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 |
|---|---|---|
| The effect of DNA structure on the catalytic efficiency and fidelity of human DNA polymerase beta on templates with platinum-DNA adducts. | 2001-06-01 |
|
| DNA methyltransferase inhibition in normal human fibroblasts induces a p21-dependent cell cycle withdrawal. | 2001-06-01 |
|
| Akt, MAPK (Erk1/2), and p38 act in concert to promote apoptosis in response to ErbB receptor family inhibition. | 2001-05-04 |
|
| Enhancement of sensitivity to capecitabine in human renal carcinoma cells transfected with thymidine phosphorylase cDNA. | 2001-05-01 |
|
| Integrating the oral fluoropyrimidines into the management of advanced colorectal cancer. | 2001-05 |
|
| Deoxynucleoside anabolic enzyme levels in acute myelocytic leukemia and chronic lymphocytic leukemia cells. | 2001-04-26 |
|
| Gemcitabine following radiotherapy with concurrent 5-fluorouracil for nonmetastatic adenocarcinoma of the pancreas. | 2001-04-20 |
|
| 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. | 2001-04-15 |
|
| [Capecitabine in the treatment of colorectal cancer]. | 2001-04-13 |
|
| Combined use of gemcitabine and radiation in mice. | 2001-04-13 |
|
| Schedule dependency of antitumor activity in combination therapy with capecitabine/5'-deoxy-5-fluorouridine and docetaxel in breast cancer models. | 2001-04 |
|
| 2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentofuranosylcytosine: a novel anticancer nucleoside analog that causes both DNA strand breaks and G(2) arrest. | 2001-04 |
|
| Cotton-wool spots associated with pancreatic carcinoma. | 2001-03-26 |
|
| Steroids affect collateral sensitivity to gemcitabine of multidrug-resistant human lung cancer cells. | 2001-03-23 |
|
| Effect of chemical modifications of cytosine and guanine in a CpG-motif of oligonucleotides: structure-immunostimulatory activity relationships. | 2001-03 |
|
| Optimizing chemoradiation in locally advanced non-small-cell lung cancer. | 2001-03 |
|
| Gemcitabine and cisplatin combination in early-stage non-small-cell lung cancer. | 2001-03 |
|
| Gemcitabine for the treatment of non-small-cell lung cancer. | 2001-03 |
|
| Gemcitabine and nonplatinum combinations in non-small-cell lung cancer. | 2001-03 |
|
| Gemcitabine in combination with new platinum compounds: an update. | 2001-03 |
|
| Irinotecan/gemcitabine combination chemotherapy in pancreatic cancer. | 2001-03 |
|
| Unexpected severe myelotoxicity of gemcitabine in pretreated breast cancer patients. | 2001-03 |
|
| Capecitabine (Xeloda) improves medical resource use compared with 5-fluorouracil plus leucovorin in a phase III trial conducted in patients with advanced colorectal carcinoma. | 2001-03 |
|
| Gemcitabine and vinorelbine as first-line chemotherapy for advanced non-small cell lung cancer: a phase II trial. | 2001-03 |
|
| Latent hematopoietic stem cell toxicity associated with protracted drug administration. | 2001-03 |
|
| [A case of primary malignant hemangiopericytoma of the lung with marked response to combination chemotherapy with cisplatin, ifosfamide and gemcitabine]. | 2001-03 |
|
| Neoadjuvant chemoradiotherapy for adenocarcinoma of the pancreas: treatment variables and survival duration. | 2001-03 |
|
| Phase II trial of two-weekly gemcitabine in patients with advanced biliary tract cancer. | 2001-02 |
|
| Challenging the platinum combinations: docetaxel (Taxotere) combined with gemcitabine or vinorelbine in non-small cell lung cancer. | 2001-02 |
|
| 5-fluorouracil/leucovorin versus capecitabine in patients with stage III colon cancer. | 2001-02 |
|
| [Palliative therapy of pancreatic adenocarcinoma]. | 2001-02 |
|
| Biweekly gemcitabine, doxorubicin, and paclitaxel as first-line treatment in metastatic breast cancer. Final results from a phase II trial. | 2001-02 |
|
| The gemcitabine/epirubicin/paclitaxel trials in advanced breast cancer. | 2001-02 |
|
| Gemcitabine, paclitaxel, and trastuzumab in metastatic breast cancer. | 2001-02 |
|
| Gemcitabine and Pemetrexed disodium in treating breast cancer. | 2001-02 |
|
| Gemcitabine plus cisplatin in breast cancer. | 2001-02 |
|
| Gemcitabine and paclitaxel as salvage therapy in metastatic breast cancer. | 2001-02 |
|
| Docetaxel/gemcitabine: salvage chemotherapy in anthracycline-pretreated patients with advanced breast cancer. | 2001-02 |
|
| Treatment of advanced breast cancer with gemcitabine and vinorelbine. | 2001-02 |
|
| Gemcitabine as single-agent therapy in the management of advanced breast cancer. | 2001-02 |
|
| Gemcitabine-associated posterior reversible encephalopathy syndrome: MR imaging and MR spectroscopy findings. | 2001-01 |
|
| Phase I trial of gemcitabine in patients with advanced pancreatic cancer. | 2001-01 |
|
| [The potential of capecitabine (Xeloda) in the treatment of disseminated solid tumors]. | 2001 |
|
| Treatment of classical Kaposi's sarcoma with gemcitabine. | 2001 |
|
| Excellent response to gemcitabine in a massively pre-treated woman with extensive cutaneous involvement after recurrence of breast cancer. | 2001 |
|
| The oral fluorinated pyrimidines. | 2001 |
|
| Achievement of complete remission in refractory Hodgkin's disease with prolonged infusion of gemcitabine. | 2001 |
|
| Recent advances in bladder cancer chemotherapy. | 2001 |
|
| Clinical pharmacokinetics of capecitabine. | 2001 |
|
| The Twenty-third Annual San Antonio Breast Cancer Symposium. | 2001 |
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
|
| Record UNII |
X8FX60E66D
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
X8FX60E66D
Created by
admin on Mon Mar 31 17:46:21 GMT 2025 , Edited by admin on Mon Mar 31 17:46:21 GMT 2025
|
PRIMARY | |||
|
25203-63-8
Created by
admin on Mon Mar 31 17:46:21 GMT 2025 , Edited by admin on Mon Mar 31 17:46:21 GMT 2025
|
NON-SPECIFIC STOICHIOMETRY | |||
|
223-639-9
Created by
admin on Mon Mar 31 17:46:21 GMT 2025 , Edited by admin on Mon Mar 31 17:46:21 GMT 2025
|
PRIMARY | |||
|
300000026391
Created by
admin on Mon Mar 31 17:46:21 GMT 2025 , Edited by admin on Mon Mar 31 17:46:21 GMT 2025
|
PRIMARY | |||
|
83251
Created by
admin on Mon Mar 31 17:46:21 GMT 2025 , Edited by admin on Mon Mar 31 17:46:21 GMT 2025
|
PRIMARY | |||
|
107488
Created by
admin on Mon Mar 31 17:46:21 GMT 2025 , Edited by admin on Mon Mar 31 17:46:21 GMT 2025
|
PRIMARY | |||
|
246-732-6
Created by
admin on Mon Mar 31 17:46:21 GMT 2025 , Edited by admin on Mon Mar 31 17:46:21 GMT 2025
|
ALTERNATIVE | |||
|
3992-42-5
Created by
admin on Mon Mar 31 17:46:21 GMT 2025 , Edited by admin on Mon Mar 31 17:46:21 GMT 2025
|
PRIMARY | |||
|
DTXSID2074956
Created by
admin on Mon Mar 31 17:46:21 GMT 2025 , Edited by admin on Mon Mar 31 17:46:21 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |