Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H6O3.2H2O |
| Molecular Weight | 162.1406 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.OC1=CC(O)=CC(O)=C1
InChI
InChIKey=MPYXTIHPALVENR-UHFFFAOYSA-N
InChI=1S/C6H6O3.2H2O/c7-4-1-5(8)3-6(9)2-4;;/h1-3,7-9H;2*1H2
| Molecular Formula | C6H6O3 |
| Molecular Weight | 126.11 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24876726Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/phloroglucinol.html | http://www.druginfosys.com/drug.aspx?drugcode=963&type=1 | https://www.ncbi.nlm.nih.gov/pubmed/17439513 | https://www.ncbi.nlm.nih.gov/pubmed/9136853
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24876726
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/phloroglucinol.html | http://www.druginfosys.com/drug.aspx?drugcode=963&type=1 | https://www.ncbi.nlm.nih.gov/pubmed/17439513 | https://www.ncbi.nlm.nih.gov/pubmed/9136853
Phloroglucinol is an organic compound that is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is a phenol derivative with antispasmodic properties that is used primarily as a laboratory reagent. The mechanism of action is most likely based on the direct inhibition of the voltage-dependent calcium channels of smooth muscle; however, the modulation of prostaglandin or nitric oxide release has also been suggested. Although it has long been used in clinical practice as an antispasmodic for painful urogenital and gastrointestinal conditions, in an early study on anesthetized rats, phloroglucinol was found to be inactive toward the contraction of the duodenum, ileum and colon. Similarly, in anesthetized dogs, phloroglucinol plus trimethyl-phloroglucinol failed to antagonize acetylcholine-induced contraction of the colon. In parallel with animal studies, phloroglucinol plus trimethyl-phloroglucinol had no clear effects in humans on ascending and sigmoid colon hypermotility evoked by neostigmine. However in Irritable bowel syndrome (IBS) patients iv phloroglucinol effectively reduced postprandial rectosigmoid motility increases after a test meal, compared to placebo. In another study of IBS patients, phloroglucinol inhibited phasic contractions provoked by intrarectally injected glycerol, but it did not modify colonic tone. In an open-label study of 100 IBS patients selected according to the Rome II criteria, po 50 mg phloroglucinol was administered three times daily for two months. The 68 patients who completed the study reported significant improvement in abdominal pain, frequency of stools per day, urgency, passage of mucus per the rectum, sense of incomplete defecation and bloating. Nevertheless, straining was unchanged. Further, a multicenter, randomized, double-blind, placebo-controlled trial examined the effects of phloroglucinol/trimethylphloroglucinol (62.2 mg P plus 80 mg TMP three times daily) or placebo for 7 d in 307 IBS patients diagnosed using the Rome II criteria. The relative decrease in pain intensity and the responder rate were significantly higher in the P/TMP-treated group, compared to the placebo-treated group. Further, the treatment effect persisted up to the 7th day in a higher percentage of patients treated with P/TMP than in those treated with placebo.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20462757 |
36470.0 nM [IC50] | ||
Target ID: CHEMBL2363032 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24876726 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | SPASFON Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
515.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28485775/ |
160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHLOROGLUCINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
466.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28485775/ |
160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHLOROGLUCINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.384 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28485775/ |
160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHLOROGLUCINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
80 mg 3 times / day multiple, oral Recommended Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
80 mg single, intravenous Recommended Dose: 80 mg Route: intravenous Route: single Dose: 80 mg Sources: |
pregnant, ADULT Health Status: pregnant Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
|
80 mg single, intramuscular Recommended Dose: 80 mg Route: intramuscular Route: single Dose: 80 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Casein kinase 1 regulates connexin-43 gap junction assembly. | 2002-11-22 |
|
| Determination of hyperforin in human plasma using solid-phase extraction and high-performance liquid chromatography with ultraviolet detection. | 2002-11-15 |
|
| Targeted synthesis of ferromagnetically coupled complexes with modified 1,3,5-trihydroxybenzene ligands. | 2002-10-18 |
|
| The involvement of sodium and calcium ions in the release of amino acid neurotransmitters from mouse cortical slices elicited by hyperforin. | 2002-10-18 |
|
| Biosynthesis of hyperforin in Hypericum perforatum. | 2002-10-10 |
|
| O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction. | 2002-10 |
|
| Fucosylated arabinogalactan-proteins are required for full root cell elongation in arabidopsis. | 2002-10 |
|
| Inhibition of vesicular uptake of monoamines by hyperforin. | 2002-09-27 |
|
| Simultaneous determination of hypericin and hyperforin in human plasma and serum using liquid-liquid extraction, high-performance liquid chromatography and liquid chromatography-tandem mass spectrometry. | 2002-09-25 |
|
| Synthesis of poly(alkyl aryl ether) dendrimers. | 2002-08-23 |
|
| O-methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals. | 2002-08 |
|
| Biosynthesis of the major scent components 3,5-dimethoxytoluene and 1,3,5-trimethoxybenzene by novel rose O-methyltransferases. | 2002-07-17 |
|
| Quantitative analysis of the active components and the by-products of eight dry extracts of Hypericum perforatum L. (St John's Wort). | 2002-07-09 |
|
| In vitro receptor screening of pure constituents of St. John's wort reveals novel interactions with a number of GPCRs. | 2002-07 |
|
| Prostaglandin E(2) production and induction of prostaglandin endoperoxide synthase-2 is inhibited in a murine macrophage-like cell line, RAW 264.7, by Mallotus japonicus phloroglucinol derivatives. | 2002-06-06 |
|
| Progress toward the Synthesis of garsubellin A and related phloroglucins: the direct diastereoselective synthesis of the bicyclo[3.3.1]nonane core. | 2002-05-30 |
|
| Rapid quantification of constituents in St. John's wort extracts by NIR spectroscopy. | 2002-05-15 |
|
| Dapsone a new diazotizing reagent for the spectrophotometric determination of nitrite in waste and natural water samples. | 2002-05-08 |
|
| Supercritical fluid extraction and high-performance liquid chromatographic determination of phloroglucinols in St. John's Wort (Hypericum perforatum L.). | 2002-05-08 |
|
| A preliminary approach to nonenolizable beta,beta-tricarbonyls: assembly of a hyperevolutin prototype. | 2002-05-03 |
|
| Release of an acid phosphatase activity during lily pollen tube growth involves components of the secretory pathway. | 2002-05 |
|
| Analysis and stability of the constituents of artichoke and St. John's wort tinctures by HPLC-DAD and HPLC-MS. | 2002-05 |
|
| Dual modulation of striatal acetylcholine release by hyperforin, a constituent of St. John's wort. | 2002-05 |
|
| Regulating natural health products. | 2002-04-05 |
|
| Synthesis and biological evaluation of hyperforin analogues. Part I. Modification of the enolized cyclohexanedione moiety. | 2002-04 |
|
| Determining hyperforin and hypericin content in eight brands of St. John's wort. | 2002-03-15 |
|
| A role for arabinogalactan proteins in gibberellin-induced alpha-amylase production in barley aleurone cells. | 2002-03 |
|
| Hypericum perforatum--chemical profiling and quantitative results of St. John's Wort products by an improved high-performance liquid chromatography method. | 2002-03 |
|
| An arabinogalactan-protein from cell culture of Malva sylvestris. | 2002-03 |
|
| Oligomeric acylphloroglucinols from myrtle (Myrtus communis). | 2002-03 |
|
| Benzoylphloroglucinol derivatives from Hypericum scabrum. | 2002-03 |
|
| Properties and substrate specificity of RppA, a chalcone synthase-related polyketide synthase in Streptomyces griseus. | 2002-02-15 |
|
| Inhibition of tumour cell growth by hyperforin, a novel anticancer drug from St. John's wort that acts by induction of apoptosis. | 2002-02-14 |
|
| Short term treatment with St. John's wort, hypericin or hyperforin fails to induce CYP450 isoforms in the Swiss Webster mouse. | 2002-02-01 |
|
| Arabinogalactan proteins, pollen tube growth, and the reversible effects of Yariv phenylglycoside. | 2002-02 |
|
| Polyprenylated phloroglucinol derivatives from Hypericum erectum. | 2002-02 |
|
| Crystallization and preliminary X-ray analysis of the molybdenum-dependent pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici. | 2002-02 |
|
| Improved procedure for the quality control of Hypericum perforatum L. | 2002-01-17 |
|
| Comparative metabolism of genistin by human and rat gut microflora: detection and identification of the end-products of metabolism. | 2002-01 |
|
| Biological activity of secondary metabolites produced by a strain of Pseudomonas fluorescens. | 2002 |
|
| [Hyperforin in St. John's wort--drug, extraction and preparations]. | 2002 |
|
| Micellar effect on the scavenging of singlet molecular oxygen by hydroxybenzenes. | 2002 |
|
| Effect of lacZY-marking of the 2,4-diacetyl-phloroglucinol producing Pseudomonas fluorescens-strain 5-2/4 on its physiological performance and root colonization ability. | 2002 |
|
| Determination of naphthodianthrones and phloroglucinols from Hypericum perforatum extracts by liquid chromatography/tandem mass spectrometry. | 2002 |
|
| Determination of hyperforin, hypericin, and pseudohypericin in human plasma using high-performance liquid chromatography analysis with fluorescence and ultraviolet detection. | 2001-12-05 |
|
| Photokilling of cultured tumour cells by the porphyrin derivative CF3. | 2001-12 |
|
| Antidepressant activity of hyperforin conjugates of the St. John's wort, Hypericum perforatum Linn.: an experimental study. | 2001-12 |
|
| Extraction parameters and capillary electrophoresis analysis of limonin glucoside and phlorin in citrus byproducts. | 2001-12 |
|
| Pulse radiolysis studies of ortho-quinone chemistry relevant to melanogenesis. | 2001-11-15 |
|
| Inhibitory effects of phloroglucinol derivatives from Mallotus japonicus on nitric oxide production by a murine macrophage-like cell line, RAW 264.7, activated by lipopolysaccharide and interferon-gamma. | 2001-11-07 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16454126
po 50 mg phloroglucinol, three times daily for two months
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20188716
Chinese hamster lung fibroblasts (V79-4) cells were used for activity evaluation. Image analysis for the generation of intracellular ROS was achieved by seeding cells on a cover-slip loaded six well plate at 2Ч105 cells/well. Sixteen hours after plating, cells were treated with phloroglucinol at a concentration of 10mkg/ml. One hour following phloroglucinol treatment, plate was exposed to 10 Gy of gamma-rays. Twenty-four hours later, 100mkM DCF-DA was added to each well and cells were incubated for an additional 30 min at 37 C. After washing with PBS, the stained cells were mounted onto a microscope slide in mounting medium (DAKO, Carpinteria, CA, USA). Microscopic images were collected using Laser Scanning Microscope 5 PASCAL (Carl Zeiss, Jena, Germany) on a confocal microscope. In addition, cells were treated with phloroglucinol at 10mkg/ml and were exposed to gamma-rays radiation 1 h later. Cells were incubated for an additional 24 h at 37 ◦C. After addition of 25mkM of DCF-DA solution, the fluorescence signal of 2’,7’ dichlorofluorescein was detected using a Perkin Elmer LS-5B spectrofluorometer and a flow cytometer
| Substance Class |
Chemical
Created
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| Record UNII |
0X7B22BRG1
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| Record Status |
Validated (UNII)
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| Record Version |
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ANHYDROUS->SOLVATE |
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ACTIVE MOIETY |