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

Description

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

CNS Non-penetrant
1014
Curator's Comment: The transfer of thymidine through the blood-brain barrier in either direction must be extremely low.

Approval Year

2020
742
Targets

Targets

Primary TargetPharmacologyConditionPotency
Thymidine kinase 2, mitochondrial
1
Target ID: O00142
Gene ID: 7084.0
Gene Symbol: TK2
Target Organism: Homo sapiens (Human)
Substrate
661
Thymidine kinase, cytosolic
1
Target ID: P04183
Gene ID: 7083.0
Gene Symbol: TK1
Target Organism: Homo sapiens (Human)
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
120 min
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10561372
75 mg/m² 1 times / day steady-state, intravenous
dose: 75 mg/m²
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: CARBOPLATIN
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 (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
DLT: Myelosuppression...
Other AEs: Indigestion, Hiccoughs...
Dose limiting toxicities:
Myelosuppression (7 patients)
Other AEs:
Indigestion (22%)
Hiccoughs (22%)
Leukopenia (57%)
thrombocytopenia (29%)
Somnolence (82%)
anemia (52%)
headache (73%)
Nausea (91%)
vomiting (91%)
anorexia (91%)
Illusion (56%)
Diarrhea (73%)
Memory impairment (22%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
AEs

AEs

AESignificanceDosePopulation
Hiccoughs 22%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
Indigestion 22%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
Memory impairment 22%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
thrombocytopenia 29%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
anemia 52%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
Illusion 56%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
Leukopenia 57%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
Myelosuppression 7 patients
DLT
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
Diarrhea 73%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
headache 73%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
Somnolence 82%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
Nausea 91%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
anorexia 91%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
vomiting 91%
75 g/m2 1 times / day multiple, intravenous (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/7471098/
PubMed

PubMed

TitleDatePubMed
Delayed methotrexate clearance in a patient with sickle cell anemia and osteosarcoma.
1999 Mar-Apr
Metabolism and mode of inhibition of varicella-zoster virus by L-beta-5-bromovinyl-(2-hydroxymethyl)-(1,3-dioxolanyl)uracil is dependent on viral thymidine kinase.
2000 Nov
Bone morphogenetic protein-7 modulates genes that maintain the vascular smooth muscle cell phenotype in culture.
2001
Evaluation of a nonradioactive colorimetric assay for analysis of lymphocyte proliferation in healthy cats.
2001 Apr
Mechanisms of thrombin-induced MAPK activation associated with cell proliferation in human cultured tracheal smooth muscle cells.
2001 Apr
Effects of synthetic serine protease inhibitors on proliferation and collagen synthesis of human pancreatic periacinar fibroblast-like cells.
2001 Apr
Characterization of the CC chemokine receptor 3 on human keratinocytes.
2001 Apr
Human uterine myometrial smooth muscle cell proliferation and vascular endothelial growth-factor production in response to platelet-derived growth factor.
2001 Apr
Evaluation of an in vitro endothelialized vascular graft under pulsatile shear stress with a novel radiolabeling procedure.
2001 Apr
5-Lipoxygenase is required for proliferation of immature cerebellar granule neurons in vitro.
2001 Apr 20
Oxidative stress effect on the activation of hepatic stellate cells.
2001 Feb
Opposite effects on human colon cancer cell proliferation of two dietary Thomsen-Friedenreich antigen-binding lectins.
2001 Feb
Dual effect of oxidized LDL on cell cycle in human endothelial cells through oxidative stress.
2001 Feb
Labeling DNA with stable isotopes: economical and practical considerations.
2001 Jan
Role of stimulatory guanine nucleotide binding protein (GSalpha) in proliferation of PC-3M prostate cancer cells.
2001 Jan 1
Arginine modulated cyclosporine-induced immune suppression in rats transplanted with gastric cancer cells.
2001 Jan-Feb
Nitric oxide induces oxidative stress and mediates cytotoxicity to human cavernosal cells in culture.
2001 Jan-Feb
Cell-mediated immune response to high-passage Borrelia spirochetes in C57bl/6 mice is strictly dependent on antigen specificity.
2001 Mar
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 Mar
Endothelin receptor blockade inhibits proliferation of Kaposi's sarcoma cells.
2001 Mar
Cytogenetic subgroups in acute myeloid leukemia differ in proliferative activity and response to GM-CSF.
2001 Mar
Adenosine receptor-adenylate cyclase system in the trout testis: involvement in the regulation of germ cell proliferation.
2001 Mar
Patents

Patents

06025482
1
06596857
1
JP2000514307A
1
JP2004143049A
1
JP2008048741A
1
JP2008286729A
1
JPH02227096A
1
JPH02291298A
1
JPH03216188A
1
JPH0543424A
1
JPH06206823A
2
JPH06247859A
2
JPH0827008A
3
JPH08280385A
4
JPH09509323A
2
JPH11137289A
1
JPH11137290A
1
JPS59106297A
1
JPS60126221A
1
JPS62138190A
1
JPS6356298A
1
JPS6359886A
1
JPS6434282A
5
JPS6443200A
1

Sample Use Guides

In Vivo Use Guide
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 Fri Dec 15 15:21:10 GMT 2023
Edited
by admin
on Fri Dec 15 15:21:10 GMT 2023
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-β-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
THYMIDINE [INCI]
Common Name 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-β-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 Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
EU-Orphan Drug EU/3/17/1870
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
LOINC 48162-2
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
NCI_THESAURUS C707
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
LOINC 75156-0
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
Code System Code Type Description
USAN
KL-167
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
INN
11756
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
MESH
D013936
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-070-4
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
PUBCHEM
5789
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
CHEBI
17748
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
WIKIPEDIA
THYMIDINE
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
CAS
50-89-5
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
RS_ITEM_NUM
1724543
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
NCI_THESAURUS
C880
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
EVMPD
SUB15554MIG
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
NSC
21548
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
MERCK INDEX
m10822
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB04485
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
DAILYMED
VC2W18DGKR
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
FDA UNII
VC2W18DGKR
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
RXCUI
1372538
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID5023661
Created by admin on Fri Dec 15 15:21:10 GMT 2023 , Edited by admin on Fri Dec 15 15:21:10 GMT 2023
PRIMARY
Related Record Type Details
Structure of ZIDOVUDINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of STAVUDINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of STAVUDINE
PARENT -> IMPURITY
Amount Not Specified
INTERNATIONAL PHARMACOPEIA
Related Record Type Details
Structure of Doxribtimine
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966