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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6O3
Molecular Weight 126.11
Optical Activity NONE
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
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
St John's Wort and literature quotations.
2001 Apr 9
Degradation of natural polyphenols by methanogenic consortia enriched from digested municipal sludge.
2001 Aug
Extraction parameters and capillary electrophoresis analysis of limonin glucoside and phlorin in citrus byproducts.
2001 Dec
Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity.
2001 Feb 23
Three new hyperforin analogues from Hypericum perforatum.
2001 Jan
Hyperforin--antidepressant activity by a novel mechanism of action.
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
A study of the antidepressant activity of Hypericum perforatum on animal models.
2001 Jul
Researching the antidepressant actions of Hypericum perforatum (St. John's wort) in animals and man.
2001 Jul
In vitro effects of St. John's wort extract and hyperforin on 5 HT uptake and efflux in human blood platelets.
2001 Jul
A current review of the antimicrobial activity of Hypericum perforatum L.
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
Phenols in citrus peel byproducts. Concentrations of hydroxycinnamates and polymethoxylated flavones in citrus peel molasses.
2001 Jul
Comparison of German St. John's wort products according to hyperforin and total hypericin content.
2001 Jul-Aug
Six new diarylheptanoids from the seeds of Alpinia blepharocalyx.
2001 Mar
Comparative evaluation of St. John's wort from different Italian regions.
2001 May-Jul
Composition of grape skin proanthocyanidins at different stages of berry development.
2001 Nov
Pulse radiolysis studies of ortho-quinone chemistry relevant to melanogenesis.
2001 Nov 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 Nov 7
Micellar effect on the scavenging of singlet molecular oxygen by hydroxybenzenes.
2002
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
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
A preliminary approach to nonenolizable beta,beta-tricarbonyls: assembly of a hyperevolutin prototype.
2002 May 3
Targeted synthesis of ferromagnetically coupled complexes with modified 1,3,5-trihydroxybenzene ligands.
2002 Oct 18
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
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
PHLOROGLUCINOL [EP MONOGRAPH]
Common Name English
NSC-1572
Code English
Classification Tree Code System Code
WHO-ATC A03AX12
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
WHO-VATC QA03AX12
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
203-611-2
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
FDA UNII
DHD7FFG6YS
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
EPA CompTox
DTXSID9048354
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
CHEBI
16204
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
DRUG BANK
DB12944
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
CAS
108-73-6
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
PUBCHEM
359
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
MERCK INDEX
M8709
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
PHLOROGLUCINOL
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
DRUG CENTRAL
2153
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
MESH
D010696
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
ChEMBL
CHEMBL473159
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
SMS_ID
100000079455
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
NSC
1572
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY
RXCUI
8196
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY RxNorm
EVMPD
SUB14845MIG
Created by admin on Thu Jul 06 00:05:47 UTC 2023 , Edited by admin on Thu Jul 06 00:05:47 UTC 2023
PRIMARY