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
Unnatural enantiomers of 5-azacytidine analogues: syntheses and enzymatic properties.	2000 Nov	11137229
Phosphorylation of the anti-HIV compound (S,S)-isodideoxyadenosine by human recombinant deoxycytidine kinase.	2000 Nov 15	11020453
[The potential of capecitabine (Xeloda) in the treatment of disseminated solid tumors].	2001	11317529
Clinical pharmacokinetics of capecitabine.	2001	11286326
Treatment of extensive stage small cell lung cancer.	2001	11224990
Induction chemotherapy followed by concomitant chemoradiotherapy for non-small cell lung cancer.	2001	11182002
Options in advanced non-small cell lung cancer: a review and report on a phase II study of vinorelbine plus gemcitabine.	2001	11182000
Topotecan and gemcitabine in platinum/paclitaxel-resistant ovarian cancer.	2001	11150903
Gemcitabine: progress in the treatment of pancreatic cancer.	2001	11150902
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
Deoxynucleoside anabolic enzyme levels in acute myelocytic leukemia and chronic lymphocytic leukemia cells.	2001 Apr 26	11275369
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
[Palliative therapy of pancreatic adenocarcinoma].	2001 Feb	11253511
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
Radiation concurrent with gemcitabine for locally advanced head and neck cancer: a phase I trial and intracellular drug incorporation study.	2001 Feb 1	11157033
Gemcitabine for malignant mesothelioma: A phase II trial by the Cancer and Leukemia Group B.	2001 Feb-Mar	11165412
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	11165408
Decreased myelotoxicity of gemcitabine and cisplatin in advanced non-small cell lung cancer (NSCLC) with cisplatin infusion on day 15.	2001 Feb-Mar	11165407
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	11165406
Phase I trial of gemcitabine in patients with advanced pancreatic cancer.	2001 Jan	11256843
High-dose thiotepa and melphalan with hemopoietic progenitor support following induction therapy with epirubicin-paclitaxel-containing regimens in metastatic breast cancer (MBC).	2001 Jan	11249051
The role of laparoscopy in second-look evaluations for ovarian cancer.	2001 Jan	11136568
Simultaneous treatment with 1-beta-D-arabinofuranosylcytosine and daunorubicin induces cross-resistance to both drugs due to a combination-specific mechanism in HL60 cells.	2001 Jan 1	11196156
Quantitative analysis of etheno-2'-deoxycytidine DNA adducts using on-line immunoaffinity chromatography coupled with LC/ES-MS/MS detection.	2001 Jan 15	11199982
The significance of thymidine phosphorylase expression in colorectal cancer.	2001 Jan-Feb	11115583
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
DNA methyltransferase inhibition in normal human fibroblasts induces a p21-dependent cell cycle withdrawal.	2001 Jun 1	11259405
Effect of chemical modifications of cytosine and guanine in a CpG-motif of oligonucleotides: structure-immunostimulatory activity relationships.	2001 Mar	11310616
Gemcitabine for the treatment of non-small-cell lung cancer.	2001 Mar	11301846
Gemcitabine and vinorelbine as first-line chemotherapy for advanced non-small cell lung cancer: a phase II trial.	2001 Mar	11290433
Latent hematopoietic stem cell toxicity associated with protracted drug administration.	2001 Mar	11274755
Neoadjuvant chemoradiotherapy for adenocarcinoma of the pancreas: treatment variables and survival duration.	2001 Mar	11258776
Cytogenetic subgroups in acute myeloid leukemia differ in proliferative activity and response to GM-CSF.	2001 Mar	11237060
Cytosolic high K(m) 5'-nucleotidase and 5'(3')-deoxyribonucleotidase in substrate cycles involved in nucleotide metabolism.	2001 Mar 2	11083867
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
Human cytosolic 5'-nucleotidase I: characterization and role in nucleoside analog resistance.	2001 Mar 30	11133996
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
Akt, MAPK (Erk1/2), and p38 act in concert to promote apoptosis in response to ErbB receptor family inhibition.	2001 May 4	11278435

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