Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H30O16.3H2O |
| Molecular Weight | 664.5633 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C3=O)C(O)=CC(O)=C4)C5=CC=C(O)C(O)=C5)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
InChI
InChIKey=NLLBWFFSGHKUSY-JPRRWYCFSA-N
InChI=1S/C27H30O16.3H2O/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;3*1H2/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-;;;/m0.../s1
| Molecular Formula | C27H30O16 |
| Molecular Weight | 610.5175 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: http://phenol-explorer.eu/contents/polyphenol/296 | https://www.ncbi.nlm.nih.gov/pubmed/22731245
Curator's Comment: http://phenol-explorer.eu/contents/polyphenol/296 | https://www.ncbi.nlm.nih.gov/pubmed/22731245
Rutin, also called rutoside, is the glycoside flavonoid found in a certain fruits and vegetables. Most rutine-rich foods are capers, olives, buckwheat (whole grain flour), asparagus, raspberry.In a clinical trial, rutin was found to aid control of intraocular pressure in patients with primary open angle glaucoma. As a component of dietary supplement Phlogenzym, rutin is used for treatment of osteoarthritis. Rutin is also used for treatment of post-surgical swelling of the arm after breast cancer surgery. Traditionally, rutin is used to prevent mucositis due to cancer treatment, to treat blood vessel disease such as varicose veins, bleeding, hemorrhoids.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2622 |
13.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | PHLOGENZYM Approved UseTaking rutin by mouth in combination with trypsin and bromelain seems to be about as effective as the medication diclofenac (Voltaren) in relieving pain and improving knee function in people with osteoarthritis. |
|||
| Primary | WOBENZYM Approved UseSwelling in the arm after breast surgery (post-surgical lymphedema). Some early research suggests that taking a specific product (Wobenzym) containing rutin, pancreatin, papain, trypsin, and chymotrypsin daily for 7 weeks reduces swelling in the arm due to breast removal surgery. |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
89.9 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
23.5 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
47.6 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1017 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
381 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
636 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11151743/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUERCETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| weak [IC50 111.5 uM] | ||||
| yes [EC50 2.32 uM] | ||||
| yes [IC50 27 uM] | ||||
| yes [IC50 60.7 uM] | ||||
| yes [IC50 7.2 uM] | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Metabolism of hydroxyethylrutosides (HR): metabolism of [14C]-HR in man. | 1976 |
|
| Effect of o-(beta-hydroxyethyl)-rutoside in lymphangiography. | 1977 Feb |
|
| Inhibitory effect of the flavonoid O-(beta-hydroxyethyl)-rutoside on increased microvascular permeability induced by various agents in rat skin. | 1983 |
|
| Effect of benzopyrone derivatives on drug activity and metabolism. | 1986 Oct-Dec |
|
| Differential inhibitory effects of various flavonoids on the activities of reverse transcriptase and cellular DNA and RNA polymerases. | 1990 Jul 5 |
|
| Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. | 1994 Aug 3 |
|
| Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
|
| Antitubercular sterols from Thalia multiflora Horkel ex Koernicke. | 2005 Oct |
|
| [Effect of polyphenols from the Mediterranean diet on proliferation and mediators of in vitro invasiveness of the MB-49 murine bladder cancer cell line]. | 2005 Sep |
|
| Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John's wort. | 2006 Jan 16 |
|
| Antiparasitic activity of flavonoids and isoflavones against Cryptosporidium parvum and Encephalitozoon intestinalis. | 2006 Jun |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
| In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
|
| Protective effect of rutin, a polyphenolic flavonoid against haloperidol-induced orofacial dyskinesia and associated behavioural, biochemical and neurochemical changes. | 2007 Oct |
|
| In vitro anti-HIV and -HSV activity and safety of sodium rutin sulfate as a microbicide candidate. | 2007 Sep |
|
| Plant polyphenols differentially modulate inflammatory responses of human keratinocytes by interfering with activation of transcription factors NFκB and AhR and EGFR-ERK pathway. | 2011 Sep 1 |
|
| Plant polyphenols regulate chemokine expression and tissue repair in human keratinocytes through interaction with cytoplasmic and nuclear components of epidermal growth factor receptor system. | 2012 Feb 15 |
Patents
Sample Use Guides
As a dietary supplement and natural nutrient, rutin is administered orally. For osteoarthritis: 2 tablets of a combination product (Phlogenzym), which contains 100 mg of rutin, 48 mg of trypsin, and 90 mg of bromelain, 3 times daily.
Route of Administration:
Oral
Inhibition of aldose reductase from rat lens homogenate was measured using DL-glyceraldehyde as a substrate. The reaction was initiated by addition of NADPH at 30°C. After 30 min the reaction was stopped, and 10mM imidazole was added to convert NADP to a fluorescent product. IC50 for rutin was 13 uM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:58:36 GMT 2023
by
admin
on
Fri Dec 15 18:58:36 GMT 2023
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| Record UNII |
RF4N03853G
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| Record Status |
Validated (UNII)
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| Record Version |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |