Thymidine

HCID 5789CAS 146183-25-7

기본 정보

표준 SMILES
Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O
InChIKey
IQFYYKKMVGJFEH-XLPZGREQSA-N
분자식
C10H14N2O5
평균 분자량
242.23 g/mol
단동위원소 질량
242.09027155

이름 및 식별자

우선 이름
Thymidine
IUPAC
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
영어명
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione
분자식
C10H14N2O5
분자량
242.23

이름 및 동의어

thymidine50-89-52'-DeoxythymidineDThydThymidinThymine-2-desoxyriboside5-Methyl-2'-deoxyuridineThyminedeoxyribosideDeoxyribothymidineDoxribtiminedThd2'-thymidine
이름 더 보기
DTXSID50236611-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dionethymine 2'-deoxyribosideVC2W18DGKR1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione2'-deoxy-5-methyluridineCHEBI:17748NSC-21548

데이터베이스 식별자

CAS
146183-25-7、50-88-4、50-89-5
PubChem CID
5789
DTXSID
DTXSID5023661
ChEMBL
CHEMBL52609
ChEBI
CHEBI:17748
UNII
VC2W18DGKR
EC Number
200-070-4
Nikkaji
J4.548I

물성

구조 계산 물성

XLogP
-1.2
극성 표면적
99.1 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
5
회전 가능 결합 수
2
무거운 원자 수
17

실험 및 물리화학적 성질

LogP · 2건

-0.93

-0.93

Solubility · 2건

73.5 mg/mL

Water 50 (mg/mL)

Melting Point187-189
Optical Rotation(c = 1, H2O) [a]25 D = +18 ± 0.5°
Physical Description · 2건

Solid; [Merck Index] White odorless powder; [Alfa Aesar MSDS]

Solid

Stability/Shelf LifeSolution: A 1% solution of thymidine in water, kept at room temperature, is stable for at least 24 hours (HPLC).

안전 및 규제

GHS 분류

GHS Classification · 3건

This chemical does not meet GHS hazard criteria for 97.6% (121 of 124) of all reports.

Not Classified;Reported as not meeting GHS hazard criteria by 121 of 124 companies (only 2.4% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

Aggregated GHS information provided per 124 reports by companies from 4 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 121 of 124 reports by companies.;There are 3 notifications provided by 3 of 124 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

유해성 정보

Regulatory Information · 3건

Chemical: Thymidine

Status: Active Update: 02-09-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/15994

Thymidine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryCauses somnolence and changes in motor activity in intraperitoneal lethal-dose studies of mice (LD50 = 2,512 mg/kg); [RTECS] May cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesNot Classified

독성 정보

Toxicity DataMouse(ip): LD50 2512 mg/kg

규제 정보

Regulatory Information · 3건

Chemical: Thymidine

Status: Active Update: 02-09-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/15994

Thymidine: Does not have an individual approval but may be used under an appropriate group standard

화학 및 산업

약리 정보

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

Thymidine acts systemically as a biochemical modulator to optimize the efficacy and reduce the toxicity of standard anti-metabolite chemotherapeutic agents. Its core action is the metabolic modulation of key enzymes in the DNA salvage pathway, which results in the potentiation of anti-tumor effects (e.g., when combined with 5-Fluorouracil) or protection against host toxicity (e.g., host cell rescue from Methotrexate toxicity). Furthermore, TdR, through its conversion to dTTP, significantly accelerates DNA replication fork progression and helps alleviate replication stress in rapidly proliferating cells, a fundamental effect that contributes to its role in preserving genomic stability and altering the selectivity of drug therapy.

Mechanism of Action · 1건

The primary molecular function of Thymidine is its role as a precursor in the DNA salvage pathway, which it exploits to act as a potent biochemical modulator of anti-metabolite chemotherapy. Unlike its use as a traditional drug, thymidine's effect is achieved by manipulating the intracellular balance of deoxyribonucleotide triphosphate (dNTP) pools, which are essential for DNA synthesis and repair. Upon administration, thymidine is rapidly salvaged and phosphorylated by thymidine kinases to form dTTP (deoxythymidine triphosphate). This supplementation significantly increases the intracellular concentration of both dTTP and dGTP pools. This alteration of dNTP balance is directly responsible for thymidine's observed therapeutic effects, which are dependent on the co-administered drug. The elevated dTTP pools influence the metabolism of cytotoxic drugs. For example, it is thought to enhance the activation and incorporation of the active cytotoxic form of 5-Fluorouracil (FU) into DNA and RNA. The increase in dTTP and dGTP is linked to the observed acceleration of DNA replication fork progression in various cell types.

Biological Half-LifeThe mean half-life was approximately five hours following a single oral administration of 133 mg/kg dose under fed conditions in healthy adults.
Metabolism/Metabolites · 1건

Thymidine is primarily degraded (catabolized) by thymidine phosphorylase to the nucleobases and the 2-deoxy-α-D-ribose 1-phosphate moiety. Thymine, the pyrimidine nucleobase of doxribtimine, is subsequently catabolized to dihydrothymine and ultimately to γ-amino-isobutyric acid and CO2.

Absorption, Distribution and Excretion · 3건

The absolute bioavailability of thymidine following oral administration has not been determined. The median time to peak plasma concentration (Tmax) was approximately four hours.

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

Thymidine's transfer across the blood-brain barrier is generally considered extremely low, with studies suggesting an active transport system in the choroid plexus transfers it into the cerebrospinal fluid (CSF) before it enters brain cells.

용도 및 제조

UsesComponent of DNA; [Merck Index]
General Manufacturing InformationThymidine: ACTIVE

관련 반응

195건

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