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 (total)
Highest studied dose
Dose: 75 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 g/m2, 1 times / day
Sources:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
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:
unhealthy
n = 11
Health Status: unhealthy
Condition: cancer
Sex: M+F
Food Status: UNKNOWN
Population Size: 11
Sources:
PubMed

PubMed

TitleDatePubMed
Role of endothelin in the human craniofacial morphogenesis.
1998 Oct-Dec
Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds.
1999 Aug 26
Delayed methotrexate clearance in a patient with sickle cell anemia and osteosarcoma.
1999 Mar-Apr
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
Angiotensin II and serotonin potentiate endothelin-1-induced vascular smooth muscle cell proliferation.
2001 Apr
Immediate-early protooncogene expression and liver function following various extents of partial hepatectomy in the rat.
2001 Apr
Lipidation of T helper sequences from hepatitis C virus core significantly enhances T-cell activity in vitro.
2001 Apr
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
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
Loss of cyclin A and G1-cell cycle arrest are a prerequisite of ceramide-induced toxicity in human arterial endothelial cells.
2001 Apr
Immunohistochemical localization of Betacellulin, a member of epidermal growth factor family, in atherosclerotic plaques of human aorta.
2001 Apr
Basic calcium phosphate crystals activate human osteoarthritic synovial fibroblasts and induce matrix metalloproteinase-13 (collagenase-3) in adult porcine articular chondrocytes.
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
Cholecystokinin octapeptide induces both proliferation and apoptosis in the rat pancreas.
2001 Apr 2
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
Enterocyte digestive enzyme activity along the crypt-villus and longitudinal axes in the neonatal pig small intestine.
2001 Feb
Troglitazone and rosiglitazone induce apoptosis of vascular smooth muscle cells through an extracellular signal-regulated kinase-independent pathway.
2001 Feb
Combined effects of estrogen and progesterone on the anterior cruciate ligament.
2001 Feb
Dual effect of oxidized LDL on cell cycle in human endothelial cells through oxidative stress.
2001 Feb
Adrenomedullin expression and growth inhibitory effects in distinct pulmonary artery smooth muscle cell subpopulations.
2001 Feb
Myostatin inhibits cell proliferation and protein synthesis in C2C12 muscle cells.
2001 Feb
Role of PKC and TGF-beta receptor in glucose-induced proliferation of smooth muscle cells.
2001 Feb 16
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 Jan
Semifluorinated symmetrical diethers for intraocular use: synthesis, characterization, and in vitro biocompatibility.
2001 Jan
Short chain fatty acids differentially modulate cellular phenotype and c-myc protein levels in primary human nonmalignant and malignant colonocytes.
2001 Jan
Labeling DNA with stable isotopes: economical and practical considerations.
2001 Jan
Okadaic acid-induced inhibition of protein phosphatase 2A enhances chondrogenesis in chicken limb bud micromass cell cultures.
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
Role of stimulatory guanine nucleotide binding protein (GSalpha) in proliferation of PC-3M prostate cancer cells.
2001 Jan 1
Coexpression of granulocyte colony stimulating factor and its receptor in primary ovarian carcinomas.
2001 Jan 10
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
Taenia solium: germinal cell precursors in tapeworms grown in hamster intestine.
2001 Jan-Feb
The immune response to alkaline phosphatase and other immunogens in patients with primary biliary cirrhosis.
2001 Jan-Feb
[Characteristic of proliferative processes in colonic mucosa in acute salmonellosis].
2001 Jan-Feb
17Beta-estradiol inhibits proliferation of cultured vascular smooth muscle cells induced by lysophosphatidylcholine via a nongenomic antioxidant mechanism.
2001 Jan-Feb
A mechanistic study of proliferation induced by Angelica sinensis in a normal gastric epithelial cell line.
2001 Jun 1
Growth-inhibitory effects of CD40 ligand (CD154) and its endogenous expression in human breast cancer.
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
Lipid peroxidation product 4-hydroxy-2-nonenal acts synergistically with serotonin in inducing vascular smooth muscle cell proliferation.
2001 Mar
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 Mar 1
STAT5 pathway: target of anti-CD4 antibody in attenuation of IL-2 receptor signaling.
2001 Mar 27
Glucocorticoids stimulate p21(CIP1) in mesangial cells and in anti-GBM glomerulonephritis.
2001 May
Flow-induced DNA synthesis requires signaling to a translational control pathway.
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 Fri Dec 15 15:21:10 UTC 2023
Edited
by admin
on Fri Dec 15 15:21:10 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
EU-Orphan Drug EU/3/17/1870
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
LOINC 48162-2
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
NCI_THESAURUS C707
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
LOINC 75156-0
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
Code System Code Type Description
USAN
KL-167
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
INN
11756
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
MESH
D013936
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-070-4
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
PUBCHEM
5789
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
CHEBI
17748
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
WIKIPEDIA
THYMIDINE
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
CAS
50-89-5
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
RS_ITEM_NUM
1724543
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
NCI_THESAURUS
C880
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
EVMPD
SUB15554MIG
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
NSC
21548
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
MERCK INDEX
m10822
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB04485
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
DAILYMED
VC2W18DGKR
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
FDA UNII
VC2W18DGKR
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY
RXCUI
1372538
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID5023661
Created by admin on Fri Dec 15 15:21:10 UTC 2023 , Edited by admin on Fri Dec 15 15:21:10 UTC 2023
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