Identification
- Summary
Flurandrenolide is a corticosteroid used to treat corticosteroid-responsive dermatoses.
- Brand Names
- Cordran, Nolix
- Generic Name
- Flurandrenolide
- DrugBank Accession Number
- DB00846
- Background
A corticosteroid used topically in the treatment of various skin disorders. It is usually employed as a cream or an ointment, and is also used as a polyethylene tape with an adhesive. (From Martindale, The Extra Pharmacopoeia, 30th ed, p733)
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Flurandrenolide (DB00846)
- Weight
- Average: 436.5136
Monoisotopic: 436.226116993 - Chemical Formula
- C24H33FO6
- Synonyms
- Fludroxicortida
- Fludroxicortide
- Fludroxycortid
- Fludroxycortide
- Fludroxycortidum
- Flurandrenolide
- Flurandrenolone
- External IDs
- 33379
- Lilly 33379
Pharmacology
- Indication
For relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses, particularly dry, scaling localized lesions
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Dermatoses •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Flurandrenolide is primarily effective because of its anti-inflammatory, antipruritic, and vasoconstrictive actions.
- Mechanism of action
Flurandrenolide is a topical corticosteroid. It is normally applied to a plastic tape called Cordran. Cordran is primarily effective because of its anti-inflammatory, antipruritic, and vasoconstrictive actions. Flurandrenolide, which is slowly released from the Cordran tape, binds to the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. Cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In another words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Like other glucocorticoid agents Fluocinolone acetonide acts as a physiological antagonist to insulin by decreasing glycogenesis (formation of glycogen). It also promotes the breakdown of lipids (lipolysis), and proteins, leading to the mobilization of extrahepatic amino acids and ketone bodies. This leads to increased circulating glucose concentrations (in the blood). There is also decreased glycogen formation in the liver.
Target Actions Organism AGlucocorticoid receptor agonistHumans - Absorption
Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to those of systemically administered corticosteroids
- Volume of distribution
Not Available
- Protein binding
Corticosteroids are bound to plasma proteins in varying degrees.
- Metabolism
Primarily hepatic
- Route of elimination
Topical corticosteroids can be absorbed from normal intact skin. They are metabolized primarily in the liver and then excreted in the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Systemic absorption of topical corticosteroids has produced reversible hypothalamic-pituitary- adrenal (HPA) axis suppression, manifestations of Cushing's syndrome, hyperglycemia, and glucosuria in some patients
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Flurandrenolide can be increased when it is combined with Abametapir. Acarbose The risk or severity of hyperglycemia can be increased when Flurandrenolide is combined with Acarbose. Acetohexamide The risk or severity of hyperglycemia can be increased when Flurandrenolide is combined with Acetohexamide. Acetyldigitoxin The risk or severity of adverse effects can be increased when Flurandrenolide is combined with Acetyldigitoxin. Albiglutide The risk or severity of hyperglycemia can be increased when Flurandrenolide is combined with Albiglutide. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Drenison (Biolab) / Haelan (Typharm Limited)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cordran Ointment 0.25 mg/1g Topical Watson Pharma, Inc. 1965-10-18 2011-08-30 US 
Cordran Cream 0.25 mg/1g Topical Almirall, LLC 2018-10-12 2021-07-30 US Cordran Ointment 0.25 mg/1g Topical Aqua Pharmaceuticals, LLC. 2007-05-31 2007-05-31 US Cordran Tape 4 ug/1cm2 Topical Watson Labs 1969-07-29 2010-11-17 US Cordran Tape 4 ug/1cm2 Topical Almirall, LLC 2018-09-24 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Flurandrenolide Ointment 0.5 mg/1g Topical Mayne Pharma Inc. 2019-11-29 Not applicable US Flurandrenolide Lotion 0.5 mg/1mL Topical Padagis Israel Pharmaceuticals Ltd 2016-10-06 Not applicable US Flurandrenolide Cream 0.5 mg/1g Topical Teligent Pharma, Inc. 2016-04-13 2016-04-20 US Flurandrenolide Lotion 0.5 mg/1mL Topical Cintex Services, Llc 2016-12-22 2022-06-30 US Flurandrenolide Ointment 0.5 mg/1g Topical Teligent Pharma, Inc. 2016-12-30 Not applicable US
Categories
- ATC Codes
- D07CC03 — Fludroxycortide and antibiotics
- D07CC — Corticosteroids, potent, combinations with antibiotics
- D07C — CORTICOSTEROIDS, COMBINATIONS WITH ANTIBIOTICS
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- Drug Categories
- Adrenal Cortex Hormones
- Anti-Inflammatory Agents
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Potent (Group III)
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Dermatologicals
- Fused-Ring Compounds
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Immunosuppressive Agents
- Pregnanes
- Pregnenediones
- Pregnenes
- Steroids
- Steroids, Fluorinated
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Hydroxysteroids
- Direct Parent
- 21-hydroxysteroids
- Alternative Parents
- Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 11-beta-hydroxysteroids / 3-oxo delta-4-steroids / Halogenated steroids / Delta-4-steroids / Ketals / Cyclohexenones / 1,3-dioxolanes / Alpha-hydroxy ketones show 8 more
- Substituents
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / 6-halo-steroid / Acetal / Alcohol / Aliphatic heteropolycyclic compound show 25 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 8EUL29XUQT
- CAS number
- 1524-88-5
- InChI Key
- POPFMWWJOGLOIF-XWCQMRHXSA-N
- InChI
- InChI=1S/C24H33FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h7,13-14,16-17,19-20,26,28H,5-6,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1
- IUPAC Name
- (1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-17-en-16-one
- SMILES
- CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@@]2(O1)C(=O)CO
References
- Synthesis Reference
Casas-Campillo, C.; U.S. Patent 3,119,748; January 28, 1964; assigned to Syntex Corporation, Panama. Ringold, H.J., Zderic, J.A., Djerassi, C. and Bowers, A.; U.S. Patent 3,126,375; March 24, 1964; assigned to Syntex Corporation, Panama.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014984
- KEGG Drug
- D00328
- PubChem Compound
- 15209
- PubChem Substance
- 46505159
- ChemSpider
- 14475
- BindingDB
- 50240003
- 4500
- ChEBI
- 5127
- ChEMBL
- CHEMBL1201012
- ZINC
- ZINC000004097308
- Therapeutic Targets Database
- DAP000418
- PharmGKB
- PA164750513
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Fludroxycortide
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Continuous ambulatory peritoneal dialysis therapy / End-stage Renal Failure (ESRF) / Peritoneal dialysis therapy / Renal Failure, Chronic Renal Failure 1 2 Terminated Treatment Anorexia / Cachexia / Weight Loss 1
Pharmacoeconomics
- Manufacturers
- Watson pharmaceuticals inc
- Watson laboratories inc
- Alpharma us pharmaceuticals division
- Packagers
- Aqua Pharmaceuticals
- DPT Laboratories Ltd.
- Oclassen Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Cream Topical 0.5 mg/1g Lotion Topical 0.5 mg/1mL Ointment Topical 0.25 mg/1g Ointment Topical 0.5 mg/1g Tape Topical 4 ug/1cm2 Cream Topical 0.25 mg/1g Cream Topical Ointment Topical Tape Topical 4 mcg / sq cm - Prices
Unit description Cost Unit Cordran (80 X 3 Inch) Box Box 105.02USD box Cordran 4 mcg/sqcm Tape (24 X 3 Inch) Box 53.63USD box Cordran 0.05% lotion 4.8USD ml Cordran sp 0.05% cream 4.8USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 251 °C PhysProp water solubility Insoluble Not Available logP 0.6 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0578 mg/mL ALOGPS logP 2.02 ALOGPS logP 1.56 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 13.74 Chemaxon pKa (Strongest Basic) -2.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 93.06 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 110.79 m3·mol-1 Chemaxon Polarizability 45.51 Å3 Chemaxon Number of Rings 5 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 + 0.9796 Blood Brain Barrier + 0.9739 Caco-2 permeable + 0.5279 P-glycoprotein substrate Substrate 0.8046 P-glycoprotein inhibitor I Non-inhibitor 0.6488 P-glycoprotein inhibitor II Non-inhibitor 0.7127 Renal organic cation transporter Non-inhibitor 0.7839 CYP450 2C9 substrate Non-substrate 0.862 CYP450 2D6 substrate Non-substrate 0.8911 CYP450 3A4 substrate Substrate 0.7258 CYP450 1A2 substrate Non-inhibitor 0.9294 CYP450 2C9 inhibitor Non-inhibitor 0.9269 CYP450 2D6 inhibitor Non-inhibitor 0.9481 CYP450 2C19 inhibitor Non-inhibitor 0.9398 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9098 Ames test Non AMES toxic 0.8398 Carcinogenicity Non-carcinogens 0.934 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.2002 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9652 hERG inhibition (predictor II) Non-inhibitor 0.5679
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 210.276699 predictedDarkChem Lite v0.1.0 [M-H]- 209.423399 predictedDarkChem Lite v0.1.0 [M-H]- 205.55095 predictedDeepCCS 1.0 (2019) [M+H]+ 209.402399 predictedDarkChem Lite v0.1.0 [M+H]+ 210.673699 predictedDarkChem Lite v0.1.0 [M+H]+ 207.27467 predictedDeepCCS 1.0 (2019) [M+Na]+ 207.564299 predictedDarkChem Lite v0.1.0 [M+Na]+ 208.698199 predictedDarkChem Lite v0.1.0 [M+Na]+ 213.95103 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
- Gene Name
- NR3C1
- Uniprot ID
- P04150
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
References
- Baschant U, Tuckermann J: The role of the glucocorticoid receptor in inflammation and immunity. J Steroid Biochem Mol Biol. 2010 May 31;120(2-3):69-75. doi: 10.1016/j.jsbmb.2010.03.058. Epub 2010 Mar 24. [Article]
- Fitzgerald P, O'Brien SM, Scully P, Rijkers K, Scott LV, Dinan TG: Cutaneous glucocorticoid receptor sensitivity and pro-inflammatory cytokine levels in antidepressant-resistant depression. Psychol Med. 2006 Jan;36(1):37-43. Epub 2005 Oct 28. [Article]
- Issar M, Sahasranaman S, Buchwald P, Hochhaus G: Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids. Eur Respir J. 2006 Mar;27(3):511-6. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- NCI/NIH [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Steroid binding
- Specific Function
- Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
- Gene Name
- SERPINA6
- Uniprot ID
- P08185
- Uniprot Name
- Corticosteroid-binding globulin
- Molecular Weight
- 45140.49 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. [Article]
- 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. [Article]
- Emptoz-Bonneton A, Cousin P, Seguchi K, Avvakumov GV, Bully C, Hammond GL, Pugeat M: Novel human corticosteroid-binding globulin variant with low cortisol-binding affinity. J Clin Endocrinol Metab. 2000 Jan;85(1):361-7. [Article]
- Smith CL, Power SG, Hammond GL: A Leu----His substitution at residue 93 in human corticosteroid binding globulin results in reduced affinity for cortisol. J Steroid Biochem Mol Biol. 1992 Aug;42(7):671-6. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55