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    Gemcitabine hydrochloride

    Available from stock

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      Gemcitabine hydrochloride

      SKU
      G0063

      Category: API's & Intermediates

      Synonyms
      2'-Deoxy-2',2'-difluorocytidine , dFdC , Gemzar (Lilly) , LY-188011 , dFdC , dFdCyd , NSC613327
      122111-03-9
      CAS-Number
      C9H11F2N3O4 · HCl
      Molecular Formula
      299.66
      Molecular Weight

      • Product Data
      • Handling
      • Safety Information
      • Details

      Specifications

      Purity
      ≥98% (HPLC)
      Identity
      1H-NMR
      Appearance
      White to off-white powder

      Properties

      Solvents
      water (20mg/ml), DMSO (slightly), ethanol (insoluble)
      Handling Advice
      Protect from light and moisture.
      Use / Stability
      This product should not be used if colour has changed or if there are
      Long Term Storage
      RT
      Short Term Storage
      RT
      Shipping
      AMBIENT
      Transportation
      Not dangerous goods
      Signal word
      Danger
      GHS Symbol
      GHS08
      Precautionary statements
      P201-P308 + P313
      Hazard statements
      H360
      Description
      Widely used antitumor agent in vitro and in vivo. Deoxycytidine analog with cytotoxic effects. Inhibits DNA synthesis and induces apoptosis through inhibition of ribonucleotide reductase (R1 and R2). Following the uptake of this prodrug into cells by nucleoside transporters it is phosphorylated to its mono(dFdCMP), di(dFdCDP), and triphosphorylated(dFdCTP) forms by deoxycytidine kinase. dFdCDP and dFdCTP are reported to inhibit the activity of ribonucleotide reductase and impede DNA synthesis and repair mechanisms and induce cell death. The triphosphate form is incorporated into DNA which induces masked chain termination and cell death. By specifically inhibiting growth arrest and DNA damage inducible protein 45 a (Gadd45a), a key mediator of active DNA demethylation, inhibits repair-mediated DNA demethylation in a methylation-sensitive reporter assay at concentrations ranging from 34-134nM. This anticancer nucleoside analog inhibits the growth of HL-60 promyelocytic leukemia cells with an LC50 value of 40nM. It inhibits the growth of MX-1 mammary, CX-1, HC-1, GC3, and VRC5 colon, LX-1, Calu-6 and NCI-H460 lung, and HS766T, PaCa-2, PANC-1, and BxPC-3 pancreatic cancer tumors in mouse xenograft models (45-93% inhibition). Also shown to block mitochondrial DNA polymerase ?. Works synergistically with other chemotherapeutic agents to enhance their cytotoxicity. Has also broad antiretroviral activity, decreasing MuLV cell infectivity, a murine AIDS model, in cell culture (EC50 = ~1.5nM) and inhibits the progression of murine AIDS in vivo at a dose of 1-2 mg/kg per day.
      References
      (1) L.W. Hertel, et al., Cancer Res. 50, 4417 (1990) , (2) V. Heinemann, et al., Cancer Res. 52, 533 (1992) , (3) D.D. Ross & D.P. Cuddy, Biochem. Pharmacol. 48, 1619 (1994) , (5) W. Plunkett, et al., Se≥ Oncol. 22, 3 (1995) , (6) R.L. Merriman, et al., New Drugs 14, 243 (1996) , (7) J.R. Mackey, et al., Cancer Res. 58, 4349 (1998) , (8) R.P. McGeary, et al., Mini Rev. Med. Chem. 8, 1384 (2008) , (9) C.L. Clouser, et al., PLoS One 6, 1 (2011) , (10) S.W. Hung, et al., Cancer Lett. 320, 138 (2012)
      InChi Key
      OKKDEIYWILRZIA-OSZBKLCCSA-N
      Smiles
      OC[C@@H]1[C@@H](O)C(F)(F)[C@H](N2C=CC([NH3+])=NC2=O)O1.[Cl-]

      Widely used antitumor agent in vitro and in vivo. Deoxycytidine analog with cytotoxic effects. Inhibits DNA synthesis and induces apoptosis through inhibition of ribonucleotide reductase (R1 and R2). Following the uptake of this prodrug into cells by nucleoside transporters it is phosphorylated to its mono(dFdCMP), di(dFdCDP), and triphosphorylated(dFdCTP) forms by deoxycytidine kinase. dFdCDP and dFdCTP are reported to inhibit the activity of ribonucleotide reductase and impede DNA synthesis and repair mechanisms and induce cell death. The triphosphate form is incorporated into DNA which induces masked chain termination and cell death. By specifically inhibiting growth arrest and DNA damage inducible protein 45 a (Gadd45a), a key mediator of active DNA demethylation, inhibits repair-mediated DNA demethylation in a methylation-sensitive reporter assay at concentrations ranging from 34-134nM. This anticancer nucleoside analog inhibits the growth of HL-60 promyelocytic leukemia cells with an LC50 value of 40nM. It inhibits the growth of MX-1 mammary, CX-1, HC-1, GC3, and VRC5 colon, LX-1, Calu-6 and NCI-H460 lung, and HS766T, PaCa-2, PANC-1, and BxPC-3 pancreatic cancer tumors in mouse xenograft models (45-93% inhibition). Also shown to block mitochondrial DNA polymerase ?. Works synergistically with other chemotherapeutic agents to enhance their cytotoxicity. Has also broad antiretroviral activity, decreasing MuLV cell infectivity, a murine AIDS model, in cell culture (EC50 = ~1.5nM) and inhibits the progression of murine AIDS in vivo at a dose of 1-2 mg/kg per day.

      SKU: G0063 Category: API's & Intermediates
      • Additional information

      Additional information

      Synonyms

      2'-Deoxy-2',2'-difluorocytidine, dFdC, Gemzar (Lilly), LY-188011, dFdC, dFdCyd, NSC613327

      Purity

      ≥98% (HPLC)

      Appearance

      White to off-white powder

      CAS-Number

      122111-03-9

      Molecular Formula

      C9H11F2N3O4 · HCl

      Molecular Weight

      299.66

      Identity

      1H-NMR

      Solvents

      water (20mg/ml), DMSO (slightly), ethanol (insoluble)

      Smiles

      OC[C@@H]1[C@@H](O)C(F)(F)[C@H](N2C=CC([NH3+])=NC2=O)O1.[Cl-]

      InChi Key

      OKKDEIYWILRZIA-OSZBKLCCSA-N

      Shipping

      AMBIENT

      Short Term Storage

      RT

      Long Term Storage

      RT

      Handling Advice

      Protect from light and moisture.

      Use / Stability

      This product should not be used if colour has changed or if there are

      Hazard statements

      H360

      Precautionary statements

      P201-P308 + P313

      GHS Symbol

      GHS08

      Signal word

      Danger

      Transportation

      Not dangerous goods

      References

      (1) L.W. Hertel, et al., Cancer Res. 50, 4417 (1990), (2) V. Heinemann, et al., Cancer Res. 52, 533 (1992), (3) D.D. Ross & D.P. Cuddy, Biochem. Pharmacol. 48, 1619 (1994), (5) W. Plunkett, et al., Se≥ Oncol. 22, 3 (1995), (6) R.L. Merriman, et al., New Drugs 14, 243 (1996), (7) J.R. Mackey, et al., Cancer Res. 58, 4349 (1998), (8) R.P. McGeary, et al., Mini Rev. Med. Chem. 8, 1384 (2008), (9) C.L. Clouser, et al., PLoS One 6, 1 (2011), (10) S.W. Hung, et al., Cancer Lett. 320, 138 (2012)

      Quantity

      10 mg, 50 mg, Bulk

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