110714-48-2

Basic information

• Product Name: 7-Ethyl-10-hydroxycamptothecin
• Synonyms: 1h-pyrano3,4:6,7indolizino1,2-bquinoline-3,14(4h,12h)-dione, 4-ethyl-4,10-dihydroxy-; 7-ethyl-10-hydroxy camptothecin; 7-ethyl-10-hydroxy-camptothecine; 4,11-diethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione; (4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 7-Ethyl-10-Hydroxy-Camptothecin; SN-38; 7-Ethyl-10-hydroxycamptothecine; Intermediate of Irinotecan 1
• CAS NO: 110714-48-2
• Molecular Formula: C₂₂H₂₀N₂O₅
• Molecular Weight: 392.4
• Mol File: 110714-48-2.mol
• Article Data: 44

Chemical Properties

• Refractive Index: 1.776
• CAS DataBase Reference: 7-Ethyl-10-hydroxycamptothecin(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Ethyl-10-hydroxycamptothecin(110714-48-2)
• EPA Substance Registry System: 7-Ethyl-10-hydroxycamptothecin(110714-48-2)

Safety Data

• Hazardous Substances Data: 110714-48-2(Hazardous Substances Data)

Usage

General Description

7-Ethyl-10-hydroxycamptothecin is a semi-synthetic derivative of camptothecin, a natural plant alkaloid. It is a topoisomerase inhibitor, which means it interferes with the action of enzymes that are involved in DNA replication and transcription. This mechanism of action makes it a potential anti-cancer agent, as it can inhibit the growth and spread of cancer cells. It has been studied for its potential use in the treatment of various types of cancer, including colorectal, ovarian, and lung cancer. Additionally, its water-soluble properties make it a promising candidate for use in drug delivery systems and formulations. Overall, 7-Ethyl-10-hydroxycamptothecin shows promise as a potent and versatile chemical with potential applications in cancer therapy and drug delivery.

Upstream product

• 35364-15-9 2'-amino-5'-hydroxypropiophenone 
• 110351-94-5 (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 
• 99-11-6 citrazinic acid 
• 5398-44-7 2,6-dichloropyridine-4-carboxylic acid 
• 19685-09-7 (S)-10-hydroxycamptothecin 
• 123-38-6 propionaldehyde 
• 955939-04-5 7-ethyl-10-hydroxy-18,19-dehydrocamptothecin 
• 97682-44-5 irinotecan 
• 102978-40-5 4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 
• 924648-17-9 1-(5-fluoro-2-nitrophenyl)propan-1-one 
• 453518-19-9 1-(5-hydroxy-2-nitrophenyl)propan-1-one 
• 456-48-4 3-Fluorobenzaldehyde 
• 458-02-6 3-fluorobenzaldehyde oxime 
• 403-54-3 m-Fluorobenzonitrile 

Downstream Products

• 113853-62-6 Phosphoric acid dibenzyl ester (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 
• 549520-67-4 3,4,5-triacetoxy-6-{2-[(4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yloxycarbonyl)-methyl-amino]-4-nitro-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 97682-44-5 irinotecan 
• 100286-90-6 irinotecan hydrochloirde 
• 946062-01-7 7-ethyl-10-O-t-butyldiphenylsilylcamptothecin 
• 850728-18-6 tocopherol succinate 7-ethyl-10-hydroxycamptothecin 
• 1346434-22-7 C₅₂H₅₁N₇O₈ 
• 1436411-08-3 O-trityl-7ethyl-10-hydroxycamptothecintriazolylbutahydroxamate 
• 1436411-10-7 O-trityl-7-ethyl-10-hydroxycamptothecintriazolylpentahydroxamate 
• 1436411-12-9 O-trityl-7-ethyl-10-hydroxycamptothecintriazolylhexahydroxamate 
• 1436411-14-1 O-trityl-7-ethyl-10-hydroxycamptothecintriazolylheptahydroxamate 
• 1436411-16-3 O-trityl-7-ethyl-10-hydroxycamptothecintriazolyloctahydroxamate 
• 1454575-12-2 7-ethyl-10-benzyloxy-(20S, 21S)-fluorcamptothecin 

Relevant articles and documents

Chemical decontamination of iPS cell-derived neural cell mixtures

This report describes the design and evaluation of phosphorylated 7-ethyl-10-hydroxycamptothecin (SN38-P), which selectively eliminates tumor-forming proliferative stem cells, including human induced pluripotent stem cells (hiPSCs) and neural stem cells, from iPSC-derived neural cell mixtures. Results of the present study demonstrate that simple phosphorylation of an anticancer drug can provide a safe, cost-effective, and chemically-defined tool for decontaminating hiPSC-derived neuron.

Copper-free Sonogashira reaction using 7-chloro camptothecins

We studied copper-free Sonogashira reaction using 7-chloro camptothecins, and determined that rac-BINAP/Pd(OAc)2 was an efficient catalyst for the coupling reaction. With this process, a number of 7-substituted camptothecins with a wide range of functional groups are potentially accessible. Besides, two drugs, SN-38 and BNP-1350, could be prepared by this method.

Different hydrolases involved in bioactivation of prodrug-type angiotensin receptor blockers: Carboxymethylenebutenolidase and carboxylesterase 1

Olmesartan medoxomil (OM) is a prodrug-type angiotensin II type 1 receptor blocker (ARB). We recently identified carboxymethylenebutenolidase homolog (CMBL) as the responsible enzyme for OM bioactivation in humans. In the present study, we compared the bioactivating properties of OM with those of other prodrug-type ARBs, candesartan cilexetil (CC) and azilsartan medoxomil (AM), by focusing on interspecies differences and tissue specificity. In invitro experiments with pooled tissue subcellular fractions of mice, rats, monkeys, dogs, and humans, substantial OM-hydrolase activities were observed in cytosols of the liver, intestine, and kidney in all the species tested except for dog intestine, which showed negligible activity, whereas lung cytosols showed relatively low activities compared with the other tissues. AM-hydrolase activities were well correlated with the OM-hydrolase activities. In contrast, liver microsomes exhibited the highest CC-hydrolase activity among various tissue subcellular fractions in all the species tested. As a result of Western blot analysis with the tissue subcellular fractions, the band intensities stained with anti-human CMBL and carboxylesterase 1 (CES1) antibodies well reflected OM- and AM-hydrolase activities and CC-hydrolase activity, respectively, in animals and humans. Recombinant human CMBL and CES1 showed significant AM- and CC-hydrolase activities, respectively, whereas CC hydrolysis was hardly catalyzed with recombinant carboxylesterase 2 (CES2). In conclusion, OM is bioactivated mainly via intestinal and additionally hepatic CMBL not only in humans but also in mice, rats, and monkeys, while CC is bioactivated via hepatic CES1 rather than intestinal enzymes, including CES2. AM is a substrate for CMBL. Copyright

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.

On-Demand Activation of a Bioorthogonal Prodrug of SN-38 with Fast Reaction Kinetics and High Releasing Efficiency in Vivo

Although a myriad of bioorthogonal prodrugs have been developed, very few of them present both fast reaction kinetics and complete cleavage. Herein, we report a new bioorthogonal prodrug strategy with both fast reaction kinetics (k2: ～103 M-1 s-1) and complete cleavage (>90% within minutes) using the bioorthogonal reaction pair of N-oxide and boron reagent. Distinctively, an innovative 1,6-elimination-based self-immolative linker is masked by N-oxide, which can be bioorthogonally demasked by a boron reagent for the release of both amino and hydroxy-containing payload in live cells. Such a strategy was applied to prepare a bioorthogonal prodrug for a camptothecin derivative, SN-38, resulting in 10-fold weakened cytotoxicity against A549 cells, 300-fold enhanced water solubility, and on-demand activation upon a click reaction both in vitro and in vivo. This novel bioorthogonal prodrug strategy presents significant advances over the existing ones and may find wide applications in drug delivery in the future.

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)