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 |
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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 (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%) Sources: 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%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
Title | Date | PubMed |
---|---|---|
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 |
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Differences in intracellular sites of action of Adriamycin in neoplastic and normal differentiated cells. | 2001 |
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Dilazep hydrochloride, an antiplatelet drug, inhibits lipopolysaccharide-induced mouse mesangial cell IL-6 secretion and proliferation. | 2001 |
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Angiotensin II and serotonin potentiate endothelin-1-induced vascular smooth muscle cell proliferation. | 2001 Apr |
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Immediate-early protooncogene expression and liver function following various extents of partial hepatectomy in the rat. | 2001 Apr |
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Vascular endothelial growth factor-A activates Ca2+ -activated K+ channels in human endothelial cells in culture. | 2001 Apr |
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Effects of synthetic serine protease inhibitors on proliferation and collagen synthesis of human pancreatic periacinar fibroblast-like cells. | 2001 Apr |
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Characterization of the CC chemokine receptor 3 on human keratinocytes. | 2001 Apr |
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Loss of cyclin A and G1-cell cycle arrest are a prerequisite of ceramide-induced toxicity in human arterial endothelial cells. | 2001 Apr |
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Effects of sodium butyrate on expression of members of the IGF-binding protein superfamily in human mammary epithelial cells. | 2001 Apr |
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Human uterine myometrial smooth muscle cell proliferation and vascular endothelial growth-factor production in response to platelet-derived growth factor. | 2001 Apr |
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Basic calcium phosphate crystals activate human osteoarthritic synovial fibroblasts and induce matrix metalloproteinase-13 (collagenase-3) in adult porcine articular chondrocytes. | 2001 Apr |
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Evaluation of an in vitro endothelialized vascular graft under pulsatile shear stress with a novel radiolabeling procedure. | 2001 Apr |
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Cholecystokinin octapeptide induces both proliferation and apoptosis in the rat pancreas. | 2001 Apr 2 |
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5-Lipoxygenase is required for proliferation of immature cerebellar granule neurons in vitro. | 2001 Apr 20 |
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Oxidative stress effect on the activation of hepatic stellate cells. | 2001 Feb |
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Tephrosia purpurea alleviates phorbol ester-induced tumor promotion response in murine skin. | 2001 Feb |
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Lupeol, a triterpene, inhibits early responses of tumor promotion induced by benzoyl peroxide in murine skin. | 2001 Feb |
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Enterocyte digestive enzyme activity along the crypt-villus and longitudinal axes in the neonatal pig small intestine. | 2001 Feb |
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Troglitazone and rosiglitazone induce apoptosis of vascular smooth muscle cells through an extracellular signal-regulated kinase-independent pathway. | 2001 Feb |
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The effects of particulate wear debris, cytokines, and growth factors on the functions of MG-63 osteoblasts. | 2001 Feb |
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Evidence for mitogen-associated protein kinase activation and transduction of mitogenic signals by platelet-derived growth factor in human meningioma cells. | 2001 Feb |
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Combined effects of estrogen and progesterone on the anterior cruciate ligament. | 2001 Feb |
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Role of PKC and TGF-beta receptor in glucose-induced proliferation of smooth muscle cells. | 2001 Feb 16 |
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Effects of vasoactive intestinal peptide (VIP) and somatostatin (SST) on lipoprotein receptor expression by A431 tumor cells. | 2001 Feb 2 |
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The chondrogenic potential of periosteum decreases with age. | 2001 Jan |
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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 |
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Regulation of retinal capillary cells by basic fibroblast growth factor, vascular endothelial growth factor, and hypoxia. | 2001 Jan |
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Labeling DNA with stable isotopes: economical and practical considerations. | 2001 Jan |
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Okadaic acid-induced inhibition of protein phosphatase 2A enhances chondrogenesis in chicken limb bud micromass cell cultures. | 2001 Jan |
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Arginine modulated cyclosporine-induced immune suppression in rats transplanted with gastric cancer cells. | 2001 Jan-Feb |
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Changes in thymidine incorporation into tumor cells induced by supernatants of calcium-ionophore-treated macrophages incubated with tumor cells. | 2001 Jan-Feb |
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Taenia solium: germinal cell precursors in tapeworms grown in hamster intestine. | 2001 Jan-Feb |
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[Characteristic of proliferative processes in colonic mucosa in acute salmonellosis]. | 2001 Jan-Feb |
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[Effect of cytomegalovirus on cell cycle progression and formation of pathological mitoses in cultured human diploid fibroblasts]. | 2001 Jan-Feb |
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17Beta-estradiol inhibits proliferation of cultured vascular smooth muscle cells induced by lysophosphatidylcholine via a nongenomic antioxidant mechanism. | 2001 Jan-Feb |
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Nitric oxide induces oxidative stress and mediates cytotoxicity to human cavernosal cells in culture. | 2001 Jan-Feb |
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A mechanistic study of proliferation induced by Angelica sinensis in a normal gastric epithelial cell line. | 2001 Jun 1 |
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Cell-mediated immune response to high-passage Borrelia spirochetes in C57bl/6 mice is strictly dependent on antigen specificity. | 2001 Mar |
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Growth-inhibitory effects of CD40 ligand (CD154) and its endogenous expression in human breast cancer. | 2001 Mar |
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The migration of cells in multicell tumor spheroids. | 2001 Mar |
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Pulsed electromagnetic fields increase growth factor release by nonunion cells. | 2001 Mar |
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Peroxisome proliferators do not increase DNA synthesis in purified rat hepatocytes. | 2001 Mar |
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Endothelin receptor blockade inhibits proliferation of Kaposi's sarcoma cells. | 2001 Mar |
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Cytogenetic subgroups in acute myeloid leukemia differ in proliferative activity and response to GM-CSF. | 2001 Mar |
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Synergistic efficacy of 3n-butyrate and 5-fluorouracil in human colorectal cancer xenografts via modulation of DNA synthesis. | 2001 Mar |
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Total cell-associated Zn2+ and Cu2+ and proliferative responsiveness of peripheral blood mononuclear cells from patients on chronic hemodialysis. | 2001 Mar |
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Lipid peroxidation product 4-hydroxy-2-nonenal acts synergistically with serotonin in inducing vascular smooth muscle cell proliferation. | 2001 Mar |
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STAT5 pathway: target of anti-CD4 antibody in attenuation of IL-2 receptor signaling. | 2001 Mar 27 |
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Development of non-radio isotopic endpoint of murine local lymph node assay based on 5-bromo-2'-deoxyuridine (BrdU) incorporation. | 2001 Mar 8 |
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
by
admin
on
Edited
Fri Dec 15 15:21:10 GMT 2023
by
admin
on
Fri Dec 15 15:21:10 GMT 2023
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Record UNII |
VC2W18DGKR
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Record Status |
Validated (UNII)
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Record Version |
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LOINC |
59215-4
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EU-Orphan Drug |
EU/3/17/1870
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LOINC |
48162-2
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NCI_THESAURUS |
C707
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LOINC |
75156-0
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KL-167
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11756
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D013936
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200-070-4
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5789
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17748
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THYMIDINE
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50-89-5
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1724543
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C880
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SUB15554MIG
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21548
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m10822
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DB04485
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VC2W18DGKR
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1372538
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DTXSID5023661
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
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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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