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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:
122111-03-9
Molecular Weight:
299.66
MDL number:
MFCD01735988
UNSPSC Code:
12352200
PubChem Substance ID:
329799951
NACRES:
NA.77

product name

Gemcitabine hydrochloride, ≥98% (HPLC)

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

Gene Information

human ... POLA1(5422) , POLA2(23649) , POLD1(5424) , POLD2(5425) , POLD3(10714) , POLD4(57804) , POLE(5426) , POLE2(5427) , POLE3(54107) , PRIM1(5557) , PRIM2(5558) , RRM1(6240) , RRM2(6241) , RRM2B(50484)

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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
GHS08

Signal Word

Danger

Hazard Statements

H360

Hazard Classifications

Repr. 1B

Storage Class Code

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

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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M Barton-Burke
Cancer nursing, 22(2), 176-183 (1999-04-27)
There have been exciting new developments in anticancer therapy over the past few years. One such therapy uses gemcitabine (GemzarR), an antimetabolite approved in 1996 by the Food and Drug Administration (FDA) for first-line treatment of locally advanced (nonresectable stage
Abdullah Shopit et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 91, 153711-153711 (2021-08-28)
Gemcitabine (GCB) is a first-line chemotherapeutic drug for pancreatic cancer (PCa). However, the resistance begins developing within weeks of chemotherapy. SPINK1 overexpression enhances resistance to chemotherapy. In a recent study, our laboratory established that the oleanolic acid (OA) derivative, K73-03
Yuan Chi et al.
Frontiers in oncology, 11, 671082-671082 (2021-12-07)
Pancreatic cancer is associated with poor prognosis and dismal survival rates. This study aims to investigate roles of lncRNA UCA1-loaded exosomes secreted by pancreatic stellate cells (PSCs) in Gemcitabine (Gem) resistance of pancreatic cancer under hypoxia, which involves the methylation
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
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