138685-83-3

Basic information

• Product Name: N-Carboxybenzyl GeMcitabine
• Synonyms: N-Carboxybenzyl GeMcitabine;[1-(2-Deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)-1,2-dihydro-2-oxo-4-pyriMidinyl]- carbaMic Acid PhenylMethyl Ester;2'-Deoxy-2',2'-difluoro-N-[(phenylMethoxy)carbonyl]-cytidine;N-Cbz gemcitabine
• CAS NO: 138685-83-3
• Molecular Formula: C₁₇H₁₇F₂N₃O₆
• Molecular Weight: 397.3301864
• Product Categories: Amines;Bases & Related Reagents;Heterocycles;Nucleotides;Amines, Heterocycles, Nucleotides, Bases & Related Reagents
• Mol File: 138685-83-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: N-Carboxybenzyl GeMcitabine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Carboxybenzyl GeMcitabine(138685-83-3)
• EPA Substance Registry System: N-Carboxybenzyl GeMcitabine(138685-83-3)

Safety Data

• Hazardous Substances Data: 138685-83-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Powder

Uses

Gemcitabine (G305000) derivative.

Upstream product

• 122111-03-9 gemcitabine hydrochloride 
• 1151528-36-7 4-amino-1-((2R,4R,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3,3-difluoro-4-hydroxytetrahydrofuran-2-yl)pyrimidin-2(1H)-one 
• 1613293-13-2 4-(benzyloxycarbonylamino)-1-(2-deoxy-2,2-difluoro-5-O-[tertbutyl(dimethyl)silyl]-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one 
• 1155265-38-5 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-(trimethylsilyloxy)-5-((trimethylsilyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2(1H)-one 
• 501-53-1 benzyl chloroformate 
• 95058-81-4 gemcitabine 
• 1613293-14-3 4-(propargyloxycarbonylamino)-1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one 

Downstream Products

• 95058-81-4 gemcitabine 

Relevant articles and documents

A pharmacokinetic and pharmacodynamic evaluation of the anti-hepatocellular carcinoma compound 4-N-Carbobenzoxy-gemcitabine (Cbz-dFdC)

Gemcitabine (dFdC) demonstrates significant effectiveness against solid tumors in vitro and in vivo; however, its clinical application is limited because it tends to easily undergo deamination metabolism. Therefore, we synthesized 4-N-carbobenzoxy-gemcitabine (Cbz-dFdC) as a lead prodrug and conducted a detailed pharmacokinetic, metabolic, and pharmacodynamic evaluation. After intragastric Cbz-dFdC administration, the Cmax of Cbz-dFdC and dFdC was 451.1 ± 106.7 and 1656.3 ± 431.5 ng/mL, respectively. The Tmax of Cbz-dFdC and dFdC was 2 and 4 h, respectively. After intragastric administration of Cbz-dFdC, this compound was mainly distributed in the intestine due to low carboxylesterase-1 (CES1) activity. Cbz-dFdC is activated by CES1 in both humans and rats. The enzyme kinetic curves were well fitted by the Michaelis-Menten equation in rats' blood, plasma, and tissue homogenates and S9 of the liver and kidney, as well as human liver S9 and CES1 recombinase. The pharmacodynamic results showed that the Cbz-dFdC have a good antitumor effect in the HepG2 cell and in tumor-bearing mice, respectively. In general, Cbz-dFdC has good pharmaceutical characteristics and is therefore a good candidate for a potential prodrug.

CYTIDINE DERIVATIVE DIMERS AND APPLICATIONS THEREOF

The present disclosure provides cytidine derivative dimers, salts and compositions of the cytidine derivative dimers, and methods of making and using the cytidine derivative dimers that are useful for treating a neoplasm in mammalian subjects. A cytidine derivative dimer may have the following general formula (I): By molecularly designing such cytidine-based compounds, the disclosed cytidine-based derivative dimers/salts show significant inhibiting effects on HCT-116 human colon cancer cells, and exhibit strong growth inhibiting effects on HCT-116 human colon cancer xenografts grown in nude mice. The disclosed cytidine derivative dimers/salts provide high anti-tumor activity with low toxicity and are useful for treating cancers.

TREATMENT OR PROPHYLAXIS OF PROLIFERATIVE CONDITIONS

The invention relates to novel compounds for use in the treatment or prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express cytochrome P450 1B1 (CYP1B1) and allelic variants thereof. The invention also provides pharmaceutical compositions comprising one or more such compounds for use in medical therapy, for example in the treatment of prophylaxis of cancers or other proliferative conditions, as well as methods for treating cancers or other conditions in human or non-human animal patients. The invention also provides methods for identifying novel compounds for use in the treatment of prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express CYP1 B1 and allelic variants thereof. The invention also provides a method for determining the efficacy of a compound of the invention in treating cancer.