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Key Documents

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H0165

Sigma-Aldrich

7-Ethyl-10-hydroxycamptothecin

powder, ≥98% (HPLC)

Sinónimos:

SN-38

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About This Item

Fórmula empírica (notación de Hill):
C22H20N2O5
Número de CAS:
86639-52-3
Peso molecular:
392.40
MDL number:
MFCD00871873
UNSPSC Code:
12352204
PubChem Substance ID:
329815105
NACRES:
NA.77

product name

7-Ethyl-10-hydroxycamptothecin, ≥98% (HPLC), powder

biological source

Artemisia annua

assay

≥98% (HPLC)

form

powder

solubility

DMSO: 1 mg/mL

storage temp.

−20°C

SMILES string

OC1=CC2=C(CC)C(C3)=C(N=C2C=C1)C(N3C4=O)=CC5=C4COC([C@]5(O)CC)=O

InChI

1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1

InChI key

FJHBVJOVLFPMQE-QFIPXVFZSA-N

Application

7-Ethyl-10-hydroxycamptothecin has been used:
  • to inhibit enterovirus 71 (EV71) (H) infection
  • to screen the chemosensitivity of pancreatic adenocarcinoma cells
  • as a chemical to study its ability to reverse multidrug resistance (MDR), due to ATP binding cassette (ABC) transporters

Biochem/physiol Actions

Active metabolite of irinotecan. Inhibitor of topoisomerase I.. Gene expression analysis of colon cancer cell lines treated with SN-38 showed differential effects: the majority of affected genes were down-regulated (including, most strongly, genes related to receptor and kinase activity, signal transduction, apoptosis, RNA processing, protein metabolism and transport, cell cycle and transcription. Some of the up-regulated genes were involved in apoptosis, transcription, development and differentiation.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B - STOT RE 1

target_organs

Gastro-intestinal system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Mélanie Rouleau et al.
Molecular pharmacology, 85(1), 29-36 (2013-10-22)
Transcripts of the UGT1A gene, encoding half of human UDP-glucuronosyltransferase (UGT) enzymes, undergo alternative splicing, resulting in active enzymes named isoforms 1 (i1s) and novel truncated isoforms 2 (i2s). Here, we investigated the effects of depleting endogenous i2 on drug
Shuichi Hironaka et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 31(35), 4438-4444 (2013-11-06)
This phase III study compared treatment with weekly paclitaxel and biweekly irinotecan in patients with advanced gastric cancer refractory to treatment with fluoropyrimidine plus platinum. Patients were randomly assigned to receive either paclitaxel (80 mg/m(2) on days 1, 8, and
Josep Tabernero et al.
European journal of cancer (Oxford, England : 1990), 50(2), 320-331 (2013-10-22)
The antiangiogenic agent aflibercept (ziv-aflibercept in the United States) in combination with 5-fluorouracil, leucovorin and irinotecan (FOLFIRI) significantly improved survival in a phase III study of patients with metastatic colorectal cancer (mCRC) previously treated with an oxaliplatin-based regimen. In the
J Hu et al.
Clinical and experimental immunology, 172(3), 490-499 (2013-04-23)
Recent studies indicate that chemotherapeutic agents may increase the anti-tumoral immune response. Based on the pivotal role of dendritic cells (DCs) in host tumour-specific immune responses, we investigated the effect of commonly used chemotherapeutic drugs dexamethasone, doxorubicin, cisplatin and irinotecan
Kan Xing Wu et al.
Antiviral research, 143, 122-133 (2017-04-22)
Enterovirus 71 (EV71) is one of the causative agents of hand, foot and mouth disease (HFMD) associated with severe neurological disease. EV71's pathogenesis remains poorly understood and the lack of approved antiviral has led to its emergence as a clinically
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