Identification
- Summary
Rutin is a flavonoid found in over-the-counter vitamin supplements.
- Generic Name
- Rutin
- DrugBank Accession Number
- DB01698
- Background
A flavonol glycoside found in many plants, including buckwheat; tobacco; forsythia; hydrangea; viola, etc. It has been used therapeutically to decrease capillary fragility.
- Type
- Small Molecule
- Groups
- Approved, Experimental, Investigational
- Structure
Structure for Rutin (DB01698)
- Weight
- Average: 610.5175
Monoisotopic: 610.153384912 - Chemical Formula
- C27H30O16
- Synonyms
- 3-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
- 3-Rhamnoglucosylquercetin
- 3-Rutinosyl quercetin
- Phytomelin
- Quercetin 3-rutinoside
- Quercetin-3-rutinoside
- Rutin
- Rutoside
- Rutosido
- Rutosidum
- Sophorin
- Vitamin P
- External IDs
- C.I. 75730
- NSC-9220
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form For therapy Anemia ••• ••• •••••• For therapy Anemia ••• ••• •••••• For therapy General surgery ••• ••• •••••• For therapy Pregnancy ••• ••• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UCarbonyl reductase [NADPH] 1 Not Available Humans UAldo-keto reductase family 1 member C3 Not Available 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 softwareAcenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Rutin. Alfuzosin The metabolism of Alfuzosin can be decreased when combined with Rutin. Alprazolam The metabolism of Alprazolam can be decreased when combined with Rutin. Aripiprazole The metabolism of Aripiprazole can be decreased when combined with Rutin. Aripiprazole lauroxil The metabolism of Aripiprazole lauroxil can be decreased when combined with Rutin. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Rutoside trihydrate RF4N03853G 250249-75-3 NLLBWFFSGHKUSY-JPRRWYCFSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image NAT-C Rutin (50 mg) + Ascorbic acid (421.053 mg) + Calcium ascorbate dihydrate (412.372 mg) + Citrus bioflavonoids (50 mg) + Hesperidin (50 mg) + Malpighia emarginata extract (12.5 mg) + Rosa canina fruit (62.5 mg) + Sodium ascorbate (353.535 mg) Tablet, film coated บริษัท เมก้า ไลฟ์ไซแอ็นซ์ จำกัด (มหาชน) 2009-08-06 Not applicable Thailand 
NAT-C 1000 Rutin (50 mg) + Ascorbic acid (421.053 mg) + Calcium ascorbate (412.372 mg) + Citrus bioflavonoids (50 mg) + Hesperidin (50 mg) + Malpighia emarginata extract (12.5 mg) + Rosa canina fruit (62.5 mg) + Sodium ascorbate (353.535 mg) Tablet, film coated บริษัท เมก้า ไลฟ์ไซแอ็นซ์ จำกัด (มหาชน) 2019-04-18 Not applicable Thailand Phlogenzym - Filmtabletten Rutoside trihydrate (100 mg) + Bromelains (250 FIP units) + Trypsin (1440 FIP units) Tablet, film coated Oral Mucos Pharma Gmb H & Co.Kg 1998-10-28 Not applicable Austria 
Rose Hips 500plus Nu Life Rutin (50 mg) + Ascorbic acid (500 mg) + Citrus bioflavonoids (100 mg) + Hesperidin (100 mg) Tablet Oral Nu Life Nutrition Ltd. 1972-12-31 2005-03-15 Canada 
Rutozym - Filmtabletten Rutoside trihydrate (100 mg) + Bromelains (450 FIP units) + Trypsin (1440 FIP units) Tablet, film coated Oral Mucos Pharma Gmb H & Co.Kg 2001-08-02 Not applicable Austria
Categories
- ATC Codes
- C05CA51 — Rutoside, combinations
- C05CA — Bioflavonoids
- C05C — CAPILLARY STABILIZING AGENTS
- C05 — VASOPROTECTIVES
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Benzopyrans
- Capillary Stabilizing Agents
- Chromones
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Flavonoids
- Flavonols
- Heterocyclic Compounds, Fused-Ring
- Pyrans
- Vasoprotectives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Flavonoids
- Sub Class
- Flavonoid glycosides
- Direct Parent
- Flavonoid-3-O-glycosides
- Alternative Parents
- 3'-hydroxyflavonoids / 4'-hydroxyflavonoids / 5-hydroxyflavonoids / 7-hydroxyflavonoids / Flavones / O-glycosyl compounds / Chromones / Disaccharides / Catechols / Pyranones and derivatives show 12 more
- Substituents
- 1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 3'-hydroxyflavonoid / 4'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Acetal / Alcohol / Aromatic heteropolycyclic compound show 25 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- rutinoside, disaccharide derivative, tetrahydroxyflavone, quercetin O-glucoside (CHEBI:28527) / flavonols (C05625)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 5G06TVY3R7
- CAS number
- 153-18-4
- InChI Key
- IKGXIBQEEMLURG-NVPNHPEKSA-N
- InChI
- InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
- IUPAC Name
- 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(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}-4H-chromen-4-one
- SMILES
- C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
References
- Synthesis Reference
Yukio Suzuki, Kei Suzuki, Masaru Yoneyama, Toshio Miyake, "4.sup.G -alpha-D-glucopyranosyl rutin, and its preparation and uses." U.S. Patent US5171573, issued October, 1979.
US5171573- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0003249
- KEGG Compound
- C05625
- PubChem Compound
- 5280805
- PubChem Substance
- 46508549
- ChemSpider
- 4444362
- 9500
- ChEBI
- 28527
- ChEMBL
- CHEMBL226335
- ZINC
- ZINC000004096846
- PharmGKB
- PA451291
- PDBe Ligand
- RUT
- Wikipedia
- Rutin
- PDB Entries
- 1ry8 / 8c3q
- MSDS
- Download (72 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Anemia, Pernicious / Megaloblastic anemia 1 Not Available Completed Not Available Glaucoma 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- V Sab Medical Labs Inc.
- Dosage Forms
Form Route Strength Capsule Oral Tablet Oral Tablet, film coated Tablet, film coated Oral Tablet, delayed release Oral Capsule - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 125 °C PhysProp water solubility 125 mg/L MERCK (1989) - Predicted Properties
Property Value Source Water Solubility 3.54 mg/mL ALOGPS logP 0.15 ALOGPS logP -0.87 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 6.37 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 16 Chemaxon Hydrogen Donor Count 10 Chemaxon Polar Surface Area 265.52 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 140.15 m3·mol-1 Chemaxon Polarizability 57.08 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8041 Blood Brain Barrier - 0.8542 Caco-2 permeable - 0.9172 P-glycoprotein substrate Substrate 0.6901 P-glycoprotein inhibitor I Non-inhibitor 0.8759 P-glycoprotein inhibitor II Non-inhibitor 0.8546 Renal organic cation transporter Non-inhibitor 0.8977 CYP450 2C9 substrate Non-substrate 0.7639 CYP450 2D6 substrate Non-substrate 0.8962 CYP450 3A4 substrate Non-substrate 0.5374 CYP450 1A2 substrate Non-inhibitor 0.8673 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9545 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9249 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6787 Ames test Non AMES toxic 0.5118 Carcinogenicity Non-carcinogens 0.9608 Biodegradation Not ready biodegradable 0.8339 Rat acute toxicity 2.4984 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9814 hERG inhibition (predictor II) Non-inhibitor 0.7469
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 228.272102 predictedDarkChem Lite v0.1.0 [M-H]- 214.9401103 predictedDarkChem Standard v0.1.0 [M-H]- 233.031302 predictedDarkChem Lite v0.1.0 [M-H]- 228.78703 predictedDeepCCS 1.0 (2019) [M+H]+ 228.355802 predictedDarkChem Lite v0.1.0 [M+H]+ 227.7752149 predictedDarkChem Standard v0.1.0 [M+H]+ 234.857302 predictedDarkChem Lite v0.1.0 [M+H]+ 230.89938 predictedDeepCCS 1.0 (2019) [M+Na]+ 229.211902 predictedDarkChem Lite v0.1.0 [M+Na]+ 247.7863025 predictedDarkChem Standard v0.1.0 [M+Na]+ 234.122302 predictedDarkChem Lite v0.1.0 [M+Na]+ 236.91771 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Prostaglandin-e2 9-reductase activity
- Specific Function
- NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. ...
- Gene Name
- CBR1
- Uniprot ID
- P16152
- Uniprot Name
- Carbonyl reductase [NADPH] 1
- Molecular Weight
- 30374.73 Da
References
- Carlquist M, Frejd T, Gorwa-Grauslund MF: Flavonoids as inhibitors of human carbonyl reductase 1. Chem Biol Interact. 2008 Jul 30;174(2):98-108. doi: 10.1016/j.cbi.2008.05.021. Epub 2008 May 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
- Specific Function
- Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....
- Gene Name
- AKR1C3
- Uniprot ID
- P42330
- Uniprot Name
- Aldo-keto reductase family 1 member C3
- Molecular Weight
- 36852.89 Da
References
- Skarydova L, Zivna L, Xiong G, Maser E, Wsol V: AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids. Chem Biol Interact. 2009 Mar 16;178(1-3):138-44. doi: 10.1016/j.cbi.2008.10.015. Epub 2008 Oct 19. [Article]
- Barski OA, Tipparaju SM, Bhatnagar A: The aldo-keto reductase superfamily and its role in drug metabolism and detoxification. Drug Metab Rev. 2008;40(4):553-624. doi: 10.1080/03602530802431439. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Yu CP, Wu PP, Hou YC, Lin SP, Tsai SY, Chen CT, Chao PD: Quercetin and rutin reduced the bioavailability of cyclosporine from Neoral, an immunosuppressant, through activating P-glycoprotein and CYP 3A4. J Agric Food Chem. 2011 May 11;59(9):4644-8. doi: 10.1021/jf104786t. Epub 2011 Apr 5. [Article]
Drug created at June 13, 2005 13:24 / Updated at May 06, 2021 01:09