Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H31F3O5S |
Molecular Weight | 500.571 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@@H](C)[C@](OC(=O)CC)(C(=O)SCF)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])C[C@H](F)C4=CC(=O)C=C[C@]34C
InChI
InChIKey=WMWTYOKRWGGJOA-CENSZEJFSA-N
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
DescriptionSources: http://www.drugbank.ca/drugs/DB00588Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/fluticasone.html
Sources: http://www.drugbank.ca/drugs/DB00588
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/fluticasone.html
Fluticasone propionate, a medium-potency synthetic corticosteroid, is used topically to relieve inflammatory and pruritic symptoms of dermatoses and psoriasis, intranasally to manage symptoms of allergic and non-allergic rhinitis, and orally for the treatment of asthma. Fluticasone proprionate is marketed under several different brand names such as Flonase®. Fluticasone propionate is also available as a combination product of azelastine hydrochloride and fluticasone propionate called Dymista™. Dymista™ is indicated in patients over 12 years old for symptomatic relief of seasonal allergic rhinitis. Fluticasone propionate binds to the glucocorticoid receptor. Unbound corticosteroids cross the membranes of cells such as mast cells and eosinophils, binding with high affinity to glucocorticoid receptors (GR). The results include alteration of transcription and protein synthesis, a decreased release of leukocytic acid hydrolases, reduction in fibroblast proliferation, prevention of macrophage accumulation at inflamed sites, reduction of collagen deposition, interference with leukocyte adhesion to the capillary wall, reduction of capillary membrane permeability and subsequent edema, reduction of complement components, inhibition of histamine and kinin release, and interference with the formation of scar tissue. In the management of asthma, the glucocorticoid receptor complexes down-regulates proinflammatory mediators such as interleukin-(IL)-1, 3, and 5, and up-regulates anti-inflammatory mediators such as IkappaB [inhibitory molecule for nuclear factor kappaB1], IL-10, and IL-12. The antiinflammatory actions of corticosteroids are also thought to involve inhibition of cytosolic phospholipase A2 (through activation of lipocortin-1 (annexin)) which controls the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL208 Sources: http://www.drugbank.ca/drugs/DB00588 |
1.0 nM [EC50] | ||
Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB00588 |
0.7 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CUTIVATE Approved UseCUTIVATE® Ointment is a corticosteroid indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses in adult patients. Launch Date1990 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23364 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12680886 |
1000 μg single, intravenous dose: 1000 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
FLUTICASONE PROPIONATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14148 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12680886 |
1000 μg single, intravenous dose: 1000 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
FLUTICASONE PROPIONATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12680886 |
1000 μg single, intravenous dose: 1000 μg route of administration: Intravenous experiment type: SINGLE co-administered: |
FLUTICASONE PROPIONATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9% |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FLUTICASONE PROPIONATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
16 mg single, oral Highest studied dose Dose: 16 mg Route: oral Route: single Dose: 16 mg Sources: |
healthy, adult Health Status: healthy Age Group: adult Sources: |
|
2 mg 2 times / day multiple, intranasal Highest studied dose Dose: 2 mg, 2 times / day Route: intranasal Route: multiple Dose: 2 mg, 2 times / day Sources: |
healthy, adult Health Status: healthy Age Group: adult Sources: |
|
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
healthy, adult Health Status: healthy Age Group: adult Sources: |
|
1320 ug 1 times / day multiple, respiratory Highest studied dose Dose: 1320 ug, 1 times / day Route: respiratory Route: multiple Dose: 1320 ug, 1 times / day Sources: |
healthy, adult Health Status: healthy Age Group: adult Sources: |
|
3520 ug single, respiratory Highest studied dose Dose: 3520 ug Route: respiratory Route: single Dose: 3520 ug Sources: |
healthy, adult Health Status: healthy Age Group: adult Sources: |
|
25 ug 2 times / day steady, respiratory Dose: 25 ug, 2 times / day Route: respiratory Route: steady Dose: 25 ug, 2 times / day Sources: |
unhealthy, children n = 211 Health Status: unhealthy Condition: Asthma Age Group: children Population Size: 211 Sources: |
Other AEs: Pneumonia mycoplasmal... Other AEs: Pneumonia mycoplasmal (serious, 1 patient) Sources: |
50 ug 2 times / day steady, respiratory Dose: 50 ug, 2 times / day Route: respiratory Route: steady Dose: 50 ug, 2 times / day Sources: |
unhealthy, children n = 208 Health Status: unhealthy Condition: Asthma Age Group: children Population Size: 208 Sources: |
Other AEs: Disruptive mood dysregulation disorder... Other AEs: Disruptive mood dysregulation disorder (serious, 1 patient) Sources: |
200 ug 1 times / day steady, intranasal Dose: 200 ug, 1 times / day Route: intranasal Route: steady Dose: 200 ug, 1 times / day Sources: |
unhealthy n = 314 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Population Size: 314 Sources: |
Other AEs: Thirst, Gastrointestinal viral infection... Other AEs: Thirst (below serious, 1 patient) Sources: Gastrointestinal viral infection (below serious, 1 patient) Headache (below serious, 2 patients) Throat irritation (below serious, 1 patient) Palpitations (below serious, 1 patient) Laceration (below serious, 1 patient) Hypertension (below serious, 1 patient) |
880 ug 2 times / day steady, oral Dose: 880 ug, 2 times / day Route: oral Route: steady Dose: 880 ug, 2 times / day Sources: |
unhealthy n = 19 Health Status: unhealthy Condition: Eosinophilic Esophagitis Population Size: 19 Sources: |
Other AEs: Esophageal candidiasis... Other AEs: Esophageal candidiasis (below serious, 5 patients) Sources: |
880 ug 2 times / day steady, oral Dose: 880 ug, 2 times / day Route: oral Route: steady Dose: 880 ug, 2 times / day Sources: |
unhealthy n = 28 Health Status: unhealthy Condition: Eosinophilic Esophagitis Population Size: 28 Sources: |
Other AEs: General system disorders NEC, General system disorders NEC... Other AEs: General system disorders NEC (below serious, 7 patients) Sources: General system disorders NEC (below serious, 2 patients) General system disorders NEC (below serious, 1 patient) General system disorders NEC (below serious, 5 patients) General system disorders NEC (below serious, 4 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Pneumonia mycoplasmal | serious, 1 patient | 25 ug 2 times / day steady, respiratory Dose: 25 ug, 2 times / day Route: respiratory Route: steady Dose: 25 ug, 2 times / day Sources: |
unhealthy, children n = 211 Health Status: unhealthy Condition: Asthma Age Group: children Population Size: 211 Sources: |
Disruptive mood dysregulation disorder | serious, 1 patient | 50 ug 2 times / day steady, respiratory Dose: 50 ug, 2 times / day Route: respiratory Route: steady Dose: 50 ug, 2 times / day Sources: |
unhealthy, children n = 208 Health Status: unhealthy Condition: Asthma Age Group: children Population Size: 208 Sources: |
Gastrointestinal viral infection | below serious, 1 patient | 200 ug 1 times / day steady, intranasal Dose: 200 ug, 1 times / day Route: intranasal Route: steady Dose: 200 ug, 1 times / day Sources: |
unhealthy n = 314 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Population Size: 314 Sources: |
Hypertension | below serious, 1 patient | 200 ug 1 times / day steady, intranasal Dose: 200 ug, 1 times / day Route: intranasal Route: steady Dose: 200 ug, 1 times / day Sources: |
unhealthy n = 314 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Population Size: 314 Sources: |
Laceration | below serious, 1 patient | 200 ug 1 times / day steady, intranasal Dose: 200 ug, 1 times / day Route: intranasal Route: steady Dose: 200 ug, 1 times / day Sources: |
unhealthy n = 314 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Population Size: 314 Sources: |
Palpitations | below serious, 1 patient | 200 ug 1 times / day steady, intranasal Dose: 200 ug, 1 times / day Route: intranasal Route: steady Dose: 200 ug, 1 times / day Sources: |
unhealthy n = 314 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Population Size: 314 Sources: |
Thirst | below serious, 1 patient | 200 ug 1 times / day steady, intranasal Dose: 200 ug, 1 times / day Route: intranasal Route: steady Dose: 200 ug, 1 times / day Sources: |
unhealthy n = 314 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Population Size: 314 Sources: |
Throat irritation | below serious, 1 patient | 200 ug 1 times / day steady, intranasal Dose: 200 ug, 1 times / day Route: intranasal Route: steady Dose: 200 ug, 1 times / day Sources: |
unhealthy n = 314 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Population Size: 314 Sources: |
Headache | below serious, 2 patients | 200 ug 1 times / day steady, intranasal Dose: 200 ug, 1 times / day Route: intranasal Route: steady Dose: 200 ug, 1 times / day Sources: |
unhealthy n = 314 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Population Size: 314 Sources: |
Esophageal candidiasis | below serious, 5 patients | 880 ug 2 times / day steady, oral Dose: 880 ug, 2 times / day Route: oral Route: steady Dose: 880 ug, 2 times / day Sources: |
unhealthy n = 19 Health Status: unhealthy Condition: Eosinophilic Esophagitis Population Size: 19 Sources: |
General system disorders NEC | below serious, 1 patient | 880 ug 2 times / day steady, oral Dose: 880 ug, 2 times / day Route: oral Route: steady Dose: 880 ug, 2 times / day Sources: |
unhealthy n = 28 Health Status: unhealthy Condition: Eosinophilic Esophagitis Population Size: 28 Sources: |
General system disorders NEC | below serious, 2 patients | 880 ug 2 times / day steady, oral Dose: 880 ug, 2 times / day Route: oral Route: steady Dose: 880 ug, 2 times / day Sources: |
unhealthy n = 28 Health Status: unhealthy Condition: Eosinophilic Esophagitis Population Size: 28 Sources: |
General system disorders NEC | below serious, 4 patients | 880 ug 2 times / day steady, oral Dose: 880 ug, 2 times / day Route: oral Route: steady Dose: 880 ug, 2 times / day Sources: |
unhealthy n = 28 Health Status: unhealthy Condition: Eosinophilic Esophagitis Population Size: 28 Sources: |
General system disorders NEC | below serious, 5 patients | 880 ug 2 times / day steady, oral Dose: 880 ug, 2 times / day Route: oral Route: steady Dose: 880 ug, 2 times / day Sources: |
unhealthy n = 28 Health Status: unhealthy Condition: Eosinophilic Esophagitis Population Size: 28 Sources: |
General system disorders NEC | below serious, 7 patients | 880 ug 2 times / day steady, oral Dose: 880 ug, 2 times / day Route: oral Route: steady Dose: 880 ug, 2 times / day Sources: |
unhealthy n = 28 Health Status: unhealthy Condition: Eosinophilic Esophagitis Population Size: 28 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubs.acs.org/doi/abs/10.1021/tx100124k Page: - |
weak | |||
Sources: https://pubs.acs.org/doi/abs/10.1021/tx100124k Page: - |
yes | |||
Page: - |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
no | |||
Page: - |
weak | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
yes [Km 3.8 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16565171/ Page: - |
yes [Km 5.2 uM] | |||
yes [Km 5.3 uM] | yes (co-administration study) Comment: Ritonavir A drug interaction trial with fluticasone propionate aqueous nasal spray in healthy subjects has shown that ritonavir (a strong CYP3A4 inhibitor) can significantly increase plasma fluticasone propionate exposure, resulting in significantly reduced serum cortisol concentrations Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209022Orig1s000ClinPharmR_rev.pdf#page=14 Page: 14.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Small airway inflammation in asthma. | 2001 |
|
Using clinical measures of disease control to reduce the burden of asthma. | 2001 |
|
Inhaled fluticasone propionate for chronic asthma. | 2001 |
|
Cost-efficacy analysis of fluticasone propionate versus zafirlukast in patients with persistent asthma. | 2001 |
|
Should inhaled corticosteroids be used in the long term treatment of chronic obstructive pulmonary disease? | 2001 |
|
Clinical prescribing of allergic rhinitis medication in the preschool and young school-age child: what are the options? | 2001 |
|
Systemic availability of inhaled budesonide and fluticasone propionate: healthy versus asthmatic lungs. | 2001 |
|
Inhaled mometasone furoate: a review of its use in adults and adolescents with persistent asthma. | 2001 |
|
Improvement in health care utilization and pulmonary function with fluticasone propionate in patients with steroid-dependent asthma at a National Asthma Referral Center. | 2001 Aug |
|
Effects of single-dose fluticasone on exercise-induced asthma in asthmatic children: a pilot study. | 2001 Aug |
|
A comparison of short-term treatment with inhaled fluticasone propionate and zafirlukast for patients with persistent asthma. | 2001 Aug 15 |
|
Dose-response relation of inhaled fluticasone propionate in adolescents and adults with asthma: meta-analysis. | 2001 Aug 4 |
|
Cost-effectiveness of fluticasone propionate administered via metered-dose inhaler plus babyhaler spacer in the treatment of asthma in preschool-aged children. | 2001 Dec |
|
One-year treatment with different dosing schedules of fluticasone propionate in childhood asthma. Effects on hyperresponsiveness, lung function, and height. | 2001 Dec 1 |
|
The cost effectiveness of early treatment with fluticasone propionate 250 microg twice a day in subjects with obstructive airway disease. Results of the DIMCA program. | 2001 Dec 1 |
|
Fluticasone propionate and budesonide do not influence bone metabolism in the long term treatment of asthma. | 2001 Jan-Feb |
|
Fluticasone and salmeterol downregulate in vitro, fibroblast proliferation and ICAM-1 or H-CAM expression. | 2001 Jul |
|
Drugs for the treatment of allergic diseases. | 2001 Jul |
|
Fluticasone propionate compared with zafirlukast in controlling persistent asthma: a randomized double-blind, placebo-controlled trial. | 2001 Jul |
|
Dose-response for adrenal suppression with hydrofluoroalkane formulations of fluticasone propionate and beclomethasone dipropionate. | 2001 Jul |
|
Effects of intranasal corticosteroids on the hypothalamic-pituitary-adrenal axis in children. | 2001 Jul |
|
Pharmacokinetics of intranasal corticosteroids. | 2001 Jul |
|
A novel pharmacologic action of glucocorticosteroids on leukotriene C4 catabolism. | 2001 Jul |
|
GRbeta expression in nasal polyp inflammatory cells and its relationship to the anti-inflammatory effects of intranasal fluticasone. | 2001 Jul |
|
A comparison of clinical use of fluticasone propionate and beclomethasone dipropionate in pediatric asthma. | 2001 Jun |
|
[Effect of FP inhalation and airway inflammation assessed by ECP in asthma]. | 2001 Jun |
|
[Peak inspiratory flow rates attained by asthmatic patients through a dry-powder inhaler of fluticasone propionate]. | 2001 Jun |
|
Topical corticosteroids in chronic rhinosinusitis: a randomized, double-blind, placebo-controlled trial using fluticasone propionate aqueous nasal spray. | 2001 Jun |
|
Improved asthma control after changing from low-to-medium doses of other inhaled corticosteroids to low-dose fluticasone propionate. | 2001 Jun 8 |
|
Pharmacokinetics and systemic activity of fluticasone via Diskus and pMDI, and of budesonide via Turbuhaler. | 2001 Nov |
|
Suppression of hypothalamic-pituitary-adrenal axis activity with inhaled flunisolide and fluticasone propionate in adult asthma patients. | 2001 Nov |
|
Effects of 2 inhaled corticosteroids on growth: results of a randomized controlled trial. | 2001 Nov |
|
Novel anti-inflammatory effects of the inhaled corticosteroid fluticasone propionate during lung myofibroblastic differentiation. | 2001 Nov 1 |
|
Beclomethasone, budesonide and fluticasone propionate inhibit human neutrophil apoptosis. | 2001 Nov 23 |
|
Superiority of an intranasal corticosteroid compared with an oral antihistamine in the as-needed treatment of seasonal allergic rhinitis. | 2001 Nov 26 |
|
Comparison of the tissue affinity of glucocorticoids to human lung, nasal and skin tissue in vitro. | 2001 Oct |
|
The effect of low-dose inhaled fluticasone propionate on exhaled nitric oxide in asthmatic patients and comparison with oral zafirlukast. | 2001 Oct |
|
Fluticasone propionate aqueous nasal spray in pregnancy rhinitis. | 2001 Oct |
|
[Combination treatment with inhaled corticosteroid/long-acting beta 2-adrenergic bronchodilator in the treatment of asthma]. | 2001 Oct |
|
[Japanese guideline for the diagnosis and management of bronchial asthma (1998)--its results and reversion]. | 2001 Oct |
|
Serum dehydroepiandrosterone sulfate concentration as an indicator of adrenocortical suppression in asthmatic children treated with inhaled steroids. | 2001 Oct |
|
Response of preschool children with asthma symptoms to fluticasone propionate. | 2001 Oct |
|
A comparison of asthma-related expenditures for patients started on montelukast versus fluticasone propionate as monotherapy. | 2001 Sep |
|
A review of the pharmacology and pharmacokinetics of inhaled fluticasone propionate and mometasone furoate. | 2001 Sep |
|
Improved safety with equivalent asthma control in adults with chronic severe asthma on high-dose fluticasone propionate. | 2001 Sep |
|
The penetration of 0.005% fluticasone propionate ointment in eyelid skin. | 2001 Sep |
|
Comparison of fluticasone propionate-salmeterol combination therapy and montelukast in patients who are symptomatic on short-acting beta(2)-agonists alone. | 2001 Sep 1 |
|
Intracranial hypertension and nasal fluticasone propionate. | 2001 Sep 22 |
|
Quantification of epimeric budesonide and fluticasone propionate in human plasma by liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry. | 2001 Sep 25 |
|
Aerosol characterization of nebulized intranasal glucocorticoid formulations. | 2001 Summer |
Patents
Sample Use Guides
Usual Adult Dose for Dermatitis
Cream/Ointment: Apply a thin film to affected area twice a day
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10100995
Pretreatment with Fluticasone propionate (10(-11) M to about 10(-7) M, 24 h) inhibited TNF-alpha-induced VCAM-1 mRNA expression in BEAS-2B in a dose-dependent manner
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
273208
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EU-Orphan Drug |
EU/3/16/1815
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FDA ORPHAN DRUG |
319410
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FDA ORPHAN DRUG |
499815
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NCI_THESAURUS |
C521
Created by
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Code System | Code | Type | Description | ||
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444036
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PRIMARY | |||
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SUB02241MIG
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m5510
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PRIMARY | Merck Index | ||
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FLUTICASONE PROPIONATE
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CHEMBL1473
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O2GMZ0LF5W
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100000092718
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1225
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759889
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O2GMZ0LF5W
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DB00588
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W-145
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80474-14-2
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1285873
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50121
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7080
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C29061
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DTXSID8045511
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31441
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ACTIVE MOIETY
METABOLITE INACTIVE (PARENT)