H0165

7-Ethyl-10-hydroxycamptothecin

Name: 7-Ethyl-10-hydroxycamptothecin
Brand: SIGMA

powder, ≥98% (HPLC)

Synonym(s):

SN-38

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All Photos(2)

About This Item

Empirical Formula (Hill Notation):

C₂₂H₂₀N₂O₅

CAS Number:

86639-52-3

Molecular Weight:

392.40

UNSPSC Code:

12352204

PubChem Substance ID:

329815105

NACRES:

NA.77

MDL number:

MFCD00871873

Product Name

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

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

biological source

Artemisia annua

assay

≥98% (HPLC)

form

powder

solubility

DMSO: 1 mg/mL

storage temp.

−20°C

Quality Level

200

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.

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

GHS08,GHS07

signalword

Danger

hcodes

H302,H360D,H372

pcodes

P201 - P202 - P260 - P264 - P301 + P312 - P308 + P313

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Randomized, open-label, phase III study comparing irinotecan with paclitaxel in patients with advanced gastric cancer without severe peritoneal metastasis after failure of prior combination chemotherapy using fluoropyrimidine plus platinum: WJOG 4007 trial.

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

Aflibercept versus placebo in combination with fluorouracil, leucovorin and irinotecan in the treatment of previously treated metastatic colorectal cancer: prespecified subgroup analyses from the VELOUR trial.

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

Dual roles for splice variants of the glucuronidation pathway as regulators of cellular metabolism.

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

Antiviral screen identifies EV71 inhibitors and reveals camptothecin-target, DNA topoisomerase 1 as a novel EV71 host factor.

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

The effects of chemotherapeutic drugs on human monocyte-derived dendritic cell differentiation and antigen presentation.

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

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