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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N2O5
Molecular Weight 242.229
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THYMIDINE

SMILES

Cc1cn([C@@]2([H])C[C@@]([H])([C@@]([H])(CO)O2)O)c(=O)nc1O

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 242.229
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
Gene Symbol: TK2
Target Organism: Homo sapiens (Human)
Target ID: P04183
Gene ID: 7083
Gene Symbol: TK1
Target Organism: Homo sapiens (Human)
Conditions
PubMed

PubMed

TitleDatePubMed
Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain.
2000 Dec 1
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
Thymidine phosphorylase induces carcinoma cell oxidative stress and promotes secretion of angiogenic factors.
2000 Nov 15
Differences in intracellular sites of action of Adriamycin in neoplastic and normal differentiated cells.
2001
Dilazep hydrochloride, an antiplatelet drug, inhibits lipopolysaccharide-induced mouse mesangial cell IL-6 secretion and proliferation.
2001
Short-term effects of four antibiotics on DNA synthesis in endothelial cells.
2001 Apr
Effects of C5a and FMLP on interleukin-8 production and proliferation of human umbilical vein endothelial cells.
2001 Apr
Human uterine myometrial smooth muscle cell proliferation and vascular endothelial growth-factor production in response to platelet-derived growth factor.
2001 Apr
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 Apr 16
5-Lipoxygenase is required for proliferation of immature cerebellar granule neurons in vitro.
2001 Apr 20
Induction of unscheduled DNA synthesis in hairless mouse epidermis by 8-methoxypsoralen plus ultraviolet A (PUVA).
2001 Feb
Tephrosia purpurea alleviates phorbol ester-induced tumor promotion response in murine skin.
2001 Feb
The effects of particulate wear debris, cytokines, and growth factors on the functions of MG-63 osteoblasts.
2001 Feb
Interleukin-11 receptor expression in primary ovarian carcinomas.
2001 Feb
Myostatin inhibits cell proliferation and protein synthesis in C2C12 muscle cells.
2001 Feb
Biological action of angiopoietin-2 in a fibrin matrix model of angiogenesis is associated with activation of Tie2.
2001 Feb 16
Short chain fatty acids differentially modulate cellular phenotype and c-myc protein levels in primary human nonmalignant and malignant colonocytes.
2001 Jan
Pityrosporum and Candida specific and non-specific humoral, cellular and cytokine responses in atopic dermatitis patients.
2001 Jan
Dopamine induces ERK activation in renal epithelial cells through H2O2 produced by monoamine oxidase.
2001 Jan
Antidepressants alter cell proliferation in the adult brain in vivo and in neural cultures in vitro.
2001 Jan 5
Arginine modulated cyclosporine-induced immune suppression in rats transplanted with gastric cancer cells.
2001 Jan-Feb
A mechanistic study of proliferation induced by Angelica sinensis in a normal gastric epithelial cell line.
2001 Jun 1
Lamina propria lymphocytes produce interferon-gamma and develop suppressor activity in response to lactoglobulin.
2001 Mar
Nuclear factor-kappaB regulates cyclooxygenase-2 expression and cell proliferation in human gastric cancer cells.
2001 Mar
Endothelin receptor blockade inhibits proliferation of Kaposi's sarcoma cells.
2001 Mar
Lipid peroxidation product 4-hydroxy-2-nonenal acts synergistically with serotonin in inducing vascular smooth muscle cell proliferation.
2001 Mar
Adenosine receptor-adenylate cyclase system in the trout testis: involvement in the regulation of germ cell proliferation.
2001 Mar
Bile salt stimulates intestinal epithelial cell migration through TGFbeta after wounding.
2001 May 1
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 Sat Jun 26 10:57:41 UTC 2021
Edited
by admin
on Sat Jun 26 10:57:41 UTC 2021
Record UNII
VC2W18DGKR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THYMIDINE
INCI   MART.   MI   WHO-DD   WHO-IP  
INCI  
Official Name English
1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE
Common Name English
1-(2-DEOXY-.BETA.-D-RIBOFURANOSYL)-5-METHYLURACIL
Common Name English
ZIDOVUDINE RELATED COMPOUND D
USP-RS  
Common Name English
THYMIDINE [MART.]
Common Name English
THYMIDINE [MI]
Common Name English
THYMIDINE [WHO-IP]
Common Name English
ZIDOVUDINE RELATED COMPOUND D [USP-RS]
Common Name English
NSC-21548
Code English
THYMIDINE [WHO-DD]
Common Name English
THYMIDINE [INCI]
Common Name English
ZIDOVUDINE IMPURITY E [EP]
Common Name English
1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE [WHO-IP]
Systematic Name English
THYMINE-2-DESOXYRIBOSIDE
Common Name English
DEOXYRIBOTHYMIDINE
Common Name English
STAVUDINE IMPURITY C [WHO-IP]
Common Name English
STAVUDINE IMPURITY C [EP]
Common Name English
ZIDOVUDINE RELATED COMPOUND D RS [USP]
Common Name English
Classification Tree Code System Code
LOINC 59215-4
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
EU-Orphan Drug EU/3/17/1870
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
LOINC 48162-2
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
NCI_THESAURUS C707
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
LOINC 75156-0
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
Code System Code Type Description
MESH
D013936
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-070-4
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY
PUBCHEM
5789
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY
WIKIPEDIA
THYMIDINE
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY
CAS
50-89-5
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY
NCI_THESAURUS
C880
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY
EVMPD
SUB15554MIG
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY
USP_CATALOG
1724543
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M10822
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB04485
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY
FDA UNII
VC2W18DGKR
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY
RXCUI
1372538
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY RxNorm
EPA CompTox
50-89-5
Created by admin on Sat Jun 26 10:57:41 UTC 2021 , Edited by admin on Sat Jun 26 10:57:41 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
Amount Not Specified
INTERNATIONAL PHARMACOPEIA
Related Record Type Details
ACTIVE MOIETY