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MedKoo Cat#: 206589 | Name: Namitecan

Description:

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

Namitecan, also known as ST-1968, is a new water-soluble camptothecin analogue which showed high antitumor activity in preclinical models. ST1968 exhibited an impressive activity against several tumors including models of ovarian and colon carcinoma in which a high rate of cures was observed. t ST1968 was able to overcome the most relevant mechanisms associated with the development of topotecan resistance (i.e., slow proliferation and target downregulation) owing to its peculiar pharmacokinetic behaviour.

Chemical Structure

Namitecan
Namitecan
CAS#372105-27-6

Theoretical Analysis

MedKoo Cat#: 206589

Name: Namitecan

CAS#: 372105-27-6

Chemical Formula: C23H22N4O5

Exact Mass: 434.1590

Molecular Weight: 434.45

Elemental Analysis: C, 63.59; H, 5.10; N, 12.90; O, 18.41

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
ST-1968; ST 1968; ST1968; Namitecan.
IUPAC/Chemical Name
(4S)-11-((E)-((2-Aminoethoxy)imino)methyl)-4-ethyl-4-hydroxy-1,12-dihydro-14H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H)-dione
InChi Key
IBTISPLPBBHVSU-UVOOVGFISA-N
InChi Code
InChI=1S/C23H22N4O5/c1-2-23(30)17-9-19-20-15(11-27(19)21(28)16(17)12-31-22(23)29)14(10-25-32-8-7-24)13-5-3-4-6-18(13)26-20/h3-6,9-10,30H,2,7-8,11-12,24H2,1H3/b25-10+/t23-/m0/s1
SMILES Code
O=C1[C@](O)(CC)C2=C(CO1)C(N3CC4=C(/C=N/OCCN)C5=CC=CC=C5N=C4C3=C2)=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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 434.45 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
1: Joerger M, Hess D, Delmonte A, Gallerani E, Barbieri P, Pace S, Sessa C. Phase-I dose finding and pharmacokinetic study of the novel hydrophilic camptothecin ST-1968 (namitecan) in patients with solid tumors. Invest New Drugs. 2015 Apr;33(2):472-9. doi: 10.1007/s10637-015-0219-5. Epub 2015 Feb 20. PubMed PMID: 25693886. 2: Joerger M, Hess D, Delmonte A, Gallerani E, Fasolo A, Gianni L, Cresta S, Barbieri P, Pace S, Sessa C. Integrative population pharmacokinetic and pharmacodynamic dose finding approach of the new camptothecin compound namitecan (ST1968). Br J Clin Pharmacol. 2015 Jul;80(1):128-38. doi: 10.1111/bcp.12583. Epub 2015 Jun 3. PubMed PMID: 25580946; PubMed Central PMCID: PMC4500332. 3: De Cesare M, Lauricella C, Veronese SM, Cominetti D, Pisano C, Zunino F, Zaffaroni N, Zuco V. Synergistic antitumor activity of cetuximab and namitecan in human squamous cell carcinoma models relies on cooperative inhibition of EGFR expression and depends on high EGFR gene copy number. Clin Cancer Res. 2014 Feb 15;20(4):995-1006. doi: 10.1158/1078-0432.CCR-13-1684. Epub 2013 Dec 10. PubMed PMID: 24327272. 4: Meco D, Di Francesco AM, Cusano G, Bucci F, Pierri F, Patriarca V, Torella AR, Pisano C, Riccardi R. Preclinical evaluation of the novel 7-substituted camptothecin Namitecan (ST1968) in paediatric tumour models. Cancer Chemother Pharmacol. 2012 Dec;70(6):811-22. doi: 10.1007/s00280-012-1973-0. Epub 2012 Sep 25. PubMed PMID: 23007316. 5: Beretta GL, Zuco V, De Cesare M, Perego P, Zaffaroni N. Namitecan: a hydrophilic camptothecin with a promising preclinical profile. Curr Med Chem. 2012;19(21):3488-501. Review. PubMed PMID: 22680917. 6: Cassinelli G, Zuco V, Petrangolini G, De Cesare M, Tortoreto M, Lanzi C, Cominetti D, Zaffaroni N, Orlandi A, Passeri D, Meco D, Di Francesco AM, Riccardi R, Bucci F, Pisano C, Zunino F. The curative efficacy of namitecan (ST1968) in preclinical models of pediatric sarcoma is associated with antiangiogenic effects. Biochem Pharmacol. 2012 Jul 15;84(2):163-71. doi: 10.1016/j.bcp.2012.04.005. Epub 2012 Apr 13. PubMed PMID: 22525722. 7: Dal Pozzo A, Esposito E, Ni M, Muzi L, Pisano C, Bucci F, Vesci L, Castorina M, Penco S. Conjugates of a novel 7-substituted camptothecin with RGD-peptides as α(v)β₃ integrin ligands: An approach to tumor-targeted therapy. Bioconjug Chem. 2010 Nov 17;21(11):1956-67. doi: 10.1021/bc100097r. Epub 2010 Oct 15. PubMed PMID: 20949910. 8: Zuco V, Benedetti V, Zunino F. ATM- and ATR-mediated response to DNA damage induced by a novel camptothecin, ST1968. Cancer Lett. 2010 Jun 28;292(2):186-96. doi: 10.1016/j.canlet.2009.12.001. Epub 2009 Dec 29. PubMed PMID: 20042274. 9: Badaloni E, Cabri W, Ciogli A, D'Acquarica I, Deias R, Gasparrini F, Giorgi F, Kotoni D, Villani C. Extending the use of "Inverted Chirality Columns Approach" for enantiomeric excess determination in absence of reference samples: Application to a water-soluble camptothecin derivative. J Chromatogr A. 2010 Feb 12;1217(7):1024-32. doi: 10.1016/j.chroma.2009.10.035. Epub 2009 Oct 17. PubMed PMID: 19863967. 10: Zuco V, Supino R, Favini E, Tortoreto M, Cincinelli R, Croce AC, Bucci F, Pisano C, Zunino F. Efficacy of ST1968 (namitecan) on a topotecan-resistant squamous cell carcinoma. Biochem Pharmacol. 2010 Feb 15;79(4):535-41. doi: 10.1016/j.bcp.2009.09.012. Epub . PubMed PMID: 19765546. 11: Pisano C, De Cesare M, Beretta GL, Zuco V, Pratesi G, Penco S, Vesci L, Foderà R, Ferrara FF, Guglielmi MB, Carminati P, Dallavalle S, Morini G, Merlini L, Orlandi A, Zunino F. Preclinical profile of antitumor activity of a novel hydrophilic camptothecin, ST1968. Mol Cancer Ther. 2008 Jul;7(7):2051-9. doi: 10.1158/1535-7163.MCT-08-0266. PubMed PMID: 18645015. 12: Pisano C, Zuco V, De Cesare M, Benedetti V, Vesci L, Foderà R, Bucci F, Aulicino C, Penco S, Carminati P, Zunino F. Intracellular accumulation and DNA damage persistence as determinants of human squamous cell carcinoma hypersensitivity to the novel camptothecin ST1968. Eur J Cancer. 2008 Jun;44(9):1332-40. doi: 10.1016/j.ejca.2008.04.004. Epub 2008 Apr 27. PubMed PMID: 18445521. 13: De Cesare M, Beretta GL, Tinelli S, Benedetti V, Pratesi G, Penco S, Dallavalle S, Merlini L, Pisano C, Carminati P, Zunino F. Preclinical efficacy of ST1976, a novel camptothecin analog of the 7-oxyiminomethyl series. Biochem Pharmacol. 2007 Mar 1;73(5):656-64. Epub 2006 Nov 9. PubMed PMID: 17169332.

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