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Deoxycytidine

HCID 13711
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
56905-41-0
標準SMILES
Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
InChIKey
CKTSBUTUHBMZGZ-SHYZEUOFSA-N
分子式
C9H13N3O4
平均分子量
227.22 g/mol
単同位体質量
227.0906059

概要

2'-deoxycytidine is a pyrimidine 2'-deoxyribonucleoside having cytosine as the nucleobase. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is functionally related to a cytosine.

名称と識別子

優先名称
Deoxycytidine
IUPAC
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
英語名
951-77-9
分子式
C9H13N3O4
分子量
227.22

名称と別名

2'-deoxycytidine951-77-9deoxycytidineCYTIDINE, 2'-DEOXY-Deoxyribose cytidinedCYDCytosine deoxyribosideDoxecitineDesoxycytidinCytosine, deoxyribonucleoside4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one0W860991D6
名称をさらに表示
CHEBI:15698DTXSID70883620MT-1621 COMPONENT 2'-DEOXYCYTIDINE4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2-dihydropyrimidin-2-one4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidin-2-oneDeoxyriboside, CytosineRefChem:585745

データベース識別子

CAS
56905-41-0、951-77-9
PubChem CID
13711
DTXSID
DTXSID70883620
ChEMBL
CHEMBL66115
ChEBI
CHEBI:15698
UNII
0W860991D6
EC Number
213-454-1
Nikkaji
J14.406A

物性

構造計算による物性

XLogP
-1.8
極性表面積
108 Ų
水素結合供与体数
3
水素結合受容体数
4
回転可能結合数
2
重原子数
16
形式電荷
0
複雑度
355

実験および物理化学的性質

Chemical ClassesBiological Agents -> Nucleic Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
LogP-1.77
Solubility870 mg/mL
Human Drugs · 2 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point207 - 210 °C
Physical Description · 2 件

White powder; [Sigma-Aldrich MSDS]

Solid

Collision Cross Section · 4 件

158.41 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

146.84 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

158.5 Ų [M+K]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

149.1 Ų [M-H]-

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 3 件

This chemical does not meet GHS hazard criteria for 92.3% (12 of 13) of all reports.

Not Classified

Aggregated GHS information provided per 13 reports by companies from 2 notifications to the ECHA C&L Inventory.

危険有害性情報

Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesNot Classified

化学と産業

薬理情報

Protein BindingIn vitro plasma protein binding of doxecitine was less than 10% over the concentration range between 0.23 mcg/mL and 23 mcg/mL.
Pharmacodynamics · 1 件

Doxecitine's primary action is a substrate enhancement therapy that corrects the nucleoside imbalance caused by TK2d deficiency. The goal is to provide a high systemic concentration of deoxycytidine and deoxythymidine that can be utilized by unaffected salvage pathways. This action restores the synthesis of mitochondrial DNA (mtDNA) precursors, leading to the restoration of mtDNA copy number and subsequent improvement in respiratory chain enzyme (RCE) activities in affected tissues. This systemic correction counteracts the relentless muscle weakness and respiratory failure characteristic of TK2d, resulting in the amelioration of myopathy, delay of disease onset, and significantly prolonged survival in both preclinical models and patients.

Mechanism of Action · 1 件

The progressive, often fatal myopathy seen in Thymidine Kinase 2 deficiency (TK2d) is caused by mutations in the nuclear TK2 gene, leading to a dysfunctional or deficient mitochondrial TK2 enzyme. This enzyme is essential for phosphorylating the pyrimidine nucleosides doxecitine (dC) and thymidine (dT) into dCMP and dTMP, which are precursors for the deoxyribonucleotide triphosphates (dNTPs) required for mitochondrial DNA (mtDNA) maintenance and replication. The resulting metabolic block causes severe mtDNA depletion and dysfunction of the mitochondrial respiratory chain.[] Doxecitine, in combination with doxribtimine, functions as a nucleoside substrate enhancement therapy that successfully bypasses the defective mitochondrial pathway. The high concentrations of exogenous dC and dT are primarily phosphorylated by intact cytosolic salvage enzymes, specifically Deoxycytidine Kinase (dCK) and Thymidine Kinase 1 (TK1). The nucleosides are actively transported into cells and across the blood-brain barrier via equilibrative nucleoside transporters. The resulting phosphorylated dNTP precursors are then made available to the mitochondria. This replenishes the critically depleted dNTP pools, which facilitates the replication of mtDNA by the mitochondrial DNA Polymerase gamma.

Biological Half-LifeThe mean half-life was approximately 1 hour for doxecitine following a single oral administration of 133 mg/kg doxecitine under fed conditions in healthy adult subjects.

関連反応

25 件
反応記録を作成
HRID 1725 の反応式
HRID 1725反応物としてuspto-grants-1998_03
HRID 25468 の反応式
HRID 25468反応物としてuspto-grants-2005_02
HRID 84065 の反応式
HRID 84065反応物としてuspto-grants-2014_09
HRID 366970 の反応式
HRID 366970反応物としてuspto-grants-2000_10
HRID 366972 の反応式
HRID 366972反応物としてuspto-grants-2000_10
HRID 600111 の反応式
HRID 600111反応物としてuspto-grants-2011_03
HRID 844537 の反応式
HRID 844537生成物としてuspto-grants-2002_04
HRID 844538 の反応式
HRID 844538生成物としてuspto-grants-2002_04
1 / 4 ページ

化合物ノート

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Metabolism/Metabolites · 1 件

Doxecitine is primarily degraded by cytidine deaminase to its nucleobases and the 2-deoxy-α-D-ribose 1-phosphate moiety. Intermediate products of doxecitine catabolism are deoxyuridine, uracil, and dihydrouracil with the end products β-alanine, ammonia, and carbon dioxide (CO2).

Absorption, Distribution and Excretion · 2 件

Doxecitine is administered orally, with rapid absorption and plasma concentrations returning to near baseline within 8 to 12 hours. The absolute bioavailability of doxecitine following oral administration has not been determined. The median time to peak plasma concentration (Tmax) was approximately two hours for doxecitine.

Urinary excretion of intact doxecitine and doxribtimine was <1% of the dose in healthy subjects following an oral administration of doxecitine and doxribtimine.

Tissue LocationsAll Tissues
Cellular LocationsExtracellular
Metabolite PathwaysBeta Ureidopropionase Deficiency

用途と製造

General Manufacturing InformationCytidine, 2'-deoxy-: ACTIVE