Identification

Name
Esculin
Accession Number
DB13155
Type
Small Molecule
Groups
Approved
Description

Esculin is found in barley. Vitamin C2 is generally considered a bioflavanoid, related to vitamin P esculin is a glucoside that naturally occurs in the horse chestnut (Aesculus hippocastanum), California Buckeye (Aesculus californica) and in daphnin (the dark green resin of Daphne mezereum). Esculin belongs to the family of Glycosyl Compounds. These are carbohydrate derivatives in which a sugar group is bonded through its anmoeric carbonA to another group via a C-, S-,N-,O-, or Se- glycosidic bond.

Structure
Thumb
Synonyms
  • 6-(beta-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one
  • 6-(beta-D-Glucopyranosyloxy)-7-hydroxy-cumarin
  • 6,7-Dihydroxycoumarin 6-glucoside
  • 6,7-Dihydroxycoumarin-6-O-glucoside
  • Aesculin
  • Aesculinum
  • Esculetin 6-O-glucoside
  • esculetin 6-β-D-glucoside
  • Esculina
  • Esculoside
Product Ingredients
IngredientUNIICASInChI Key
Esculin sodium951F046A5J96997-92-1ZVHOSRMJDHCBSF-QWFKVUSTSA-M
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Proctol OintmentEsculin (1 %) + Dibucaine hydrochloride (0.5 %) + Framycetin sulfate (1 %) + Hydrocortisone (0.5 %)OintmentRectalOdan Laboratories Ltd2003-08-06Not applicableCanada
Proctol SuppositoriesEsculin (10 mg) + Dibucaine hydrochloride (5 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalOdan Laboratories Ltd2004-03-15Not applicableCanada
Proctosedyl OintmentEsculin (10 mg) + Dibucaine hydrochloride (5 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg)OintmentRectalRoussel Canada Inc.1959-12-311997-08-05Canada
Proctosedyl OintmentEsculin (10 mg) + Dibucaine hydrochloride (5 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg)OintmentRectalHoechst Roussel Canada Inc.1971-12-312006-07-28Canada
Proctosedyl OintmentEsculin (1 %) + Dibucaine hydrochloride (0.5 %) + Framycetin sulfate (1 %) + Hydrocortisone (0.5 %)OintmentRectalAptalis Pharma Canada Ulc2003-04-01Not applicableCanada
Proctosedyl SupEsculin (10 mg) + Dibucaine hydrochloride (5 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalRoussel Canada Inc.1959-12-311996-09-09Canada
Proctosedyl SuppositoriesEsculin (10 mg) + Dibucaine hydrochloride (5 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalAptalis Pharma Canada Ulc1997-01-23Not applicableCanada
Proctosedyl SuppositoriesEsculin (10 mg) + Dibucaine hydrochloride (5 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalHoechst Roussel Canada Inc.1959-12-311999-08-11Canada
Proctosone OntEsculin (1 %) + Dibucaine hydrochloride (.5 %) + Hydrocortisone acetate (.5 %) + Neomycin sulfate (1 %)OintmentRectalTechnilab Pharma Inc.1981-12-312004-08-03Canada
Proctosone SupEsculin (10 mg) + Dibucaine hydrochloride (5 mg) + Hydrocortisone acetate (5 mg) + Neomycin sulfate (10 mg)SuppositoryRectalTechnilab Pharma Inc.1981-12-312004-08-03Canada
Categories
UNII
1Y1L18LQAF
CAS number
531-75-9
Weight
Average: 340.284
Monoisotopic: 340.079432095
Chemical Formula
C15H16O9
InChI Key
XHCADAYNFIFUHF-TVKJYDDYSA-N
InChI
InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1
IUPAC Name
7-hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
SMILES
OC[C@H]1O[C@@H](OC2=C(O)C=C3OC(=O)C=CC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

Pharmacology

Indication

As medication, esculin is sometimes used as a vasoprotective agent. Esculin is also used in a microbiology laboratory to aid in the identification of bacterial species (especially Enterococci and Listeria). In fact, all strains of Group D Streptococci hydrolyze æsculin in 40% bile.

Pharmacodynamics

Topically applied Esculine increases the “capillary density” (the number of capillaries open to flow per surface unit) and improves the morphological aspect of the smallest blood vessels.

Mechanism of action

The main activities of Esculine focus on capillary protection, as it improves capillary permeability and fragility. It is reported to inhibit catabolic enzymes such as hyaluronidase and collagenase, thus preserving the integrity of the perivascular connective tissue. Esculine also showed good antioxidant properties, protecting triglycerides against auto-oxidation at high temperatures . The antioxidant property might as well explain some of the anti-inflammatory activity of the product, making it a suitable product for after sun treatments, for example.

TargetActionsOrganism
UAndrogen receptor
agonist
Human
Absorption

Rarely, absorbed into the blood stream if used as a combination with other ingredients in suppository form. But, Applying cream or ointment form to open wound or skin may lead this drug to absorb and circulate into blood stream.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

After oral administration of esculin (100 mg/kg) for rats, plasma, urine, feces and bile samples were collected to screen metabolites. As a result, a total of 19 metabolites (10 phase I metabolites and 9 phase II metabolites) were found and identified. It was also found that after oral administration of esculin, the esculin could be metabolized to esculetin in vivo via deglycosylation, and esculetin was found in all biological samples.

Route of elimination
Not Available
Half life

Absorption half life about 1 hour and elimination half life about 20 hours

Clearance
Not Available
Toxicity

Organism : Mouse Test type : LD50 Route: Intraperitoneal Reported dose: 1900mg/kg No reported effects known other than LD50

Affected organisms
  • Aerococcus viridans
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Wang Y, Zhao M, Ou Y, Zeng B, Lou X, Wang M, Zhao C: Metabolic profile of esculin in rats by ultra high performance liquid chromatography combined with Fourier transform ion cyclotron resonance mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 May 1;1020:120-8. doi: 10.1016/j.jchromb.2016.03.027. Epub 2016 Mar 21. [PubMed:27038404]
  2. HMDB [Link]
  3. Wikipedia [Link]
  4. Indena [Link]
  5. Toxnet [Link]
External Links
KEGG Compound
C09264
PubChem Compound
5281417
PubChem Substance
347829265
ChemSpider
4444765
ChEBI
4853
ChEMBL
CHEMBL482581
Wikipedia
Aesculin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
OintmentRectal
SuppositoryRectal
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility10.3 mg/mLALOGPS
logP-0.53ALOGPS
logP-1.1ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)8.12ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity77.65 m3·mol-1ChemAxon
Polarizability31.4 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Mass Spectrum (Electron Ionization)MSsplash10-0fb9-8900000000-f07e5f4d396dfa02a8ec
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-004i-0901000000-4baa83a9d2df1615a0bb
MS/MS Spectrum - , negativeLC-MS/MSsplash10-014i-4321100129-8dd728a7ffce4137b185
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0900000000-f430c535996e7a3911ce
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0900000000-6f75f8f80ff5ba44b19a
1H NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Coumarins and derivatives
Sub Class
Coumarin glycosides
Direct Parent
Coumarin glycosides
Alternative Parents
Phenolic glycosides / 7-hydroxycoumarins / Hexoses / O-glycosyl compounds / 1-benzopyrans / Pyranones and derivatives / 1-hydroxy-2-unsubstituted benzenoids / Oxanes / Heteroaromatic compounds / Lactones
show 7 more
Substituents
Coumarin o-glycoside / Coumarin-6-o-glycoside / Phenolic glycoside / 7-hydroxycoumarin / Hydroxycoumarin / Hexose monosaccharide / O-glycosyl compound / Glycosyl compound / Benzopyran / 1-benzopyran
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
beta-D-glucoside, hydroxycoumarin (CHEBI:4853) / coumarins (C09264)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. ChEMBL [Link]
  2. UniProt [Link]
  3. KEGG [Link]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Glutaminase activity
Specific Function
Catalyzes the first reaction in the primary pathway for the renal catabolism of glutamine. Plays a role in maintaining acid-base homeostasis. Regulates the levels of the neurotransmitter glutamate ...
Gene Name
GLS
Uniprot ID
O94925
Uniprot Name
Glutaminase kidney isoform, mitochondrial
Molecular Weight
73460.56 Da
References
  1. CHEMbl [Link]
  2. UniProt [Link]
  3. KEGG [Link]

Drug created on December 03, 2016 17:13 / Updated on November 02, 2018 09:00