Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H13N3O4.ClH |
| Molecular Weight | 263.678 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NC1=NC(=O)N(C=C1)[C@H]2C[C@H](O)[C@@H](CO)O2
InChI
InChIKey=LTKCXZGFJFAPLY-OERIEOFYSA-N
InChI=1S/C9H13N3O4.ClH/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8;/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15);1H/t5-,6+,8+;/m0./s1
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C9H13N3O4 |
| Molecular Weight | 227.2172 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
2′-Deoxycytidine (deoxyC) is one of the deoxy nucleosides, which after phosphorylation to dCTP is used to synthesize DNA via various DNA polymerases or reverse transcriptases. Deoxycytidine is phosphorylated by deoxycytidine kinase (dCK). This enzyme catalyzes the initial conversion of the nucleosides deoxyadenosine (dA), deoxyguanosine (dG), and deoxycytidine (dC) into their monophosphate forms, with subsequent phosphorylation to the triphosphate forms performed by additional enzymes.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Unnatural enantiomers of 5-azacytidine analogues: syntheses and enzymatic properties. | 2000 Nov |
|
| Phosphorylation of the anti-HIV compound (S,S)-isodideoxyadenosine by human recombinant deoxycytidine kinase. | 2000 Nov 15 |
|
| [The potential of capecitabine (Xeloda) in the treatment of disseminated solid tumors]. | 2001 |
|
| Treatment of classical Kaposi's sarcoma with gemcitabine. | 2001 |
|
| Clinical pharmacokinetics of capecitabine. | 2001 |
|
| Treatment of extensive stage small cell lung cancer. | 2001 |
|
| Induction chemotherapy followed by concomitant chemoradiotherapy for non-small cell lung cancer. | 2001 |
|
| The role of capecitabine, an oral, enzymatically activated fluoropyrimidine, in the treatment of metastatic breast cancer. | 2001 |
|
| Activity of gemcitabine and continuous infusion fluorouracil in advanced pancreatic cancer. | 2001 |
|
| Topotecan and gemcitabine in platinum/paclitaxel-resistant ovarian cancer. | 2001 |
|
| Gemcitabine: progress in the treatment of pancreatic cancer. | 2001 |
|
| Schedule dependency of antitumor activity in combination therapy with capecitabine/5'-deoxy-5-fluorouridine and docetaxel in breast cancer models. | 2001 Apr |
|
| Comparison of oral capecitabine versus intravenous fluorouracil plus leucovorin as first-line treatment in 605 patients with metastatic colorectal cancer: results of a randomized phase III study. | 2001 Apr 15 |
|
| Deoxynucleoside anabolic enzyme levels in acute myelocytic leukemia and chronic lymphocytic leukemia cells. | 2001 Apr 26 |
|
| 5-fluorouracil/leucovorin versus capecitabine in patients with stage III colon cancer. | 2001 Feb |
|
| Biweekly gemcitabine, doxorubicin, and paclitaxel as first-line treatment in metastatic breast cancer. Final results from a phase II trial. | 2001 Feb |
|
| Radiation concurrent with gemcitabine for locally advanced head and neck cancer: a phase I trial and intracellular drug incorporation study. | 2001 Feb 1 |
|
| Gemcitabine and cisplatin for advanced, metastatic bladder cancer. | 2001 Feb 15 |
|
| Phase II trial of paclitaxel plus gemcitabine in patients with locally advanced or metastatic non-small-cell lung cancer. | 2001 Feb 15 |
|
| DNA structure and aspartate 276 influence nucleotide binding to human DNA polymerase beta. Implication for the identity of the rate-limiting conformational change. | 2001 Feb 2 |
|
| Deoxynucleoside kinases encoded by the yaaG and yaaF genes of Bacillus subtilis. Substrate specificity and kinetic analysis of deoxyguanosine kinase with UTP as the preferred phosphate donor. | 2001 Feb 23 |
|
| Orf135 from Escherichia coli Is a Nudix hydrolase specific for CTP, dCTP, and 5-methyl-dCTP. | 2001 Feb 23 |
|
| Gemcitabine for malignant mesothelioma: A phase II trial by the Cancer and Leukemia Group B. | 2001 Feb-Mar |
|
| Activity and toxicity of gemcitabine and gemcitabine + vinorelbine in advanced non-small-cell lung cancer elderly patients: Phase II data from the Multicenter Italian Lung Cancer in the Elderly Study (MILES) randomized trial. | 2001 Feb-Mar |
|
| Decreased myelotoxicity of gemcitabine and cisplatin in advanced non-small cell lung cancer (NSCLC) with cisplatin infusion on day 15. | 2001 Feb-Mar |
|
| Cisplatin and vinorelbine as second-line chemotherapy in patients with advanced non-small cell lung cancer (NSCLC) resistant to taxol plus gemcitabine. | 2001 Feb-Mar |
|
| Second-line chemotherapy for non-small-cell lung cancer with monthly docetaxel and weekly gemcitabine: a phase II trial. | 2001 Jan |
|
| Clinical status of capecitabine in the treatment of breast cancer. | 2001 Jan |
|
| [Refractory non-small-cell lung cancer responding to combination chemotherapy with docetaxel, gemcitabine and cisplatin]. | 2001 Jan |
|
| Preclinical in vivo antitumor efficacy of nedaplatin with gemcitabine against human lung cancer. | 2001 Jan |
|
| Fatal pulmonary veno-occlusive disease possibly related to gemcitabine. | 2001 Jan |
|
| The role of laparoscopy in second-look evaluations for ovarian cancer. | 2001 Jan |
|
| Induction of differentiation of acute promyelocytic leukemia cells by a cytidine deaminase-resistant analogue of 1-beta-D-arabinofuranosylcytosine, 1-(2-deoxy-2-methylene-beta-D-erythro-pentofuranosyl)cytidine. | 2001 Jan 1 |
|
| Preirradiation gemcitabine chemotherapy for newly diagnosed glioblastoma. A phase II study. | 2001 Jan 15 |
|
| Activation of deoxycytidine kinase by inhibition of DNA synthesis in human lymphocytes. | 2001 Jan 15 |
|
| Evidence against apoptosis as a major mechanism for reproductive cell death following treatment of cell lines with anti-cancer drugs. | 2001 Jan 5 |
|
| The significance of thymidine phosphorylase expression in colorectal cancer. | 2001 Jan-Feb |
|
| Effect of chemical modifications of cytosine and guanine in a CpG-motif of oligonucleotides: structure-immunostimulatory activity relationships. | 2001 Mar |
|
| Gemcitabine for the treatment of non-small-cell lung cancer. | 2001 Mar |
|
| Gemcitabine and nonplatinum combinations in non-small-cell lung cancer. | 2001 Mar |
|
| Capecitabine (Xeloda) improves medical resource use compared with 5-fluorouracil plus leucovorin in a phase III trial conducted in patients with advanced colorectal carcinoma. | 2001 Mar |
|
| Gemcitabine and vinorelbine as first-line chemotherapy for advanced non-small cell lung cancer: a phase II trial. | 2001 Mar |
|
| Combined radiochemotherapy of locally advanced unresectable pancreatic adenocarcinoma with mitomycin C plus 24-hour continuous infusional gemcitabine. | 2001 Mar 1 |
|
| Production of brominating intermediates by myeloperoxidase. A transhalogenation pathway for generating mutagenic nucleobases during inflammation. | 2001 Mar 16 |
|
| Cytosolic high K(m) 5'-nucleotidase and 5'(3')-deoxyribonucleotidase in substrate cycles involved in nucleotide metabolism. | 2001 Mar 2 |
|
| Steroids affect collateral sensitivity to gemcitabine of multidrug-resistant human lung cancer cells. | 2001 Mar 23 |
|
| Cotton-wool spots associated with pancreatic carcinoma. | 2001 Mar 26 |
|
| Human cytosolic 5'-nucleotidase I: characterization and role in nucleoside analog resistance. | 2001 Mar 30 |
|
| Integrating the oral fluoropyrimidines into the management of advanced colorectal cancer. | 2001 May |
|
| Enhancement of sensitivity to capecitabine in human renal carcinoma cells transfected with thymidine phosphorylase cDNA. | 2001 May 1 |
Sample Use Guides
It was examined the effect of supraphysiologic concentrations of the naturally occurring nucleoside deoxycytidine (dCyd) on the in vitro growth of normal (CFU-GM) and leukemic (L-CFU) myeloid progenitor cells. Bone marrow samples obtained from 34 consecutive patients undergoing routine diagnostic bone marrow aspirations for nonmalignant hematologic disorders exhibited nearly a twofold increment in CFU-GM when continuously cultured in the presence of 10(-4) mol/L dCyd. Higher dCyd concentrations were associated with a smaller degree of enhancement of colony formation. In contrast, the growth of leukemic blast progenitors obtained from patients with acute nonlymphocytic leukemia were not enhanced by any of the dCyd concentrations tested. Treatment of normal bone marrow cells with dCyd at concentrations ranging from 10(-6) to 5 X 10(-3) mol/L for 24 hours had only a minor effect on the fraction of CFU-GM in S phase. Coadministration of 10(-4) mol/L dCyd was able to reverse the inhibitory effects of several putative regulators of normal myelopoiesis, including leukemia inhibitory activity (LIA), acidic isoferritins (AIF), and prostaglandin E1 (PGE1). Leukemic myeloblasts exposed to 10(-4) mol/L dCyd exhibited substantial expansion of intracellular pools of dCyd triphosphate (dCTP), demonstrating that inability to metabolize dCyd could not be solely responsible for the absence of growth potentiation in these cells. It was suggested that supraphysiologic concentrations of dCyd might the former from the inhibitory effects of several potential negative regulators of myelopoiesis.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:46:21 GMT 2025
by
admin
on
Mon Mar 31 17:46:21 GMT 2025
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| Record UNII |
X8FX60E66D
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| Record Status |
Validated (UNII)
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| Record Version |
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X8FX60E66D
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25203-63-8
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223-639-9
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300000026391
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83251
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107488
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246-732-6
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3992-42-5
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DTXSID2074956
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