Name: Chimmitecan
Brand: BOC Sciences
Price: 298 USD
Availability: MadeToOrder

Size

Price

Stock

Quantity

5 mg

$298

In stock

Synonyms

1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4,9-dihydroxy-10-(2-propen-1-yl)-, (4S)-; (4S)-4-Ethyl-4,9-dihydroxy-10-(2-propen-1-yl)-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4,9-dihydroxy-10-(2-propenyl)-, (4S)-; 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4,9-dihydroxy-10-(2-propenyl)-, (S)-; (S)-9-Allyl-10-Hydroxycamptothecin; (S)-10-allyl-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

IUPAC Name

(19S)-19-ethyl-7,19-dihydroxy-8-prop-2-enyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

Canonical SMILES

CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=C(C5=C4)CC=C)O)O

InChI

InChI=1S/C23H20N2O5/c1-3-5-13-14-8-12-10-25-18(20(12)24-17(14)6-7-19(13)26)9-16-15(21(25)27)11-30-22(28)23(16,29)4-2/h3,6-9,26,29H,1,4-5,10-11H2,2H3/t23-/m0/s1

InChIKey

AXXPNDLHTNUMIK-QHCPKHFHSA-N

Density

1.49±0.1 g/cm3

Solubility

Soluble in DMSO, Water (Insoluble)

Appearance

Light Yellow to Off-white Powder

Storage

Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)

Boiling Point

803.0±65.0°C at 760 mmHg

Current Developer

Shanghai Institute of Materia Medica.

Chimmitecan, a potent derivative of camptothecin renowned for its efficacy in inhibiting topoisomerase I enzymes, finds diverse applications across various fields. Here are four key applications of Chimmitecan:

Cancer Therapy: In the realm of oncology, Chimmitecan emerges as a powerful weapon against different cancer types by specifically targeting topoisomerase I, a pivotal enzyme essential for DNA replication. By blocking this enzyme, Chimmitecan inflicts DNA damage in cancer cells, triggering cellular demise and shrinkage of tumors. This compound showcases remarkable effectiveness against cancers characterized by rapid cell division, such as colorectal and ovarian cancers.

Drug Development: Serving as a cornerstone in the realm of anticancer drug development, Chimmitecan undergoes structural modifications to enhance pharmacokinetics, mitigate side effects, and elevate therapeutic efficacy. These altered derivatives offer fresh avenues for treating patients resistant to current therapies, ushering in novel solutions in the fight against cancer.

Pharmacological Research: Within laboratory settings, Chimmitecan takes center stage in unraveling the intricacies of topoisomerase I inhibition and DNA damage response. By dissecting the interactions between Chimmitecan and cellular components, researchers pave the way for innovative strategies to combat drug resistance and elevate the efficacy of cancer treatments. This body of research not only enriches our understanding of DNA-interactive drugs but also propels advancements in cancer therapeutics.

Combination Therapy: Embraced as a cornerstone in combination therapies, Chimmitecan synergizes with other chemotherapeutic agents to magnify anticancer effects. Paired with compounds like paclitaxel or cisplatin, Chimmitecan potentiates the eradication of cancer cells while enabling lower dosages of each drug, thereby reducing overall toxicity. This collaborative approach not only enhances the efficacy of cancer treatments but also fosters more tolerable and efficient regimens in the battle against cancer.

1.Accurate determination of the anticancer prodrug simmitecan and its active metabolite chimmitecan in various plasma samples based on immediate deactivation of blood carboxylesterases.

Hu Z1, Sun Y, Du F, Niu W, Xu F, Huang Y, Li C. J Chromatogr A. 2011 Sep 23;1218(38):6646-53. doi: 10.1016/j.chroma.2011.07.042. Epub 2011 Jul 23.

Simmitecan (L-P) is an anticancer ester prodrug, which involves activation to chimmitecan (L-2-Z). In the current study, a liquid chromatography/tandem mass spectrometry-based method was developed for simultaneous determination of L-P and L-2-Z in various plasma samples. Because L-P is rapidly converted to L-2-Z by blood carboxylesterase during and after sampling, which hampers accurate determination of L-P and L-2-Z in the biological samples, different carboxylesterase inhibitors were tested. As a result, bis(4-nitrophenyl)phosphate gave the best results with respect to inhibitory capability, hemolysis, and matrix effects and was used to deactivate blood carboxylesterases when sampling. The plasma samples were precipitated with acetonitrile and the resulting supernatants were separated using a pulse gradient method on a C18 column. Irinotecan and camptothecin were used as internal standards for quantification of L-P and L-2-Z, respectively.

2.Chimmitecan, a novel 9-substituted camptothecin, with improved anticancer pharmacologic profiles in vitro and in vivo.

Huang M1, Gao H, Chen Y, Zhu H, Cai Y, Zhang X, Miao Z, Jiang H, Zhang J, Shen H, Lin L, Lu W, Ding J. Clin Cancer Res. 2007 Feb 15;13(4):1298-307. Epub 2007 Feb 7.

PURPOSE: This study aimed to evaluate antitumor activities and pharmacologic profiles of chimmitecan, a novel 9-small-alkyl-substituted lipophilic camptothecin, in comparison with irinotecan (CPT-11) and topotecan.