FLUTICASONE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H27F3O4S
Molecular Weight	444.508
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)SCF

InChI

InChIKey=MGNNYOODZCAHBA-GQKYHHCASA-N

InChI=1S/C22H27F3O4S/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-19(15,2)21(14,25)17(27)9-20(13,3)22(11,29)18(28)30-10-23/h4-5,7,11,13-14,16-17,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H27F3O4S
Molecular Weight	444.508
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29999824 | https://www.ncbi.nlm.nih.gov/pubmed/29999836 |

Fluticasone is a medium-potency synthetic trifluorinated corticosteroid which is used in some countries to manage nasal symptoms of allergic and non-allergic rhinitis. Fluticasone binds and activates glucocorticoid receptor, resulting in the activation of lipocortin. Lipocortin, in turn, inhibits cytosolic phospholipase A2, which triggers a cascade of reactions involved in the synthesis of inflammatory mediators, such as prostaglandins and leukotrienes. Both the furoate and propanoate esters, fluticasone furoate and fluticasone propionate, are much more commonly used as topical anti-inflammatories and inhaled corticosteroids.

Approval Year

C_max

Value	Dose	Co-administered	Analyte	Population
0.09 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9551705/	0.25 mg single, respiratory dose: 0.25 mg route of administration: Respiratory experiment type: SINGLE co-administered:		FLUTICASONE PROPIONATE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.15 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9551705/	0.5 mg single, respiratory dose: 0.5 mg route of administration: Respiratory experiment type: SINGLE co-administered:		FLUTICASONE PROPIONATE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
0.69 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9551705/	0.25 mg single, respiratory dose: 0.25 mg route of administration: Respiratory experiment type: SINGLE co-administered:		FLUTICASONE PROPIONATE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.47 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9551705/	0.5 mg single, respiratory dose: 0.5 mg route of administration: Respiratory experiment type: SINGLE co-administered:		FLUTICASONE PROPIONATE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9551705/	0.25 mg single, respiratory dose: 0.25 mg route of administration: Respiratory experiment type: SINGLE co-administered:		FLUTICASONE PROPIONATE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9551705/	0.5 mg single, respiratory dose: 0.5 mg route of administration: Respiratory experiment type: SINGLE co-administered:		FLUTICASONE PROPIONATE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.7% EXPERIMENT https://www.jacionline.org/article/S0091-6749(04)03286-5/fulltext	unknown, unknown		FLUTICASONE PROPIONATE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

PubMed

Title	Date	PubMed
Symptomatic adrenal insufficiency during inhaled corticosteroid treatment.	2001-10	11567945
Intracranial hypertension and nasal fluticasone propionate.	2001-09-22	11566840
Treatment update: nonallergic rhinitis.	2001-09-13	11552668
Comparison of fluticasone propionate-salmeterol combination therapy and montelukast in patients who are symptomatic on short-acting beta(2)-agonists alone.	2001-09-01	11549529
Dual components of optimal asthma therapy: scientific and clinical rationale for the use of long-acting beta-agonists with inhaled corticosteroids.	2001-09	11575039
Comparison of prevalence, cost, and outcomes of a combination of salmeterol and fluticasone therapy to common asthma treatments.	2001-09	11570024
Improved safety with equivalent asthma control in adults with chronic severe asthma on high-dose fluticasone propionate.	2001-09	11555383
Inhaled steroids for COPD?	2001-09	11514699
The penetration of 0.005% fluticasone propionate ointment in eyelid skin.	2001-09	11511836
A comparison of short-term treatment with inhaled fluticasone propionate and zafirlukast for patients with persistent asthma.	2001-08-15	11530030
Dose-response relation of inhaled fluticasone propionate in adolescents and adults with asthma: meta-analysis.	2001-08-04	11485952
Improvement in health care utilization and pulmonary function with fluticasone propionate in patients with steroid-dependent asthma at a National Asthma Referral Center.	2001-08	11515977
Effects of single-dose fluticasone on exercise-induced asthma in asthmatic children: a pilot study.	2001-08	11477728
Persistent wheezing in infants with an atopic tendency responds to inhaled fluticasone.	2001-08	11466189
[Bronchial asthma. Patient management still has deficits].	2001-07-26	11524993
Fluticasone propionate and budesonide do not influence bone metabolism in the long term treatment of asthma.	2001-07-14	11449531
Effect of a long-acting beta2-agonist over three months on airway wall vascular remodeling in asthma.	2001-07-01	11435249
Systemic bioavailability of inhaled corticosteroids: appropriate and comparable methodology.	2001-07	11510799
Fluticasone and salmeterol downregulate in vitro, fibroblast proliferation and ICAM-1 or H-CAM expression.	2001-07	11510784
Fluticasone propionate compared with zafirlukast in controlling persistent asthma: a randomized double-blind, placebo-controlled trial.	2001-07	11485708
[Inhalational corticosteroids in COPD. THe ISOLDE Study (Inhaled Steroids in Obstructive Lung Disease in Europe)].	2001-07	11476049
Dose-response for adrenal suppression with hydrofluoroalkane formulations of fluticasone propionate and beclomethasone dipropionate.	2001-07	11453895
Pharmacokinetics of intranasal corticosteroids.	2001-07	11449203
Risk factors for lack of asthma self-management knowledge among ED patients not on inhaled steroids.	2001-07	11447507
A novel pharmacologic action of glucocorticosteroids on leukotriene C4 catabolism.	2001-07	11447392
GRbeta expression in nasal polyp inflammatory cells and its relationship to the anti-inflammatory effects of intranasal fluticasone.	2001-07	11447383
The linear relationship between changes in childhood growth velocity and topical glucocorticoid dose.	2001-06-27	11424876
The comparison of the efficacy of fluticasone propionate with cetirizine in perennial allergic rhinitis.	2001-06-23	11420028
[Controlling inflammation plus bronchodilation. Advantages of fixed combinations].	2001-06-14	11469024
Improved asthma control after changing from low-to-medium doses of other inhaled corticosteroids to low-dose fluticasone propionate.	2001-06-08	11549975
[Chronic bronchitis. Gold standard from the internet].	2001-06-07	11460425
A comparison of clinical use of fluticasone propionate and beclomethasone dipropionate in pediatric asthma.	2001-06	11559968
[Effect of FP inhalation and airway inflammation assessed by ECP in asthma].	2001-06	11530386
[Peak inspiratory flow rates attained by asthmatic patients through a dry-powder inhaler of fluticasone propionate].	2001-06	11517519
Topical corticosteroids in chronic rhinosinusitis: a randomized, double-blind, placebo-controlled trial using fluticasone propionate aqueous nasal spray.	2001-06	11486442
The problem of dose-response and therapeutic ratio of inhaled steroids.	2001-06	11458876
Safety of inhaled corticosteroid therapy in young children with asthma.	2001-06	11428737
Comparison of once daily fluticasone propionate aqueous nasal spray with once daily budesonide reservoir powder device in patients with perennial rhinitis.	2001-06	11422149
Presence of fluticasone propionate on human nasal mucosal surface and in human nasal tissue over a period of 24 h after intranasal application.	2001-06	11421898
The problem of dose-response and therapeutic ratio of inhaled steroids.	2001-06	11401902
[Effective in more than asthma patients. Good reasons for inhaled steroids].	2001-05-17	11400616
[Precise direction or flexible self-control. How strictly must the asthma patient adhere to medical advice?].	2001-05-10	11400630
The feasibility of airways hyperresponsiveness as an inclusion criterion for studies on childhood asthma.	2001-05	11488321
Is overall asthma control being achieved? A hypothesis-generating study.	2001-04	11401050
Systemic availability of inhaled budesonide and fluticasone propionate: healthy versus asthmatic lungs.	2001	11520251
Combination therapy improves the recovery of the skin barrier function: an experimental model using a contact allergy patch test combined with TEWL measurements.	2001	11455143
Comparative efficacy of inhaled corticosteroids and antileukotriene drugs in asthma.	2001	11437689
[Changes in biochemical inflammation markers in evaluation of the effectiveness of basic chemotherapy in bronchial asthma].	2001	11417175
Holding chambers versus nebulisers for inhaled steroids in chronic asthma.	2001	11405994
Inhaled steroids as prophylaxis for delayed pulmonary toxicity syndrome in breast cancer patients undergoing high-dose chemotherapy and autologous stem cell transplantation.	2001	11400949

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:09:45 GMT 2025` Edited by `admin` on `Mon Mar 31 18:09:45 GMT 2025`
Record UNII	CUT2W21N7U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLUTICAPS

Preferred Name

English

FLUTICASONE

Official Name

English

FLUTICASONE [MART.]

Common Name

English

Fluticasone [WHO-DD]

Common Name

English

OPTINOSE

Common Name

English

S-(FLUOROMETHYL) (6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-6,9-DIFLUORO-11,17-DIHYDROXY-16-METHYL-3-OXOANDROSTA-1,4-DIENE-17-CARBOTHIOATE

Common Name

English

FLUTICASONE [VANDF]

Common Name

English

fluticasone [INN]

Common Name

English

OPN-375

Code

English

R01AD08

Code

English

FLUTICASONE [HSDB]

Common Name

English

Classification Tree Code System Code

WHO-ATC

R03AK11