Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H4N2O2 |
Molecular Weight | 112.0868 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1NC=CC(=O)N1
InChI
InChIKey=ISAKRJDGNUQOIC-UHFFFAOYSA-N
InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
Molecular Formula | C4H4N2O2 |
Molecular Weight | 112.0868 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB03419 | https://www.drugs.com/international/uracil.html | https://www.ncbi.nlm.nih.gov/pubmed/28347333 | https://www.ncbi.nlm.nih.gov/pubmed/4053028
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB03419 | https://www.drugs.com/international/uracil.html | https://www.ncbi.nlm.nih.gov/pubmed/28347333 | https://www.ncbi.nlm.nih.gov/pubmed/4053028
Uracil is a common and naturally occurring pyrimidine derivative, one of the four nucleobases in the nucleic acid of RNA In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by it’s methylated form -- thymine. Originally discovered in 1900 by Alberto Ascoli, it was isolated by hydrolysis of yeast nuclein;[4] it was also found in bovine thymus and spleen, herring sperm, and wheat germ. It is a planar, unsaturated compound that has the ability to absorb light. Uracil readily undergoes regular reactions including oxidation, nitration, and alkylation. While in the presence of phenol (PhOH) and sodium hypochlorite (NaOCl), uracil can be visualized in ultraviolet light. Uracil also has the capability to react with elemental halogens because of the presence of more than one strongly electron donating group. Uracil readily undergoes addition to ribose sugars and phosphates to partake in synthesis and further reactions in the body. Uracil becomes uridine, uridine monophosphate (UMP), uridine diphosphate (UDP), uridine triphosphate (UTP), and uridine diphosphate glucose (UDP-glucose). Each one of these molecules is synthesized in the body and has specific functions. Uracil's use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates. Uracil serves as allosteric regulator and coenzyme for reactions in the human body and in plants. Uracil can be used for drug delivery and as a pharmaceutical. When elemental fluorine is reacted with uracil, 5-fluorouracil is produced. 5-Fluorouracil is an anticancer drug (antimetabolite) used to masquerade as uracil during the nucleic acid replication process. In combination with Tegafur, uracil used as a chemotherapy drug (called UFT or UFUR) used in the treatment of cancer, primarily bowel cancer. UFT is an anticancer medication composed of a fixed molar ratio (1:4) of tegafur and uracil to be administered with calcium folinate.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2806259 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Uftoral Approved UseINDICATIONS. UFT is indicated for the first-line treatment of metastatic colorectal cancer with calcium folinate |
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Primary | Uftoral Approved UseINDICATIONS. UFT is indicated for the first-line treatment of metastatic colorectal cancer with calcium folinate |
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Primary | Uftoral Approved UseINDICATIONS. UFT is indicated for the first-line treatment of metastatic colorectal cancer with calcium folinate |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20.3 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8612313/ |
350 mg/m² 1 times / day steady-state, oral dose: 350 mg/m² route of administration: Oral experiment type: STEADY-STATE co-administered: TEGAFUR |
URACIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20.1 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8612313/ |
350 mg/m² 1 times / day steady-state, oral dose: 350 mg/m² route of administration: Oral experiment type: STEADY-STATE co-administered: TEGAFUR |
URACIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1000 mg/m2 single, oral Highest studied dose Dose: 1000 mg/m2 Route: oral Route: single Dose: 1000 mg/m2 Sources: |
healthy, 38 ± 9 years n = 4 Health Status: healthy Age Group: 38 ± 9 years Sex: M+F Population Size: 4 Sources: |
|
248.4 mg/m2 1 times / day steady, oral RP2D Dose: 248.4 mg/m2, 1 times / day Route: oral Route: steady Dose: 248.4 mg/m2, 1 times / day Co-administed with:: TEGAFUR(111.6 mg/m2) Sources: |
unhealthy, 54 years n = 6 Health Status: unhealthy Condition: carcinoma Age Group: 54 years Sex: M+F Population Size: 6 Sources: |
Other AEs: Fatigue, Nausea... Other AEs: Fatigue (grade 1-2, 3 patients) Sources: Nausea (grade 1-2, 2 patients) |
552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Co-administed with:: TEGAFUR(248 mg/m2) Sources: |
unhealthy, 59 years n = 8 Health Status: unhealthy Condition: carcinoma Age Group: 59 years Sex: M+F Population Size: 8 Sources: |
Other AEs: Granulocytopenia, Nausea... Other AEs: Granulocytopenia (grade 4, 1 patient) Sources: Nausea (grade 3, 1 patient) Thrombocytopenia (grade 3, 1 patient) Vomiting (grade 1-2, 5 patients) Fatigue (grade 1-2, 4 patients) Diarrhoea (grade 1-2, 4 patients) |
310.5 mg/m2 1 times / day steady, oral Highest studied dose Dose: 310.5 mg/m2, 1 times / day Route: oral Route: steady Dose: 310.5 mg/m2, 1 times / day Co-administed with:: TEGAFUR(139.5 mg/m2) Sources: |
unhealthy n = 6 |
DLT: Diarrhea... Dose limiting toxicities: Diarrhea (grade 3-4, 3 patients) Sources: |
621 mg/m2 1 times / day steady, oral Highest studied dose Dose: 621 mg/m2, 1 times / day Route: oral Route: steady Dose: 621 mg/m2, 1 times / day Co-administed with:: TEGAFUR(279 mg/m2) Sources: |
unhealthy n = 5 |
DLT: Granulocytopenia... Dose limiting toxicities: Granulocytopenia (grade 4, 4 patients) Sources: |
276 mg/m2 1 times / day steady, oral Dose: 276 mg/m2, 1 times / day Route: oral Route: steady Dose: 276 mg/m2, 1 times / day Co-administed with:: TEGAFUR(124 mg/m2) Sources: |
unhealthy n = 8 |
DLT: Diarrhea... Dose limiting toxicities: Diarrhea (grade 3-4, 3 patients) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | grade 1-2, 2 patients | 248.4 mg/m2 1 times / day steady, oral RP2D Dose: 248.4 mg/m2, 1 times / day Route: oral Route: steady Dose: 248.4 mg/m2, 1 times / day Co-administed with:: TEGAFUR(111.6 mg/m2) Sources: |
unhealthy, 54 years n = 6 Health Status: unhealthy Condition: carcinoma Age Group: 54 years Sex: M+F Population Size: 6 Sources: |
Fatigue | grade 1-2, 3 patients | 248.4 mg/m2 1 times / day steady, oral RP2D Dose: 248.4 mg/m2, 1 times / day Route: oral Route: steady Dose: 248.4 mg/m2, 1 times / day Co-administed with:: TEGAFUR(111.6 mg/m2) Sources: |
unhealthy, 54 years n = 6 Health Status: unhealthy Condition: carcinoma Age Group: 54 years Sex: M+F Population Size: 6 Sources: |
Diarrhoea | grade 1-2, 4 patients | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Co-administed with:: TEGAFUR(248 mg/m2) Sources: |
unhealthy, 59 years n = 8 Health Status: unhealthy Condition: carcinoma Age Group: 59 years Sex: M+F Population Size: 8 Sources: |
Fatigue | grade 1-2, 4 patients | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Co-administed with:: TEGAFUR(248 mg/m2) Sources: |
unhealthy, 59 years n = 8 Health Status: unhealthy Condition: carcinoma Age Group: 59 years Sex: M+F Population Size: 8 Sources: |
Vomiting | grade 1-2, 5 patients | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Co-administed with:: TEGAFUR(248 mg/m2) Sources: |
unhealthy, 59 years n = 8 Health Status: unhealthy Condition: carcinoma Age Group: 59 years Sex: M+F Population Size: 8 Sources: |
Nausea | grade 3, 1 patient | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Co-administed with:: TEGAFUR(248 mg/m2) Sources: |
unhealthy, 59 years n = 8 Health Status: unhealthy Condition: carcinoma Age Group: 59 years Sex: M+F Population Size: 8 Sources: |
Thrombocytopenia | grade 3, 1 patient | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Co-administed with:: TEGAFUR(248 mg/m2) Sources: |
unhealthy, 59 years n = 8 Health Status: unhealthy Condition: carcinoma Age Group: 59 years Sex: M+F Population Size: 8 Sources: |
Granulocytopenia | grade 4, 1 patient | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Co-administed with:: TEGAFUR(248 mg/m2) Sources: |
unhealthy, 59 years n = 8 Health Status: unhealthy Condition: carcinoma Age Group: 59 years Sex: M+F Population Size: 8 Sources: |
Diarrhea | grade 3-4, 3 patients DLT |
310.5 mg/m2 1 times / day steady, oral Highest studied dose Dose: 310.5 mg/m2, 1 times / day Route: oral Route: steady Dose: 310.5 mg/m2, 1 times / day Co-administed with:: TEGAFUR(139.5 mg/m2) Sources: |
unhealthy n = 6 |
Granulocytopenia | grade 4, 4 patients DLT |
621 mg/m2 1 times / day steady, oral Highest studied dose Dose: 621 mg/m2, 1 times / day Route: oral Route: steady Dose: 621 mg/m2, 1 times / day Co-administed with:: TEGAFUR(279 mg/m2) Sources: |
unhealthy n = 5 |
Diarrhea | grade 3-4, 3 patients DLT |
276 mg/m2 1 times / day steady, oral Dose: 276 mg/m2, 1 times / day Route: oral Route: steady Dose: 276 mg/m2, 1 times / day Co-administed with:: TEGAFUR(124 mg/m2) Sources: |
unhealthy n = 8 |
PubMed
Title | Date | PubMed |
---|---|---|
Adenine-induced selective apoptosis toward HIV chronically infected cells in vitro. | 2000 Jul 14 |
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Applications of microarray technology in breast cancer research. | 2001 |
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Oral combination of cyclophosphamide, uracil plus tegafur and estramustine for hormone-refractory prostate cancer. | 2001 |
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RNA fragmentation studied in a matrix-assisted laser desorption/ionisation tandem quadrupole/orthogonal time-of-flight mass spectrometer. | 2001 |
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Photocatalytic degradation of the cyanotoxin cylindrospermopsin, using titanium dioxide and UV irradiation. | 2001 Apr |
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DNA repair and aging in mouse liver: 8-oxodG glycosylase activity increase in mitochondrial but not in nuclear extracts. | 2001 Apr 15 |
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DNA damage from micronutrient deficiencies is likely to be a major cause of cancer. | 2001 Apr 18 |
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Characterization of the full length uracil-DNA glycosylase in the extreme thermophile Thermotoga maritima. | 2001 Apr 4 |
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N(1)-C(5')-linked dimer hydrates of 5-substituted uracils produced by anodic oxidation in aqueous solution. | 2001 Apr 6 |
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Caffeine metabolism before and after liver transplantation. | 2001 Feb |
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Characterization of plant beta-ureidopropionase and functional overexpression in Escherichia coli. | 2001 Feb |
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Dual antitumor effects of 5-fluorouracil on the cell cycle in colorectal carcinoma cells: a novel target mechanism concept for pharmacokinetic modulating chemotherapy. | 2001 Feb 1 |
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Human DNA repair genes. | 2001 Feb 16 |
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UFT plus oral leucovorin calcium (Orzel) and radiation in combined modality therapy: a comprehensive review. | 2001 Feb 20 |
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Uracil moiety is required for toxicity of the cyanobacterial hepatotoxin cylindrospermopsin. | 2001 Feb 23 |
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Synthesis of analogues of the O-beta-D-ribofuranosyl nucleoside moiety of liposidomycins. Part 1: contribution of the amino group and the uracil moiety upon the inhibition of MraY. | 2001 Feb 26 |
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In vitro quantitative analysis of (3)H-uracil incorporation by Sarcocytis neurona to determine efficacy of anti-protozoal agents. | 2001 Feb 26 |
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5-Formyluracil and its nucleoside derivatives confer toxicity and mutagenicity to mammalian cells by interfering with normal RNA and DNA metabolism. | 2001 Feb 3 |
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A phase II trial of oral UFT plus cisplatin (CDDP) in patients with non-small cell lung cancer (NSCLC). | 2001 Feb-Mar |
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The effect of UV irradiation on uracil thin layer measured by optical waveguide lightmode spectroscopy. | 2001 Jan |
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An electrochemical evidence of free radicals formation from flutamide and its reactivity with endo/xenobiotics of pharmacological relevance. | 2001 Jan |
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[Long survival in a case of unresectable hepatic metastasis from rectal carcinoma treated with second-look hepatectomy plus pharmacokinetic modulating chemotherapy (PMC)]. | 2001 Jan |
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[A patient with obstructive jaundice due to recurrence after gastric cancer surgery responding remarkably to FLP combination therapy]. | 2001 Jan |
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Microsoft Word macro for analysis of cytosine methylation by the bisulfite deamination reaction. | 2001 Jan |
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Potential use of antiviral L(-)nucleoside analogues for the prevention or treatment of viral associated cancers. | 2001 Jan |
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Apoptosis and p53 status predict the efficacy of postoperative administration of UFT in non-small cell lung cancer. | 2001 Jan |
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WW domains of Rsp5p define different functions: determination of roles in fluid phase and uracil permease endocytosis in Saccharomyces cerevisiae. | 2001 Jan |
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Regulation of prohormone convertase 1 (PC1) by thyroid hormone. | 2001 Jan |
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Synthesis, characterisation, X-ray structure and biological activity of three new 5-formyluracil thiosemicarbazone complexes. | 2001 Jan 15 |
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Amino acid residues in ribonuclease MC1 from bitter gourd seeds which are essential for uridine specificity. | 2001 Jan 16 |
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Calcium inhibits willardiine-induced responses in kainate receptor GluR6(Q)/KA-2. | 2001 Jan 22 |
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DNA synthesis and dRPase activities of polymerase beta are both essential for single-nucleotide patch base excision repair in mammalian cell extracts. | 2001 Jan 23 |
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Molecular dynamics simulation reveals conformational switching of water-mediated uracil-cytosine base-pairs in an RNA duplex. | 2001 Jan 26 |
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The characteristics of nucleobase transport and metabolism by the perfused sheep choroid plexus. | 2001 Jan 5 |
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Preparation of oligodeoxynucleotides containing 5-(N-methylpiperazinyl) and 5-benzyloxymethyl uracils. | 2001 Jan-Feb |
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[New drugs for colorectal cancer: UFT]. | 2001 Jan-Feb |
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Postsurgical sequential methotrexate/5-FU and leucovorin on outpatient basis for advanced colorectal carcinoma. | 2001 Jan-Feb |
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[A case of advanced gastric cancer complicated with liver metastases responding remarkably to combined chemotherapy with 5-fluorouracil and low-dose cisplatin, with UFT and low-dose cisplatin for maintenance on an outpatient basis]. | 2001 Mar |
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P2Y receptor-mediated inhibition of voltage-activated Ca(2+) currents in PC12 cells. | 2001 Mar |
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Recent progress in the biology, chemistry and structural biology of DNA glycosylases. | 2001 Mar |
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HuR, a RNA stability factor, is expressed in malignant brain tumors and binds to adenine- and uridine-rich elements within the 3' untranslated regions of cytokine and angiogenic factor mRNAs. | 2001 Mar 1 |
|
[Long-term survival of hormone-refractory prostate cancer: a case report]. | 2001 Mar 1 |
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Identification and quantification of base and nucleoside markers in extracts of Ganoderma lucidum, Ganoderma japonicum and Ganoderma capsules by micellar electrokinetic chromatography. | 2001 Mar 9 |
|
Role of MED1 (MBD4) Gene in DNA repair and human cancer. | 2001 May |
|
The role of leucine 191 of Escherichia coli uracil DNA glycosylase in the formation of a highly stable complex with the substrate mimic, ugi, and in uracil excision from the synthetic substrates. | 2001 May 18 |
Sample Use Guides
UFT (tegafur- uracil) is an anticancer medication composed of a fixed molar ratio (1:4) of tegafur and uracil to be administered with calcium folinate. The usual dose is 300 mg/m2/day tegafur-uracil 90 mg/day calcium folinate (30 mg/dose) administered in three divided doses (every 8 hours) orally one hour before or one hour after meals for 28 consecutive days.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6929529
A cultured line of human lymphoid cells (8866) was grown in suspension in modified Eagle's medium plus 10% (vol/vol) fetal calf serum. All experiments were carried out with 20-S0 ml of cells in logarithmic phase of growth (6-9 X 105 cells per ml). Cells were incubated with methotrexate (10 ,gM) plus hypoxanthine (25 jM) (serine and glycine were already present in the medium) for 4 hr, after which [5-3H]dUrd (15-20 Ci/mmol, 1 Ci = 3.7 X 1010 becquerels; Moravek, City of Industry, CA) was added at levels specified and incubation was continued for an additional 2 hr. Cultures not treated with methotrexate were labeled for 30 rmin (in the presence of hypoxanthine alone). Ura, when present, was added at 10 mM 10 min before [3H]dUrd.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:06:24 GMT 2023
by
admin
on
Fri Dec 15 15:06:24 GMT 2023
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Record UNII |
56HH86ZVCT
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Record Status |
Validated (UNII)
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Record Version |
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LOINC |
75152-9
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LOINC |
30485-7
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NCI_THESAURUS |
C789
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LOINC |
13819-8
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75128-9
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25140-5
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C917
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m11305
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1174
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D014498
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CHEMBL566
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DTXSID4021424
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1705753
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66-22-8
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10995
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17568
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DB03419
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SUB20762
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URACIL
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KK-14
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200-621-9
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3970
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56HH86ZVCT
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100000086536
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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