Esculin
Identification
- Brand Names
- Proctol, Proctosedyl
- Generic Name
- Esculin
- DrugBank Accession Number
- DB13155
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 340.284
Monoisotopic: 340.079432095 - Chemical Formula
- C15H16O9
- 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
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), as all strains of Group D Streptococci hydrolyze æsculin in 40% bile.
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- 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.
Target Actions Organism UAndrogen receptor agonistHumans - 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
- Adverse Effects
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- Toxicity
Organism : Mouse Test type : LD50 Route: Intraperitoneal Reported dose: 1900mg/kg No reported effects known other than LD50
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Esculin. Chlorpropamide The therapeutic efficacy of Chlorpropamide can be increased when used in combination with Esculin. Dexmethylphenidate The serum concentration of the active metabolites of Esculin can be increased when Esculin is used in combination with Dexmethylphenidate. Diazoxide The serum concentration of Esculin can be increased when it is combined with Diazoxide. Doxycycline The therapeutic efficacy of Esculin can be increased when used in combination with Doxycycline. Gliclazide The therapeutic efficacy of Gliclazide can be increased when used in combination with Esculin. Glimepiride The therapeutic efficacy of Glimepiride can be increased when used in combination with Esculin. Glipizide The therapeutic efficacy of Glipizide can be increased when used in combination with Esculin. Gliquidone The therapeutic efficacy of Gliquidone can be increased when used in combination with Esculin. Glyburide The therapeutic efficacy of Glyburide can be increased when used in combination with Esculin. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- No interactions found.
Products
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- Product Ingredients
Ingredient UNII CAS InChI Key Esculin sodium 951F046A5J 96997-92-1 ZVHOSRMJDHCBSF-QWFKVUSTSA-M - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Odan Proctomyxin HC Esculin (1 %) + Cinchocaine hydrochloride (0.5 %) + Framycetin sulfate (1 %) + Hydrocortisone (0.5 %) Ointment Rectal Odan Laboratories Ltd 2001-03-09 2021-08-11 Canada Odan Proctomyxin HC Suppositories Esculin (10 mg) + Cinchocaine hydrochloride (5 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg) Suppository Rectal Odan Laboratories Ltd 2001-01-05 2021-10-07 Canada Proctol Ointment Esculin (1 %) + Cinchocaine hydrochloride (0.5 %) + Framycetin sulfate (1 %) + Hydrocortisone (0.5 %) Ointment Rectal Odan Laboratories Ltd 2003-08-06 Not applicable Canada Proctol Suppositories Esculin (10 mg) + Cinchocaine hydrochloride (5 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg) Suppository Rectal Odan Laboratories Ltd 2004-03-15 Not applicable Canada Proctosedyl Esculin (1 %) + Cinchocaine hydrochloride (0.5 %) + Framycetin sulfate (1 %) + Hydrocortisone (0.5 %) Ointment Rectal Aptalis Pharma Canada Ulc 2003-04-01 Not applicable Canada Proctosedyl Esculin (10 mg) + Cinchocaine hydrochloride (5 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg) Suppository Rectal Aptalis Pharma Canada Ulc 1997-01-23 2020-05-27 Canada Proctosedyl Ointment Esculin (10 mg / g) + Cinchocaine hydrochloride (5 mg / g) + Framycetin sulfate (10 mg / g) + Hydrocortisone (5 mg / g) Ointment Rectal Hoechst Roussel Canada Inc. 1971-12-31 2006-07-28 Canada PROCTOSEDYL OINTMENT Esculin (1 % w/w) + Cinchocaine hydrochloride (0.5 % w/w) + Framycetin sulfate (1 % w/w) + Hydrocortisone (0.5 % w/w) Ointment Topical OPELLA HEALTHCARE SINGAPORE PTE. LTD. 1988-08-06 Not applicable Singapore Proctosedyl Ointment Esculin (10 mg / g) + Cinchocaine hydrochloride (5 mg / g) + Framycetin sulfate (10 mg / g) + Hydrocortisone (5 mg / g) Ointment Rectal Roussel Canada Inc. 1959-12-31 1997-08-05 Canada PROCTOSEDYL OINTMENT Esculin (10 mg) + Cinchocaine hydrochloride (5 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg) Ointment Rectal; Topical DKSH MALAYSIA SDN BHD 2020-09-08 Not applicable Malaysia
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 7-hydroxycoumarin / Acetal / Alcohol / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Coumarin o-glycoside / Coumarin-6-o-glycoside show 20 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- beta-D-glucoside, hydroxycoumarin (CHEBI:4853) / coumarins (C09264)
- Affected organisms
- Aerococcus viridans
Chemical Identifiers
- UNII
- 1Y1L18LQAF
- CAS number
- 531-75-9
- 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
References
- General References
- 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. [Article]
- HMDB [Link]
- Indena [Link]
- Toxnet [Link]
- Health Canada Product Monograph: Proctosedyl (hydrocortisone/framycetin/cinchocaine/aesculin) for rectal administration [Link]
- External Links
- PDB Entries
- 7vl7
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Rectal Suppository Rectal 5 MG Ointment Rectal Ointment Rectal; Topical Ointment Topical Suppository Rectal - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 10.3 mg/mL ALOGPS logP -0.53 ALOGPS logP -1.1 Chemaxon logS -1.5 ALOGPS pKa (Strongest Acidic) 8.12 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 145.91 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 77.65 m3·mol-1 Chemaxon Polarizability 31.4 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Mass Spectrum (Electron Ionization) MS splash10-0fb9-8900000000-f07e5f4d396dfa02a8ec Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-QTOF , negative LC-MS/MS splash10-004i-0901000000-4baa83a9d2df1615a0bb MS/MS Spectrum - , negative LC-MS/MS splash10-014i-4321100129-8dd728a7ffce4137b185 LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-004i-0900000000-f430c535996e7a3911ce MS/MS Spectrum - , positive LC-MS/MS splash10-004i-0900000000-6f75f8f80ff5ba44b19a 1H NMR Spectrum 1D NMR Not Applicable
Targets

- Kind
- Protein
- Organism
- Humans
- 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
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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
Drug created at December 04, 2016 00:13 / Updated at October 20, 2021 17:29