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G6423

Sigma-Aldrich

Gemcitabine hydrochloride

≥98% (HPLC), powder, antitumor agent

Synonym(s):

2′-Deoxy-2′,2′-difluorocytidine; dFdC, Gemzar (Lilly), LY-188011, dFdC, dFdCyd

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About This Item

Empirical Formula (Hill Notation):
C9H11F2N3O4 · HCl
CAS Number:
Molecular Weight:
299.66
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

product name

Gemcitabine hydrochloride, ≥98% (HPLC)

Quality Level

assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

solubility

H2O: ≥10 mg/mL

originator

Eli Lilly

storage temp.

room temp

SMILES string

Cl.NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)C2(F)F

InChI

1S/C9H11F2N3O4.ClH/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17;/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17);1H/t4-,6-,7-;/m1./s1

InChI key

OKKDEIYWILRZIA-OSZBKLCCSA-N

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General description

Gemcitabineis a pyrimidine nucleoside analog of deoxycytidine. It exhibits anticancereffects against various cancers.

Application

Gemcitabinehydrochloride has been used as a chemotherapeutic agent to study its effects onthe human pancreatic adenocarcinoma cell lineIt has been used as a chemotherapeutic to study its resistance inpancreatic stellate cells (PSCs)It has also been used to study its effects on patient-derivedxenograft (PDX) organoids.

Biochem/physiol Actions

Gemcitabine is a widely used antitumor agents in both clinics and research labs. It is an antineoplastic agent and antimetabolite.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Eli Lilly. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Health hazard

signalword

Danger

hcodes

Hazard Classifications

Repr. 1B

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


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bei-Ping Miao et al.
Cellular & molecular immunology, 12(6), 750-756 (2014-12-30)
The prevalence of nasopharyngeal cancer (NPC) is high in the southern area of China and some other districts in the world. The pathogenesis of NPC is unclear. It is reported that some microRNAs (miR) are involved in the progression of
Jun Young Park et al.
Molecular therapy. Nucleic acids, 12, 543-553 (2018-09-10)
Gemcitabine has been considered a first-line chemotherapy agent for the treatment of pancreatic cancer. However, the initial response rate of gemcitabine is low and chemoresistance occurs frequently. Aptamers can be effectively internalized into cancer cells via binding to target molecules
Nikki K Lytle et al.
Cell, 177(3), 572-586 (2019-04-09)
Drug resistance and relapse remain key challenges in pancreatic cancer. Here, we have used RNA sequencing (RNA-seq), chromatin immunoprecipitation (ChIP)-seq, and genome-wide CRISPR analysis to map the molecular dependencies of pancreatic cancer stem cells, highly therapy-resistant cells that preferentially drive tumorigenesis
Jin Soo Shin et al.
Viruses, 10(6) (2018-05-26)
The Middle East respiratory syndrome-coronavirus (MERS-CoV), first identified in Saudi Arabia, is an emerging zoonotic pathogen that causes severe acute respiratory illness in humans with a high fatality rate. Since its emergence, MERS-CoV continues to spread to countries outside of
Katsumi Fukamachi et al.
PloS one, 9(10), e111481-e111481 (2014-10-28)
Pancreatic ductal adenocarcinoma (PDA) is a highly lethal disease, which is usually diagnosed in an advanced stage. We have established transgenic rats carrying a mutated K-ras gene controlled by Cre/loxP activation. The animals develop PDA which is histopathologically similar to

Articles

Neoplastic cells are highly dependent on the de novo synthesis of nucleotides to maintain sufficient pools to support DNA replication and the production of RNA.

Related Content

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

n proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during the synthesis (S) phase, which is followed by a second gap phase (G2) during which growth and preparation for cell division occurs. Together, these three stages comprise the interphase phase of the cell cycle. Interphase is followed by the mitotic (M) phase.

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