Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H6O3 |
Molecular Weight | 138.1207 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=C(O)C=CC=C1
InChI
InChIKey=YGSDEFSMJLZEOE-UHFFFAOYSA-N
InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
Molecular Formula | C7H6O3 |
Molecular Weight | 138.1207 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00936https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdfCurator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/salicylic-acid.html
Sources: http://www.drugbank.ca/drugs/DB00936https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/salicylic-acid.html
Methyl salicylate (or methyl 2-hydroxybenzoate), also known as wintergreen oil, is a natural product and is present in white wine, tea, porcini mushroom Boletus edulis, Bourbon vanilla, clary sage, red sage and fruits including cherry, apple, raspberry, papaya and plum. Methyl salicylate is topically used in combination with methanol and under brand name SALONPAS to temporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises. The precise mechanism of action of methyl salicylate is not known, but there is suggested, that it cause dilation of the capillaries thereby increasing blood flow to the area.
Originator
Sources: http://www.casinapioiv.va/content/dam/accademia/pdf/acta18/acta18-szczeklik.pdfhttps://books.google.ru/books?id=iUpwBAAAQBAJ&pg=PT83&lpg=PT83&dq=Methyl+salicylate+Auguste+Andr%C3%A9+Thomas+Cahours&source=bl&ots=nFDf2n2bpT&sig=wAKTDamdc7xWWgRxOrTeokeji8g&hl=ru&sa=X&ved=0ahUKEwj-q8769PzTAhVFfhoKHYEqDgkQ6AEIODAD#v=onepage&q=Methyl%20salicylate%20Auguste%20Andr%C3%A9%20Thomas%20Cahours&f=false
Curator's Comment: first isolated in 1843
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00936 |
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Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00936 |
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Target ID: CHEMBL2311236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26101955 |
1.48 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | SALONPAS Approved UseTemporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date2008 |
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Palliative | SALONPAS Approved UseTemporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date2008 |
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Palliative | SALONPAS Approved UseTemporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date2008 |
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Palliative | SALONPAS Approved UseTemporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date2008 |
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Primary | Salicylic Acid Approved UseSalicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date2012 |
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Primary | Salicylic Acid Approved UseSalicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date2012 |
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Primary | Salicylic Acid Approved UseSalicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date2012 |
Doses
Dose | Population | Adverse events |
---|---|---|
30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: |
unhealthy, 23.05 ± 5.7 years Health Status: unhealthy Age Group: 23.05 ± 5.7 years Sex: M+F Sources: |
Other AEs: Redness, Scales... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Redness | 30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: |
unhealthy, 23.05 ± 5.7 years Health Status: unhealthy Age Group: 23.05 ± 5.7 years Sex: M+F Sources: |
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Scales | 30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: |
unhealthy, 23.05 ± 5.7 years Health Status: unhealthy Age Group: 23.05 ± 5.7 years Sex: M+F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/9207195/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
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likely | ||||
likely | ||||
major | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
False-high blood salicylate levels in neonates with hyperbilirubinemia. | 2000 Dec |
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Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries. | 2001 |
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Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
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Nitric oxide: comparative synthesis and signaling in animal and plant cells. | 2001 Apr |
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Sodium salicylate increases CYP2E1 levels and enhances arachidonic acid toxicity in HepG2 cells and cultured rat hepatocytes. | 2001 Apr |
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Induction of wound response gene expression in tomato leaves by ionophores. | 2001 Feb |
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Isolation and preliminary characterization of the medium-chain fatty acid:CoA ligase responsible for activation of short- and medium-chain fatty acids in colonic mucosa from swine. | 2001 Feb |
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Acetylsalicylic acid and other salicylates in relation to Stevens-Johnson syndrome and toxic epidermal necrolysis. | 2001 Feb |
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A novel pH-sensitive membrane from chitosan--TEOS IPN; preparation and its drug permeation characteristics. | 2001 Feb |
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A hot pepper cDNA encoding a pathogenesis-related protein 4 is induced during the resistance response to tobacco mosaic virus. | 2001 Feb 28 |
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Molecular cloning of the nahG gene encoding salicylate hydroxylase from Pseudomonas fluorescens. | 2001 Feb 28 |
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Manipulation of salicylate content in Arabidopsis thaliana by the expression of an engineered bacterial salicylate synthase. | 2001 Jan |
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Effect of 4-trifluoromethyl derivatives of salicylate on nuclear factor kappaB-dependent transcription in human astrocytoma cells. | 2001 Jan |
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The possibility of achieving an interactive mixture with high dose homogeneity containing an extremely low proportion of a micronised drug. | 2001 Jan |
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Induction of cell death in arabidopsis by superoxide in combination with salicylic acid or with protein synthesis inhibitors. | 2001 Jan 1 |
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Reversed-phase high-performance liquid chromatography versus spectrophotometric assay for thimerosal in Cuban recombinant hepatitis B vaccine. | 2001 Jan 12 |
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Salicylates inhibit T cell adhesion on endothelium under nonstatic conditions: induction of L-selectin shedding by a tyrosine kinase-dependent mechanism. | 2001 Jan 15 |
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Characterization of a rice (Oryza sativa L.) Bowman-Birk proteinase inhibitor: tightly light regulated induction in response to cut, jasmonic acid, ethylene and protein phosphatase 2A inhibitors. | 2001 Jan 24 |
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Selective suppression of CCAAT/enhancer-binding protein beta binding and cyclooxygenase-2 promoter activity by sodium salicylate in quiescent human fibroblasts. | 2001 Jun 1 |
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A recessive mutation in the Arabidopsis SSI2 gene confers SA- and NPR1-independent expression of PR genes and resistance against bacterial and oomycete pathogens. | 2001 Mar |
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Signaling mediated by the closely related mammalian Rho family GTPases TC10 and Cdc42 suggests distinct functional pathways. | 2001 Mar |
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The Arabidopsis downy mildew resistance gene, RPP13-Nd, functions independently of NDR1 and EDS1 and does not require the accumulation of salicylic acid. | 2001 Mar |
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Effect of lipophilicity on in vivo iontophoretic delivery. I. NSAIDs. | 2001 Mar |
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Identification of free radicals produced during phacoemulsification. | 2001 Mar |
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Microdialysis of salicylic acid from viscous emulsion samples prior to high-performance liquid chromatographic determination. | 2001 Mar 30 |
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Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection. | 2001 Mar 5 |
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Anti-inflammatory and antipyretic effects of Trigonella foenum-graecum leaves extract in the rat. | 2001 May |
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Binding of cosalane--a novel highly lipophilic anti-HIV agent--to albumin and glycoprotein. | 2001 May |
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In vitro dermal absorption of methyl salicylate, ethyl parathion, and malathion: first responder safety. | 2007 Jun |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/salicylic-acid.html
The preferable method of use is to apply Salicylic Acid 6% thoroughly to the affected area and to cover the treated area at night after washing and before retiring. Preferably, the skin should be hydrated for a least five minutes prior to application.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1811921
Salicylic acid inhibited hippuric acid formation in the homogenates obtained from the specimens of human liver with IC50 value 0.19 mM
Substance Class |
Chemical
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Record UNII |
O414PZ4LPZ
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Validated (UNII)
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 358.710
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CFR |
21 CFR 333.310
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NCI_THESAURUS |
C257
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NCI_THESAURUS |
C52588
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CFR |
21 CFR 358.510
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WHO-VATC |
QD01AE12
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CFR |
21 CFR 862.3830
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EPA PESTICIDE CODE |
76602
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CFR |
21 CFR 358.720
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WHO-VATC |
QS01BC08
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WHO-ATC |
S01BC08
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CFR |
21 CFR 358.110
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FDA ORPHAN DRUG |
359211
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WHO-VATC |
QM02AC99
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JECFA EVALUATION |
2-HYDROXYBENZOIC ACID
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WHO-ATC |
D01AE12
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WHO-ESSENTIAL MEDICINES LIST |
13.4
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9525
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891
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672
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O414PZ4LPZ
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338
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9522
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ALTERNATIVE | |||
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1609002
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PRIMARY | |||
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Salicylic Acid
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SUB15180MIG
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SALICYLIC ACID
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PRIMARY | |||
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69-72-7
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Medical uses of salicylic acid
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200-712-3
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D020156
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30762
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4306
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180
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100000090038
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2416
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16914
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O414PZ4LPZ
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m9739
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PRIMARY | Merck Index | ||
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C61934
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SALICYLIC ACID
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PRIMARY | Description: Colourless crystals, usually needle-like, or a white, crystalline powder; odourless. Solubility: Slightly soluble in water; soluble in 4 parts of ethanol (~750 g/l) TS and in 3 parts of ether R. Category: Keratolytic. Storage: Salicylic acid should be kept in a well-closed container. Definition: Salicylic acid contains not less than 99.0% and not more than 101.0% of C7H6O3, calculated with reference to the dried substance. | ||
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CHEMBL424
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DB00936
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DTXSID7026368
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Salicylic acid content for water extract of plant callus was 3.22+/-0.06 as expressed as mg/100 g of dry base of extract.
For the analysis of phenolic acids, a Nova pack C18 UG120 equipped with a Guard column, a JASCO HPLC system consisting of a column oven, a UV-Vis diode array detector set at 280 nm, a Liquid chromatography pump and a ChromNAV software program were used.
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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DERIVATIVE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE | |||
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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IMPURITY -> PARENT |
INTERNATIONAL PHARMACOPEIA
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
INTERNATIONAL PHARMACOPEIA
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IMPURITY -> PARENT |
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
USP
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PARENT -> IMPURITY |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
Correction factors: for the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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