7-Ethyl-10-hydroxycamptothecin

Base Information

• Chemical Name: 7-Ethyl-10-hydroxycamptothecin
• CAS No.: 86639-52-3
• Deprecated CAS: 113015-38-6
• Molecular Formula: C₂₂H₂₀N₂O₅
• Molecular Weight: 392.411
• Hs Code.: 29399990
• European Community (EC) Number: 643-093-9
• NSC Number: 673596
• UNII: 0H43101T0J
• DSSTox Substance ID: DTXSID4040399
• Nikkaji Number: J353.490A
• Wikipedia: SN-38
• Wikidata: Q1750127
• NCI Thesaurus Code: C61618
• Pharos Ligand ID: 39QM3LS7DRND
• Metabolomics Workbench ID: 68075
• ChEMBL ID: CHEMBL837
• Mol file: 86639-52-3.mol

Synonyms:7 Ethyl 10 hydroxycamptothecin;7-ethyl-10-hydroxycamptothecin;Camptosar;Camptothecin 11;camptothecin-11;CPT 11;CPT-11;CPT11;irinotecan;irinotecan hydrochloride;Irrinotecan;NK012 compound;SN 38;SN 38 11;SN-38;SN-38-11;SN3811

Chemical Property of 7-Ethyl-10-hydroxycamptothecin

Chemical Property:

• Appearance/Colour: light-yellow solid
• Melting Point: 217 °C
• Refractive Index: 21.5 ° (C=0.2, THF)
• Boiling Point: 810.3 °C at 760 mmHg
• PKA: 9.13±0.40(Predicted)
• Flash Point: 443.8 °C
• PSA: 101.65000
• Density: 1.51 g/cm³
• LogP: 2.34760
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble1mg/mL
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 392.13722174
• Heavy Atom Count: 29
• Complexity: 820

Purity/Quality:

99% ^*data from raw suppliers

7-Ethyl-10-Hydroxy-Camptothecin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)O
• Isomeric SMILES: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)O
• Recent ClinicalTrials: Safety and Pharmacokinetic Study of IT-141 in Monotherapy in Patients With Advanced Cancer
• Description: SN-38 (86639-52-3) is the active metabolite of CPT-11 that inhibits DNA topoisomerase I (IC50 values are 0.74 and 1.9 μM in P388 and Ehrlich cells respectively). Inhibits DNA and RNA synthesis (IC50 values are 0.077 and 1.3 μM respectively) but does not affect protein synthesis. SN-38 displays potent antitumor activity against a range of human tumor cell lines (IC50 values are 3.3, 13, 19 and 22 nM for HCT-116, BEL-7402, HL60 and HeLa cells respectively).
• Uses: 7-ethyl-10-hydroxycamptothecin (SN 38) is a metabolite of Irinotecan, a DNA topoisomerase inhibitor. SN 38 has been used in trials studying the treatment of Cancer, Advanced Solid Tumors, Small Cell Lung Cancer, Metastatic Colorectal Cancer, and Triple Negative Breast Cancer, among others.

Technology Process of 7-Ethyl-10-hydroxycamptothecin

There total 112 articles about 7-Ethyl-10-hydroxycamptothecin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

(S)-4,11-diethyl-4-hydroxy-9-methoxy-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4H,12H)-dione (86639-53-4) → 7-ethyl-10-hydroxycamptothecin (86639-52-3,110714-48-2,130144-34-2,113015-38-6,647852-82-2)

Guidance literature:

With boron tribromide; sodium iodide; In N,N-dimethyl-formamide; at -10 - 20 ℃; for 3h; Reagent/catalyst;

Reference yield: 92.0%

2'-amino-5'-hydroxypropiophenone (35364-15-9) + (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione (110351-94-5) → 7-ethyl-10-hydroxycamptothecin (86639-52-3,110714-48-2,130144-34-2,113015-38-6,647852-82-2)

Guidance literature:

With trifluoroacetic acid; In toluene; at 80 ℃; for 6h;

DOI:10.1080/00397911.2012.658947

Reference yield: 80.3%

7-ethylcamptothecin (78287-27-1) → 7-ethyl-10-hydroxycamptothecin (86639-52-3,110714-48-2,130144-34-2,113015-38-6,647852-82-2)

Guidance literature:

With dihydrogen peroxide; acetic anhydride; acetic acid; at 50 ℃;

upstream raw materials:

7-Ethylcamptothecin 1-Oxide

SN 38 Carboxylate

4-isocyanophenol

(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

Downstream raw materials:

SN 38 Carboxylate

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

irinotecan

irinotecan hydrochloirde

Refernces

• 1、 Feng, Shun,Ji, Xingyue,Long, Ya-Qiu,Zhou, Jujun,Zhou, Zhou. "On-Demand Activation of a Bioorthogonal Prodrug of SN-38 with Fast Reaction Kinetics and High Releasing Efficiency in Vivo". . . Retrieved 2022/01/14.
• 2、 Ito, Kei,Tatsumi, Toshifumi,Takahashi, Kazuki,Shimizu, Yohei,Yamatsugu, Kenzo,Kanai, Motomu. "A stable and cleavable o-linked spacer for drug delivery systems". . p. 212 - 215. Retrieved 2020/11/26.