Explore a selection of our essential drug information below, or:
Identification
- Summary
Fluticasone propionate is a glucocorticoid used to treat asthma, inflammatory pruritic dermatoses, and nonallergic rhinitis.
- Brand Names
- Advair, Airduo, Airduo Respiclick, Aller-flo, Armonair, Beser, Cutivate, Dymista, Flonase, Flovent, Fluticare, Ticanase, Wixela, Xhance
- Generic Name
- Fluticasone propionate
- DrugBank Accession Number
- DB00588
- Background
Fluticasone propionate is a synthetic glucocorticoid9,10Label. These drugs are available as inhalers, nasal, sprays, and topical treatments for various inflammatory indications9,10Label. Fluticasone propionate was first approved in 19907.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Fluticasone propionate (DB00588)
- Weight
- Average: 500.571
Monoisotopic: 500.184429407 - Chemical Formula
- C25H31F3O5S
- Synonyms
- Fluticasone propionate
- External IDs
- CCI 18781
- CCI-18781
- PF-00241939
Pharmacology
- Indication
Fluticasone propionate is indicated as an inhaler for the treatment and management of asthma by prophylaxisLabelas well as inflammatory and pruritic dermatoses9. Fluticasone propionate nasal spray is indicated for managing allergic and nonallergic rhinitis8,10.
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 Adjunct therapy in treatment of Acute bacterial rhinosinusitis ••• ••••• ••••• Prophylaxis of Allergic rhinitis ••• ••••• ••••• Treatment of Allergic rhinitis •••••••••••• ••••• Used in combination to treat Allergy to mold Combination Product in combination with: Azelastine (DB00972) •••••••••••• •••••• •••••••••• Used in combination to treat Allergy; dander Combination Product in combination with: Azelastine (DB00972) •••••••••••• •••••• •••••••••• - 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
Systemically, fluticasone propionate activates glucocorticoid receptors, and inhibits lung eosinophilia in rats10Label. Fluticasone propionate as a topical formulation is also associated with vasoconstriction in the skin9,3.
- Mechanism of action
Fluticasone propionate works through an unknown mechanism to affect the action of various cell types and mediators of inflammation10. Fluticasone propionate activates glucocorticoid receptors and inhibits lung eosinophilia in rats10,9.
Target Actions Organism AGlucocorticoid receptor agonistHumans UProgesterone receptor agonistHumans UCytosolic phospholipase A2 inhibitorHumans UMineralocorticoid receptor antagonistHumans - Absorption
Intranasal bioavailability of fluticasone propionate is <2%, and oral bioavailability is <1%10Label. Intranasal exposure results in the majority of the dose being swallowed3. Topical absorption of fluticasone propionate is very low but can change depending on a number of factors including integrity of the skin and the presence of inflammation or disease9. A study of 24 healthy Caucasian males showed an inhaled bioavailability of 9.0%1.
- Volume of distribution
The volume of distribution of intravenous fluticasone propionate is 4.2L/kg10Label. A study of 24 healthy Caucasian males showed a volume of distribution at steady state of 577L following intravenous administration1.
- Protein binding
Fluticasone propionate is 99% protein bound in serum10. Topical fluticasone propionate is only 91% protein bound in serum however9.
- Metabolism
Fluticasone propionate is cleared from hepatic metabolism by cytochrome P450 3A410,4Label. Fluticasone propionate is hydrolysed at the FIVE-S-fluoromethyl carbothioate group, forming an inactive metabolite9,3Label.
Hover over products below to view reaction partners
- Route of elimination
Fluticasone propionate is mainly eliminated in the feces with <5% eliminated in the urine10,5Label.
- Half-life
7.8 hours for intravenous fluticasone propionate10Label. A study of 24 healthy Caucasian males shows a half life of 14.0 hours following intravenous administration and 10.8 hours following inhalation1.
- Clearance
1093mL/min for fluticasone propionate10. A study of 24 healthy Caucasian males showed a clearance of 63.9L/h following intravenous administration1.
- Adverse Effects
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Fluticasone propionate's use in specific populations has not been well studied10. Fluticasone propionate is not carcinogenic, mutagenic, or clastogenic, nor did it affect fertility in animal studies10Label. Subcutaneous fluticasone propionate has been shown to produce teratogenic effects in rats though oral administration does not9Label. Generally, there are no reported adverse effects with fluticasone in pregnancy6. Fluticasone propionate in human milk may cause growth suppression, effects on endogenous corticosteroid production, or other effects9,2. Pediatric patients treated with fluticasone propionate ointment experienced adrenal suppression9. Geriatric patients treated with fluticasone propionate did not show any difference in safety or efficacy compared to other patient groups, though older patients may be more sensitive to adverse effects9. There is no difference in the clearance of fluticasone propionate across genders or raceLabel. Patients with hepatic impairment should be closely monitored due to the elimination mechanismLabel5.
- 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 Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Fluticasone propionate is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Fluticasone propionate can be increased when it is combined with Abametapir. Abatacept The metabolism of Fluticasone propionate can be increased when combined with Abatacept. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Fluticasone propionate. Acalabrutinib The serum concentration of Acalabrutinib can be increased when it is combined with Fluticasone propionate. - 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
- Ezicas (Intas) / Flixonase (GlaxoSmithKline) / Flixotide (GlaxoSmithKline) / FLOVENTHFA / Flunase (GlaxoSmithKline) / Nasofan (Teva) / Pirinase (GlaxoSmithKline) / Seretide (GlaxoSmithKline)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aermony Respiclick Powder, metered 55 mcg / act Respiratory (inhalation) Teva Italia S.R.L. 2020-09-30 Not applicable Canada 
Aermony Respiclick Powder, metered 232 mcg / act Respiratory (inhalation) Teva Italia S.R.L. 2020-09-30 Not applicable Canada Aermony Respiclick Powder, metered 113 mcg / act Respiratory (inhalation) Teva Italia S.R.L. 2020-09-30 Not applicable Canada ArmonAir Digihaler Powder, metered 232 ug/1 Respiratory (inhalation) Teva Respiratory, LLC 2020-09-15 2025-09-30 US 
ArmonAir Digihaler Powder, metered 232 ug/1 Respiratory (inhalation) Teva Respiratory, LLC 2020-09-15 2025-09-30 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-fluticasone Spray, metered 50 mcg / act Nasal Apotex Corporation 2007-07-05 Not applicable Canada Apo-fluticasone HFA Aerosol, metered 50 mcg / act Respiratory (inhalation) Apotex Corporation Not applicable Not applicable Canada Apo-fluticasone HFA Aerosol, metered 250 mcg / act Respiratory (inhalation) Apotex Corporation 2021-04-26 Not applicable Canada Apo-fluticasone HFA Aerosol, metered 125 mcg / act Respiratory (inhalation) Apotex Corporation 2022-11-22 Not applicable Canada Beser Kit 0.5 mg/1mL Topical Medimetriks Pharmaceuticals, Inc. 2019-04-01 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 24 Hour Allergy Nasal Spray, metered 50 ug/1 Nasal Walgreen Company 2016-05-27 Not applicable US 24 Hour Allergy Nasal Spray, metered 50 ug/1 Nasal HYVEE INC 2016-08-08 2019-05-01 US 24 Hour Allergy Nasal Spray, metered 50 ug/1 Nasal Shopko Stores Operating Co., LLC 2016-08-23 Not applicable US 24 Hour Allergy Relief nasal Spray, metered 50 ug/1 Nasal Kroger Company 2016-05-27 Not applicable US 24 Hour Allergy Relief Nasal Spray, metered 50 ug/1 Nasal Meijer Distribution Inc 2016-11-17 2023-02-01 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image \- Fluticasone propionate (250 mcg) + Salmeterol xinafoate (50 mcg) บริษัท แกล็กโซสมิทไคล์น (ประเทศไทย) 2019-07-23 Not applicable Thailand 
ABRIFF Fluticasone propionate (50 mcg) + Formoterol fumarate (5 mcg) Aerosol; Suspension Respiratory (inhalation) Mundipharma Pharmaceuticals S.R.L. 2018-09-18 2021-02-01 Italy 
ABRIFF Fluticasone propionate (125 mcg) + Formoterol fumarate (5 mcg) Aerosol; Suspension Respiratory (inhalation) Mundipharma Pharmaceuticals S.R.L. 2018-09-18 2021-02-01 Italy ABRIFF Fluticasone propionate (125 mcg) + Formoterol fumarate (5 mcg) Aerosol; Suspension Respiratory (inhalation) Mundipharma Pharmaceuticals S.R.L. 2014-07-08 Not applicable Italy ABRIFF Fluticasone propionate (50 mcg) + Formoterol fumarate (5 mcg) Aerosol; Suspension Respiratory (inhalation) Mundipharma Pharmaceuticals S.R.L. 2018-09-18 2021-02-01 Italy - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image AIRPLUS 25/125 MCG INHALASYON ICIN OLCULU DOZLU AEROSOL 120 DOZ Fluticasone propionate (125 mcg) + Salmeterol (25 mcg) Aerosol, metered Respiratory (inhalation) Takeda Pharma A/S 2018-02-20 Not applicable Turkey 
Cenovia Fluticasone propionate (0.025 g/0.025g) + Hydroquinone (2 g/2g) + Tretinoin (0.025 g/0.025g) Kit Topical Accumix Pharmaceuticals 2014-12-15 2015-07-17 US Fluticasone Propionate 0.05% / Niacinamide 4% Fluticasone propionate (0.05 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-14 Not applicable US Ticanase Fluticasone propionate (50 ug/1) Kit Nasal PureTek Corporation 2016-01-11 Not applicable US Validerm Fluticasone propionate (0.05 g/0.05g) + Calcitriol (0.2 mg/0.2mg) + Tacrolimus hydrate (0.05 g/0.05g) Kit Topical Accumix Pharmaceuticals 2014-12-15 2015-07-17 US
Categories
- Drug Categories
- Adrenal Cortex Hormones
- Adrenals
- Agents to Treat Airway Disease
- Androstadienes
- Androstanes
- Androstenes
- Anti-Allergic Agents
- Anti-Asthmatic Agents
- Anti-Inflammatory Agents
- Autonomic Agents
- Bronchodilator Agents
- Central Nervous System Depressants
- Corticosteroids
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Potent (Group III)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strong)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Fused-Ring Compounds
- Glucocorticoids
- Immunosuppressive Agents
- OATP1B1/SLCO1B1 Inhibitors
- P-glycoprotein substrates
- Peripheral Nervous System Agents
- Respiratory System Agents
- Steroids
- Thyroxine-binding globulin inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Steroid esters
- Direct Parent
- Steroid esters
- Alternative Parents
- Androgens and derivatives / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Thioesters / Secondary alcohols / Carbothioic S-esters / Carboxylic acid esters / Cyclic alcohols and derivatives show 8 more
- Substituents
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 6-halo-steroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl fluoride / Alkyl halide show 28 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- thioester, propanoate ester, 11beta-hydroxy steroid, steroid ester, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, corticosteroid (CHEBI:31441)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- O2GMZ0LF5W
- CAS number
- 80474-14-2
- InChI Key
- WMWTYOKRWGGJOA-CENSZEJFSA-N
- InChI
- InChI=1S/C25H31F3O5S/c1-5-20(31)33-25(21(32)34-12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15+,16+,18+,19+,22+,23+,24+,25+/m1/s1
- IUPAC Name
- (1R,2R,3aS,3bS,5S,9aS,9bR,10S,11aS)-5,9b-difluoro-1-{[(fluoromethyl)sulfanyl]carbonyl}-10-hydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl propanoate
- SMILES
- [H][C@@]12C[C@@H](C)[C@](OC(=O)CC)(C(=O)SCF)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C
References
- Synthesis Reference
Joseph Kaspi, Oded Arad, Michael Brand, Moty Shookrun, Simona Malka, Mohammed Alnabari, Shalom Hazan, Vlado Malesevic, "Synthesis and powder preparation of fluticasone propionate." U.S. Patent US20060009435, issued January 12, 2006.
US20060009435- General References
- Allen A, Bareille PJ, Rousell VM: Fluticasone furoate, a novel inhaled corticosteroid, demonstrates prolonged lung absorption kinetics in man compared with inhaled fluticasone propionate. Clin Pharmacokinet. 2013 Jan;52(1):37-42. doi: 10.1007/s40262-012-0021-x. [Article]
- Allen A, Schenkenberger I, Trivedi R, Cole J, Hicks W, Gul N, Jacques L: Inhaled fluticasone furoate/vilanterol does not affect hypothalamic-pituitary-adrenal axis function in adolescent and adult asthma: randomised, double-blind, placebo-controlled study. Clin Respir J. 2013 Oct;7(4):397-406. doi: 10.1111/crj.12026. Epub 2013 Jun 5. [Article]
- Phillipps GH: Structure-activity relationships of topically active steroids: the selection of fluticasone propionate. Respir Med. 1990 Nov;84 Suppl A:19-23. [Article]
- Harding SM: The human pharmacology of fluticasone propionate. Respir Med. 1990 Nov;84 Suppl A:25-9. [Article]
- Crim C, Pierre LN, Daley-Yates PT: A review of the pharmacology and pharmacokinetics of inhaled fluticasone propionate and mometasone furoate. Clin Ther. 2001 Sep;23(9):1339-54. [Article]
- Choi JS, Han JY, Kim MY, Velazquez-Armenta EY, Nava-Ocampo AA: Pregnancy outcomes in women using inhaled fluticasone during pregnancy: a case series. Allergol Immunopathol (Madr). 2007 Nov-Dec;35(6):239-42. [Article]
- FDA Approved Drug Products December 1990 [Link]
- FDA Approved Drugs: Dymista nasal spray [Link]
- Fluticasone Propionate (Cutivate) Ointment FDA Label [File]
- Fluticasone Propionate (Flonase) Nasal Spray FDA Label [File]
- External Links
- Human Metabolome Database
- HMDB0005036
- KEGG Drug
- D01708
- PubChem Compound
- 444036
- PubChem Substance
- 46506140
- ChemSpider
- 392059
- BindingDB
- 50354849
- 50121
- ChEBI
- 31441
- ChEMBL
- CHEMBL1473
- ZINC
- ZINC000003920027
- Therapeutic Targets Database
- DAP001039
- PharmGKB
- PA449686
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Fluticasone_propionate
- FDA label
- Download (651 KB)
- MSDS
- Download (53.4 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Diagnostic Chronic Sinusitis 1 somestatus stop reason just information to hide Not Available Available Not Available Eosinophilic Esophagitis 1 somestatus stop reason just information to hide Not Available Completed Not Available Allergic Rhinitis (AR) 1 somestatus stop reason just information to hide Not Available Completed Not Available Asthma 14 somestatus stop reason just information to hide Not Available Completed Not Available Asthma / Atopy 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Glaxosmithkline
- Glaxo group ltd dba glaxosmithkline
- Altana inc
- G and w laboratories inc
- Kv pharmaceutical co
- Perrigo new york inc
- Tolmar inc
- Nycomed us inc
- Taro pharmaceutical industries ltd
- Apotex inc richmond hill
- Hi tech pharmacal co inc
- Roxane laboratories inc
- Packagers
- Apotex Inc.
- A-S Medication Solutions LLC
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- E. Fougera and Co.
- G & W Labs
- GlaxoSmithKline Inc.
- Hi Tech Pharmacal Co. Inc.
- Letco Medical Inc.
- Nycomed Inc.
- Palmetto Pharmaceuticals Inc.
- Penn Labs
- Perrigo Co.
- Pharmaderm
- Physicians Total Care Inc.
- Professional Co.
- Promex Medical Inc.
- Rebel Distributors Corp.
- Redpharm Drug
- Roxane Labs
- Sandoz
- Stat Scripts LLC
- Taro Pharmaceuticals USA
- Tolmar Inc.
- Dosage Forms
Form Route Strength Powder Oral; Respiratory (inhalation) Powder Respiratory (inhalation) Aerosol, metered Respiratory (inhalation) Powder, metered Respiratory (inhalation) 113 mcg / act Powder, metered Respiratory (inhalation) 232 mcg / act Powder, metered Respiratory (inhalation) 55 mcg / act Aerosol Respiratory (inhalation) Aerosol Respiratory (inhalation) 100 cg Gas Respiratory (inhalation) Powder, metered Respiratory (inhalation) 0.500 mg Aerosol; suspension Respiratory (inhalation) Suspension Intrasinal; Nasal Spray, metered Nasal 50 mcg / act Spray, metered Nasal 0.05 G/100G Powder, metered Respiratory (inhalation) 113 ug/1 Powder, metered Respiratory (inhalation) 232 ug/1 Powder, metered Respiratory (inhalation) 55 ug/1 Suspension Nasal 50.000 mcg Kit Topical 0.5 mg/1mL Lotion Topical 0.5 mg/1mL Suspension Respiratory (inhalation) 0.5 mg/2ml Powder Buccal 0.012 mg Cream Cutaneous 0.050 g Cream Topical 0.05 % Cream Topical 0.05 % w/w Spray Nasal 50 mcg/100mg Spray, metered Nasal Spray, suspension Respiratory (inhalation) Spray, suspension Respiratory (inhalation) 50 mcg Suspension Nasal Aerosol Buccal 2.9410 mg Suspension Respiratory (inhalation) 2 mg/2ml Suspension Respiratory (inhalation) 0.208 % w/w Suspension Respiratory (inhalation) 0.417 % w/w Solution Respiratory (inhalation) 125 mcg Solution Respiratory (inhalation) Solution Respiratory (inhalation) 50 mcg Suspension Respiratory (inhalation) 0.05 g Spray Nasal 0.05 % Spray Nasal 0.05 %w/w Spray Nasal 0.05 % w/w Solution / drops Nasal 400 mcg Suspension Nasal; Respiratory (inhalation) 400 cg Aerosol Buccal 0.830 mg Aerosol Respiratory (inhalation) 0.5 mg Aerosol; solution Respiratory (inhalation) 50 mcg Powder Respiratory (inhalation) 0.8 g Powder Respiratory (inhalation) 2 g Powder Respiratory (inhalation) 50 mcg Powder Respiratory (inhalation) 500 Mikrogramm Powder Respiratory (inhalation) 100 Mikrogramm Powder Respiratory (inhalation) 250 Mikrogramm Aerosol, spray Respiratory (inhalation) 125 mcg Aerosol, spray Respiratory (inhalation) 250 mcg Aerosol, spray Respiratory (inhalation) 50 mcg Aerosol, metered Respiratory (inhalation) 250 Mikrogramm Aerosol Respiratory (inhalation) 0.2941 g Aerosol Respiratory (inhalation) 0.0588 g Aerosol, metered Respiratory (inhalation) 25 mcg Aerosol, metered Respiratory (inhalation) 50 mg Aerosol, metered Respiratory (inhalation) 50 Mikrogramm Suspension Respiratory (inhalation) 2.000 mg Solution Respiratory (inhalation) 0.5 mg/2ml Aerosol, metered Respiratory (inhalation) 125 Mikrogramm Aerosol Respiratory (inhalation) 0.17 % w/v Suspension Respiratory (inhalation) 0.5 mg Suspension Respiratory (inhalation) 0.083 % w/w Suspension Respiratory (inhalation) 0.25 mg Suspension Respiratory (inhalation) Suspension Buccal Suspension Respiratory (inhalation) 125 mcg Spray, metered Respiratory (inhalation) 125 mcg Suspension Respiratory (inhalation) 50 mcg Spray, metered Nasal 50 mcg Aerosol, metered; suspension Nasal 50 mcg / act Aerosol, metered Respiratory (inhalation) 110 ug/1 Aerosol, metered Respiratory (inhalation) 220 ug/1 Aerosol, metered Respiratory (inhalation) 44 ug/1 Powder Respiratory (inhalation) 100 ug/1 Powder Respiratory (inhalation) 250 ug/1 Powder Respiratory (inhalation) 50 ug/1 Powder Respiratory (inhalation) 100 mcg / act Powder Respiratory (inhalation) 250 mcg / act Powder Respiratory (inhalation) 50 mcg / blister Powder Respiratory (inhalation) 500 mcg / act Powder, metered Respiratory (inhalation) 100 ug/1 Powder, metered Respiratory (inhalation) 250 ug/1 Powder, metered Respiratory (inhalation) 50 ug/1 Aerosol, metered Respiratory (inhalation) 125 mcg / act Aerosol, metered Respiratory (inhalation) 250 mcg / act Aerosol, metered Respiratory (inhalation) 50 mcg / act Aerosol, metered Respiratory (inhalation) 25 mcg / act Suspension Buccal; Respiratory (inhalation) Solution Oral; Respiratory (inhalation) 20 mg Solution Respiratory (inhalation) 0.062 % w/w Cream Topical 0.05 g Suspension Respiratory (inhalation) 5 mg Suspension Respiratory (inhalation) 14.175 mg Aerosol, metered Respiratory (inhalation) 125 mcg Aerosol, metered Respiratory (inhalation) 250 mcg Aerosol, metered Respiratory (inhalation) 50 mcg Aerosol; suspension Respiratory (inhalation) 50 mcg Aerosol, powder Respiratory (inhalation) Aerosol; suspension Respiratory (inhalation) 125 mcg Aerosol; suspension Respiratory (inhalation) 250 mcg Powder Respiratory (inhalation) 100 mcg Powder Respiratory (inhalation) 250 mcg Powder Respiratory (inhalation) 500 mcg Capsule Respiratory (inhalation) Aerosol; aerosol, metered Respiratory (inhalation) Spray Nasal 50 UG Gas Respiratory (inhalation) 125 UG Gas Respiratory (inhalation) 250 UG Aerosol Respiratory (inhalation) 0.05 mg Spray, suspension Nasal 50 mcg Cream Topical 0.5 mg/1 Cream Topical 0.5 mg/1g Ointment Topical 0.05 mg/1g Spray, metered Nasal 50 ug/0.1g Spray, metered Nasal 50 ug/1 Cream Topical Powder, metered Respiratory (inhalation) Powder Respiratory (inhalation) Aerosol, metered Respiratory (inhalation) Powder Respiratory (inhalation) 250 UG Powder Respiratory (inhalation) 500 UG Suspension Respiratory (inhalation) 0.07 g Powder Respiratory (inhalation) 50 ug Powder Respiratory (inhalation) 100 µg Gas Respiratory (inhalation) 50 µg Spray Nasal 50 µg Suspension Respiratory (inhalation) Aerosol, spray Respiratory (inhalation) Suspension Oral; Respiratory (inhalation) Aerosol Buccal 0.062 g Aerosol Respiratory (inhalation) 0.05 % w/v Spray Nasal 50 mcg Spray Nasal Solution Respiratory (inhalation) 0.125 mg Suspension Nasal 0.500 mg Aerosol Respiratory (inhalation) 125 cg Aerosol Respiratory (inhalation) 0.4167 g Suspension Respiratory (inhalation) 50 cg Cream 0.05 % Solution / drops Nasal 0.1 % Suspension Intrasinal; Nasal 0.05 g Solution Intrasinal; Nasal 50 mg Suspension Intrasinal; Nasal 50 mg Powder, metered Respiratory (inhalation) 100 mcg Powder, metered Respiratory (inhalation) 250 mcg Powder, metered Respiratory (inhalation) 500 mcg Ointment Cutaneous Aerosol Respiratory (inhalation) 250 mcg Powder, metered Respiratory (inhalation) 100 mcg/inhalation Powder, metered Respiratory (inhalation) 250 mcg/inhalation Powder, metered Respiratory (inhalation) 500 mcg/inhalation Aerosol Buccal Aerosol, spray Respiratory (inhalation) 125 mcg Aerosol, spray Respiratory (inhalation) 250 mcg Aerosol, spray Respiratory (inhalation) 50 mcg Powder Buccal 0.0725 mg Spray Nasal Kit Nasal 50 ug/1 Spray Nasal 50 ug/1 Powder Buccal Kit Topical Spray, metered Nasal 93 ug/1 Spray, suspension Nasal 50 mcg/1dose Spray, suspension Nasal - Prices
Unit description Cost Unit Fluticasone propionate powder 1500.0USD g Cutivate 0.05% Lotion 120ml Bottle 454.6USD bottle Advair Diskus 60 500-50 mcg/dose Aerosol Disp Pack 328.14USD disp Advair Diskus 60 250-50 mcg/dose Aerosol Disp Pack 249.48USD disp Flovent HFA 220 mcg/act Aerosol 12 gm Inhaler 237.67USD inhaler Cutivate 0.05% Cream 60 gm Tube 217.11USD tube Advair Diskus 60 100-50 mcg/dose Aerosol Disp Pack 200.79USD disp Advair Diskus 14 500-50 mcg/dose Aerosol Disp Pack 156.64USD disp Flovent HFA 110 mcg/act Aerosol 12 gm Inhaler 153.01USD inhaler Cutivate 0.005% Ointment 60 gm Tube 128.28USD tube Flovent HFA 44 mcg/act Aerosol 10.6 gm Inhaler 114.27USD inhaler Flovent Diskus 60 50 mcg/blist Aerosol Inhaler 104.74USD inhaler Flonase 50 mcg/act Suspension 16 gm Bottle 94.59USD bottle Fluticasone Propionate 50 mcg/act Suspension 16 gm Bottle 78.28USD bottle Cutivate 0.05% Cream 30 gm Tube 62.99USD tube Fluticasone Propionate 0.005% Ointment 60 gm Tube 56.27USD tube Fluticasone Propionate 0.05% Cream 60 gm Tube 56.27USD tube Cutivate 0.005% Ointment 30 gm Tube 44.99USD tube Fluticasone Propionate 0.005% Ointment 30 gm Tube 35.67USD tube Fluticasone Propionate 0.05% Cream 30 gm Tube 35.67USD tube Cutivate 0.005% Ointment 15 gm Tube 32.99USD tube Cutivate 0.05% Cream 15 gm Tube 32.99USD tube Advair hfa 230-21 mcg inhaler 25.04USD g Fluticasone Propionate 0.005% Ointment 15 gm Tube 23.14USD tube Fluticasone Propionate 0.05% Cream 15 gm Tube 23.14USD tube Advair hfa 115-21 mcg inhaler 18.13USD g Flovent hfa 220 mcg inhaler 15.54USD g Advair hfa 45-21 mcg inhaler 14.59USD g Flovent hfa 110 mcg inhaler 12.26USD g Flovent hfa 44 mcg inhaler 10.99USD g Flonase 0.05% nasal spray 5.68USD g Advair 500-50 diskus 5.26USD each Advair 250-50 diskus 4.0USD each Cutivate 0.05% cream 3.48USD g Advair 100-50 diskus 3.22USD each Flovent 250 mcg diskus 2.45USD each Flovent 100 mcg diskus 1.83USD each Flovent 50 mcg diskus 1.74USD each Flovent Diskus 500 mcg/dose Metered Inhalation Powder 1.55USD dose Flovent Diskus 250 mcg/dose Metered Inhalation Powder 0.77USD dose Flovent Hfa 250 mcg/dose Metered Dose Aerosol 0.77USD dose Flovent Hfa 125 mcg/dose Metered Dose Aerosol 0.39USD dose Flovent Hfa 50 mcg/dose Metered Dose Aerosol 0.22USD dose DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region USRE40045 No 2008-02-05 2010-09-07 US CA2317999 No 2004-11-09 2020-09-11 Canada CA2125667 No 2000-03-13 2012-12-04 Canada US5873360 Yes 1999-02-23 2016-08-23 US US6446627 No 2002-09-10 2017-12-18 US US6743413 Yes 2004-06-01 2021-12-01 US US6938796 Yes 2005-09-06 2018-07-16 US US6997349 Yes 2006-02-14 2018-07-16 US US6431168 Yes 2002-08-13 2018-12-08 US US7107986 Yes 2006-09-19 2018-12-06 US US7500444 Yes 2009-03-10 2026-08-26 US US6315173 Yes 2001-11-13 2018-06-23 US US7143908 Yes 2006-12-05 2018-07-16 US US6170717 Yes 2001-01-09 2018-06-23 US US7350676 Yes 2008-04-01 2019-02-24 US US7832351 Yes 2010-11-16 2023-12-19 US US6161724 Yes 2000-12-19 2018-07-16 US US6510969 Yes 2003-01-28 2018-06-23 US US6966467 Yes 2005-11-22 2018-06-23 US US6435372 Yes 2002-08-20 2018-07-16 US US7300669 No 2007-11-27 2019-10-20 US US8163723 Yes 2012-04-24 2024-02-29 US US9259428 Yes 2016-02-16 2023-12-13 US US8168620 Yes 2012-05-01 2026-08-24 US US6871646 No 2005-03-29 2021-06-23 US US8978966 Yes 2015-03-17 2032-07-13 US US6701917 No 2004-03-09 2021-06-23 US US7540282 Yes 2009-06-02 2023-11-06 US US6748947 No 2004-06-15 2021-06-23 US US8006690 No 2011-08-30 2021-06-23 US US6718972 No 2004-04-13 2021-06-23 US US9216260 Yes 2015-12-22 2031-12-28 US US8651103 Yes 2014-02-18 2028-09-26 US US8327844 No 2012-12-11 2023-10-03 US US7975690 No 2011-07-12 2025-08-18 US US6715485 No 2004-04-06 2020-03-03 US US8550073 No 2013-10-08 2029-10-22 US US8978647 No 2015-03-17 2030-12-06 US US9463288 Yes 2016-10-11 2025-11-19 US US8714149 Yes 2014-05-06 2032-08-25 US US9616024 Yes 2017-04-11 2025-03-01 US US9066957 Yes 2015-06-30 2035-04-06 US US9415008 Yes 2016-08-16 2035-04-06 US US9731087 Yes 2017-08-15 2031-11-18 US US9072857 No 2015-07-07 2021-04-10 US US9468727 No 2016-10-18 2020-07-30 US US8522778 No 2013-09-03 2022-05-11 US US8555878 No 2013-10-15 2020-03-20 US US9901585 No 2018-02-27 2023-06-13 US US9861771 No 2018-01-09 2020-10-11 US US9987229 Yes 2018-06-05 2025-03-01 US US10022510 Yes 2018-07-17 2031-11-18 US US10076615 No 2018-09-18 2029-07-30 US US10076614 No 2018-09-18 2034-10-20 US US10124132 No 2018-11-13 2027-03-06 US US10124131 Yes 2018-11-13 2031-11-18 US US9782550 Yes 2017-10-10 2036-02-28 US US9782551 Yes 2017-10-10 2036-02-28 US US10179216 No 2019-01-15 2033-07-08 US US10195375 Yes 2019-02-05 2031-08-14 US US10252010 No 2019-04-09 2031-02-07 US US10300229 No 2019-05-28 2035-07-07 US US10478574 No 2019-11-19 2033-11-04 US US10569034 Yes 2020-02-25 2037-02-16 US US10561808 Yes 2020-02-18 2032-07-01 US US10765820 Yes 2020-09-08 2025-11-19 US US10918816 Yes 2021-02-16 2036-06-14 US US11000653 Yes 2021-05-11 2039-06-18 US US11033696 No 2021-06-15 2033-05-20 US US11173259 Yes 2021-11-16 2041-01-06 US US11266796 Yes 2021-08-22 2041-08-22 US US11344685 Yes 2020-03-26 2040-03-26 US US11351317 Yes 2018-08-10 2038-08-10 US US11357935 Yes 2019-03-24 2039-03-24 US US11439777 Yes 2020-11-24 2040-11-24 US US11464923 Yes 2020-12-19 2040-12-19 US US11554229 No 2016-02-23 2036-02-23 US US11602603 No 2008-10-27 2028-10-27 US US11969544 Yes 2020-02-20 2040-02-20 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 261-273 °C [MSDS] water solubility Insoluble [MSDS] logP 2.78 [MSDS] - Predicted Properties
Property Value Source Water Solubility 0.0114 mg/mL ALOGPS logP 3.69 ALOGPS logP 3.72 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 13.61 Chemaxon pKa (Strongest Basic) -3.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 80.67 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 121.65 m3·mol-1 Chemaxon Polarizability 49.29 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9964 Blood Brain Barrier + 0.9701 Caco-2 permeable + 0.5417 P-glycoprotein substrate Substrate 0.7099 P-glycoprotein inhibitor I Inhibitor 0.7192 P-glycoprotein inhibitor II Non-inhibitor 0.8636 Renal organic cation transporter Non-inhibitor 0.8689 CYP450 2C9 substrate Non-substrate 0.868 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.7407 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Inhibitor 0.8988 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682 Ames test Non AMES toxic 0.798 Carcinogenicity Non-carcinogens 0.8901 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.3753 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.99 hERG inhibition (predictor II) Non-inhibitor 0.6125
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 219.2258571 predictedDarkChem Lite v0.1.0 [M-H]- 209.7664 predictedDeepCCS 1.0 (2019) [M+H]+ 218.9559571 predictedDarkChem Lite v0.1.0 [M+H]+ 211.66183 predictedDeepCCS 1.0 (2019) [M+Na]+ 218.9665571 predictedDarkChem Lite v0.1.0 [M+Na]+ 218.35823 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for glucocorticoids (GC) (PubMed:27120390, PubMed:37478846). 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 modulator of other transcription factors (PubMed:28139699). Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Involved in chromatin remodeling (PubMed:9590696). Plays a role in rapid mRNA degradation by binding to the 5' UTR of target mRNAs and interacting with PNRC2 in a ligand-dependent manner which recruits the RNA helicase UPF1 and the mRNA-decapping enzyme DCP1A, leading to RNA decay (PubMed:25775514). Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth (By similarity)
- Specific Function
- core promoter sequence-specific DNA binding
- Gene Name
- NR3C1
- Uniprot ID
- P04150
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
References
- Andersson O, Cassel TN, Gronneberg R, Bronnegard M, Stierna P, Nord M: In vivo modulation of glucocorticoid receptor mRNA by inhaled fluticasone propionate in bronchial mucosa and blood lymphocytes in subjects with mild asthma. J Allergy Clin Immunol. 1999 Apr;103(4):595-600. [Article]
- Lumry WR: A review of the preclinical and clinical data of newer intranasal steroids used in the treatment of allergic rhinitis. J Allergy Clin Immunol. 1999 Oct;104(4 Pt 1):S150-8. [Article]
- Zhang X, Moilanen E, Kankaanranta H: Beclomethasone, budesonide and fluticasone propionate inhibit human neutrophil apoptosis. Eur J Pharmacol. 2001 Nov 23;431(3):365-71. [Article]
- Hogger P, Rohdewald P: Binding kinetics of fluticasone propionate to the human glucocorticoid receptor. Steroids. 1994 Oct;59(10):597-602. [Article]
- Johnson M: Fluticasone propionate: safety profile. Cutis. 1996 Feb;57(2 Suppl):10-2. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Depending on the isoform, progesterone receptor functions as a transcriptional activator or repressor
- Specific Function
- ATPase binding
- Gene Name
- PGR
- Uniprot ID
- P06401
- Uniprot Name
- Progesterone receptor
- Molecular Weight
- 98979.96 Da
References
- 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]
- Austin RJ, Maschera B, Walker A, Fairbairn L, Meldrum E, Farrow SN, Uings IJ: Mometasone furoate is a less specific glucocorticoid than fluticasone propionate. Eur Respir J. 2002 Dec;20(6):1386-92. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Has primarily calcium-dependent phospholipase and lysophospholipase activities, with a major role in membrane lipid remodeling and biosynthesis of lipid mediators of the inflammatory response (PubMed:10358058, PubMed:14709560, PubMed:16617059, PubMed:17472963, PubMed:18451993, PubMed:27642067, PubMed:7794891, PubMed:8619991, PubMed:8702602, PubMed:9425121). Plays an important role in embryo implantation and parturition through its ability to trigger prostanoid production (By similarity). Preferentially hydrolyzes the ester bond of the fatty acyl group attached at sn-2 position of phospholipids (phospholipase A2 activity) (PubMed:10358058, PubMed:17472963, PubMed:18451993, PubMed:7794891, PubMed:8619991, PubMed:9425121). Selectively hydrolyzes sn-2 arachidonoyl group from membrane phospholipids, providing the precursor for eicosanoid biosynthesis via the cyclooxygenase pathway (PubMed:10358058, PubMed:17472963, PubMed:18451993, PubMed:7794891, PubMed:9425121). In an alternative pathway of eicosanoid biosynthesis, hydrolyzes sn-2 fatty acyl chain of eicosanoid lysophopholipids to release free bioactive eicosanoids (PubMed:27642067). Hydrolyzes the ester bond of the fatty acyl group attached at sn-1 position of phospholipids (phospholipase A1 activity) only if an ether linkage rather than an ester linkage is present at the sn-2 position. This hydrolysis is not stereospecific (PubMed:7794891). Has calcium-independent phospholipase A2 and lysophospholipase activities in the presence of phosphoinositides (PubMed:12672805). Has O-acyltransferase activity. Catalyzes the transfer of fatty acyl chains from phospholipids to a primary hydroxyl group of glycerol (sn-1 or sn-3), potentially contributing to monoacylglycerol synthesis (PubMed:7794891)
- Specific Function
- calcium ion binding
- Gene Name
- PLA2G4A
- Uniprot ID
- P47712
- Uniprot Name
- Cytosolic phospholipase A2
- Molecular Weight
- 85238.2 Da
References
- Sano A, Munoz NM, Sano H, Choi J, Zhu X, Jacobs B, Leff AR: Inhibition of cPLA2 translocation and leukotriene C4 secretion by fluticasone propionate in exogenously activated human eosinophils. Am J Respir Crit Care Med. 1999 Jun;159(6):1903-9. [Article]
- Myo S, Zhu X, Myou S, Meliton AY, Liu J, Boetticher E, Lambertino AT, Xu C, Munoz NM, Leff AR: Additive blockade of beta 2-integrin adhesion of eosinophils by salmeterol and fluticasone propionate. Eur Respir J. 2004 Apr;23(4):511-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels
- Specific Function
- DNA-binding transcription factor activity
- Gene Name
- NR3C2
- Uniprot ID
- P08235
- Uniprot Name
- Mineralocorticoid receptor
- Molecular Weight
- 107080.615 Da
References
- Austin RJ, Maschera B, Walker A, Fairbairn L, Meldrum E, Farrow SN, Uings IJ: Mometasone furoate is a less specific glucocorticoid than fluticasone propionate. Eur Respir J. 2002 Dec;20(6):1386-92. [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
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Pearce RE, Leeder JS, Kearns GL: Biotransformation of fluticasone: in vitro characterization. Drug Metab Dispos. 2006 Jun;34(6):1035-40. Epub 2006 Mar 24. [Article]
- Murai T, Reilly CA, Ward RM, Yost GS: The inhaled glucocorticoid fluticasone propionate efficiently inactivates cytochrome P450 3A5, a predominant lung P450 enzyme. Chem Res Toxicol. 2010 Aug 16;23(8):1356-64. doi: 10.1021/tx100124k. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins during embryogenesis (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone, DHEA), a precursor in the biosynthesis of androgen and estrogen steroid hormones (PubMed:17178770, PubMed:9555064). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1), particularly D-ring hydroxylated estrone at the C16-alpha position (PubMed:12865317, PubMed:14559847). Mainly hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in atRA clearance during fetal development (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics including anticonvulsants (PubMed:9555064)
- Specific Function
- all-trans retinoic acid 18-hydroxylase activity
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57469.95 Da
References
- Pearce RE, Leeder JS, Kearns GL: Biotransformation of fluticasone: in vitro characterization. Drug Metab Dispos. 2006 Jun;34(6):1035-40. Epub 2006 Mar 24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Pearce RE, Leeder JS, Kearns GL: Biotransformation of fluticasone: in vitro characterization. Drug Metab Dispos. 2006 Jun;34(6):1035-40. Epub 2006 Mar 24. [Article]
- Murai T, Reilly CA, Ward RM, Yost GS: The inhaled glucocorticoid fluticasone propionate efficiently inactivates cytochrome P450 3A5, a predominant lung P450 enzyme. Chem Res Toxicol. 2010 Aug 16;23(8):1356-64. doi: 10.1021/tx100124k. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10358072, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (dehydroepiandrosterone 3-sulfate, 17-beta-glucuronosyl estradiol, and estrone 3-sulfate), as well as eicosanoids (prostaglandin E2, thromboxane B2, leukotriene C4, and leukotriene E4), and thyroid hormones (T4/L-thyroxine, and T3/3,3',5'-triiodo-L-thyronine) (PubMed:10358072, PubMed:10601278, PubMed:10873595, PubMed:11159893, PubMed:12196548, PubMed:12568656, PubMed:15159445, PubMed:15970799, PubMed:16627748, PubMed:17412826, PubMed:19129463, PubMed:26979622). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Involved in the clearance of endogenous and exogenous substrates from the liver (PubMed:10358072, PubMed:10601278). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins), such as pravastatin and pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:10601278, PubMed:15159445, PubMed:15970799). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drug methotrexate (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748). Shows a pH-sensitive substrate specificity towards prostaglandin E2 and T4 which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- FDA reports [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species
- Specific Function
- serine-type endopeptidase inhibitor activity
- Gene Name
- SERPINA6
- Uniprot ID
- P08185
- Uniprot Name
- Corticosteroid-binding globulin
- Molecular Weight
- 45140.49 Da
References
- Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- FDA reports [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10358072, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (dehydroepiandrosterone 3-sulfate, 17-beta-glucuronosyl estradiol, and estrone 3-sulfate), as well as eicosanoids (prostaglandin E2, thromboxane B2, leukotriene C4, and leukotriene E4), and thyroid hormones (T4/L-thyroxine, and T3/3,3',5'-triiodo-L-thyronine) (PubMed:10358072, PubMed:10601278, PubMed:10873595, PubMed:11159893, PubMed:12196548, PubMed:12568656, PubMed:15159445, PubMed:15970799, PubMed:16627748, PubMed:17412826, PubMed:19129463, PubMed:26979622). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Involved in the clearance of endogenous and exogenous substrates from the liver (PubMed:10358072, PubMed:10601278). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins), such as pravastatin and pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:10601278, PubMed:15159445, PubMed:15970799). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drug methotrexate (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748). Shows a pH-sensitive substrate specificity towards prostaglandin E2 and T4 which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- FDA reports [Link]
Drug created at June 13, 2005 13:24 / Updated at October 29, 2024 18:03