Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H30O16 |
Molecular Weight | 610.5175 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]5(OC[C@H]1O[C@@H](OC2=C(OC3=C(C2=O)C(O)=CC(O)=C3)C4=CC=C(O)C(O)=C4)[C@H](O)[C@@H](O)[C@@H]1O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O
InChI
InChIKey=IKGXIBQEEMLURG-NVPNHPEKSA-N
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
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 |
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
Originator
Sources: https://naldc.nal.usda.gov/download/IND43894155/PDF
Curator's Comment: Rutin was first isolated in 1842 by GFerman chemist AUgust Weiss from garden ruc, Ruta graveolens
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12193020 |
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. |
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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. |
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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 |
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Inhibitory effect of the flavonoid O-(beta-hydroxyethyl)-rutoside on increased microvascular permeability induced by various agents in rat skin. | 1983 |
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Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. | 1994 Aug 3 |
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Flavonoids as phospholipase A2 inhibitors: importance of their structure for selective inhibition of group II phospholipase A2. | 1997 Jun |
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Identification and quantification of flavonoids in human urine samples by column-switching liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry. | 2000 Apr 1 |
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Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
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Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta. | 2001 Jan 30 |
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A pharmacophore for human pregnane X receptor ligands. | 2002 Jan |
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Search of antimicrobial activity of selected non-antibiotic drugs. | 2002 Nov-Dec |
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Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. | 2003 Jun |
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Dietary rutin, but not its aglycone quercetin, ameliorates dextran sulfate sodium-induced experimental colitis in mice: attenuation of pro-inflammatory gene expression. | 2005 Feb 1 |
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Antitubercular sterols from Thalia multiflora Horkel ex Koernicke. | 2005 Oct |
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Influence of quercetin and rutin on growth and antioxidant defense system of a human hepatoma cell line (HepG2). | 2006 Feb |
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Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John's wort. | 2006 Jan 16 |
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Antiparasitic activity of flavonoids and isoflavones against Cryptosporidium parvum and Encephalitozoon intestinalis. | 2006 Jun |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Flavonoids inhibit histamine release and expression of proinflammatory cytokines in mast cells. | 2008 Oct |
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Gastroprotective effect of rutin against indomethacin-induced ulcers in rats. | 2010 Sep |
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Phenolic compounds from Achillea millefolium L. and their bioactivity. | 2011 |
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Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. | 2011 Dec 15 |
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Differential protective effects of quercetin, resveratrol, rutin and epigallocatechin gallate against mitochondrial dysfunction induced by indomethacin in Caco-2 cells. | 2012 Feb 5 |
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Antiplasmodial activity of flavonol quercetin and its analogues in Plasmodium falciparum: evidence from clinical isolates in Bangladesh and standardized parasite clones. | 2012 Jun |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12193020
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 16 15:58:43 UTC 2022
by
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on
Fri Dec 16 15:58:43 UTC 2022
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Record UNII |
5G06TVY3R7
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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DSLD |
120 (Number of products:1322)
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WHO-ATC |
C05CA01
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WHO-VATC |
QC05CA01
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DSLD |
1394 (Number of products:104)
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WHO-VATC |
QC05CA51
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WHO-ATC |
C05CA51
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NCI_THESAURUS |
C792
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Code System | Code | Type | Description | ||
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RUTIN
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28527
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3535
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153-18-4
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5G06TVY3R7
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205-814-1
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61606
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1606503
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CHEMBL226335
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5280805
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SUB10407MIG
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2213
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D012431
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DTXSID3022326
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M9708
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5G06TVY3R7
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4055
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DB01698
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C819
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9500
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PRIMARY | RxNorm | ||
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9220
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SOLVATE->ANHYDROUS | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
CALENDULA OFFICINALIS FLOWER flavonoid
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
IN-VIVO
URINE
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METABOLITE -> PARENT |
Quantity of quercetin-3-glucuronide in urine of six healthy human subjects 0-24hr (total) after consumption of tomato juice containing 176 micromoles of rutin; Unit: nmoles
IN-VIVO
URINE
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METABOLITE -> PARENT |
Cmax: 4.3 +/- 1.5 nM; Tmax: 5.4 +/- 0.2 hr; T1/2: 6.9 +/- 0.3 hr (n=6)
IN-VIVO
PLASMA
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METABOLITE -> PARENT |
IN-VIVO
PLASMA; URINE
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METABOLITE -> PARENT |
IN-VIVO
URINE
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METABOLITE -> PARENT |
Quantity of Isorhamnetin-3-glucuronide in urine of six healthy human subjects 0-24hr (total) after consumption of tomato juice containing 176 micromoles of rutin; Unit: nmoles
IN-VIVO
URINE
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METABOLITE -> PARENT |
Cmax: 12 +/- 2 nM; Tmax: 4.7 +/- 0.3 hr; T1/2: 5.7 +/- 0.6 hr (n=6)
IN-VIVO
PLASMA
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METABOLITE -> PARENT |
IN-VIVO
URINE
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METABOLITE -> PARENT |
Excretion of 3-Hydroxyphenylacetic acid in the urine of human subjects (n=6, 0-24hr total) after rutin (176 micromoles) supplemented tomato juice; Unit: micromoles
IN-VIVO
URINE
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METABOLITE -> PARENT |
Quantity of Quercetin-4'-glucuronide in urine of five healthy human subjects 0-24hr (total) after consumption of tomato juice containing 176 micromoles of rutin; Unit: nmoles
IN-VIVO
URINE
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METABOLITE -> PARENT |
IN-VIVO
URINE
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METABOLITE -> PARENT |
Excretion of 3,4-Dihydroxyphenylacetic acid in the urine of human subjects (n=6, 0-24hr total) after rutin (176 micromoles) supplemented tomato juice; Unit: micromoles
IN-VIVO
URINE
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METABOLITE -> PARENT |
IN-VIVO
PLASMA; URINE
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METABOLITE -> PARENT |
Excretion of 3-Methoxy-4-Hydroxyphenylacetic acid in the urine of human subjects (n=6, 0-24hr total) after rutin (176 micromoles) supplemented tomato juice; Unit: micromoles
IN-VIVO
URINE
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METABOLITE -> PARENT |
IN-VIVO
URINE
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METABOLITE -> PARENT |
IN-VIVO
PLASMA; URINE
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METABOLITE -> PARENT |
IN-VIVO
PLASMA; URINE
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METABOLITE -> PARENT |
Quantity of Quercetin-3'-glucuronide in urine of six healthy human subjects 0-24hr (total) after consumption of tomato juice containing 176 micromoles of rutin; Unit: nmoles
IN-VIVO
URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
NMT 2%
USP
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IMPURITY -> PARENT |
USP
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IMPURITY -> PARENT |
NMT 2%
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |