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CAS NO.122111-03-9
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| Gemcitabine hydrochloride Basic information |
| Product Description Content Determination Distinguish Adverse reactions and side effects application |
| Product Name: | Gemcitabine hydrochloride |
| Synonyms: | 2’,2’-difluorodeoxycytidinemonohydrochloride;2’-deoxy-2’,2’-difluorocytidinemonohydrochloride;2’-deoxy-2’,2’-difluoro-cytidinmonohydrochloride;gemzar;ly188011;ly188011hydrochloride;2',2'-DIFLUORO-2'-DEOXYCYTIDINE;2'-DEOXY-2',2'-DIFLUOROCYTIDINE |
| CAS: | 122111-03-9 |
| MF: | C9H12ClF2N3O4 |
| MW: | 299.66 |
| EINECS: | |
| Product Categories: | Active Pharmaceutical Ingredients;API;Antineoplastic;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Antineoplastic drug, difluorine nucleoside analog;Anti-cancer&immunity;Inhibitors |
| Mol File: | 122111-03-9.mol |
|
|
|
| Gemcitabine hydrochloride Chemical Properties |
| mp | >250°C dec. |
| storage temp. | Desiccate at +4°C |
| CAS DataBase Reference | 122111-03-9(CAS DataBase Reference) |
| Safety Information |
| Hazard Codes | Xn,Xi |
| Risk Statements | 21-36/38-46-62-63 |
| Safety Statements | 25-26-36/37-53 |
| Gemcitabine hydrochloride Usage And Synthesis |
| Product Description |
Gemcitabine hydrochloride is a synthetic novel difluoro nucleoside drug that is anti-metabolic and antineoplastic. It is researched and developed by the Eli Lilly and Company and approved to be listed in South Africa, Sweden, the Netherlands, Australia and other countries in 1995. The United States Food and Drug Administration ( referred FDA) approved it as the first-line therapy for the clinical treatment of non-small cell lung cancer and pancreatic cancer. The main manufacturers of gemcitabine hydrochloride in domestic are Jiangsu Stock hausen Pharmaceutical Co., Ltd., and Harbin, Yu Heng Pharmaceutical company. Gemcitabine hydrochloride, as a pro-drug, is a good substrate for the acidification of deoxygenation of thymine kinase phosphorus in the cell, and under the action of the enzyme, it can be converted into the following metabolites: gemcitabine mono-phosphate (dFdCMP), gemcitabine diphosphate (dFdCDP) and gemcitabine triphosphate (dFdCTP), among which the latter two are the active products. In recent years, new drugs such as gemcitabine, paclitaxel, docetaxel, vinorebine are effective drugs for the treatment of non-small cell lung cancer (abbreviated NSCLC). Compared with traditional chemotherapy drugs, these drugs have the advantages of high curative effect and low toxicity. Gemcitabine hydrochloride is a new generation of anti-metabolites drug and a type of special medicine for cell cycle, playing a major role in DNA synthesis phase, namely S phase of cells. Under certain conditions, this medicine can prevent progression of cells from G1 phase to S phase, and have a strong anti-cancer activity non-small cell lung cancer(NSCLC). Foreign studies have shown that the efficient of the single treatment for NSCLC with gemcitabine hydrochloride only is about 18%~35%, while combined the treatment with cisplatin the efficiency for NSCLC is 41.7%. In advanced NSCLC, effective rate of carboplatin is 16%, which is similar to cisplatin, but has low toxicity, especially for gastrointestinal reactions, bone marrow suppression and the toxic reaction of kidney and nerve ending. In combination with carboplatin, both of them have mutual coordination and additive effect, and can produce higher curative effects. |
| Content Determination |
According to the efficient chromatography (Chinese Pharmacopoeia Edition 2000 Part two Appendix VD) determination. Chromatography conditions and system suitability test Use octadecylsilane bonded silica as a filler and ammonium acetate buffer (ammonium acetate 3.85g, add water 800ml to dissolve and glacial acetic acid to adjust the pH to 5.7, adding water to 1000ml) - methanol (90:10) as mobile phase, detecting the wavelength of 268nm. The theoretical plate number calculated according to the peak of gemcitabine hydrochloride should not be less than 2000 and the resolution between the peaks of gemcitabine hydrochloride and cytosine should be greater than 2.0. Measurements Take this product about 25mg, weigh it accurately, and put it into a 25ml volumetric flask, dissolved in water and diluted to the scale. Precisely measure this solution 5ml and put the solution into 50ml volumetric flask, diluted with water to the mark. Shake well and use this solution as the test solution. Precisely measure 20μl injection fluid into chromatography and record the chromatograms; Take another appropriate amount of gemcitabine hydrochloride and dry it to constant weight under the temperature of 105℃, using the processed product as the reference. Operate the reference with the same method mentioned above, and calculate it by peak area on the basis of the external standard method. The above information is edited by the Chemicalbook of Bai Linlin. |
| Distinguish |
1.Take appropriate amount of gemcitabine hydrochloride, make into solution containing the 10μg per ml by adding water and measure it according to the spectrophotometric method (Chinese Pharmacopoeia Edition 2000 Part 2 Appendix Ⅳ A). It has the maximum absorption at the wavelength of 269nm, and the minimum absorption at the wavelength of 249nm. 2.In the chromatogram recorded in content determination, the retention time of the major peak in the test solution should correspond to that in the reference solution. 3.The infrared absorption spectrum should be consistent with the reference standard spectrum. 4.Identification reaction that aqueous solution is chloride. (Chinese Pharmacopoeia Edition 2000 Part two Appendix III) |
| Adverse reactions and side effects |
The effect of bone marrow suppression. Symptoms such as anemia, leucopenia and thrombocytopenia will appear. Approximately 66% of patients have liver aminotransferase abnormalities, which mostly are mild, non-progressive damage. About 33% of patients experience nausea and vomiting. About 50% of patients have the symptoms of mild proteinuria and hematuria. There are some cases of unexplained renal failure. About 25% of patients have skin rash, 10% patients with itching. Less than 1% of patients experience bronchial spasms. Gemcitabine hydrochloride has significant cytotoxic activity on cultured human and mouse tumors, whose antitumor activity is associated with the administration. For example, daily dosing can lead to death of the animal, but the anti-cancer activity is very small; and when giving the drug every 3-4 days at a time, drug dose is non-lethal dose and has good anti-tumor activities on many tumors. |
| application | Suitable for the treatment of inoperable advanced or metastatic pancreatic cancer and the treatment of locally advanced or metastatic non-small cell lung cancer, and the treatment for mid-term and advanced non-small cell lung cancer, non-small cell lung cancer, pancreatic cancer, bladder cancer, breast cancer and other solid tumors. |
| Chemical Properties | White crystalline granular, odorless |
| Usage | An antineoplastic |
| Biological Activity | Deoxycytidine analog that inhibits DNA synthesis. Metabolized to form gemcitabine triphosphate (dFdCTP) and gemcitabine diphosphate (dFdCDP). dFdCTD inhibits ribonucleotide reductase causing a reduction in cellular nucleotides. dFdCTP is incorporated in DNA resulting in DNA strand termination. Displays antitumor activity in vitro and in vivo . |
| Gemcitabine hydrochloride Basic information |
| Product Description Content Determination Distinguish Adverse reactions and side effects application |
| Product Name: | Gemcitabine hydrochloride |
| Synonyms: | 2’,2’-difluorodeoxycytidinemonohydrochloride;2’-deoxy-2’,2’-difluorocytidinemonohydrochloride;2’-deoxy-2’,2’-difluoro-cytidinmonohydrochloride;gemzar;ly188011;ly188011hydrochloride;2',2'-DIFLUORO-2'-DEOXYCYTIDINE;2'-DEOXY-2',2'-DIFLUOROCYTIDINE |
| CAS: | 122111-03-9 |
| MF: | C9H12ClF2N3O4 |
| MW: | 299.66 |
| EINECS: | |
| Product Categories: | Active Pharmaceutical Ingredients;API;Antineoplastic;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Antineoplastic drug, difluorine nucleoside analog;Anti-cancer&immunity;Inhibitors |
| Mol File: | 122111-03-9.mol |
|
|
|
| Gemcitabine hydrochloride Chemical Properties |
| mp | >250°C dec. |
| storage temp. | Desiccate at +4°C |
| CAS DataBase Reference | 122111-03-9(CAS DataBase Reference) |
| Safety Information |
| Hazard Codes | Xn,Xi |
| Risk Statements | 21-36/38-46-62-63 |
| Safety Statements | 25-26-36/37-53 |
| Gemcitabine hydrochloride Usage And Synthesis |
| Product Description |
Gemcitabine hydrochloride is a synthetic novel difluoro nucleoside drug that is anti-metabolic and antineoplastic. It is researched and developed by the Eli Lilly and Company and approved to be listed in South Africa, Sweden, the Netherlands, Australia and other countries in 1995. The United States Food and Drug Administration ( referred FDA) approved it as the first-line therapy for the clinical treatment of non-small cell lung cancer and pancreatic cancer. The main manufacturers of gemcitabine hydrochloride in domestic are Jiangsu Stock hausen Pharmaceutical Co., Ltd., and Harbin, Yu Heng Pharmaceutical company. Gemcitabine hydrochloride, as a pro-drug, is a good substrate for the acidification of deoxygenation of thymine kinase phosphorus in the cell, and under the action of the enzyme, it can be converted into the following metabolites: gemcitabine mono-phosphate (dFdCMP), gemcitabine diphosphate (dFdCDP) and gemcitabine triphosphate (dFdCTP), among which the latter two are the active products. In recent years, new drugs such as gemcitabine, paclitaxel, docetaxel, vinorebine are effective drugs for the treatment of non-small cell lung cancer (abbreviated NSCLC). Compared with traditional chemotherapy drugs, these drugs have the advantages of high curative effect and low toxicity. Gemcitabine hydrochloride is a new generation of anti-metabolites drug and a type of special medicine for cell cycle, playing a major role in DNA synthesis phase, namely S phase of cells. Under certain conditions, this medicine can prevent progression of cells from G1 phase to S phase, and have a strong anti-cancer activity non-small cell lung cancer(NSCLC). Foreign studies have shown that the efficient of the single treatment for NSCLC with gemcitabine hydrochloride only is about 18%~35%, while combined the treatment with cisplatin the efficiency for NSCLC is 41.7%. In advanced NSCLC, effective rate of carboplatin is 16%, which is similar to cisplatin, but has low toxicity, especially for gastrointestinal reactions, bone marrow suppression and the toxic reaction of kidney and nerve ending. In combination with carboplatin, both of them have mutual coordination and additive effect, and can produce higher curative effects. |
| Content Determination |
According to the efficient chromatography (Chinese Pharmacopoeia Edition 2000 Part two Appendix VD) determination. Chromatography conditions and system suitability test Use octadecylsilane bonded silica as a filler and ammonium acetate buffer (ammonium acetate 3.85g, add water 800ml to dissolve and glacial acetic acid to adjust the pH to 5.7, adding water to 1000ml) - methanol (90:10) as mobile phase, detecting the wavelength of 268nm. The theoretical plate number calculated according to the peak of gemcitabine hydrochloride should not be less than 2000 and the resolution between the peaks of gemcitabine hydrochloride and cytosine should be greater than 2.0. Measurements Take this product about 25mg, weigh it accurately, and put it into a 25ml volumetric flask, dissolved in water and diluted to the scale. Precisely measure this solution 5ml and put the solution into 50ml volumetric flask, diluted with water to the mark. Shake well and use this solution as the test solution. Precisely measure 20μl injection fluid into chromatography and record the chromatograms; Take another appropriate amount of gemcitabine hydrochloride and dry it to constant weight under the temperature of 105℃, using the processed product as the reference. Operate the reference with the same method mentioned above, and calculate it by peak area on the basis of the external standard method. The above information is edited by the Chemicalbook of Bai Linlin. |
| Distinguish |
1.Take appropriate amount of gemcitabine hydrochloride, make into solution containing the 10μg per ml by adding water and measure it according to the spectrophotometric method (Chinese Pharmacopoeia Edition 2000 Part 2 Appendix Ⅳ A). It has the maximum absorption at the wavelength of 269nm, and the minimum absorption at the wavelength of 249nm. 2.In the chromatogram recorded in content determination, the retention time of the major peak in the test solution should correspond to that in the reference solution. 3.The infrared absorption spectrum should be consistent with the reference standard spectrum. 4.Identification reaction that aqueous solution is chloride. (Chinese Pharmacopoeia Edition 2000 Part two Appendix III) |
| Adverse reactions and side effects |
The effect of bone marrow suppression. Symptoms such as anemia, leucopenia and thrombocytopenia will appear. Approximately 66% of patients have liver aminotransferase abnormalities, which mostly are mild, non-progressive damage. About 33% of patients experience nausea and vomiting. About 50% of patients have the symptoms of mild proteinuria and hematuria. There are some cases of unexplained renal failure. About 25% of patients have skin rash, 10% patients with itching. Less than 1% of patients experience bronchial spasms. Gemcitabine hydrochloride has significant cytotoxic activity on cultured human and mouse tumors, whose antitumor activity is associated with the administration. For example, daily dosing can lead to death of the animal, but the anti-cancer activity is very small; and when giving the drug every 3-4 days at a time, drug dose is non-lethal dose and has good anti-tumor activities on many tumors. |
| application | Suitable for the treatment of inoperable advanced or metastatic pancreatic cancer and the treatment of locally advanced or metastatic non-small cell lung cancer, and the treatment for mid-term and advanced non-small cell lung cancer, non-small cell lung cancer, pancreatic cancer, bladder cancer, breast cancer and other solid tumors. |
| Chemical Properties | White crystalline granular, odorless |
| Usage | An antineoplastic |
| Biological Activity | Deoxycytidine analog that inhibits DNA synthesis. Metabolized to form gemcitabine triphosphate (dFdCTP) and gemcitabine diphosphate (dFdCDP). dFdCTD inhibits ribonucleotide reductase causing a reduction in cellular nucleotides. dFdCTP is incorporated in DNA resulting in DNA strand termination. Displays antitumor activity in vitro and in vivo . |