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Calcipotriol
Identification
- Name
- Calcipotriol
- Accession Number
- DB02300
- Description
Calcipotriol (INN) or calcipotriene (USAN) is a sythetic derivative of calcitriol or Vitamin D.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Calcipotriol (DB02300)
- Weight
- Average: 412.6047
Monoisotopic: 412.297745146 - Chemical Formula
- C27H40O3
- Synonyms
- Calcipotriene
- Calcipotriol
- External IDs
- MC 903
- MC-903
Pharmacology
- Indication
For the treatment of moderate plaque psoriasis in adults.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Calcipotriene is a synthetic analog of vitamin D. In humans, the natural supply of vitamin D depends mainly on exposure to the ultraviolet rays of the sun for conversion of 7-dehydrocholesterol to vitamin D3 (cholecalciferol) in the skin.
- Mechanism of action
The precise mechanism of calcipotriol in remitting psoriasis is not well-understood, however, it has been shown to have comparable affinity with calcitriol for the Vitamin D receptor while being less than 1% the activity in regulating calcium metabolism. The Vitamin D receptor (VDR) belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. T cells are known to play a role in psoriasis and are believed to undergo modulation of gene expression with binding of calcipotriol to the VDR. This modulation is thought to affect gene products related to cell differentiation and proliferation.
Target Actions Organism UVitamin D3 receptor antagonistHumans - Absorption
Clinical studies with radiolabeled ointment indicate that approximately 6% (+3%, SD) of the applied dose of calcipotriene is absorbed systemically when the ointment is applied topically to psoriasis plaques or 5% (+2.6%, SO) when applied to normal skin.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Hepatic. Calcipotriene metabolism following systemic uptake is rapid, and occurs via a similar pathway to the natural hormone. The primary metabolites are much less potent than the parent compound.
- Route of elimination
The active form of the vitamin, 1,25-dihydroxy vitamin D3 (calcitriol), is known to be recycled via the liver and excreted in the bile. There is evidence that maternal 1,25-dihydroxy vitamin D3 (calcitriol) may enter the fetal circulation, but it is not known whether it is excreted in human milk.
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Topically applied calcipotriene can be absorbed in sufficient amounts to produce systemic effects. Elevated serum calcium has been observed with excessive use of calcipotriene.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Unlock Additional DataCalcium acetate The risk or severity of adverse effects can be increased when Calcium acetate is combined with Calcipotriol. Calcium carbonate The risk or severity of adverse effects can be increased when Calcium carbonate is combined with Calcipotriol. Calcium chloride The risk or severity of adverse effects can be increased when Calcium chloride is combined with Calcipotriol. Calcium citrate The risk or severity of adverse effects can be increased when Calcium citrate is combined with Calcipotriol. Calcium glubionate anhydrous The risk or severity of adverse effects can be increased when Calcium glubionate anhydrous is combined with Calcipotriol. Calcium glucoheptonate The risk or severity of adverse effects can be increased when Calcium glucoheptonate is combined with Calcipotriol. Calcium gluconate The risk or severity of adverse effects can be increased when Calcium gluconate is combined with Calcipotriol. Calcium lactate The risk or severity of adverse effects can be increased when Calcium lactate is combined with Calcipotriol. Calcium levulinate The risk or severity of adverse effects can be increased when Calcium levulinate is combined with Calcipotriol. Calcium Phosphate The risk or severity of adverse effects can be increased when Calcium Phosphate is combined with Calcipotriol. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Calcipotriol hydrate S7499TYY6G 147657-22-5 XBKHACNRWFKJNC-MANNPBRJSA-N - International/Other Brands
- Daivonex
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataCalcipotriene 0.005% 60 gram Foam Aerosol, foam 50 ug/1g Topical Trifluent Pharma LLC 2020-08-24 Not applicable US 
Calcipotriene Foam Aerosol, foam 50 ug/1g Topical Ayurax 2020-01-08 2020-05-07 US Dovonex Cream 50 ug/1g Topical Physicians Total Care, Inc. 2006-09-15 Not applicable US Dovonex Solution 0.05 mg/1mL Topical Leo Pharma 1997-06-01 2013-04-01 US Dovonex Ointment 50 ug/1g Topical Bristol Myers Squibb Pharma Company 2009-06-01 2012-10-15 US Dovonex Solution 0.05 mg/1mL Topical Physicians Total Care, Inc. 2009-08-12 Not applicable US Dovonex Solution 0.05 mg/1mL Topical Allergan 2006-01-01 2012-03-31 US Dovonex Ointment 50 ug/1g Topical Physicians Total Care, Inc. 2004-06-30 2010-12-29 US Dovonex Cream 50 ug/1g Topical LEO Pharma Inc. 1996-10-01 Not applicable US Dovonex Cream 50 ug/1g Topical Allergan 2006-01-01 2012-03-31 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataCalcipotriene Cream 50 ug/1g Topical North Star Rx Llc 2015-06-01 Not applicable US Calcipotriene Solution 0.05 mg/1mL Topical Amneal Pharmaceuticals of New York Llc 2009-11-20 Not applicable US Calcipotriene Ointment 50 ug/1g Topical Prasco Laboratories 2013-07-01 Not applicable US Calcipotriene Ointment 0.05 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 2010-03-24 Not applicable US Calcipotriene Cream 50 ug/1g Topical Glenmark Pharmaceuticals Inc.,Usa 2015-06-10 Not applicable US Calcipotriene Ointment 50 ug/1g Topical Glenmark Pharmaceuticals Inc., USA 2010-03-24 Not applicable US Calcipotriene Solution 0.05 mg/1mL Topical Sandoz 2009-11-20 2013-10-31 US Calcipotriene Solution 0.05 mg/1mL Topical Hi-Tech Pharmacal Co., Inc. 2014-10-06 Not applicable US Calcipotriene Cream 0.05 mg/1g Topical Sandoz Inc. 2012-07-27 Not applicable US Calcipotriene Solution 0.05 mg/1mL Topical Fougera Pharmaceuticals Inc. 2008-05-06 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Calcipotriene and Betamethasone Dipropionate Calcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g) Ointment Topical Prasco Laboratories 2020-01-28 Not applicable US Calcipotriene and Betamethasone Dipropionate Calcipotriol (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g) Ointment Topical Sandoz Inc. 2014-03-31 Not applicable US Calcipotriene and Betamethasone Dipropionate Calcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g) Ointment Topical Perrigo New York Inc 2008-06-01 Not applicable US Calcipotriene and Betamethasone Dipropionate Calcipotriol (50 ug/1g) + Betamethasone dipropionate (.643 mg/1g) Ointment Topical Perrigo New York Inc 2020-01-30 Not applicable US Calcipotriene and Betamethasone Dipropionate Calcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g) Suspension Topical Prasco Laboratories 2020-01-07 Not applicable US Calcipotriene and Betamethasone Dipropionate Calcipotriol (50 ug/1g) + Betamethasone dipropionate (50 mg/1g) Suspension Topical Taro Pharmaceuticals U.S.A., Inc. 2020-09-02 Not applicable US Calcipotriene and Betamethasone Dipropionate Calcipotriol (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g) Suspension Topical TOLMAR Inc. 2020-05-11 Not applicable US Dovobet Gel Calcipotriol (50 mcg) + Betamethasone (0.5 mg) Gel Topical Leo Pharma 2009-01-28 Not applicable Canada 
Dovobet Ointment Calcipotriol (50 mcg) + Betamethasone (0.5 mg) Ointment Topical Leo Pharma 2001-11-29 Not applicable Canada Enstilar Calcipotriol (50 mcg) + Betamethasone (0.5 mg) Aerosol, foam Topical Leo Pharma 2016-11-11 Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Calcipotriene 0.005% / Clobetasol Propionate 0.05% Calcipotriol (0.005 g/100g) + Clobetasol propionate (0.05 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-20 Not applicable US Calcipotriene 0.005% / Diclofenac Sodium 3% / Hyaluronic Acid Sodium Salt 2% / Niacinamide 2% Calcipotriol (0.005 g/100g) + Diclofenac sodium (3 g/100g) + Sodium hyaluronate (2 g/100g) + Nicotinamide (2 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-07 Not applicable US Calcipotriene 0.005% / Niacinamide 4% Calcipotriol (0.005 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-14 Not applicable US Calcipotriene 0.005% / Triamcinolone Acetonide 0.1% Calcipotriol (0.005 g/100g) + Triamcinolone acetonide (0.1 g/100g) Ointment Topical Sincerus Florida, LLC 2019-05-11 Not applicable US
Categories
- ATC Codes
- D05AX52 — Calcipotriol, combinations
- D05AX — Other antipsoriatics for topical use
- D05A — ANTIPSORIATICS FOR TOPICAL USE
- D05 — ANTIPSORIATICS
- D — DERMATOLOGICALS
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Vitamin D and derivatives
- Direct Parent
- Vitamin D and derivatives
- Alternative Parents
- Triterpenoids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Secondary alcohol / Triterpenoid
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- seco-cholestane, hydroxy seco-steroid (CHEBI:50749) / Vitamin D3 and derivatives (LMST03020106)
Chemical Identifiers
- UNII
- 143NQ3779B
- CAS number
- 112965-21-6
- InChI Key
- LWQQLNNNIPYSNX-UROSTWAQSA-N
- InChI
- InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1
- IUPAC Name
- (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
- SMILES
- O[[email protected]](\C=C\[[email protected]@H](C)[[email protected]@]1([H])CC[[email protected]@]2([H])\C(CCC[[email protected]]12C)=C\C=C1\C[[email protected]@H](O)C[[email protected]](O)C1=C)C1CC1
References
- Synthesis Reference
Andrzej Kutner, Michal Chodynski, Teresa Ryznar, Hanna Fitak, Jerzy Winiarski, Bartlomiej Gorecki, Agnieszka Burzynska, Wieslaw Szelejewski, "Process for Preparation of Pharmaceutically Pure Anhydrous Calcipotriol." U.S. Patent US20080214876, issued September 04, 2008.
US20080214876- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015567
- KEGG Drug
- D01125
- PubChem Compound
- 5288783
- PubChem Substance
- 46507122
- ChemSpider
- 4450880
- BindingDB
- 50369964
- 29365
- ChEBI
- 50749
- ChEMBL
- CHEMBL1200666
- ZINC
- ZINC000003921872
- Therapeutic Targets Database
- DAP000292
- PharmGKB
- PA448714
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- MC9
- RxList
- RxList Drug Page
- Wikipedia
- Calcipotriol
- AHFS Codes
- 84:92.00 — Misc. Skin and Mucous Membrane Agents
- PDB Entries
- 1s19
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Other Psoriasis Vulgaris (Plaque Psoriasis) 1 4 Completed Supportive Care Adherence 1 4 Completed Treatment Psoriasis 5 4 Completed Treatment Psoriasis Vulgaris (Plaque Psoriasis) 7 4 Completed Treatment Psoriasis / Psoriasis Vulgaris (Plaque Psoriasis) 1 4 Not Yet Recruiting Treatment Nail Psoriasis 1 4 Recruiting Treatment Psoriasis 3 4 Recruiting Treatment Psoriasis Vulgaris (Plaque Psoriasis) 1 4 Terminated Treatment Psoriasis Vulgaris (Plaque Psoriasis) 2 3 Completed Treatment Chronic Plaque Psoriasis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Contract Pharm
- Dispensing Solutions
- E. Fougera and Co.
- Glenmark Generics Ltd.
- Hi Tech Pharmacal Co. Inc.
- LEO Pharma Inc.
- Nycomed Inc.
- Physicians Total Care Inc.
- Sandoz
- Warner Chilcott Co. Inc.
- WC Pharmaceuticals
- Dosage Forms
Form Route Strength Cream Topical 0.05 mg/1g Solution Topical .05 mg/1mL Solution Topical Cream Topical Ointment Cutaneous 0.05 MG/G Solution Cutaneous 0.05 MG/ML Ointment Topical 0.05 mg/1g Ointment Gel Topical 50 mg Ointment Topical 0.5 mg Cream 0.005 % Ointment Cutaneous 0.005 % Solution 50 MICROGRAMMI/ML Ointment Topical 0.005 g Gel Topical Cream Topical 50 ug/1g Ointment Topical 50 ug/1g Solution Topical 0.05 mg/1mL Cream Topical Ointment Topical Solution Topical Aerosol, foam Topical Kit Topical Ointment Topical 0.005 % Ointment Topical 0.5 mg/g Ointment 0.005 % Solution Topical 0.05 mg/ml Ointment Topical 50 mcg/g Cream 30 g Aerosol, foam Topical 50 ug/1g Ointment Topical Spray, metered Topical Suspension Topical - Prices
Unit description Cost Unit Dovonex 0.005% Cream 120 gm Tube 607.03USD tube Dovonex 0.005% Solution 60ml Bottle 323.98USD bottle Dovonex 0.005% Cream 60 gm Tube 303.51USD tube Dovonex 0.005% cream 4.23USD g Dovonex 50 mcg/ml Solution 0.84USD ml Dovonex 50 mcg/g Cream 0.83USD g Dovonex 50 mcg/g Ointment 0.81USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS5763426 No 1998-06-09 2015-06-09 US US6753013 No 2004-06-22 2020-01-27 US US6787529 No 2004-09-07 2020-01-27 US US8263580 No 2012-09-11 2028-09-27 US US8629128 No 2014-01-14 2026-05-26 US US9119781 Yes 2015-09-01 2031-12-10 US US10130640 Yes 2018-11-20 2031-12-10 US US9566286 No 2017-02-14 2031-06-10 US US10617698 No 2011-06-10 2031-06-10 US US10660908 No 2011-06-10 2031-06-10 US US10688108 No 2011-06-10 2031-06-10 US US10682364 No 2011-06-10 2031-06-10 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0135 mg/mL ALOGPS logP 4.63 ALOGPS logP 3.84 ChemAxon logS -4.5 ALOGPS pKa (Strongest Acidic) 14.39 ChemAxon pKa (Strongest Basic) -1.6 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 60.69 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 125.45 m3·mol-1 ChemAxon Polarizability 49.59 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9945 Blood Brain Barrier + 0.8426 Caco-2 permeable + 0.7643 P-glycoprotein substrate Substrate 0.7718 P-glycoprotein inhibitor I Non-inhibitor 0.7297 P-glycoprotein inhibitor II Non-inhibitor 0.9687 Renal organic cation transporter Non-inhibitor 0.813 CYP450 2C9 substrate Non-substrate 0.8383 CYP450 2D6 substrate Non-substrate 0.8975 CYP450 3A4 substrate Substrate 0.7113 CYP450 1A2 substrate Non-inhibitor 0.7455 CYP450 2C9 inhibitor Non-inhibitor 0.7898 CYP450 2D6 inhibitor Non-inhibitor 0.9336 CYP450 2C19 inhibitor Non-inhibitor 0.7994 CYP450 3A4 inhibitor Non-inhibitor 0.8014 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7475 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9332 Biodegradation Not ready biodegradable 0.9871 Rat acute toxicity 3.9699 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9198 hERG inhibition (predictor II) Non-inhibitor 0.8018
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B...
- Gene Name
- VDR
- Uniprot ID
- P11473
- Uniprot Name
- Vitamin D3 receptor
- Molecular Weight
- 48288.64 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Peroxidase activity
- Specific Function
- Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
- Gene Name
- MPO
- Uniprot ID
- P05164
- Uniprot Name
- Myeloperoxidase
- Molecular Weight
- 83867.71 Da
References
- Sato H, Ogino Y, Takagi H, Hata J, Asano S, Ohta T, Komoriya K: Pharmacological profiles of high-concentration (20 microg/g) tacalcitol ointment: effects on cutaneous inflammation, epidermal proliferation, and differentiation in mice. J Dermatol. 2003 Jul;30(7):510-24. [PubMed:12928540]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidoreductase activity
- Specific Function
- Has a role in maintaining calcium homeostasis. Catalyzes the NADPH-dependent 24-hydroxylation of calcidiol (25-hydroxyvitamin D(3)) and calcitriol (1-alpha,25-dihydroxyvitamin D(3)). The enzyme can...
- Gene Name
- CYP24A1
- Uniprot ID
- Q07973
- Uniprot Name
- 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial
- Molecular Weight
- 58874.695 Da
References
- Jones G, Byford V, West S, Masuda S, Ibrahim G, Kaufmann M, Knutson JC, Strugnell S, Mehta R: Hepatic activation and inactivation of clinically-relevant vitamin D analogs and prodrugs. Anticancer Res. 2006 Jul-Aug;26(4A):2589-95. [PubMed:16886668]
Drug created on June 13, 2005 07:24 / Updated on September 24, 2020 02:08
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