E-Homocamptothecin | CAS#186668-40-6 | Antineoplastic agent

MedKoo Cat#: 463279 | Name: E-Homocamptothecin

Description:

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

E-Homocamptothecin is an antineoplastic agent.

Chemical Structure

E-Homocamptothecin

CAS#186668-40-6

Theoretical Analysis

MedKoo Cat#: 463279

Name: E-Homocamptothecin

CAS#: 186668-40-6

Chemical Formula: C21H18N2O4

Exact Mass: 362.1267

Molecular Weight: 362.39

Elemental Analysis: C, 69.60; H, 5.01; N, 7.73; O, 17.66

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

E-Homocamptothecin; E Homocamptothecin; E-Homocamptothecin, (+/-)-;

IUPAC/Chemical Name

5-ethyl-5-hydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione

InChi Key

PAEZRCINULFAGO-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H18N2O4/c1-2-21(26)9-18(24)27-11-14-15(21)8-17-19-13(10-23(17)20(14)25)7-12-5-3-4-6-16(12)22-19/h3-8,26H,2,9-11H2,1H3

SMILES Code

CCC1(CC(OCC2=C1C=C3N(C2=O)Cc(c4)c3nc5c4cccc5)=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

Soluble in DMSO

Shelf Life

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 362.39 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.

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: Sun Y, Zhang Z, Xiang F, Zhang M, Chen Q, Tang L, Zhu L, Liu J, Meng Z, Hu J, Luo X, Ni Z, Wang X. Decreasing Arl4c expression by inhibition of AKT signal in human lung adenocarcinoma cells. Life Sci. 2020 Apr 1;246:117428. doi: 10.1016/j.lfs.2020.117428. Epub 2020 Feb 11. PMID: 32057901. 2: Amin SA, Adhikari N, Jha T, Gayen S. A Review on Camptothecin Analogs with Promising Cytotoxic Profile. Anticancer Agents Med Chem. 2018;18(13):1796-1814. doi: 10.2174/1871520618666180327140956. PMID: 29589546. 3: Wang G, Gao S, Tian R, Miller-Kleinhenz J, Qin Z, Liu T, Li L, Zhang F, Ma Q, Zhu L. Theranostic Hyaluronic Acid-Iron Micellar Nanoparticles for Magnetic- Field-Enhanced in vivo Cancer Chemotherapy. ChemMedChem. 2018 Jan 8;13(1):78-86. doi: 10.1002/cmdc.201700515. Epub 2017 Dec 12. PMID: 29086481. 4: Liu Y, Li D, Guo X, Xu H, Li Z, Zhang Y, Song C, Fan R, Tang X, Zhang Z. A pH-responsive prodrug delivery system of 10-HCPT for controlled release and tumor targeting. Int J Nanomedicine. 2017 Mar 22;12:2227-2242. doi: 10.2147/IJN.S125849. PMID: 28356739; PMCID: PMC5367588. 5: Xu X, Wu Y, Liu W, Sheng C, Yao J, Dong G, Fang K, Li J, Yu Z, Min X, Zhang H, Miao Z, Zhang W. Discovery of 7-Methyl-10-Hydroxyhomocamptothecins with 1,2,3-Triazole Moiety as Potent Topoisomerase I Inhibitors. Chem Biol Drug Des. 2016 Sep;88(3):398-403. doi: 10.1111/cbdd.12767. Epub 2016 May 5. PMID: 27062430. 6: Mangas-Sanjuan V, Buil-Bruna N, Garrido MJ, Soto E, Trocóniz IF. Semimechanistic cell-cycle type-based pharmacokinetic/pharmacodynamic model of chemotherapy-induced neutropenic effects of diflomotecan under different dosing schedules. J Pharmacol Exp Ther. 2015 Jul;354(1):55-64. doi: 10.1124/jpet.115.223776. Epub 2015 May 6. PMID: 25948593. 7: Wang L, Xie S, Ma L, Chen Y, Lu W. Design, synthesis and biological evaluation of novel homocamptothecin analogues as potent antitumor agents. Bioorg Med Chem. 2015 May 1;23(9):1950-62. doi: 10.1016/j.bmc.2015.03.031. Epub 2015 Mar 18. PMID: 25835359. 8: Wang Q, Liu P, Gong T, Sun X, Duan Y, Zhang Z. Uptake mechanism and endosomal fate of drug-phospholipid lipid nanoparticles in subcutaneous and in situ hepatoma. J Biomed Nanotechnol. 2014 Jun;10(6):993-1003. doi: 10.1166/jbn.2014.1776. PMID: 24749394. 9: Geng M, Wang L, Chen X, Cao R, Li P. The association between chemosensitivity and Pgp, GST-π and Topo II expression in gastric cancer. Diagn Pathol. 2013 Dec 10;8:198. doi: 10.1186/1746-1596-8-198. PMID: 24326092; PMCID: PMC3901556. 10: Li DZ, Wang CY, Liu RH, Wang YM, Ji TF, Li YR, Pan XD. Synthesis and cytotoxicity of novel 20-O-linked homocamptothecin ester derivatives as potent topoisomerase I inhibitors. J Asian Nat Prod Res. 2013 Nov;15(11):1179-88. doi: 10.1080/10286020.2013.855203. Epub 2013 Nov 11. PMID: 24215541. 11: Guo W, Dong G, Zhu L, Liu W, Zhuang C, Guo Z, Yao J, Sheng C, Zhang H, Miao Z, Zhang W. Synthesis and biological assays of 9-(acylamino) homocamptothecins as DNA topoisomerase I inhibitors. Chem Biodivers. 2013 Oct;10(10):1804-15. doi: 10.1002/cbdv.201200311. PMID: 24130024. 12: Tu LX, Xu YH, Tang CY, Deng LH, Wu CB. [In vivo imaging in tumor-bearing animals and pharmacokinetics of PEGylated liposomes modified with RGD cyclopeptide]. Yao Xue Xue Bao. 2012 May;47(5):646-51. Chinese. PMID: 22812011. 13: Zhu L, Zhang X, Lei N, Liu W, Miao Z, Zhuang C, Sheng C, Guo W, Dong G, Yao J, Cheng P, Zhang W. Synthesis and biological evaluation of 7-alkenyl homocamptothecins as potent topoisomerase I inhibitors. Chem Biodivers. 2012 Jun;9(6):1084-94. doi: 10.1002/cbdv.201100195. PMID: 22700227. 14: Trocóniz IF, Cendrós JM, Soto E, Pruñonosa J, Perez-Mayoral A, Peraire C, Principe P, Delavault P, Cvitkovic F, Lesimple T, Obach R. Population pharmacokinetic/pharmacodynamic modeling of drug-induced adverse effects of a novel homocamptothecin analog, elomotecan (BN80927), in a Phase I dose finding study in patients with advanced solid tumors. Cancer Chemother Pharmacol. 2012 Aug;70(2):239-50. doi: 10.1007/s00280-012-1906-y. Epub 2012 Jun 15. PMID: 22699813. 15: Luo Y, Yu S, Tong L, Huang Q, Lu W, Chen Y. Synthesis and biological evaluation of new homocamptothecin analogs. Eur J Med Chem. 2012 Aug;54:281-6. doi: 10.1016/j.ejmech.2012.05.002. Epub 2012 May 15. PMID: 22647222. 16: Tong JL, Zhang CP, Nie F, Xu XT, Zhu MM, Xiao SD, Ran ZH. MicroRNA 506 regulates expression of PPAR alpha in hydroxycamptothecin-resistant human colon cancer cells. FEBS Lett. 2011 Nov 16;585(22):3560-8. doi: 10.1016/j.febslet.2011.10.021. Epub 2011 Oct 22. PMID: 22036718. 17: Pu XH, Sun J, Qin YM, Zhang X, Zhang P, He ZG. [Pharmaceutical evaluation of hydroxycamptothecin nanosuspensions with the action of inhibiting P-gp]. Yao Xue Xue Bao. 2011 Jul;46(7):834-8. Chinese. PMID: 22010354. 18: Zhu L, Cheng P, Lei N, Yao J, Sheng C, Zhuang C, Guo W, Liu W, Zhang Y, Dong G, Wang S, Miao Z, Zhang W. Synthesis and biological evaluation of novel homocamptothecins conjugating with dihydropyrimidine derivatives as potent topoisomerase I inhibitors. Arch Pharm (Weinheim). 2011 Nov;344(11):726-34. doi: 10.1002/ardp.201000402. Epub 2011 Sep 29. PMID: 21956522. 19: Guo W, Miao Z, Sheng C, Yao J, Liu W, Zhu L, Zhang Y, Cheng P, Dong G, Zhuang C, Zhang W. Synthesis of 9-(heteroarylmethylidene)amino derivatives of homocamptothecin with biological activities. Chem Biodivers. 2011 Jul;8(7):1266-73. doi: 10.1002/cbdv.201000271. PMID: 21766447. 20: Liu W, Zhu L, Guo W, Zhuang C, Zhang Y, Sheng C, Cheng P, Yao J, Wang W, Dong G, Wang S, Miao Z, Zhang W. Synthesis and biological evaluation of novel 7-acyl homocamptothecins as Topoisomerase I inhibitors. Eur J Med Chem. 2011 Jun;46(6):2408-14. doi: 10.1016/j.ejmech.2011.03.024. Epub 2011 Mar 23. PMID: 21463912.