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95058-81-4 , Gemcitabine, CAS:95058-81-4

95058-81-4 , Gemcitabine,
C9H11F2N3O4 / 263.20

吉西他滨 ,Gemcitabine

Gemcitabine is as a synthetic pyrimidine nucleoside prodrug. The hydrogen atoms on the 2' carbon of deoxycytidine are replaced by fluorine atoms. Gemcitabine works by being incorporated into the DNA of cancer cells during replication and inhibiting DNA synthesis. First gemcitabine is converted into its active form, gemcitabine triphosphate, by cellular enzymes including deoxycytidine kinase (DCK), after it is taken up by cancer cells. The gemcitabine triphosphate interferes with the normal functioning of the enzymes involved in replicating DNA, leading to the termination of DNA synthesis and ultimately, cell death. Gemcitabine is used as a chemotherapy drug used to treat various types of cancer, including pancreatic, lung, breast, and ovarian cancer.

Gemcitabine is part of our Bio-X™ Range. These products are aimed at life science researchers who need high quality ready to use products for assay development, screening or other R&D work. With a solubility datasheet and convenient vials, all of our Bio-X ™ products are in stock across our global warehouses for rapid delivery and ease of use.

Gemcitabine is a nucleoside analogue that is primarily used in the treatment of several types of cancers and solid tumors. It is an antimetabolite that interferes with the synthesis of DNA and RNA molecules, thereby inhibiting the growth and proliferation of cancer cells. It was first synthesized in the late 1980s and was approved by the FDA in 1995 for the treatment of pancreatic cancer.

Physical and Chemical Properties:

Gemcitabine is a white to off-white, crystalline powder that is highly soluble in water. It has a molecular formula of C9H11F2N3O4 and a molecular weight of 263.20 g/mol. It is a prodrug that is converted to its active form, gemcitabine triphosphate, within the cell.

Synthesis and Characterization:

The synthesis of gemcitabine involves the reaction of 2'-deoxy-2',2'-difluorocytidine with triethylamine, followed by acetylation with acetic anhydride. This reaction yields gemcitabine hydrochloride, which is then converted to the free base by treatment with sodium hydroxide. Gemcitabine can be characterized by several techniques, including NMR spectroscopy, mass spectrometry, and X-ray crystallography.

Analytical Methods:

Several analytical methods have been developed for the detection and quantification of gemcitabine. These include high-performance liquid chromatography (HPLC), capillary electrophoresis (CE), and mass spectrometry (MS). These methods are highly sensitive and accurate, allowing for the detection of very small quantities of gemcitabine in biological samples.

Biological Properties:

Gemcitabine exhibits potent antitumor activity against several types of cancers, including pancreatic, non-small cell lung, breast, and bladder cancer. Its mechanism of action involves the inhibition of DNA and RNA synthesis, leading to the inhibition of cancer cell growth and proliferation. Gemcitabine has also been shown to induce apoptosis, or programmed cell death, in cancer cells.

Toxicity and Safety in Scientific Experiments:

Gemcitabine can cause several side effects, including nausea, vomiting, fatigue, and hematological toxicity, which can result in anemia, leukopenia, and thrombocytopenia. However, these side effects are generally mild and can be managed with supportive care. Toxicity studies have demonstrated that gemcitabine is relatively safe at therapeutic doses and does not cause significant damage to normal tissues or organs.

Applications in Scientific Experiments:

Gemcitabine has several applications in scientific experiments, including studies on cancer biology, drug development, and drug resistance mechanisms. It is often used as a standard chemotherapy agent in preclinical studies and clinical trials, allowing for the evaluation of the efficacy and safety of new anticancer drugs.

Current State of Research:

Gemcitabine continues to be an important chemotherapy agent for the treatment of several types of cancer. Research is currently focused on the development of new gemcitabine-based combination therapies, the identification of biomarkers for patient selection, and the development of predictive models for drug resistance.

Potential Implications in Various Fields of Research and Industry:

Gemcitabine has potential implications in several fields of research and industry, including pharmacology, oncology, and drug development. Its antitumor activity and low toxicity profile make it a promising candidate for combination therapies with other chemotherapy agents and targeted therapies.

Limitations and Future Directions:

Despite its therapeutic potential, gemcitabine has several limitations, including the development of drug resistance and the limited efficacy against certain types of cancer. Future research is focused on the development of new formulations and delivery systems, combination therapies with other drugs, and identification of predictive biomarkers of response and resistance.

Future Directions:

1. Development of gemcitabine prodrugs with improved pharmacokinetic properties and enhanced tumor-targeting properties.

2. Identification of predictive biomarkers for the selection of patients who are likely to benefit from gemcitabine-based chemotherapy.

3. Development of new gemcitabine-based combination therapies with other chemotherapy agents or targeted therapies.

4. Investigation of the molecular mechanisms underlying gemcitabine resistance and the identification of novel targets for combination therapies.

5. Development of predictive models for gemcitabine efficacy and resistance based on genomic and proteomic profiling.

6. Evaluation of the potential of gemcitabine in other therapeutic areas, such as viral infections and autoimmune diseases.

7. Development of gemcitabine-loaded nanoparticles and other drug delivery systems that can improve drug bioavailability and reduce toxicity.

8. Investigation of the potential of gemcitabine in combination with immunotherapies for the treatment of cancer.

9. Development of gemcitabine derivatives with improved pharmacological properties and therapeutic efficacy.

10. Identification of novel molecular targets for gemcitabine-based chemotherapy, such as epigenetic regulators and non-coding RNAs.

Title: Gemcitabine

CAS Registry Number: 95058-81-4

CAS Name: 2'-Deoxy-2',2'-difluorocytidine

Additional Names: 1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose; dFdC; dFdCyd

Manufacturers' Codes: LY-188011

Trademarks: Gemzar (Lilly)

Molecular Formula: C9H11F2N3O4

Molecular Weight: 263.20

Percent Composition: C 41.07%, H 4.21%, F 14.44%, N 15.97%, O 24.32%

Literature References: Prepn: L. W. Hertel, GB 2136425; idem, US 4808614 (1984, 1989 both to Lilly); L. W. Hertel et al., J. Org. Chem. 53, 2406 (1988); T. S. Chou et al., Synthesis 1992, 565. Antitumor activity: L. W. Hertel et al., Cancer Res. 50, 4417 (1990). Mode of action study: V. W. T. Ruiz et al., Biochem. Pharmacol. 46, 762 (1993). Clinical pharmacokinetics and toxicity: J. L. Abbruzzese et al., J. Clin. Oncol. 9, 491 (1991). Review of clinical studies: B. Lund et al., Cancer Treat. Rev. 19, 45-55 (1993).

Properties: Crystals from water, pH 8.5. [a]365 +425.36°; [a]D +71.51° (c = 0.96 in methanol). uv max (ethanol): 234, 268 (e 7810, 8560). LD10 i.v. in rats: 200 mg/m2 (Abbruzzese).

Optical Rotation: [a]365 +425.36°; [a]D +71.51°

Absorption maximum: uv max (ethanol): 234, 268 (e 7810, 8560)

Toxicity data: LD10 i.v. in rats: 200 mg/m2 (Abbruzzese)


Derivative Type: Hydrochloride

CAS Registry Number: 122111-03-9

Molecular Formula: C9H11F2N3O4.HCl

Molecular Weight: 299.66

Percent Composition: C 36.07%, H 4.04%, F 12.68%, N 14.02%, O 21.36%, Cl 11.83%

Properties: Crystals from water-acetone, mp 287-292° (dec). [a]D +48°; [a]365 +257.9° (c = 1.0 in deuterated water). uv max (water): 232, 268 nm (e 7960, 9360).

Melting point: mp 287-292° (dec)

Optical Rotation: [a]D +48°; [a]365 +257.9° (c = 1.0 in deuterated water)

Absorption maximum: uv max (water): 232, 268 nm (e 7960, 9360)

CAS Number95058-81-4
Product NameGemcitabine
IUPAC Name4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Molecular FormulaC9H11F2N3O4
Molecular Weight263.2 g/mol
In water, 5.13X10+4 mg/L at 25 °C (est)
2.23e+01 g/L
Synonyms2',2'-DFDC, 2',2'-difluoro-2'-deoxycytidine, 2',2'-difluorodeoxycytidine, 2'-deoxy-2',2''-difluorocytidine-5'-O-monophosphate, 2'-deoxy-2'-difluorocytidine, dFdCyd, gemcitabine, gemcitabine hydrochloride, gemcitabine, (alpha-D-threo-pentofuranosyl)-isomer, gemcitabine, (beta-D-threo-pentafuranosyl)-isomer, gemcitabine, (D-threo-pentafuranosyl)-isomer, gemicitabine, Gemzar, LY 188011, LY-188011
Canonical SMILESC1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)(F)F
Isomeric SMILESC1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F

CAS No: 95058-81-4 Synonyms: 2;-Deoxy-2',2'-difluorocytidine4-Amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one2'-Deoxy-2',2'-difluoro-D-cytidine2',2'-Difluoro-2'-deoxycytidine MDL No: MFCD00869720 Chemical Formula: C9H11F2N3O4 Molecular Weight: 263.20


Name: Gemcitabine        CAS: 95058-81-4     

M.F.: C9H11F2N3O      M.W.: 263.20      





White crystalline powder


NMR and MS

Should comply






224 -230

224 -226

Specific rotation

0.96% solution in ethanol

+68o ~ +74o



Max. 0.1%



Max. 0.1%


Total impurities

Max. 1%


Loss Weight On Dryness

Max. 0.5%


Residue On Ignition

Max. 0.2%


Heavy metal

Max. 20ppm


Assay (HPLC)

Min. 98%



1. Grunewald R, Abbruzzese JL, Tarassoff P, Plunkett W, Cancer Chemotherapy and Pharmacology 1991, Vol27, No4, p258-262


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