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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6O3
Molecular Weight 126.11
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHLOROGLUCINOL

SMILES

OC1=CC(O)=CC(O)=C1

InChI

InChIKey=QCDYQQDYXPDABM-UHFFFAOYSA-N
InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H

HIDE SMILES / InChI

Description

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

Targets

Primary TargetPharmacologyConditionPotency
36470.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SPASFON
PubMed

PubMed

TitleDatePubMed
Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol.
2001 Apr
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
Extraction parameters and capillary electrophoresis analysis of limonin glucoside and phlorin in citrus byproducts.
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
Determination of hyperforin, hypericin, and pseudohypericin in human plasma using high-performance liquid chromatography analysis with fluorescence and ultraviolet detection.
2001 Dec 5
Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity.
2001 Feb 23
Hyperforin--antidepressant activity by a novel mechanism of action.
2001 Jul
Modulation of ion channels in rat neurons by the constituents of Hypericum perforatum.
2001 Jul
Hyperforin stimulates intracellular calcium mobilisation and enhances extracellular acidification in DDT1-MF2 smooth muscle cells.
2001 Jul
In vitro binding studies with two hypericum perforatum extracts--hyperforin, hypericin and biapigenin--on 5-HT6, 5-HT7, GABA(A)/benzodiazepine, sigma, NPY-Y1/Y2 receptors and dopamine transporters.
2001 Jul
Researching the antidepressant actions of Hypericum perforatum (St. John's wort) in animals and man.
2001 Jul
In vivo neurotransmitter release in the locus coeruleus--effects of hyperforin, inescapable shock and fear.
2001 Jul
Effects of two different extracts of St. John's wort and some of their constituents on cytochrome P450 activities in rat liver microsomes.
2001 Jul
New prenylated bi- and tricyclic phloroglucinol derivatives from Hypericum papuanum.
2001 Jun
St John's wort: Prozac from the plant kingdom.
2001 Jun
A new sensitive and selective spectrophotometric method for the determination of catechol derivatives and its pharmaceutical preparations.
2001 Jun
Effect of St. John's wort on free radical production.
2001 Jun 1
Algal growth inhibition effects and inducement modes by plant-producing phenols.
2001 May
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
Variability in St. John's wort formulations is an important consideration.
2001 Nov-Dec
[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
Synthesis and biological evaluation of hyperforin analogues. Part I. Modification of the enolized cyclohexanedione moiety.
2002 Apr
Regulating natural health products.
2002 Apr 5
Synthesis of poly(alkyl aryl ether) dendrimers.
2002 Aug 23
Polyprenylated phloroglucinol derivatives from Hypericum erectum.
2002 Feb
Crystallization and preliminary X-ray analysis of the molybdenum-dependent pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici.
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
Comparative metabolism of genistin by human and rat gut microflora: detection and identification of the end-products of metabolism.
2002 Jan
Dapsone a new diazotizing reagent for the spectrophotometric determination of nitrite in waste and natural water samples.
2002 Jan-Feb
Hypericum perforatum--chemical profiling and quantitative results of St. John's Wort products by an improved high-performance liquid chromatography method.
2002 Mar
An arabinogalactan-protein from cell culture of Malva sylvestris.
2002 Mar
Oligomeric acylphloroglucinols from myrtle (Myrtus communis).
2002 Mar
Benzoylphloroglucinol derivatives from Hypericum scabrum.
2002 Mar
Determining hyperforin and hypericin content in eight brands of St. John's wort.
2002 Mar 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
O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction.
2002 Oct
Inhibition of vesicular uptake of monoamines by hyperforin.
2002 Sep 27
Patents

Sample Use Guides

In Vivo Use Guide
po 50 mg phloroglucinol, three times daily for two months
Route of Administration: Oral
In Vitro Use Guide
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
Name Type Language
PHLOROGLUCINOL
INCI   JAN   MART.   MI   WHO-DD  
INCI  
Official Name English
PHLOROGLUCINOL [MART.]
Common Name English
PHLOROGLUCINOL [JAN]
Common Name English
PHLOROGLUCINOL [MI]
Common Name English
PHLOROGLUCINOL [INCI]
Common Name English
DILOSPAN S
Brand Name English
SYM-TRIHYDROXYBENZENE
Common Name English
PHLOROGLUCIN
Common Name English
PHLOROGLUCINOL [WHO-DD]
Common Name English
SPASFON-LYOC
Brand Name English
BENEZENE-1,3,5-TRIOL
Common Name English
NSC-1572
Code English
Classification Tree Code System Code
WHO-ATC A03AX12
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
WHO-VATC QA03AX12
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
Code System Code Type Description
ECHA (EC/EINECS)
203-611-2
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
PRIMARY
EPA CompTox
108-73-6
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
PRIMARY
CAS
108-73-6
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
PRIMARY
PUBCHEM
359
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
PRIMARY
MERCK INDEX
M8709
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
PHLOROGLUCINOL
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
PRIMARY
MESH
D010696
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
PRIMARY
ChEMBL
CHEMBL473159
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
PRIMARY
RXCUI
8196
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
PRIMARY RxNorm
EVMPD
SUB14845MIG
Created by admin on Tue Oct 22 02:43:55 UTC 2019 , Edited by admin on Tue Oct 22 02:43:55 UTC 2019
PRIMARY