Doxecitine

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H13N3O4
Molecular Weight	227.2172
Optical Activity	( + )
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=O)N(C=C1)[C@H]2C[C@H](O)[C@@H](CO)O2

InChI

InChIKey=CKTSBUTUHBMZGZ-SHYZEUOFSA-N

InChI=1S/C9H13N3O4/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)/t5-,6+,8+/m0/s1

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18361501

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

Targets

Primary Target	Pharmacology	Condition	Potency
Deoxycytidine kinase 6 Target ID: P27707 Gene ID: 1633.0 Gene Symbol: DCK Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18361501	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
[The potential of capecitabine (Xeloda) in the treatment of disseminated solid tumors].	2001	11317529
Treatment of classical Kaposi's sarcoma with gemcitabine.	2001	11306832
Excellent response to gemcitabine in a massively pre-treated woman with extensive cutaneous involvement after recurrence of breast cancer.	2001	11291839
The oral fluorinated pyrimidines.	2001	11291832
Achievement of complete remission in refractory Hodgkin's disease with prolonged infusion of gemcitabine.	2001	11291828
Recent advances in bladder cancer chemotherapy.	2001	11291559
Clinical pharmacokinetics of capecitabine.	2001	11286326
The Twenty-third Annual San Antonio Breast Cancer Symposium.	2001	11268712
Treatment of extensive stage small cell lung cancer.	2001	11224990
Lung cancer: therapeutic options for stage IV and recurrent NSCLC.	2001	11224988
Chemoradiation in locally advanced non-small cell lung cancer.	2001	11224987
Schedule dependency of antitumor activity in combination therapy with capecitabine/5'-deoxy-5-fluorouridine and docetaxel in breast cancer models.	2001 Apr	11309360
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 Apr	11259616
Towards an understanding of somatic hypermutation.	2001 Apr	11228415
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	11304782
Gemcitabine following radiotherapy with concurrent 5-fluorouracil for nonmetastatic adenocarcinoma of the pancreas.	2001 Apr 20	11291097
Deoxynucleoside anabolic enzyme levels in acute myelocytic leukemia and chronic lymphocytic leukemia cells.	2001 Apr 26	11275369
Phase II trial of two-weekly gemcitabine in patients with advanced biliary tract cancer.	2001 Feb	11300321
Challenging the platinum combinations: docetaxel (Taxotere) combined with gemcitabine or vinorelbine in non-small cell lung cancer.	2001 Feb	11284620
5-fluorouracil/leucovorin versus capecitabine in patients with stage III colon cancer.	2001 Feb	11273590
The gemcitabine/epirubicin/paclitaxel trials in advanced breast cancer.	2001 Feb	11252889
Docetaxel/gemcitabine: salvage chemotherapy in anthracycline-pretreated patients with advanced breast cancer.	2001 Feb	11252884
Treatment of advanced breast cancer with gemcitabine and vinorelbine.	2001 Feb	11252883
Gemcitabine as single-agent therapy in the management of advanced breast cancer.	2001 Feb	11252882
Effects of gemcitabine on cisplatin-induced nephrotoxicity in rats: schedule-dependent study.	2001 Feb	11243722
The role of apoptosis in 2',2'-difluoro-2'-deoxycytidine (gemcitabine)-mediated radiosensitization.	2001 Feb	11234886
The clinical implications of gemcitabine radiosensitization.	2001 Feb	11234872
End-joining deficiency and radiosensitization induced by gemcitabine.	2001 Feb 15	11245469
Gemcitabine-associated posterior reversible encephalopathy syndrome: MR imaging and MR spectroscopy findings.	2001 Jan	11295355
Second-line chemotherapy for non-small-cell lung cancer with monthly docetaxel and weekly gemcitabine: a phase II trial.	2001 Jan	11249055
[Capecitabine in the treatment of colorectal cancer].	2001 Jan-Feb	11300027
Combined use of gemcitabine and radiation in mice.	2001 Jan-Feb	11299753
The effect of DNA structure on the catalytic efficiency and fidelity of human DNA polymerase beta on templates with platinum-DNA adducts.	2001 Jun 1	11259423
Effect of chemical modifications of cytosine and guanine in a CpG-motif of oligonucleotides: structure-immunostimulatory activity relationships.	2001 Mar	11310616
Optimizing chemoradiation in locally advanced non-small-cell lung cancer.	2001 Mar	11301848
Gemcitabine and cisplatin combination in early-stage non-small-cell lung cancer.	2001 Mar	11301847
Gemcitabine for the treatment of non-small-cell lung cancer.	2001 Mar	11301846
Gemcitabine and nonplatinum combinations in non-small-cell lung cancer.	2001 Mar	11301844
Gemcitabine in combination with new platinum compounds: an update.	2001 Mar	11301843
Irinotecan/gemcitabine combination chemotherapy in pancreatic cancer.	2001 Mar	11301841
Unexpected severe myelotoxicity of gemcitabine in pretreated breast cancer patients.	2001 Mar	11290868
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	11290435
Latent hematopoietic stem cell toxicity associated with protracted drug administration.	2001 Mar	11274755
[A case of primary malignant hemangiopericytoma of the lung with marked response to combination chemotherapy with cisplatin, ifosfamide and gemcitabine].	2001 Mar	11265407
Cytogenetic subgroups in acute myeloid leukemia differ in proliferative activity and response to GM-CSF.	2001 Mar	11237060
Phase I study of stealth liposomal doxorubicin in combination with gemcitabine in the treatment of patients with metastatic breast cancer.	2001 Mar 15	11251001
Steroids affect collateral sensitivity to gemcitabine of multidrug-resistant human lung cancer cells.	2001 Mar 23	11282108
Cotton-wool spots associated with pancreatic carcinoma.	2001 Mar 26	11309222
Integrating the oral fluoropyrimidines into the management of advanced colorectal cancer.	2001 May	11313169
Enhancement of sensitivity to capecitabine in human renal carcinoma cells transfected with thymidine phosphorylase cDNA.	2001 May 1	11291085

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

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 `Fri Dec 15 15:11:23 GMT 2023` Edited by `admin` on `Fri Dec 15 15:11:23 GMT 2023`
Record UNII	0W860991D6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Doxecitine

Official Name

English

DEOXYCYTIDINE

Preferred Name

English

2′-Deoxycytidine

Systematic Name

English

DOXECITINE [USAN]

Common Name

English

CYTIDINE, 2'-DEOXY-

Systematic Name

English

DEOXYRIBOSE CYTIDINE

Systematic Name

English

MT-1621 COMPONENT 2'-DEOXYCYTIDINE

Code

English

1-(2-Deoxy-β-D-ribofuranosyl)cytosine

Common Name

English

DEOXYCYTIDINE [INCI]

Common Name

English

2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-

Systematic Name

English

4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone

Systematic Name

English

doxecitine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2459