Chimmitecan - CAS 185425-25-6

Chimmitecan - CAS 185425-25-6 Catalog number: BADC-01397

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Chimmitecan is a potent topoisomerase I inhibitor. Chimmitecan is also an active metabolite of simmitecan. Chimmitecan displays outstanding activity in vitro and in vivo. The substitution at the 9-position benefits chimmitecan a salient anti-MDR activity, stability in human serum albumin, improved solubility, and oral availability, which might favorably promise its therapeutic potential in clinical settings.

Category
ADCs Cytotoxin
Product Name
Chimmitecan
CAS
185425-25-6
Catalog Number
BADC-01397
Molecular Formula
C23H20N2O5
Molecular Weight
404.42
Purity
≥95%
Chimmitecan

Ordering Information

Catalog Number Size Price Quantity
BADC-01397 5 mg $298 Inquiry
Description
Chimmitecan is a potent topoisomerase I inhibitor. Chimmitecan is also an active metabolite of simmitecan. Chimmitecan displays outstanding activity in vitro and in vivo. The substitution at the 9-position benefits chimmitecan a salient anti-MDR activity, stability in human serum albumin, improved solubility, and oral availability, which might favorably promise its therapeutic potential in clinical settings.
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.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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