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

• 162471-15-0 4-isocyanophenol 
• 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 
• 97682-44-5 irinotecan 
• 1108204-40-5 1-trimethylsilyloxy-2-ethyl-1,3-butadiene 
• 1335104-70-5 (E)-3-ethoxy-1-(9-ethyl-3-hydroxy-7-methoxy-1H-pyrrolo[3,4-b]quinolin-2(3H)-yl)prop-2-en-1-one 
• 1335104-74-9 C₂₃H₂₂N₂O₃ 
• 1335104-64-7 ethyl 2-((benzyloxy)methyl)-4-ethyl-6-methoxyquinoline-3-carboxylate 
• 1335104-65-8 (2-((benzyloxy)methyl)-4-ethyl-6-methoxyquinolin-3-yl)methanol 
• 1335104-66-9 2-((benzyloxy)methyl)-4-ethyl-6-methoxyquinoline-3-carbaldehyde 
• 1335104-67-0 (E)-2-((benzyloxy)methyl)-4-ethyl-6-methoxyquinoline-3-carbaldehyde oxime 
• 1335104-68-1 (3-(aminomethyl)-4-ethyl-6-methoxyquinolin-2-yl)methanol 
• 1335104-69-2 (E)-3-ethoxy-N-((4-ethyl-2-(hydroxymethyl)-6-methoxyquinolin-3-yl)methyl)acrylamide 
• 60997-56-0 2'-amino-5'-methoxypropiophenone 
• 924648-17-9 1-(5-fluoro-2-nitrophenyl)propan-1-one 

Downstream Products

• 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 
• 1246815-54-2 SN-38 
• 97682-44-5 irinotecan 
• 1346434-22-7 C₅₂H₅₁N₇O₈ 
• 946821-59-6 (S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3′,4’:6,7]indolizino[1,2-b]-quinolin-9-yl acetate 

Relevant articles and documents

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.

Folate Receptor Targeting and Cathepsin B-Sensitive Drug Delivery System for Selective Cancer Cell Death and Imaging

In this work, a folate receptor (FR)-mediated dual-targeting drug delivery system was synthesized to improve the tumor-killing efficiency and inhibit the side effects of anticancer drugs. We designed and synthesized an FR-mediated fluorescence probe (FA-Rho) and FR-mediated cathepsin B-sensitive drug delivery system (FA-GFLG-SN38). FA-GFLG-SN38 is composed of the FR ligand (folic acid, FA), the tetrapeptide substrate for cathepsin B (GFLG), and an anticancer drug (SN38). The rhodamine B (Rho)-labeled probe FA-Rho is suitable for specific fluorescence imaging of SK-Hep-1 cells overexpressing FR and inactive in FR-negative A549 and 16-HBE cells. FA-GFLG-SN38 exhibited strong cytotoxicity against FR-overexpressing SK-Hep-1, HeLa, and Siha cells, with IC50 values of 2-3 μM, but had no effect on FR-negative A549 and 16-HBE cells. The experimental results show that the FA-CFLG-SN38 drug delivery system proposed by us can effectively inhibit tumor proliferation in vitro, and it can be adopted for the diagnostics of tumor tissues and provide a basis for effective tumor therapy.

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)