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Mometasone furoate
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Systematic (IUPAC) name |
(11β,16α)-9,21-dichloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl 2-furoate |
Clinical data |
Trade names |
Elocon Elocom, Elomet, Elosalic Novasone Nasonex Asmanex Twisthaler Essex pharma markets the medication under the brand name Ecural mometAid. |
AHFS/Drugs.com |
monograph |
Pregnancy cat. |
C (US) |
Legal status |
Rx Only (US) |
Routes |
topical, inhalation |
Pharmacokinetic data |
Bioavailability |
Nasal spray is virtually undetectable in plasma; but systemic availability is comparable to fluticasone.[1] |
Protein binding |
98% to 99% |
Metabolism |
hepatic |
Half-life |
5.8 hours |
Identifiers |
CAS number |
105102-22-5 Y 83919-23-7 |
ATC code |
D07AC13 R01AD09, R03BA07 |
PubChem |
CID 441336 |
DrugBank |
DB00764 |
ChemSpider |
390091 Y |
ChEBI |
CHEBI:47564 Y |
ChEMBL |
CHEMBL1161 Y |
Synonyms |
(9R,10S,11S,13S,14S,16R,17R)-9-chloro-17-(2-chloroacetyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl furan-2-carboxylate |
Chemical data |
Formula |
C22H28Cl2O4 for Mometasone
C27H30O6Cl2 as Furoate |
Mol. mass |
427.361 g/mol (Mometasone)
521.4 g/mol (Furoate) |
SMILES
- O=C(O[C@]2(C(=O)CCl)[C@H](C)C[C@H]3[C@@H]4CCC\1=C\C(=O)\C=C/[C@]/1(C)[C@@]4(Cl)[C@@H](O)C[C@]23C)c5occc5
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InChI
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InChI=1S/C27H30Cl2O6/c1-15-11-19-18-7-6-16-12-17(30)8-9-24(16,2)26(18,29)21(31)13-25(19,3)27(15,22(32)14-28)35-23(33)20-5-4-10-34-20/h4-5,8-10,12,15,18-19,21,31H,6-7,11,13-14H2,1-3H3/t15-,18+,19+,21+,24+,25+,26+,27+/m1/s1 Y
Key:WOFMFGQZHJDGCX-ZULDAHANSA-N Y
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N (what is this?) (verify) |
Mometasone furoate is a glucocorticosteroid used topically to reduce inflammation of the skin or in the airways. It is a prodrug of the free form mometasone (INN).
Contents
- 1 Uses, administration, and pharmacodynamics
- 2 Availability
- 3 References
- 4 External links
Uses, administration, and pharmacodynamics
Mometasone furoate is used in the treatment of inflammatory skin disorders (such as eczema and psoriasis), allergic rhinitis (such as hay fever), asthma[2][3] for patients unresponsive to less potent corticosteroids, and penile phimosis.[4] In terms of steroid strength, it is more potent than hydrocortisone, and less potent than dexamethasone.[5]
It reduces inflammation by causing several effects:[6][7][8]
- reversing the activation of inflammatory proteins
- activating the secretion of anti-inflammatory proteins
- stabilizing cell membranes
- decreasing the influx of inflammatory cells
The exact anti-inflammatory mechanism of action is unknown.
Availability
Merck markets the medication under the following brand names; Elocon (Elocom, Elomet, Elosalic), Elica and Novasone as a cream or ointment for skin conditions, Nasonex as a nasal spray for upper respiratory conditions such as nasal sinus inflammation, Asmanex Twisthaler as a dry powder inhaler (DPI) for lower respiratory conditions. Essex pharma markets the medication under the brand name Ecural and Progreś Laboratories markets it under mometAid. It is also marketed by Perrigo as an ointment for the scalp.In India it is marketed by Intas under the trade name 'Eziwin'.
It is also available as a veterinary drug in an otic (ears) form for treatment of otitis externa under the brand name Mometamax.[9]
References
- ^ Zia R Tayab, Tom C Fardon, Daniel K C Lee, Kay Haggart, Lesley C McFarlane, Brian J Lipworth, and Günther Hochhaus (November 2007). "Pharmacokinetic/pharmacodynamic evaluation of urinary cortisol suppression after inhalation of fluticasone propionate and mometasone furoate". Br J Clin Pharmacol 64 (5): 698–705. doi:10.1111/j.1365-2125.2007.02919.x. PMC 2203259. PMID 17509041.
- ^ Tan RA, Corren J (December 2008). "Mometasone furoate in the management of asthma: a review". Ther Clin Risk Manag 4 (6): 1201–8. PMC 2643101. PMID 19337427.
- ^ Bousquet J (May 2009). "Mometasone furoate: an effective anti-inflammatory with a well-defined safety and tolerability profile in the treatment of asthma". Int. J. Clin. Pract. 63 (5): 806–19. doi:10.1111/j.1742-1241.2009.02003.x. PMID 19392928.
- ^ Khope S (March 2010). "Topical mometasone furoate for phimosis". Indian pediatr 47 (3): 282. PMID 20371899.
- ^ Williams D. What does potency actually mean for inhaled corticosteroids?. The Journal Of Asthma: Official Journal Of The Association For The Care Of Asthma [serial online]. July 2005;42(6):409-417. Available from: MEDLINE with Full Text, Ipswich, MA. Accessed October 25, 2011.
- ^ Product Information: NASONEX(R) nasal spray, mometasone furoate monohydrate nasal spray. Schering Corporation, Kenilworth, NJ, 2010.
- ^ Publishers, Jones and Bartlett (2009-07-15). Nurse's Drug Handbook 2010. p. 677. ISBN 978-0-7637-7900-9.
- ^ Mani S. Kavuru (2007). "ch. 9 Anti-inflammatory agents". Diagnosis and Management of Asthma. ISBN 978-1-932610-38-3.
- ^ "Mometamax". Intervet USA. Retrieved 19 June 2010.
External links
- Mometasone Furoate Oral Inhalation (MedlinePlus)
- Mometasone Furoate Nasal Inhalation (MedlinePlus)
- Nasonex Home page
- Asmanex Home page
- Elica Home page
- U.S. National Library of Medicine: Drug Information Portal - Mometasone furoate
Decongestants and other nasal preparations (R01)
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Topical |
Sympathomimetics, plain
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- Cyclopentamine
- Ephedrine
- Phenylephrine
- Oxymetazoline
- Tetryzoline
- Xylometazoline
- Naphazoline
- Tramazoline
- Metizoline
- Tuaminoheptane
- Fenoxazoline
- Tymazoline
- Epinephrine
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Antiallergic agents,
excluding corticosteroids
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- histamine antagonists (Levocabastine
- Antazoline
- Thonzylamine)
- mast cell stabilizer (some are also antihistamines) (Cromoglicic acid
- Nedocromil
- Azelastine
- Olopatadine
- Lodoxamide)
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Corticosteroids
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- Beclometasone
- Prednisolone
- Dexamethasone
- Flunisolide
- Budesonide
- Betamethasone
- Tixocortol
- Fluticasone
- Mometasone furoate
- Triamcinolone
- Ciclesonide
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Other nasal preparations
|
- Cafaminol
- Calcium hexamine thiocyanate
- Retinol
- Ipratropium bromide
- Ritiometan
- Mupirocin
- Hexamidine
- Framycetin
- Hyaluronic acid
- Eucalyptus oil
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Systemic use:
Sympathomimetics |
- Phenylpropanolamine
- Pseudoephedrine (+loratadine)
- Phenylephrine
- Phenylpropylamine
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anat (n, x, l, c)/phys/devp
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noco (c, p)/cong/tumr, sysi/epon, injr
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proc, drug (R1/2/3/5/6/7)
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Corticosteroids – glucocorticoids and mineralocorticoids (H02)
(also A07EA, C05AA, D07, D10AA, R01AD, R03BA, S01BA, S02B, and S03B)
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Mineralocorticoids
(3-one, 4-ene,
no FG at 16) |
- Pregnenedione: ALDOSTERONE
- 11-DEOXYCORTICOSTERONE
- HALOGENATED AT 9: Fludrocortisone
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Glucocorticoids
(3-one, 4-ene,
11-FG,
17-hydroxy) |
Pregnene
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Pregnenedione
(+20-one)
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- HYDROCORTISONE/CORTISOL# (Hydrocortisone aceponate
- Hydrocortisone buteprate
- Hydrocortisone butyrate)
- Budesonide
- Ciclesonide
- Deflazacort
- Medrysone
- Tixocortol
- HALOGENATED AT 6: Cloprednol
- HALOGENATED, WITH FG AT 16: Halcinonide
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Pregnadiene (+1-ene)
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- Rimexolone
- HALOGENATED, WITH FG AT 16: Flunisolide
- Triamcinolone
- Amcinonide
- Fluocinolone acetonide (Fluocinonide)
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Pregnadienediol
(+21-hydroxy)
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- Prednisone (Meprednisone)
- HALOGENATED AT 9: Fluorometholone
- HALOGENATED, WITH FG AT 16: Fluocortolone (Clocortolone
- Diflucortolone
- Fluocortin)
- Desoximetasone
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Pregnadienetriol
(+11-hydroxy)
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- Prednisolone# (Methylprednisolone
- Methylprednisolone aceponate
- Prednicarbate
- Prednylidene)
- Desonide
- HALOGENATED: Fluprednisolone (Difluprednate
- Fluperolone)
- HALOGENATED, WITH FG AT 16: Dexamethasone#
- Betamethasone (Clobetasol
- Clobetasone
- Diflorasone
- Halometasone
- Ulobetasol)
- Beclometasone
- Paramethasone
- Alclometasone
- Fluclorolone acetonide
- Flumetasone
- Fluprednidene
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Pregnatriene
(+2-ene)
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Androstene
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- HALOGENATED, WITH FG AT 16: Fluticasone (Fluticasone propionate
- Fluticasone furoate)
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Other/ungrouped
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- HALOGENATED: Loteprednol
- HALOGENATED, WITH FG AT 16: Fludroxycortide
- Formocortal
- Mometasone furoate
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Aldosterone antagonists |
- Spironolactone
- Eplerenone
- Potassium canrenoate
- Canrenone
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Synthesis modifiers |
- Trilostane
- Carbenoxolone
- Aminoglutethimide
- Metyrapone
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco (d)/cong/tumr, sysi/epon
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proc, drug (A10/H1/H2/H3/H5)
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Glucocorticoids
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Receptor |
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Enzyme
(inhibitors) |
20,22-Desmolase
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- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
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17α-Hydroxylase,
17,20-Lyase
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- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
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3β-HSD
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- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Metyrapone
- Norethisterone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
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21-Hydroxylase
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- Aminoglutethimide
- Amphenone B
- Bifonazole
- Clotrimazole
- Diazepam
- Econazole
- Genistein
- Isoconazole
- Ketoconazole
- Metyrapone
- Miconazole
- Midazolam
- Tioconazole
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11β-Hydroxylase
|
- Aminoglutethimide
- Canrenone
- Etomidate
- Fadrozole
- FETO
- Ketoconazole
- Metomidate
- Metyrapone
- Mitotane
- Potassium canrenoate
- Spironolactone
- Trilostane
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18-Hydroxylase
|
- Aminoglutethimide
- Canrenone
- FAD286
- Fadrozole
- Ketoconazole
- LCI699
- Metyrapone
- Mespirenone
- Potassium canrenoate
- Spironolactone
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Other |
Endogenous
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- Glucocorticoids: Corticosterone
- Cortisone
- Cortodoxone/Deoxycortisol
- Hydrocortisone/Cortisol
- Antiglucocorticoids: 17-Hydroxyprogesterone
- Deoxycorticosterone
- Pregnenolone
- Progesterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- 17-Hydroxyprogesterone
- Progesterone
- Deoxycorticosterone
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Indirect
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- ACTH/Corticotropin
- CRH
- DHEA
- DHEA sulfate
- Plasma proteins (Transcortin, Albumin)
- Vasopressin
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Procedures
|
- Adrenalectomy
- Hypophysectomy
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UpToDate Contents
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English Journal
- Mometasone furoate hydrogel for scalp use: in vitro and in vivo evaluation.
- Salgado A1, Raposo S, Marto J, Silva AN, Simões S, Ribeiro HM.
- Pharmaceutical development and technology.Pharm Dev Technol.2014 Aug;19(5):618-22. doi: 10.3109/10837450.2013.819012. Epub 2013 Jul 22.
- Dermatological inflammatory diseases often affect the scalp and the eyebrows. Common dosage forms available on the market for those situations are lotions; however, the presence of hair limits their use. Gels, for their consistency and adhesiveness, are a suitable alternative to the lotions in these
- PMID 23869426
- Low-frequency shift dispersive Raman spectroscopy for the analysis of respirable dosage forms.
- Wang H1, Boraey MA1, Williams L2, Lechuga-Ballesteros D2, Vehring R3.
- International journal of pharmaceutics.Int J Pharm.2014 Jul 20;469(1):197-205. doi: 10.1016/j.ijpharm.2014.04.058. Epub 2014 May 1.
- A high performance Raman system equipped with a CCD (charged coupled device) sensor and recently developed optical filter technology is described. It provides high sensitivity, high resolution, and access to low-frequency vibrations enabling resolution of spectral features due to lattice vibrational
- PMID 24793839
- Structures and mechanism for the design of highly potent glucocorticoids.
- He Y1, Yi W2, Suino-Powell K1, Zhou XE1, Tolbert WD1, Tang X2, Yang J3, Yang H3, Shi J2, Hou L2, Jiang H3, Melcher K1, Xu HE4.
- Cell research.Cell Res.2014 Jun;24(6):713-26. doi: 10.1038/cr.2014.52. Epub 2014 Apr 25.
- The evolution of glucocorticoid drugs was driven by the demand of lowering the unwanted side effects, while keeping the beneficial anti-inflammatory effects. Potency is an important aspect of this evolution as many undesirable side effects are associated with use of high-dose glucocorticoids. The si
- PMID 24763108
Japanese Journal
- イネ科花粉症に対するモメタゾンフランカルボン酸エステル水和物点鼻液の治療効果
- 太田 伸男,鈴木 祐輔,青柳 優
- 耳鼻咽喉科臨床 103(12), 1147-1155, 2010-12-01
- We studied the clinical effects of mometasone furoate on subjects with seasonal grass pollinosis by comparing nasal and ocular symptom scores, medication scores and symptom-medication scores before an …
- NAID 10027449773
- Once-daily mometa-sone furoate aqueous nasal spray (Nasonex)in seasonal allergic rhinitis; an active-and placebo-controlled study
Related Links
- ナゾネックス(Nasonex)、フランカルボン酸モメタゾン鼻用スプレー(Mometasone)、【2本/7880円】を購入するならこちらへ ... ・商品名: ナゾネックス鼻用スプレー 0.05% 140dose ・英名: Nasonex Aqueous Nasal Spray ・一般名: フラン ...
- Nasonex (mometasone) is used to treat nasal allergies such as congestion, sneezing, and runny nose. Includes Nasonex side effects, interactions and indications. ... Nasonex side effects Get emergency medical help if you have ...
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★リンクテーブル★
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- フランカルボン酸モメタゾン、フロ酸モメタゾン mometasone furoate、フロ酸モメタゾン水和物 mometasone furoate hydrate、フランカルボン酸モメタゾン水和物
- 商
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