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
CCC(=O)O[C@@]1([C@H](C)C[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@]12C)C(=O)SCF
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 |
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 |
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 |
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 |
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 |
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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
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 |
|---|---|---|
| One-year treatment with different dosing schedules of fluticasone propionate in childhood asthma. Effects on hyperresponsiveness, lung function, and height. | 2001-12-01 |
|
| 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. | 2001-12-01 |
|
| Cost-effectiveness of fluticasone propionate administered via metered-dose inhaler plus babyhaler spacer in the treatment of asthma in preschool-aged children. | 2001-12 |
|
| Superiority of an intranasal corticosteroid compared with an oral antihistamine in the as-needed treatment of seasonal allergic rhinitis. | 2001-11-26 |
|
| Beclomethasone, budesonide and fluticasone propionate inhibit human neutrophil apoptosis. | 2001-11-23 |
|
| Novel anti-inflammatory effects of the inhaled corticosteroid fluticasone propionate during lung myofibroblastic differentiation. | 2001-11-01 |
|
| Pharmacokinetics and systemic activity of fluticasone via Diskus and pMDI, and of budesonide via Turbuhaler. | 2001-11 |
|
| Suppression of hypothalamic-pituitary-adrenal axis activity with inhaled flunisolide and fluticasone propionate in adult asthma patients. | 2001-11 |
|
| Effects of 2 inhaled corticosteroids on growth: results of a randomized controlled trial. | 2001-11 |
|
| Comparison of the tissue affinity of glucocorticoids to human lung, nasal and skin tissue in vitro. | 2001-10 |
|
| The effect of low-dose inhaled fluticasone propionate on exhaled nitric oxide in asthmatic patients and comparison with oral zafirlukast. | 2001-10 |
|
| Fluticasone propionate aqueous nasal spray in pregnancy rhinitis. | 2001-10 |
|
| [Combination treatment with inhaled corticosteroid/long-acting beta 2-adrenergic bronchodilator in the treatment of asthma]. | 2001-10 |
|
| [Japanese guideline for the diagnosis and management of bronchial asthma (1998)--its results and reversion]. | 2001-10 |
|
| Serum dehydroepiandrosterone sulfate concentration as an indicator of adrenocortical suppression in asthmatic children treated with inhaled steroids. | 2001-10 |
|
| Response of preschool children with asthma symptoms to fluticasone propionate. | 2001-10 |
|
| Quantification of epimeric budesonide and fluticasone propionate in human plasma by liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry. | 2001-09-25 |
|
| Intracranial hypertension and nasal fluticasone propionate. | 2001-09-22 |
|
| Comparison of fluticasone propionate-salmeterol combination therapy and montelukast in patients who are symptomatic on short-acting beta(2)-agonists alone. | 2001-09-01 |
|
| A comparison of asthma-related expenditures for patients started on montelukast versus fluticasone propionate as monotherapy. | 2001-09 |
|
| A review of the pharmacology and pharmacokinetics of inhaled fluticasone propionate and mometasone furoate. | 2001-09 |
|
| Improved safety with equivalent asthma control in adults with chronic severe asthma on high-dose fluticasone propionate. | 2001-09 |
|
| The penetration of 0.005% fluticasone propionate ointment in eyelid skin. | 2001-09 |
|
| A comparison of short-term treatment with inhaled fluticasone propionate and zafirlukast for patients with persistent asthma. | 2001-08-15 |
|
| Dose-response relation of inhaled fluticasone propionate in adolescents and adults with asthma: meta-analysis. | 2001-08-04 |
|
| 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 |
|
| Effects of single-dose fluticasone on exercise-induced asthma in asthmatic children: a pilot study. | 2001-08 |
|
| Fluticasone propionate and budesonide do not influence bone metabolism in the long term treatment of asthma. | 2001-07-14 |
|
| Fluticasone and salmeterol downregulate in vitro, fibroblast proliferation and ICAM-1 or H-CAM expression. | 2001-07 |
|
| Drugs for the treatment of allergic diseases. | 2001-07 |
|
| Fluticasone propionate compared with zafirlukast in controlling persistent asthma: a randomized double-blind, placebo-controlled trial. | 2001-07 |
|
| Dose-response for adrenal suppression with hydrofluoroalkane formulations of fluticasone propionate and beclomethasone dipropionate. | 2001-07 |
|
| Effects of intranasal corticosteroids on the hypothalamic-pituitary-adrenal axis in children. | 2001-07 |
|
| Pharmacokinetics of intranasal corticosteroids. | 2001-07 |
|
| A novel pharmacologic action of glucocorticosteroids on leukotriene C4 catabolism. | 2001-07 |
|
| GRbeta expression in nasal polyp inflammatory cells and its relationship to the anti-inflammatory effects of intranasal fluticasone. | 2001-07 |
|
| Improved asthma control after changing from low-to-medium doses of other inhaled corticosteroids to low-dose fluticasone propionate. | 2001-06-08 |
|
| A comparison of clinical use of fluticasone propionate and beclomethasone dipropionate in pediatric asthma. | 2001-06 |
|
| [Effect of FP inhalation and airway inflammation assessed by ECP in asthma]. | 2001-06 |
|
| [Peak inspiratory flow rates attained by asthmatic patients through a dry-powder inhaler of fluticasone propionate]. | 2001-06 |
|
| Topical corticosteroids in chronic rhinosinusitis: a randomized, double-blind, placebo-controlled trial using fluticasone propionate aqueous nasal spray. | 2001-06 |
|
| 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 |
|
| Aerosol characterization of nebulized intranasal glucocorticoid formulations. | 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 |
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
Created by
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EU-Orphan Drug |
EU/3/16/1815
Created by
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FDA ORPHAN DRUG |
319410
Created by
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FDA ORPHAN DRUG |
499815
Created by
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NCI_THESAURUS |
C521
Created by
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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444036
Created by
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PRIMARY | |||
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SUB02241MIG
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PRIMARY | |||
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m5510
Created by
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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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PRIMARY |
ACTIVE MOIETY
METABOLITE INACTIVE (PARENT)