103882-84-4

Basic information

• Product Name: gemcitabine
• Synonyms: 2',2'-Dfdc;2'-Deoxy-2',2''-difluorocytidine-5'-o-monophosphate;2'-Deoxy-2'-difluorocytidine;C056507;Gemcitabine, (alpha-D-threo-pentofuranosyl)-isomer
• CAS NO: 103882-84-4
• Molecular Formula: C₉H₁₁F₂N₃O₄
• Molecular Weight: 263.199
• Mol File: 103882-84-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 482.7°Cat760mmHg
• Flash Point: 245.7°C
• Appearance: /
• Density: 1.4034 (estimate)
• Vapor Pressure: 2.41E-11mmHg at 25°C
• Refractive Index: 1.652
• PKA: 11.65±0.70(Predicted)
• CAS DataBase Reference: gemcitabine(CAS DataBase Reference)
• NIST Chemistry Reference: gemcitabine(103882-84-4)
• EPA Substance Registry System: gemcitabine(103882-84-4)

Safety Data

• Hazardous Substances Data: 103882-84-4(Hazardous Substances Data)

Usage

Uses

Gemcitabine is a nucleoside analog with anti-cancer properties. An inhibitor of DNA synthesis active on solid tumors.

InChI:InChI=1/C9H11F2N3O4/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)/t4-,6-,7-/m1/s1

Upstream product

• 134877-42-2 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose 
• 122111-01-7 2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate 
• 1173824-58-2 (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate 
• 143157-23-7 1-(2'-deoxy-2',2'-difluoro-3',5'-di-O-benzoyl-D-ribofuranosyl)-4-acetamidopyrimidin-2-one 

Downstream Products

• 116371-67-6 Gemcitabine monophosphate 
• 95058-81-4 gemcitabine 
• 122111-03-9 gemcitabine hydrochloride 
• 122111-05-1 2'-deoxy-2',2'-difluorocytidine hydrochloride 
• 114248-23-6 Deoxydifluorouridine 

Related news

LW6 enhances chemosensitivity to gemcitabine (cas 103882-84-4) and inhibits autophagic flux in pancreatic cancer07/23/2019

The efficacy of gemcitabine therapy is often insufficient for the treatment of pancreatic cancer. The current study demonstrated that LW6, a chemical inhibitor of hypoxia-inducible factor 1α, is a promising drug for enhancing the chemosensitivity to gemcitabine. LW6 monotherapy and the combinat...detailed

Cytosolic 5′-nucleotidase 1A is overexpressed in pancreatic cancer and mediates gemcitabine (cas 103882-84-4) resistance by reducing intracellular gemcitabine (cas 103882-84-4) metabolites07/22/2019

BackgroundCytosolic 5′-nucleotidase 1A (NT5C1A) dephosphorylates non-cyclic nucleoside monophosphates to produce nucleosides and inorganic phosphates. Here, we investigate NT5C1A expression in pancreatic ductal adenocarcinoma (PDAC) and its impact on gemcitabine metabolism and therapeutic efficacy.detailed

HNF1A inhibition induces the resistance of pancreatic cancer cells to gemcitabine (cas 103882-84-4) by targeting ABCB107/20/2019

BackgroundPancreatic ductal adenocarcinoma (PDAC) is an aggressive disease with poor prognosis, and gemcitabine-based chemotherapy remains an effective option for the majority of PDAC patients. Hepatocyte nuclear factor 1α (HNF1A) is a tumor-suppressor in PDAC, but its role in gemcitabine chemo...detailed

Digoxin sensitizes gemcitabine (cas 103882-84-4)-resistant pancreatic cancer cells to gemcitabine (cas 103882-84-4) via inhibiting Nrf2 signaling pathway07/21/2019

Chemoresistance is a major therapeutic obstacle in the treatment of human pancreatic ductal adenocarcinoma (PDAC). As an oxidative stress responsive transcription factor, nuclear factor erythroid 2-related factor 2 (Nrf2) regulates the expression of cytoprotective genes. Nrf2 not only plays a cr...detailed

Relevant articles and documents

Stereospecific synthesis of 2-deoxy-2,2-difluororibonolactone and its use in the preparation of 2'-deoxy-2',2'-difluoro-β-D-ribofuranosyl pyrimidine nucleosides: The key role of selective crystallization

A stereospecific synthesis of 2'-deoxy-2',2'-difluorocytidine (gemcitabine), a potential anticancer agent, is described. The stereoselectivity was accomplished via two diastereoselective crystallizations, i.e. the crystallization of the key intermediate, difluororibonolactone 2a, and the crystallization of the hydrochloride salt of gemcitabine 16b from the anomeric mixture. Because of the availability of 2a in large quantities, other 2'-deoxy-2',2'-difluoropyrimidine nucleosides such as 2'-deoxy-2',2'-difluorouridine (19) were synthesized for structure-activity relationship studies.