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
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
| 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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7047684
Curator's Comment: The transfer of thymidine through the blood-brain barrier in either direction must be extremely low.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: O00142 Gene ID: 7084.0 Gene Symbol: TK2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6736109 |
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Target ID: P04183 Gene ID: 7083.0 Gene Symbol: TK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6736109 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6736109 |
Primary | Unknown Approved UseUnknown |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
THYMIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse 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%) Sources: 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%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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
| Title | Date | PubMed |
|---|---|---|
| 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 Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7471098
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6940654
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
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VC2W18DGKR
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Validated (UNII)
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LOINC |
59215-4
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EU-Orphan Drug |
EU/3/17/1870
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48162-2
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C707
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75156-0
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KL-167
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11756
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D013936
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17748
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THYMIDINE
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100000077023
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1724543
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C880
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m10822
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DB04485
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1372538
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DTXSID5023661
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
Amount Not Specified
INTERNATIONAL PHARMACOPEIA
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ACTIVE MOIETY |
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