yingweiwo

Indican

Alias: NSC87517 IndicanNSC 87517 NSC-87517
Cat No.:V11176 Purity: ≥98%
Indican(Indoxyl-β-D-glucoside) is a naturally occurring plantsglycoside of indoxyl and a colourless organic compound foundin Indigofera.
Indican
Indican Chemical Structure CAS No.: 487-60-5
Product category: Fluorescent Dye
This product is for research use only, not for human use. We do not sell to patients.
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Product Description

Indican (Indoxyl-β-D-glucoside) is a naturally occurring plantsglycoside of indoxyl and a colourless organic compound found in Indigofera. It is a precursor of the dyesindigo and indirubin.

Biological Activity I Assay Protocols (From Reference)
ln Vivo
Indican ((Indolyl-beta-D-glucoside; Oral; 20, 40 mg/kg; Single dose) increases MTX by significant metabolite inhibition of numerous anion transporters, including OAT 1, OAT 3, and MRP 4 Systemic exposure and MRT IS[1].
Animal Protocol
Animal/Disease Models: Male Spraguee Dawley rat, body weight 330-400 g[1]
Doses: 20, 40 mg/kg
Route of Administration: Oral
Experimental Results: Methotrexate (MTX) Increased systemic exposure and multidrug resistance-related protein (MRP; 5.0 mg/kg).
ADME/Pharmacokinetics
Metabolism / Metabolites
Uremic toxins often accumulate in the blood due to overeating or poor kidney filtration. Most uremic toxins are metabolic waste products that are normally excreted through urine or feces.
Toxicity/Toxicokinetics
Toxicity Summary
Uremic toxins (such as indophenol) are actively transported to the kidneys via organic ion transporters, particularly OAT3. Elevated uremic toxin levels can stimulate the production of reactive oxygen species (ROS). This appears to be mediated by the direct binding of uremic toxins to or inhibition of NADPH oxidases, particularly NOX4, which is abundant in the kidneys and heart (A7868). ROS can induce a variety of different DNA methyltransferases (DNMTs) involved in the silencing of the KLOTHO protein. KLOTHO has been shown to play an important role in anti-aging, mineral metabolism, and vitamin D metabolism. Multiple studies have shown that in acute or chronic kidney disease, KLOTHO mRNA and protein levels are decreased due to elevated local ROS levels (A7869).
References

[1]. Transporter-mediated interaction of indican and methotrexate in rats. J Food Drug Anal. 2018 Apr;26(2S):S133-S140.

[2]. Indoxyl sulfate, a uremic toxin, is biotransformed from indoxyl-beta-D-glucoside (indican) in rats. Toxicon. 2008 Sep 1;52(3):440-4.

Additional Infomation
Indolone is an indole-based carbohydrate belonging to the β-D-glucosides and extracellular polysaccharides. It has been reported in Strobilanthes cusia, Calanthe discolor, and other organisms with relevant data. Indolone is a toxic metabolite derived from dietary protein and tryptophan. In the intestine, protein and tryptophan are converted to indole by organisms expressing tryptophanase. In the liver, indole is hydroxylated to indolephenol, and indolephenol is sulfated to indolone. Excessive production of indolone is associated with glomerulosclerosis, interstitial fibrosis, and renal failure. Indolone is a uremic toxin. Based on their chemical and physical properties, uremic toxins can be classified into three main categories: 1) small molecule, water-soluble, non-protein-bound compounds, such as urea; 2) small molecule, lipid-soluble compounds and/or protein-bound compounds, such as phenols; and 3) larger so-called medium molecules, such as β2-microglobulins. Long-term exposure to uremic toxins can lead to a variety of diseases, including kidney damage, chronic kidney disease, and cardiovascular disease. Indigo is a colorless organic compound that is soluble in water and is naturally found in plants of the genus Indigo. It is a precursor to indigo dye. Indigo interferes with many commercial methods for measuring total bilirubin[6], which can be a problem for patients with kidney failure who have elevated levels of indigo in their blood. It can also cause gastrointestinal symptoms in patients with reduced protein absorption, such as Hartnap disease, because bacteria more readily break down tryptophan into indole and convert it into indigo.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H17NO6
Molecular Weight
295.29
Exact Mass
295.105
CAS #
487-60-5
Related CAS #
1328-73-0 (trihydrate);487-60-5;
PubChem CID
441564
Appearance
Off-white to light yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
606.7±55.0 °C at 760 mmHg
Melting Point
57-58ºC
Flash Point
320.7±31.5 °C
Vapour Pressure
0.0±1.8 mmHg at 25°C
Index of Refraction
1.715
LogP
-0.75
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
3
Heavy Atom Count
21
Complexity
356
Defined Atom Stereocenter Count
5
SMILES
C1=CC=C2C(=C1)C(=CN2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChi Key
XVARCVCWNFACQC-RKQHYHRCSA-N
InChi Code
InChI=1S/C14H17NO6/c16-6-10-11(17)12(18)13(19)14(21-10)20-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-19H,6H2/t10-,11-,12+,13-,14-/m1/s1
Chemical Name
(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(1H-indol-3-yloxy)oxane-3,4,5-triol
Synonyms
NSC87517 IndicanNSC 87517 NSC-87517
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~338.65 mM)
MEthanol : ~83.33 mg/mL (~282.20 mM)
H2O : ~20 mg/mL (~67.73 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.47 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (8.47 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (8.47 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 14.29 mg/mL (48.39 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.3865 mL 16.9325 mL 33.8650 mL
5 mM 0.6773 mL 3.3865 mL 6.7730 mL
10 mM 0.3387 mL 1.6933 mL 3.3865 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04117191 Completed Dietary Supplement: Doctor's Best L-Tryptophan Chronic Kidney Diseases
Healthy
Taipei Tzu Chi Hospital, Buddhist Tzu Chi Medical Foundation 2019-10-01 Not Applicable
NCT02639624 Withdrawn Drug: Low bicarbonate dialysate First
Drug: Normal bicarbonate dialysate First
Drug: Normal bicarbonate dialysate
Drug: Low bicarbonate dialysate
Hemodialysis Renal Dialysis NYU Langone Health 2016-01 Not Applicable
NCT05771350 Completed Procedure: online hemodiafiltration
Procedure: high flux hemodialysis
Procedure: low flux hemodialysis
Hemodialysis Ain Shams University 2016-11-15 Not Applicable
NCT03920982 Recruiting Diagnostic Test: Determination of the blood
concentration of indoxyl sulfate (IS)
Acute Kidney Injury
Mortality
Septic Shock
Uremic; Toxemia
Centre Hospitalier Universitaire, Amiens 2019-12-10 Not Applicable
NCT05634083 Completed Dietary Supplement: Uremic pateints with itching Pruritus Benha University 2022-11-25 Not Applicable
Biological Data
  • Structures of indican, indoxyl sulfate, phenolsulfonphthalein (PSP) and methotrexate (MTX).[1].Transporter-mediated interaction of indican and methotrexate in rats. J Food Drug Anal. 2018 Apr;26(2S):S133-S140.
  • Mean (±S.E.) serum semi-log concentration–time profiles of methotrexate (MTX) after oral MTX alone (5.0 mg/kg) (○), and coadministrations with 20.0 (●) and 40.0 mg/kg (▼) of indican, revealing that the elimination of MTX was inhibited by both dosages of indican.[1].Transporter-mediated interaction of indican and methotrexate in rats. J Food Drug Anal. 2018 Apr;26(2S):S133-S140.
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