U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N2O5
Molecular Weight 242.2286
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Doxribtimine

SMILES

CC1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)NC1=O

InChI

InChIKey=IQFYYKKMVGJFEH-XLPZGREQSA-N
InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H14N2O5
Molecular Weight 242.2286
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Thymidine is a water-soluble pyrimidine deoxynucleoside and potent thymidine kinase substrate. Thymidine is known to be converted to dTTP and utilized for DNA synthesis. It is also known that thymidine is converted by catabolic enzymes to several end products. Excess thymidine results in high levels of dTTP, which exerts a regulatory feedback inhibition in the nucleotide biosynthesis pathways leading to DNA synthesis. This property of thymidine is used when it is given in high doses to patients with solid tumors. Thymidine is being tested in Phase II of clinical trials for the treatment of cancer and 5'-Nucleotidase Syndrome.

CNS Activity

Curator's Comment: The transfer of thymidine through the blood-brain barrier in either direction must be extremely low.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O00142
Gene ID: 7084.0
Gene Symbol: TK2
Target Organism: Homo sapiens (Human)
Target ID: P04183
Gene ID: 7083.0
Gene Symbol: TK1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
120 min
75 mg/m² 1 times / day steady-state, intravenous
dose: 75 mg/m²
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: CARBOPLATIN
THYMIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
DLT: Myelosuppression...
Other AEs: Leukopenia, thrombocytopenia...
Dose limiting toxicities:
Myelosuppression (7 patients)
Other AEs:
Leukopenia (57%)
thrombocytopenia (29%)
anemia (52%)
Nausea (91%)
vomiting (91%)
anorexia (91%)
Diarrhea (73%)
Indigestion (22%)
Hiccoughs (22%)
Somnolence (82%)
headache (73%)
Illusion (56%)
Memory impairment (22%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hiccoughs 22%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Indigestion 22%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Memory impairment 22%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
thrombocytopenia 29%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
anemia 52%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Illusion 56%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Leukopenia 57%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Myelosuppression 7 patients
DLT
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Diarrhea 73%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
headache 73%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Somnolence 82%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Nausea 91%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
anorexia 91%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
vomiting 91%
75 g/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
A mechanistic study of proliferation induced by Angelica sinensis in a normal gastric epithelial cell line.
2001-06-01
Bile salt stimulates intestinal epithelial cell migration through TGFbeta after wounding.
2001-05-01
Flow-induced DNA synthesis requires signaling to a translational control pathway.
2001-05-01
Glucocorticoids stimulate p21(CIP1) in mesangial cells and in anti-GBM glomerulonephritis.
2001-05
High glucose inhibits renal proximal tubule cell proliferation and involves PKC, oxidative stress, and TGF-beta 1.
2001-05
5-Lipoxygenase is required for proliferation of immature cerebellar granule neurons in vitro.
2001-04-20
N-Nitrosomorpholine induced alterations of unscheduled DNA synthesis, mitochondrial DNA synthesis and cell proliferation in different cell types of liver, kidney, and urogenital organs in the rat.
2001-04-16
Arginine modulated cyclosporine-induced immune suppression in rats transplanted with gastric cancer cells.
2001-04-05
Changes in thymidine incorporation into tumor cells induced by supernatants of calcium-ionophore-treated macrophages incubated with tumor cells.
2001-04-05
Taenia solium: germinal cell precursors in tapeworms grown in hamster intestine.
2001-04-03
Angiotensin II and serotonin potentiate endothelin-1-induced vascular smooth muscle cell proliferation.
2001-04
Immediate-early protooncogene expression and liver function following various extents of partial hepatectomy in the rat.
2001-04
Lipidation of T helper sequences from hepatitis C virus core significantly enhances T-cell activity in vitro.
2001-04
Evaluation of a nonradioactive colorimetric assay for analysis of lymphocyte proliferation in healthy cats.
2001-04
Short-term effects of four antibiotics on DNA synthesis in endothelial cells.
2001-04
Effects of C5a and FMLP on interleukin-8 production and proliferation of human umbilical vein endothelial cells.
2001-04
Vascular endothelial growth factor-A activates Ca2+ -activated K+ channels in human endothelial cells in culture.
2001-04
Mechanisms of thrombin-induced MAPK activation associated with cell proliferation in human cultured tracheal smooth muscle cells.
2001-04
Effects of synthetic serine protease inhibitors on proliferation and collagen synthesis of human pancreatic periacinar fibroblast-like cells.
2001-04
Characterization of the CC chemokine receptor 3 on human keratinocytes.
2001-04
Estrogen inhibits mechanical strain-induced mitogenesis in human vascular smooth muscle cells via down-regulation of Sp-1.
2001-04
Loss of cyclin A and G1-cell cycle arrest are a prerequisite of ceramide-induced toxicity in human arterial endothelial cells.
2001-04
PDGF signal transduction inhibition ameliorates experimental mesangial proliferative glomerulonephritis.
2001-04
Dexfenfluramine-associated changes in 5-hydroxytryptamine transporter expression and development of hypoxic pulmonary hypertension in rats.
2001-04
Immunohistochemical localization of Betacellulin, a member of epidermal growth factor family, in atherosclerotic plaques of human aorta.
2001-04
Effects of sodium butyrate on expression of members of the IGF-binding protein superfamily in human mammary epithelial cells.
2001-04
Human uterine myometrial smooth muscle cell proliferation and vascular endothelial growth-factor production in response to platelet-derived growth factor.
2001-04
Basic calcium phosphate crystals activate human osteoarthritic synovial fibroblasts and induce matrix metalloproteinase-13 (collagenase-3) in adult porcine articular chondrocytes.
2001-04
Evaluation of an in vitro endothelialized vascular graft under pulsatile shear stress with a novel radiolabeling procedure.
2001-04
The immune response to alkaline phosphatase and other immunogens in patients with primary biliary cirrhosis.
2001-03-28
STAT5 pathway: target of anti-CD4 antibody in attenuation of IL-2 receptor signaling.
2001-03-27
Kinetics study of the biotransformation of an oligonucleotide prodrug in cells extract by matrix-assisted laser desorption-ionization time-of-flight mass spectrometry.
2001-03-25
Development of non-radio isotopic endpoint of murine local lymph node assay based on 5-bromo-2'-deoxyuridine (BrdU) incorporation.
2001-03-08
Tumor necrosis factor alpha and interleukin 11 secreted by malignant breast epithelial cells inhibit adipocyte differentiation by selectively down-regulating CCAAT/enhancer binding protein alpha and peroxisome proliferator-activated receptor gamma: mechanism of desmoplastic reaction.
2001-03-01
Lamina propria lymphocytes produce interferon-gamma and develop suppressor activity in response to lactoglobulin.
2001-03
Nuclear factor-kappaB regulates cyclooxygenase-2 expression and cell proliferation in human gastric cancer cells.
2001-03
Cell-mediated immune response to high-passage Borrelia spirochetes in C57bl/6 mice is strictly dependent on antigen specificity.
2001-03
Growth-inhibitory effects of CD40 ligand (CD154) and its endogenous expression in human breast cancer.
2001-03
The migration of cells in multicell tumor spheroids.
2001-03
Characterization of the cyclooxygenase-2 promoter in an adenoviral vector and its application for the mitigation of toxicity in suicide gene therapy of gastrointestinal cancers.
2001-03
Pulsed electromagnetic fields increase growth factor release by nonunion cells.
2001-03
Oxidative stress effect on the activation of hepatic stellate cells.
2001-02
Induction of unscheduled DNA synthesis in hairless mouse epidermis by 8-methoxypsoralen plus ultraviolet A (PUVA).
2001-02
The chondrogenic potential of periosteum decreases with age.
2001-01
The effects of reduced oxygen tension on cell proliferation and matrix synthesis in synovium and tendon explants from the rabbit carpal tunnel: an experimental study in vitro.
2001-01
Semifluorinated symmetrical diethers for intraocular use: synthesis, characterization, and in vitro biocompatibility.
2001-01
Short chain fatty acids differentially modulate cellular phenotype and c-myc protein levels in primary human nonmalignant and malignant colonocytes.
2001-01
Regulation of retinal capillary cells by basic fibroblast growth factor, vascular endothelial growth factor, and hypoxia.
2001-01
Evidence for stimulation of tumor proliferation in cell lines and histotypic cultures by clinically relevant low doses of the galactoside-binding mistletoe lectin, a component of proprietary extracts.
2001
Bone morphogenetic protein-7 modulates genes that maintain the vascular smooth muscle cell phenotype in culture.
2001
Patents

Sample Use Guides

In a clinical trial, patients with solid tumors were given thymidine intravenously as a dose of 75 g/m2/day continuously for 5 days or more.
Route of Administration: Intravenous
In Vitro Use Guide
HL-60 cells were dispersed in the fresh liquid medium at a concentration of 2.5 x 10(5) cells/ml. 48 hr later, with cells in early log phase, thymidine was added in concentrations from 10(-8) M lo 10(-2) M. Aliquots (1.5 ml) of cell medium mixture was placed in microwell plates and incubated for 5 days. The growth rate of cells incubated with 5.0 mM thymidine was inhibited >90% of control.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:54:56 GMT 2025
Edited
by admin
on Mon Mar 31 17:54:56 GMT 2025
Record UNII
VC2W18DGKR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THYMIDINE
INCI   MART.   MI   WHO-DD   WHO-IP  
INCI  
Preferred Name English
Doxribtimine
INN   USAN  
Official Name English
MT-1621 COMPONENT 2'-DEOXYTHYMIDINE
Code English
1-(2-Deoxy-?-D-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione
Common Name English
ZIDOVUDINE RELATED COMPOUND D
USP-RS  
Common Name English
STAVUDINE IMPURITY C [EP IMPURITY]
Common Name English
ZIDOVUDINE RELATED COMPOUND D [USP IMPURITY]
Common Name English
THYMIDINE [MART.]
Common Name English
THYMIDINE [MI]
Common Name English
DOXRIBTIMINE [USAN]
Common Name English
THYMIDINE [WHO-IP]
Common Name English
Thymidine [WHO-DD]
Common Name English
IMPURITY C [EP IMPURITY]
Common Name English
ZIDOVUDINE RELATED COMPOUND D [USP-RS]
Common Name English
NSC-21548
Code English
5-Methyl-2?-deoxyuridine
Systematic Name English
ZIDOVUDINE IMPURITY E [EP IMPURITY]
Common Name English
1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE [WHO-IP]
Systematic Name English
2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-?-D-erythro-pentofuranosyl)-5-methyl-
Systematic Name English
THYMINE-2-DESOXYRIBOSIDE
Common Name English
DEOXYRIBOTHYMIDINE
Common Name English
STAVUDINE IMPURITY C [WHO-IP]
Common Name English
doxribtimine [INN]
Common Name English
2?-Deoxythymidine
Common Name English
Classification Tree Code System Code
LOINC 59215-4
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
EU-Orphan Drug EU/3/17/1870
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
LOINC 48162-2
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
NCI_THESAURUS C707
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
LOINC 75156-0
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
Code System Code Type Description
USAN
KL-167
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
INN
11756
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
MESH
D013936
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-070-4
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
PUBCHEM
5789
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
CHEBI
17748
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
WIKIPEDIA
THYMIDINE
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
SMS_ID
100000077023
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
CAS
50-89-5
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
RS_ITEM_NUM
1724543
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
NCI_THESAURUS
C880
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
EVMPD
SUB15554MIG
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
NSC
21548
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
MERCK INDEX
m10822
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB04485
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
DAILYMED
VC2W18DGKR
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
FDA UNII
VC2W18DGKR
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
RXCUI
1372538
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID5023661
Created by admin on Mon Mar 31 17:54:56 GMT 2025 , Edited by admin on Mon Mar 31 17:54:56 GMT 2025
PRIMARY
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