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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6O3.2H2O
Molecular Weight 162.1408
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHLOROGLUCINOL DIHYDRATE

SMILES

c1c(cc(cc1O)O)O.O.O

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

HIDE SMILES / InChI

Molecular Formula C6H6O3
Molecular Weight 126.1103
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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
36470.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SPASFON

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Involvement of gacS and rpoS in enhancement of the plant growth-promoting capabilities of Enterobacter cloacae CAL2 and UW4.
2001 Aug
High-performance liquid chromatography-electrospray ionization mass spectrometry and multiple mass spectrometry studies of hyperforin degradation products.
2001 Aug 10
Lignification induced by pseudomonads harboring avirulent genes on Arabidopsis.
2001 Aug 31
Photokilling of cultured tumour cells by the porphyrin derivative CF3.
2001 Dec
Antidepressant activity of hyperforin conjugates of the St. John's wort, Hypericum perforatum Linn.: an experimental study.
2001 Dec
Development of a simple, rapid and reproducible HPLC assay for the simultaneous determination of hypericins and stabilized hyperforin in commercial St. John's wort preparations.
2001 Dec
Hyperforin--antidepressant activity by a novel mechanism of action.
2001 Jul
Composition of grape skin proanthocyanidins at different stages of berry development.
2001 Nov
Is St John's wort a 'Prozac-like' herbal antidepressant?
2001 Nov
Management of Xanthomonas camprestris pv. malvacearum-induced blight of cotton through phenolics of cotton rhizobacterium.
2001 Nov
Ion fluxes, auxin and the induction of elongation growth in Nicotiana tabacum cells.
2001 Nov
Pulse radiolysis studies of ortho-quinone chemistry relevant to melanogenesis.
2001 Nov 15
Release of iron from ferritin by metabolites of benzene and superoxide radical generating agents.
2001 Nov 30
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 Nov 7
Variability in St. John's wort formulations is an important consideration.
2001 Nov-Dec
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
Determination of naphthodianthrones and phloroglucinols from Hypericum perforatum extracts by liquid chromatography/tandem mass spectrometry.
2002
Synthesis and biological evaluation of hyperforin analogues. Part I. Modification of the enolized cyclohexanedione moiety.
2002 Apr
O-methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals.
2002 Aug
Synthesis of poly(alkyl aryl ether) dendrimers.
2002 Aug 23
Polyprenylated phloroglucinol derivatives from Hypericum erectum.
2002 Feb
Short term treatment with St. John's wort, hypericin or hyperforin fails to induce CYP450 isoforms in the Swiss Webster mouse.
2002 Feb 1
Inhibition of tumour cell growth by hyperforin, a novel anticancer drug from St. John's wort that acts by induction of apoptosis.
2002 Feb 14
Properties and substrate specificity of RppA, a chalcone synthase-related polyketide synthase in Streptomyces griseus.
2002 Feb 15
Separation of hypericins and hyperforins in extracts of Hypericum perforatum L. using non-aqueous capillary electrophoresis with reversed electro-osmotic flow.
2002 Jan 1
Dapsone a new diazotizing reagent for the spectrophotometric determination of nitrite in waste and natural water samples.
2002 Jan-Feb
In vitro receptor screening of pure constituents of St. John's wort reveals novel interactions with a number of GPCRs.
2002 Jul
Biosynthesis of the major scent components 3,5-dimethoxytoluene and 1,3,5-trimethoxybenzene by novel rose O-methyltransferases.
2002 Jul 17
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 Jun 6
A role for arabinogalactan proteins in gibberellin-induced alpha-amylase production in barley aleurone cells.
2002 Mar
Hypericum perforatum--chemical profiling and quantitative results of St. John's Wort products by an improved high-performance liquid chromatography method.
2002 Mar
Determining hyperforin and hypericin content in eight brands of St. John's wort.
2002 Mar 15
Release of an acid phosphatase activity during lily pollen tube growth involves components of the secretory pathway.
2002 May
Analysis and stability of the constituents of artichoke and St. John's wort tinctures by HPLC-DAD and HPLC-MS.
2002 May
Rapid quantification of constituents in St. John's wort extracts by NIR spectroscopy.
2002 May 15
A preliminary approach to nonenolizable beta,beta-tricarbonyls: assembly of a hyperevolutin prototype.
2002 May 3
Progress toward the Synthesis of garsubellin A and related phloroglucins: the direct diastereoselective synthesis of the bicyclo[3.3.1]nonane core.
2002 May 30
Supercritical fluid extraction and high-performance liquid chromatographic determination of phloroglucinols in St. John's Wort (Hypericum perforatum L.).
2002 May 8
Quantitative analysis of the active components and the by-products of eight dry extracts of Hypericum perforatum L. (St John's Wort).
2002 May-Jun
Determination of hyperforin in human plasma using solid-phase extraction and high-performance liquid chromatography with ultraviolet detection.
2002 Nov 15
Casein kinase 1 regulates connexin-43 gap junction assembly.
2002 Nov 22
O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction.
2002 Oct
Fucosylated arabinogalactan-proteins are required for full root cell elongation in arabidopsis.
2002 Oct
Biosynthesis of hyperforin in Hypericum perforatum.
2002 Oct 10
Targeted synthesis of ferromagnetically coupled complexes with modified 1,3,5-trihydroxybenzene ligands.
2002 Oct 18
The involvement of sodium and calcium ions in the release of amino acid neurotransmitters from mouse cortical slices elicited by hyperforin.
2002 Oct 18
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 Sep 25
Inhibition of vesicular uptake of monoamines by hyperforin.
2002 Sep 27
Patents

Sample Use Guides

po 50 mg phloroglucinol, three times daily for two months
Route of Administration: Oral
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
by admin
on Fri Jun 25 21:13:11 UTC 2021
Edited
by admin
on Fri Jun 25 21:13:11 UTC 2021
Record UNII
0X7B22BRG1
Record Status Validated (UNII)
Record Version
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Name Type Language
PHLOROGLUCINOL DIHYDRATE
EP   MI  
Systematic Name English
PHLOROGLUCINOL HYDRATE
Systematic Name English
PHLOROGLUCINOL DIHYDRATE [WHO-DD]
Common Name English
BENZENE-1,3,5-TRIOL DIHYDRATE
Systematic Name English
PHLOROGLUCINOL DIHYDRATE [EP MONOGRAPH]
Common Name English
PHLOROGLUCINOL DIHYDRATE [MI]
Common Name English
Code System Code Type Description
CAS
6099-90-7
Created by admin on Fri Jun 25 21:13:11 UTC 2021 , Edited by admin on Fri Jun 25 21:13:11 UTC 2021
PRIMARY
EPA CompTox
6099-90-7
Created by admin on Fri Jun 25 21:13:11 UTC 2021 , Edited by admin on Fri Jun 25 21:13:11 UTC 2021
PRIMARY
EVMPD
SUB22329
Created by admin on Fri Jun 25 21:13:11 UTC 2021 , Edited by admin on Fri Jun 25 21:13:11 UTC 2021
PRIMARY
FDA UNII
0X7B22BRG1
Created by admin on Fri Jun 25 21:13:11 UTC 2021 , Edited by admin on Fri Jun 25 21:13:11 UTC 2021
PRIMARY
PUBCHEM
80196
Created by admin on Fri Jun 25 21:13:11 UTC 2021 , Edited by admin on Fri Jun 25 21:13:11 UTC 2021
PRIMARY
MERCK INDEX
M8709
Created by admin on Fri Jun 25 21:13:11 UTC 2021 , Edited by admin on Fri Jun 25 21:13:11 UTC 2021
PRIMARY Merck Index
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