WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H100410
CAS#: 122111-03-9 (HCl)
Description: Gemcitabine hydrochloride is the hydrochloride salt of an analogue of the antimetabolite nucleoside deoxycytidine with antineoplastic activity. Gemcitabine is converted intracellularly to the active metabolites difluorodeoxycytidine di- and triphosphate (dFdCDP, dFdCTP). dFdCDP inhibits ribonucleotide reductase, thereby decreasing the deoxynucleotide pool available for DNA synthesis; dFdCTP is incorporated into DNA, resulting in DNA strand termination and apoptosis.
Hodoodo Cat#: H100410
Name: Gemcitabine Hydrochloride
CAS#: 122111-03-9 (HCl)
Chemical Formula: C9H12ClF2N3O4
Exact Mass: 0.00
Molecular Weight: 299.660
Elemental Analysis: C, 36.07; H, 4.04; Cl, 11.83; F, 12.68; N, 14.02; O, 21.36
Related CAS #: 95058-81-4 (free base) 122111-03-9 (HCl)
Synonym: LY188011; LY-188011; LY 188011; Abbreviations: dFdC; dFdCyd; gemcitabine; Gemzar.
IUPAC/Chemical Name: 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one hydrochloride
InChi Key: OKKDEIYWILRZIA-OSZBKLCCSA-N
InChi Code: 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
SMILES Code: O=C1N=C(N)C=CN1[C@@H]2O[C@H](CO)[C@@H](O)C2(F)F.[H]Cl
Appearance: white solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO at 12.5 mg/mL with slight warming; very poorly soluble in ethanol; soluble in water at 25 mg/mL with slight warming.
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in water
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | Gemcitabine Hydrochloride inhibits DNA synthesis and repair. |
| In vitro activity: | Surface expression of HLA-A,B,C was measured on a panel of tumour cell lines after culturing with equi-active concentrations of chemotherapeutic drugs for 24 hours. Representative plots are shown in Fig. 1a. GEM (Gemcitabine) significantly increased expression of HLA-A,B,C in all three cell lines (Fig. 1b). The mean change in HLA-A,B,C expression in response to culture with GEM, as measured by a change in MFI from untreated controls, was 81.3% for HCT116 cells, 67.7% for A549 cells and 41.5% for MCF-7 cells. For comparison, 1000 IU/ml IFNγ increased HLA-A,B,C by 62.2% in HCT116 cells, 142.9% in A549 cells and 367% in MCF-7 cells (data not shown). Reference: Oncoimmunology. 2018; 7(6): e1438107. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5990974/ |
| In vivo activity: | The study next investigated the anti-tumour effect of gemcitabine in vivo. Xenografted mice were intraperitoneally administrated gemcitabine (40 or 80 mg/kg) or PBS after subcutaneous implantation of PK-1 cells. Gemcitabine effectively suppressed the tumour growth from PK-1 xenografts (Figure 3A). The tumour size was significantly smaller in gemcitabine-treated mice compared with the controls (Figure 3B). This study also analysed tumour sections by immunohistochemistry to determine whether gemcitabine also affected cyclin D1 in vivo. Gemcitabine treatment resulted in decreased expression levels of cyclin D1 compared to controls (Figure 3C). The labelling index of gemcitabine-treated cell was also lower compared to controls (Figure 3D). Gemcitabine treatment had no significant effect on the body weight of animals during the treatments. Reference: In Vivo. 2020 Nov-Dec; 34(6): 3195–3203. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7811671/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 26.3 | 87.87 | |
| DMF | 2.5 | 8.34 | |
| PBS (pH 7.2) | 10.0 | 33.37 | |
| Water | 51.9 | 173.13 |
The following data is based on the product molecular weight 299.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Gravett AM, Trautwein N, Stevanović S, Dalgleish AG, Copier J. Gemcitabine alters the proteasome composition and immunopeptidome of tumour cells. Oncoimmunology. 2018 Mar 6;7(6):e1438107. doi: 10.1080/2162402X.2018.1438107. PMID: 29930882; PMCID: PMC5990974. 2. Takeda H, Okada M, Kuramoto K, Suzuki S, Sakaki H, Sanomachi T, Seino S, Yoshioka T, Hirano H, Arita K, Kitanaka C. Antitumor activity of gemcitabine against high-grade meningioma in vitro and in vivo. Oncotarget. 2017 Jun 29;8(53):90996-91008. doi: 10.18632/oncotarget.18827. PMID: 29207619; PMCID: PMC5710900. 3. Namima D, Fujihara S, Iwama H, Fujita K, Matsui T, Nakahara M, Okamura M, Hirata M, Kono T, Fujita N, Yamana H, Kato K, Kamada H, Morishita A, Kobara H, Tsutsui K, Masaki T. The Effect of Gemcitabine on Cell Cycle Arrest and microRNA Signatures in Pancreatic Cancer Cells. In Vivo. 2020 Nov-Dec;34(6):3195-3203. doi: 10.21873/invivo.12155. PMID: 33144424; PMCID: PMC7811671. 4. Shimizu T, Tomogane M, Miyashita M, Ukimura O, Ashihara E. Low dose gemcitabine increases the cytotoxicity of human Vγ9Vδ2 T cells in bladder cancer cells in vitro and in an orthotopic xenograft model. Oncoimmunology. 2018 Feb 8;7(5):e1424671. doi: 10.1080/2162402X.2018.1424671. PMID: 29721384; PMCID: PMC5927545. |
| In vitro protocol: | 1. Gravett AM, Trautwein N, Stevanović S, Dalgleish AG, Copier J. Gemcitabine alters the proteasome composition and immunopeptidome of tumour cells. Oncoimmunology. 2018 Mar 6;7(6):e1438107. doi: 10.1080/2162402X.2018.1438107. PMID: 29930882; PMCID: PMC5990974. 2. Takeda H, Okada M, Kuramoto K, Suzuki S, Sakaki H, Sanomachi T, Seino S, Yoshioka T, Hirano H, Arita K, Kitanaka C. Antitumor activity of gemcitabine against high-grade meningioma in vitro and in vivo. Oncotarget. 2017 Jun 29;8(53):90996-91008. doi: 10.18632/oncotarget.18827. PMID: 29207619; PMCID: PMC5710900. |
| In vivo protocol: | 1. Namima D, Fujihara S, Iwama H, Fujita K, Matsui T, Nakahara M, Okamura M, Hirata M, Kono T, Fujita N, Yamana H, Kato K, Kamada H, Morishita A, Kobara H, Tsutsui K, Masaki T. The Effect of Gemcitabine on Cell Cycle Arrest and microRNA Signatures in Pancreatic Cancer Cells. In Vivo. 2020 Nov-Dec;34(6):3195-3203. doi: 10.21873/invivo.12155. PMID: 33144424; PMCID: PMC7811671. 2. Shimizu T, Tomogane M, Miyashita M, Ukimura O, Ashihara E. Low dose gemcitabine increases the cytotoxicity of human Vγ9Vδ2 T cells in bladder cancer cells in vitro and in an orthotopic xenograft model. Oncoimmunology. 2018 Feb 8;7(5):e1424671. doi: 10.1080/2162402X.2018.1424671. PMID: 29721384; PMCID: PMC5927545. |
1: Iwata N, Yoshida T, Katsuta E, Aoyagi H, Takahata T, Hasegawa K, Kaneko J, Maejima S. [Long-surviving patient with hilar cholangiocarcinoma by gemcitabine monotherapy]. Gan To Kagaku Ryoho. 2012 Nov;39(12):2116-8. Review. Japanese. PubMed PMID: 23267995.
2: Federico C, Morittu VM, Britti D, Trapasso E, Cosco D. Gemcitabine-loaded liposomes: rationale, potentialities and future perspectives. Int J Nanomedicine. 2012;7:5423-36. doi: 10.2147/IJN.S34025. Epub 2012 Nov 1. Review. PubMed PMID: 23139626; PubMed Central PMCID: PMC3490684.
3: Yuh BE, Ruel N, Wilson TG, Vogelzang N, Pal SK. Pooled analysis of clinical outcomes with neoadjuvant cisplatin and gemcitabine chemotherapy for muscle invasive bladder cancer. J Urol. 2013 May;189(5):1682-6. doi: 10.1016/j.juro.2012.10.120. Epub 2012 Nov 1. Review. PubMed PMID: 23123547.
4: Sun C, Ansari D, Andersson R, Wu DQ. Does gemcitabine-based combination therapy improve the prognosis of unresectable pancreatic cancer? World J Gastroenterol. 2012 Sep 21;18(35):4944-58. Review. PubMed PMID: 23002368; PubMed Central PMCID: PMC3447278.
5: Kuramitsu Y, Wang Y, Taba K, Suenaga S, Ryozawa S, Kaino S, Sakaida I, Nakamura K. Heat-shock protein 27 plays the key role in gemcitabine-resistance of pancreatic cancer cells. Anticancer Res. 2012 Jun;32(6):2295-9. Review. PubMed PMID: 22641665.
6: Sugita Y, Hirai S, Ishkawa W, Maru N, Shimizu T, Yokota S, Nishi M, Iwamura M, Baba S. [Successful gemcitabine-nedaplatin therapy in a hemodialysis patient with ureteral carcinoma after bilateral nephroureterectomy]. Hinyokika Kiyo. 2012 Mar;58(3):159-63. Review. Japanese. PubMed PMID: 22495045.
7: Elnaggar M, Giovannetti E, Peters GJ. Molecular targets of gemcitabine action: rationale for development of novel drugs and drug combinations. Curr Pharm Des. 2012;18(19):2811-29. Review. PubMed PMID: 22390765.
8: Ying JE, Zhu LM, Liu BX. Developments in metastatic pancreatic cancer: is gemcitabine still the standard? World J Gastroenterol. 2012 Feb 28;18(8):736-45. doi: 10.3748/wjg.v18.i8.736. Review. PubMed PMID: 22371633; PubMed Central PMCID: PMC3286136.
9: Gross-Goupil M, Fourcade A, Blot E, Penel N, Négrier S, Culine S, Chaigneau L, Lesimple T, Priou F, Lortholary A, Kaminsky MC, Provencal J, Voog E, Bouzy J, Laplanche A, Fizazi K. Cisplatin alone or combined with gemcitabine in carcinomas of unknown primary: results of the randomised GEFCAPI 02 trial. Eur J Cancer. 2012 Mar;48(5):721-7. doi: 10.1016/j.ejca.2012.01.011. Epub 2012 Feb 6. Review. PubMed PMID: 22317952.
10: Shelley MD, Jones G, Cleves A, Wilt TJ, Mason MD, Kynaston HG. Intravesical gemcitabine therapy for non-muscle invasive bladder cancer (NMIBC): a systematic review. BJU Int. 2012 Feb;109(4):496-505. doi: 10.1111/j.1464-410X.2011.10880.x. Review. PubMed PMID: 22313502.
1. Pattarawat P, Hunt JT, Poloway J, Archibald CJ, Wang HR. A triple combination gemcitabine + romidepsin + cisplatin to effectively control triple-negative breast cancer tumor development, recurrence, and metastasis. Cancer Chemother Pharmacol. 2021 May 27. doi: 10.1007/s00280-021-04298-y. Epub ahead of print. PMID: 34043046.
2.
