86639-52-3

Basic information

• Product Name: 7-Ethyl-10-hydroxycamptothecin
• Synonyms: 7-10-hydroxycamptothecin;(4S)-4,9-Dihydroxy-4,11-diethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;(4S)-4,9-Dihydroxy-4α,11-diethyl-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione;EHCPT;7-Ethyl-10-hydroxy-CPT (Camptothecine), SN-38;10-Hydroxycamptothecin acetate salt ,99%;Irinotecan Related Compound B (10 mg) ((S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione);(S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• CAS NO: 86639-52-3
• Molecular Formula: C₂₂H₂₀N₂O₅
• Molecular Weight: 392.4
• EINECS: 1592732-453-0
• Product Categories: Antitumors for Research and Experimental Use;Biochemistry;Natural Plant Extract;Chiral Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Natural Anti-cancer Medical Materials and It's Derivatives;Pharmaceutical Raw Materials;Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Chiral Reagents, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Inhibitors
• Mol File: 86639-52-3.mol
• Article Data: 44

Chemical Properties

• Melting Point: 217 °C
• Boiling Point: 810.3 °C at 760 mmHg
• Flash Point: 443.8 °C
• Appearance: light-yellow solid
• Density: 1.51 g/cm³
• Refractive Index: 21.5 ° (C=0.2, THF)
• Storage Temp.: −20°C
• Solubility: DMSO: soluble1mg/mL
• PKA: 9.13±0.40(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
• CAS DataBase Reference: 7-Ethyl-10-hydroxycamptothecin(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Ethyl-10-hydroxycamptothecin(86639-52-3)
• EPA Substance Registry System: 7-Ethyl-10-hydroxycamptothecin(86639-52-3)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: 2811
• WGK Germany: 3
• RTECS: UQ0491000
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 86639-52-3(Hazardous Substances Data)

Usage

Description

7-Ethyl-10-hydroxycamptothecin, also known as SN-38, is the active metabolite of CPT-11 and Irinotecan, which are both DNA topoisomerase inhibitors. It exhibits potent antitumor activity against a range of human tumor cell lines and inhibits DNA and RNA synthesis without affecting protein synthesis.
Used in Pharmaceutical Industry:
7-Ethyl-10-hydroxycamptothecin is used as an anticancer agent for the treatment of various types of cancer, including advanced solid tumors, small cell lung cancer, metastatic colorectal cancer, and triple-negative breast cancer. It is employed in clinical trials to study its efficacy and safety in treating cancer patients.
Used in Cancer Research:
7-Ethyl-10-hydroxycamptothecin is used as a research tool to investigate the mechanisms of action of DNA topoisomerase inhibitors and their potential applications in cancer therapy. It helps researchers understand the molecular pathways involved in tumor growth and progression, as well as the development of drug resistance.

Biological Activity

Active metabolite of CPT-11 that inhibits DNA topoisomerase I (IC 50 values are 0.74 and 1.9 μ M in P388 and Ehrlich cells respectively). Inhibits DNA and RNA synthesis (IC 50 values are 0.077 and 1.3 μ M respectively) but does not affect protein synthesis. Displays potent antitumor activity against a range of human tumor cell lines (IC 50 values are 3.3, 13, 19 and 22 nM for HCT-116, BEL-7402, HL60 and HELA cells respectively).

References

1) Koizumi et al. (2006), Novel SN-38-incorporating polymeric micelles, NKK012, eradicate vascular endothelial growth factor-secreting bulky tumors; Cancer Res., 66 10048 2) Gao et al. (2005), Synthesis and antitumor activity of the hexacyclic camptothecin derivatives; Bioorg. Med. Chem. Lett., 15 3233 3) Kawato et al. (1991), Intracellular roles of SN-38, a metabolite of the camptothecin derivative CPT-11, in the antitumor effect of CPT-11; Cancer Res., 51 4187

InChI:InChI=1/C20H16N2O5/c1-2-20(26)13-7-15-17-10(6-11-14(21-17)4-3-5-16(11)23)8-22(15)18(24)12(13)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1

Upstream product

• 97682-44-5 irinotecan 
• 174092-83-2 (S)-4-ethyl-4-hydroxy-6-iodo-7-(pent-2-yn-1-yl)-1,7-dihydro-3H-pyrano[3,4-c]pyridino-3,8(4H)-dione 
• 527743-36-8 4-((tert-Butyldimethylsilyl)oxy)phenyl isocyanide 
• 113853-66-0 Phosphoric acid mono-((S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl) ester 
• 130144-34-2 4,11-diethyl-4,9-dihydroxy-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14 (4H,12H)-dione 
• 35364-15-9 2'-amino-5'-hydroxypropiophenone 
• 102978-40-5 4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 
• 145474-07-3 methyl 7-[1-(methoxycarbonyl)propyl]-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate 

Downstream Products

• 97682-44-5 irinotecan 
• 946062-02-8 7-ethyl-10-O-t-butyldiphenylsilylcamptothecin-20-O-(N-tert-butoxycarbonyl)glycine 

Relevant articles and documents

Diazaborines Are a Versatile Platform to Develop ROS-Responsive Antibody Drug Conjugates**

Antibody–drug conjugates (ADCs) are a new class of therapeutics that combine the lethality of potent cytotoxic drugs with the targeting ability of antibodies to selectively deliver drugs to cancer cells. In this study we show for the first time the synthesis of a reactive-oxygen-species (ROS)-responsive ADC (VL-DAB31-SN-38) that is highly selective and cytotoxic to B-cell lymphoma (CLBL-1 cell line, IC50 value of 54.1 nM). The synthesis of this ADC was possible due to the discovery that diazaborines (DABs) are a very effective ROS-responsive unit that are also very stable in buffer and in plasma. DFT calculations performed on this system revealed a favorable energetic profile (ΔGR=?74.3 kcal mol?1) similar to the oxidation mechanism of aromatic boronic acids. DABs’ very fast formation rate and modularity enabled the construction of different ROS-responsive linkers featuring self-immolative modules, bioorthogonal functions, and bioconjugation handles. These structures were used in the site-selective functionalization of a VL antibody domain and in the construction of the homogeneous ADC.

A stable and cleavable o-linked spacer for drug delivery systems

Anti-cancer chemotherapy with good efficacy and fewer side effects is highly desirable. A drug delivery system comprising a cancer-targeting module and a cytotoxic agent connected with a cleavable linker is promising for reducing side effects. The development of a cleavable linker satisfying the requirements of both stability and cleavability, however, is difficult, especially when a carbonate moiety is used for conjugating the linker to a hydroxy group in a drug of interest. We herein report a new stable linker comprising carbamate and ester spacers, which can be introduced on a hydroxy group of a drug. This linker is more stable in aqueous neutral buffer than a corresponding carbonate-type linker, and releases a payload anti-cancer drug, SN-38, through a two-step sequence upon cathepsin B treatment. This linker may have potential use in other drug delivery systems to lower side effects by selectively transporting cytotoxic drugs to tumor cells.

A preparation method of irinotecan hydrochloride (by machine translation)

The invention relates to a preparation method of irinotecan hydrochloride. Its steps are: parent ring to camptothecin as raw material generated by the reaction with the aldehyde 7 - ethyl camptothecin; hydrogen peroxide oxidation then N - oxide - 7 - ethyl camptothecin; by the illumination rearrangement 7 - ethyl - 10 - hydroxy camptothecin; 4 - piperidyl with dimethyl carbonate reaction to produce 4 - piperidyl carbonic acid methyl ester; 7 - ethyl - 10 - hydroxy camptothecin with 4 - piperidyl carbonic acid methyl ester reaction generating irinotecan monomer; irinotecan monomers with hydrochloric salt to obtain the finished product of the irinotecan hydrochloride. Compared with the prior art, the present invention avoid the use of phosgene in the reaction process, chloroform poisonous substance, in production with safe, convenient, less pollution and the like; in addition, the synthetic method avoids the need of the prior process in the defects of the chromatographic column separation and purification, reduces the production cost of the irinotecan, has great economic benefit. (by machine translation)