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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H30O16.3H2O
Molecular Weight 664.5644
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RUTOSIDE TRIHYDRATE

SMILES

C[C@@]1([H])[C@@]([H])([C@]([H])([C@]([H])([C@]([H])(OC[C@]2([H])[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])(O2)Oc3c(=O)c4c(cc(cc4oc3-c5ccc(c(c5)O)O)O)O)O)O)O)O1)O)O)O.O.O.O

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

HIDE SMILES / InChI

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

Molecular Formula C27H30O16
Molecular Weight 610.5186
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Originator

Curator's Comment:: Rutin was first isolated in 1842 by GFerman chemist AUgust Weiss from garden ruc, Ruta graveolens

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
13.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PHLOGENZYM

Approved Use

Taking 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 Use

Swelling 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 Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
89.9 μg/L
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
1017 μg × h/L
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
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
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

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Effect of o-(beta-hydroxyethyl)-rutoside in lymphangiography.
1977 Feb
Inhibitory effect of quercetin on carrageenan-induced inflammation in rats.
2003 Dec 26
Antiparasitic activity of flavonoids and isoflavones against Cryptosporidium parvum and Encephalitozoon intestinalis.
2006 Jun
Naturally occurring flavonoids attenuate high glucose-induced expression of proinflammatory cytokines in human monocytic THP-1 cells.
2009 Aug
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
Toxicity of clopidogrel and ticlopidine on human myeloid progenitor cells: importance of metabolites.
2012 Sep 28
Synthesis, characterization and biological evaluation of Rutin-zinc(II) flavonoid -metal complex.
2015 Sep 5
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 Fri Jun 25 21:13:41 UTC 2021
Edited
by admin
on Fri Jun 25 21:13:41 UTC 2021
Record UNII
RF4N03853G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RUTOSIDE TRIHYDRATE
EP   WHO-DD  
Common Name English
RUTIN TRIHYDRATE
Common Name English
4H-1-BENZOPYRAN-4-ONE, 3-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-, TRIHYDRATE
Common Name English
RUTOSIDE TRIHYDRATE [WHO-DD]
Common Name English
RUTIN HYDRATE
JAN  
Common Name English
RUTIN HYDRATE [JAN]
Common Name English
RUTOSIDE TRIHYDRATE [EP MONOGRAPH]
Common Name English
Code System Code Type Description
EVMPD
SUB30642
Created by admin on Fri Jun 25 21:13:41 UTC 2021 , Edited by admin on Fri Jun 25 21:13:41 UTC 2021
PRIMARY
PUBCHEM
16218542
Created by admin on Fri Jun 25 21:13:41 UTC 2021 , Edited by admin on Fri Jun 25 21:13:41 UTC 2021
PRIMARY
CAS
250249-75-3
Created by admin on Fri Jun 25 21:13:41 UTC 2021 , Edited by admin on Fri Jun 25 21:13:41 UTC 2021
PRIMARY
EPA CompTox
250249-75-3
Created by admin on Fri Jun 25 21:13:41 UTC 2021 , Edited by admin on Fri Jun 25 21:13:41 UTC 2021
PRIMARY
FDA UNII
RF4N03853G
Created by admin on Fri Jun 25 21:13:41 UTC 2021 , Edited by admin on Fri Jun 25 21:13:41 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY