Hesperidin

Identification

Summary

Hesperidin is a bioflavonoid found in a variety of nutritional supplements that is touted to have various beneficial effects on blood vessel disorders and various other conditions.

Generic Name
Hesperidin
DrugBank Accession Number
DB04703
Background

Hesperidin is a flavan-on glycoside found in citrus fruits.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 610.5606
Monoisotopic: 610.189770418
Chemical Formula
C28H34O15
Synonyms
  • (S)-(−)-hesperidin
  • Cirantin
  • Ciratin
  • Hesperetin 7-O-rutinoside
  • Hesperidin
  • Hesperidina
  • Hesperidoside
External IDs
  • NDI 590
  • NSC-44184

Pharmacology

Indication

Not Available

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAurora kinase B
regulator
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

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.
Not Available
Food Interactions
No interactions found.

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AVEFLON TABLETHesperidin (50 mg) + Diosmin (450 mg)Tablet, film coatedOralAPEX PHARMACY MARKETING SDN. BHD.2020-09-08Not applicableMalaysia flag
Cilobana Cpa TabHesperidin (75 mg / tab) + Ascorbic acid (150 mg / tab) + Bromelains (4 mg / tab) + Citrus bioflavonoids (75 mg / tab) + Vitamin A (10000 unit / tab)TabletOralAnabolic Laboratories Inc.1968-12-311996-10-02Canada flag
Daflon 1000mg Film-Coated TabletHesperidin (100 mg) + Diosmin (900 mg)Tablet, film coatedOralSERVIER MALAYSIA SDN BHD2020-09-08Not applicableMalaysia flag
Daflon 500 mg - FilmtablettenHesperidin (50 mg) + Diosmin (450 mg)Tablet, film coatedOralServier Austria Gmb H1994-11-18Not applicableAustria flag
daflon 500mg tabletsHesperidin (50 mg) + Diosmin (450 mg)Tablet, film coatedOralSERVIER MALAYSIA SDN BHD2020-09-08Not applicableMalaysia flag
DAFLON TABLET 500 mgHesperidin (50 mg) + Diosmin (450 mg)Tablet, sugar coatedOralSERVIER (S) PTE LTD1988-12-05Not applicable
Davmorid Film Coated TabletHesperidin (50 mg) + Diosmin (450 mg)Tablet, film coatedOralY.S.P. INDUSTRIES (M) SDN BHD2020-09-08Not applicableMalaysia flag
DIOFLEX TABLETHesperidin (50 mg) + Diosmin (450 mg)TabletOralPRIME PHARMACEUTICAL SDN. BHD.2020-09-08Not applicableMalaysia flag
DIOKERN 450 MG/50 MG FILM KAPLI TABLET,30 ADETHesperidin (50 mg) + Diosmin (450 mg)Tablet, coatedOralDROGSAN İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
DIOKERN 450 MG/50 MG FILM KAPLI TABLET,60 ADETHesperidin (50 mg) + Diosmin (450 mg)Tablet, coatedOralDROGSAN İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Flavonoid glycosides
Direct Parent
Flavonoid-7-O-glycosides
Alternative Parents
4'-O-methylated flavonoids / 3'-hydroxyflavonoids / 5-hydroxyflavonoids / Flavanones / Phenolic glycosides / O-glycosyl compounds / Disaccharides / Chromones / Methoxyphenols / Phenoxy compounds
show 14 more
Substituents
1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 3'-hydroxyflavonoid / 4p-methoxyflavonoid-skeleton / 5-hydroxyflavonoid / Acetal / Alcohol / Alkyl aryl ether / Anisole
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
rutinoside, disaccharide derivative, 3'-hydroxyflavanones, monomethoxyflavanone, flavanone glycoside, dihydroxyflavanone (CHEBI:28775) / flavanones (C09755)
Affected organisms
Not Available

Chemical Identifiers

UNII
E750O06Y6O
CAS number
520-26-3
InChI Key
QUQPHWDTPGMPEX-QJBIFVCTSA-N
InChI
InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
IUPAC Name
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
SMILES
COC1=CC=C(C=C1O)[C@@H]1CC(=O)C2=C(O1)C=C(O[C@@H]1O[C@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]1O)C=C2O

References

Synthesis Reference

Hiromi Hijiya, Toshio Miyake, ".alpha.-glycosyl hesperidin, and its preparation and uses." U.S. Patent US5652124, issued June, 1983.

US5652124
General References
Not Available
KEGG Drug
D01038
KEGG Compound
C09755
PubChem Compound
10621
PubChem Substance
46506898
ChemSpider
10176
BindingDB
61776
RxNav
5281
ChEBI
28775
ChEMBL
CHEMBL449317
ZINC
ZINC000008143568
PharmGKB
PA449867
PDBe Ligand
H1N
Wikipedia
Hesperidin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentLymphedema Lower Extremity1
4CompletedTreatmentVenous Insufficiency1
4Unknown StatusTreatmentPelvic Congestive Syndrome / Pelvic Varicose Veins / Venous Disease1
3CompletedPreventionOsteoporosis, Osteopenia1
3Not Yet RecruitingPreventionVinca Alkaloid Adverse Reaction1
3Unknown StatusTreatmentChronic Venous Insufficiency (CVI) / Disease1
2CompletedTreatmentAbdominal Pain / Chest Pain / Confusion / Coronavirus Disease 2019 (COVID‑19) / Cough / Dyspnea / Fever / Headache / Irritability / Joint Pain / Loss of smell / Muscle Weakness / Myalgia / Nausea / Pain / Sore Throat / Vomiting1
2Unknown StatusTreatmentEndothelial Dysfunction / Syndrome, Metabolic1
2WithdrawnTreatmentObesity / Resistance, Insulin1
1CompletedBasic ScienceBioequivalence1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
SuspensionOral1000 mg
Tablet, sugar coatedOral
Tablet, coatedOral
Tablet, coatedOral500 mg
TabletOral
Tablet, film coated
Tablet, extended releaseOral
Capsule, liquid filledOral500 mg
Tablet, film coatedOral450 mg
CapsuleOral
Powder, for suspensionOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.69 mg/mLALOGPS
logP-0.27ALOGPS
logP-0.31Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)8.61Chemaxon
pKa (Strongest Basic)-3.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count15Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area234.29 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity140.77 m3·mol-1Chemaxon
Polarizability58.87 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-0000009000-8c42f8adffac7d78b94c
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0zfr-0006009000-1f68460ef007fbd1cfa9
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0009002000-26d653ee690ce5c6cd20
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0009000000-a4d68b31e046fbf057d6
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0019000000-e9135e61d5aa11f40135
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0119003000-80c5f918f82d46fc1131
LC-MS/MS Spectrum - LC-ESI-ITTOF , negativeLC-MS/MSsplash10-0udi-0029000000-15e7bff1df4ba788d095
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ika-0003906000-8e92397c3ef59083d90b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0109500000-d16e1ccb83edc18c2285
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0109000000-44829065079eda0599e1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0209000000-edd02887a04b421dbb39
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0819000000-3ad8fb39515b5eaa0fd2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-3719300000-f2635b73560ddfd8533f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-2924000000-2288595ee1b67877de4b
13C NMR Spectrum1D NMRNot Applicable

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
General Function
Protein serine/threonine/tyrosine kinase activity
Specific Function
Serine/threonine-protein kinase component of the chromosomal passenger complex (CPC), a complex that acts as a key regulator of mitosis. The CPC complex has essential functions at the centromere in...
Gene Name
AURKB
Uniprot ID
Q96GD4
Uniprot Name
Aurora kinase B
Molecular Weight
39310.195 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
  2. de Groot CO, Hsia JE, Anzola JV, Motamedi A, Yoon M, Wong YL, Jenkins D, Lee HJ, Martinez MB, Davis RL, Gahman TC, Desai A, Shiau AK: A Cell Biologist's Field Guide to Aurora Kinase Inhibitors. Front Oncol. 2015 Dec 21;5:285. doi: 10.3389/fonc.2015.00285. eCollection 2015. [Article]

Drug created at September 11, 2007 17:49 / Updated at April 30, 2021 13:05