as Combination Therapy for Cancer. J Pharmacol Exp Ther. 2019 Apr 15. pii: jpet.119.256487. doi: 10.1124/jpet.119.256487. [Epub ahead of print] PubMed PMID: 30988010.

7: Koldysheva EV, Men'shchikova AP, Lushnikova EL, Popova NA, Kaledin VI, Nikolin VP, Zakharenko AL, Luzina OA, Salakhutdinov NF, Lavrik OI. Antimetastatic Activity of Combined Topotecan and Tyrosyl-DNA Phosphodiesterase-1 Inhibitor on Modeled Lewis Lung Carcinoma. Bull Exp Biol Med. 2019 Mar;166(5):661-666. doi: 10.1007/s10517-019-04413-3. Epub 2019 Mar 22. PubMed PMID: 30903487.

8: Yadav M, Dhagat S, Eswari JS. Structure based drug design and molecular docking studies of anti-cancer molecules paclitaxel, etoposide and topotecan using Novel ligands. Curr Drug Discov Technol. 2019 Mar 6. doi: 10.2174/1570163816666190307102033. [Epub ahead of print] PubMed PMID: 30848204.

9: Genolla J, Rodriguez T, Minguez P, Lopez-Almaraz R, Llorens V, Echebarria A. Dosimetry-based high-activity therapy with (131)I-metaiodobenzylguanidine ((131)I-mIBG) and topotecan for the treatment of high-risk refractory neuroblastoma. Eur J Nucl Med Mol Imaging. 2019 Jul;46(7):1567-1575. doi: 10.1007/s00259-019-04291-x. Epub 2019 Mar 5. PubMed PMID: 30838430.

10: Syrios J, Kouroussis C, Kotsakis A, Kentepozidis N, Kontopodis E, Kalbakis K, Vardakis N, Hatzidaki D, Polyzos A, Georgoulias V; GU Working Group of the Hellenic Oncology Research Group (HORG). Combination of weekly topotecan and gemcitabine as a salvage treatment in patients with recurrent ovarian cancer: a phase I study. Minerva Ginecol. 2019 Jun;71(3):182-190. doi: 10.23736/S0026-4784.19.04249-7. Epub 2019 Feb 6. PubMed PMID: 30727721.

11: Jin J, Xu W, Wan B, Wang X, Zhou Z, Miao Y, Lv T, Song Y. Topotecan Alleviates Lipopolysaccharide-Mediated Acute Lung Injury Via the NF-κB Signaling Pathway. J Surg Res. 2019 Mar;235:83-92. doi: 10.1016/j.jss.2018.08.057. Epub 2018 Oct 24. PubMed PMID: 30691855.

12: Wang L, Liu Y, Zhao TL, Li ZZ, He JY, Zhang BJ, Du HZ, Jiang JW, Yuan ST, Sun L. Topotecan induces apoptosis via ASCT2 mediated oxidative stress in gastric cancer. Phytomedicine. 2019 Apr;57:117-128. doi: 10.1016/j.phymed.2018.12.011. Epub 2018 Dec 11. PubMed PMID: 30668314.

13: Shackleford GM, Mahdi MY, Moats RA, Hawes D, Tran HC, Finlay JL, Hoang TQ, Meng EF, Erdreich-Epstein A. Continuous and bolus intraventricular topotecan prolong survival in a mouse model of leptomeningeal medulloblastoma. PLoS One. 2019 Jan 4;14(1):e0206394. doi: 10.1371/journal.pone.0206394. eCollection 2019. PubMed PMID: 30608927; PubMed Central PMCID: PMC6319703.

14: Mitchell AB, Vasilyeva A, Gajjar A, Santana VM, Stewart CF. Determining success rates of the current pharmacokinetically guided dosing approach of topotecan in pediatric oncology patients. Pediatr Blood Cancer. 2019 Apr;66(4):e27578. doi: 10.1002/pbc.27578. Epub 2018 Dec 11. PubMed PMID: 30548417; PubMed Central PMCID: PMC6386591.

15: Sterzyńska K, Klejewski A, Wojtowicz K, Świerczewska M, Nowicki M, Brązert J, Januchowski R. Myotilin, a New Topotecan Resistant Protein in Ovarian Cancer Cell Lines. J Cancer. 2018 Oct 22;9(23):4413-4421. doi: 10.7150/jca.27342. eCollection 2018. PubMed PMID: 30519347; PubMed Central PMCID: PMC6277650.

16: Neshasteh-Riz A, Eyvazzadeh N, Rostami A, Azzizolahi E. Cytogenetic damage from hyperthermia,6 MV X-rays, and topotecan in glioblastoma spheroids, simultaneously, and separately. J Cancer Res Ther. 2018 Oct-Dec;14(6):1273-1278. doi: 10.4103/0973-1482.189239. PubMed PMID: 30488843.

17: Guo J, Tang Q, Wang Q, Sun W, Pu Z, Wang J, Bao Y. Pifithrin-α enhancing anticancer effect of topotecan on p53-expressing cancer cells. Eur J Pharm Sci. 2019 Feb 1;128:61-72. doi: 10.1016/j.ejps.2018.11.024. Epub 2018 Nov 22. PubMed PMID: 30472223.

18: Sharma M, Khetan V. Commentary: Periocular topotecan for retinoblastoma. Indian J Ophthalmol. 2018 Dec;66(12):1838-1839. doi: 10.4103/ijo.IJO_1626_18. PubMed PMID: 30451191; PubMed Central PMCID: PMC6256899.

19: Sthapit PR, Rao R, Honavar SG. Periocular topotecan for vitreous seeds in retinoblastoma. Indian J Ophthalmol. 2018 Dec;66(12):1833-1838. doi: 10.4103/ijo.IJO_737_18. PubMed PMID: 30451190; PubMed Central PMCID: PMC6256916.

20: Sawangrat K, Yamashita S, Tanaka A, Morishita M, Kusamori K, Katsumi H, Sakane T, Yamamoto A. Modulation of Intestinal Transport and Absorption of Topotecan, a BCRP Substrate, by Various Pharmaceutical Excipients and Their Inhibitory Mechanisms of BCRP Transporter. J Pharm Sci. 2019 Mar;108(3):1315-1325. doi: 10.1016/j.xphs.2018.10.043. Epub 2018 Oct 30. PubMed PMID: 30389568.



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).