Mometasone furoate

Mometasone furoate: Mometasone furoate

Systematic (IUPAC) name

(11β,16α)-9,21-dichloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl 2-furoate

Clinical data

AHFS/Drugs.com monograph

Pregnancy cat. C(US)

Legal status Rx Only (US)

Routes topical, nasal

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 D07XC03, R01AD09, R03BA07

PubChem CID 441336

DrugBank APRD00289

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 eMolecules & PubChem

InChI

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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Mometasone furoate (also referred to as mometasone) is a glucocorticosteroid used topically to reduce inflammation of the skin or in the airways.

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

stabilising cell membranes

decreasing the influx of inflammatory cells

the exact anti-inflammatory mechanism of action is unknown

Availability

Schering-Plough markets the medication under the following brand names; Elocon (Elocom, Elomet, Elosalic) 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 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2203259.

^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2643101.

^ 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. http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=1368-5031&date=2009&volume=63&issue=5&spage=806.

^ 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 9780763779009. http://books.google.com/?id=9b8JiegivA8C&pg=PA677

^ Mani S. Kavuru (2007). "ch. 9 Anti-inflammatory agents". Diagnosis and Management of Asthma. ISBN 9781932610383. http://books.google.com/?id=Q1zF7xSRACIC

^ "Mometamax". Intervet USA. http://www.intervetusa.com/products/130_163343/productdetails_130_163679.aspx. Retrieved 19 June 2010.

External links

Mometasone Furoate Oral Inhalation (MedlinePlus)

Mometasone Furoate Nasal Inhalation (MedlinePlus)

Nasonex Home page

Asmanex Home page

U.S. National Library of Medicine: Drug Information Portal - Mometasone furoate

v · d · eCorticosteroids – glucocorticoids and mineralocorticoids (H02)
(also A07EA, C05AA, D07, D10AA, R01AD, R03BA, S01BA, S02B, and S03B)

Mineralocorticoids
(3-one, 4-ene,
no FG at 16)
Pregnenedione: ALDOSTERONE • 11-DEOXYCORTICOSTERONE • HALOGENATED AT 9: Fludrocortisone

Glucocorticoids
(3-one, 4-ene,
11-FG,
17-hydroxy)

Pregnene

CORTISONE

Pregnenedione
(+20-one)

HYDROCORTISONE/CORTISOL^# (Hydrocortisone aceponate, Hydrocortisone buteprate, Hydrocortisone butyrate) • Budesonide • Ciclesonide • Deflazacort • Medrysone • Tixocortol • HALOGENATED AT 6: Cloprednol • HALOGENATED, WITH FG AT 16: Halcinonide

Pregnadiene (+1-ene)

Rimexolone • HALOGENATED, WITH FG AT 16: Flunisolide • Triamcinolone • Amcinonide • Fluocinolone acetonide (Fluocinonide)

Pregnadienediol
(+21-hydroxy)

Prednisone (Meprednisone) • HALOGENATED AT 9: Fluorometholone • HALOGENATED, WITH FG AT 16: Fluocortolone (Clocortolone, Diflucortolone, Fluocortin) • Desoximetasone

Pregnadienetriol
(+11-hydroxy)

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 • Flumetasone • Fluprednidene

Pregnatriene
(+2-ene)

Cortivazol

Androstene

HALOGENATED, WITH FG AT 16: Fluticasone (Fluticasone propionate, Fluticasone furoate)

Other/ungrouped

HALOGENATED: Loteprednol • HALOGENATED, WITH FG AT 16: Fludroxycortide • Formocortal • Mometasone furoate

Aldosterone antagonists
Spironolactone • Eplerenone • Potassium canrenoate • Canrenone

Synthesis modifiers
Trilostane • Carbenoxolone • Aminoglutethimide • Metyrapone

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: END

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

v · d · eDecongestants and other nasal preparations (R01)

Topical

Sympathomimetics, plain

Cyclopentamine • Ephedrine • Phenylephrine • Oxymetazoline • Tetryzoline • Xylometazoline • Naphazoline • Tramazoline • Metizoline • Tuaminoheptane • Fenoxazoline • Tymazoline • Epinephrine

Antiallergic agents,
excluding corticosteroids

Spaglumic acid

histamine antagonists (Levocabastine, Antazoline, Thonzylamine)
mast cell stabilizer (some are also antihistamines) (Cromoglicic acid, Nedocromil, Azelastine, Olopatadine, Lodoxamide)

Corticosteroids

Beclometasone • Prednisolone • Dexamethasone • Flunisolide • Budesonide • Betamethasone • Tixocortol • Fluticasone • Mometasone furoate • Triamcinolone • Ciclesonide

Other nasal preparations

Cafaminol • Calcium hexamine thiocyanate • Retinol • Ipratropium bromide • Ritiometan • Mupirocin • Hexamidine • Framycetin • Hyaluronic acid • Eucalyptus oil

Systemic use:
Sympathomimetics
Phenylpropanolamine • Pseudoephedrine (+loratadine) • Phenylephrine • Phenylpropylamine

M: RES

anat(n, x, l, c)/phys/devp

noco(c, p)/cong/tumr, sysi/epon, injr

proc, drug(R1/2/3/5/6/7)

Categories:
Glucocorticoids
Asthma
Schering-Plough
Furoates
Organochlorides

Mometasone furoate

Systematic (IUPAC) name
(11β,16α)-9,21-dichloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl 2-furoate
Clinical data
AHFS/Drugs.com	monograph
Pregnancy cat.	C(US)
Legal status	Rx Only (US)
Routes	topical, nasal
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 D07XC03, R01AD09, R03BA07
PubChem	CID 441336
DrugBank	APRD00289
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	eMolecules & PubChem
InChI 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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mometasone furoate — A drug that is used in a cream to treat certain skin conditions and in a nasal spray to treat sinus problems caused by allergies. It is being studied as a way to treat inflammation of the skin caused by radiation therapy. Mometasone furoate is a… … English dictionary of cancer terms
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Fluticasone propionate — Systematic (IUPAC) name S (fluoromethyl) 6α,9 difluoro 11β, 17 dihydroxy 16α methyl 3 oxoandrosta 1, 4 diene 17β carbothioate, 17 propanoate Clinical data … Wikipedia
Triamcinolone — Systematic (IUPAC) name (11β,16α) 9 fluoro 11,16,17,21 tetrahydroxypregna 1,4 diene 3,20 dione Clinical data Trade names … Wikipedia
Budesonide — Systematic (IUPAC) name 16,17 (butylidenebis(oxy)) 11,21 dihydroxy , (11 β,16 α) pregna 1,4 diene 3,20 dione Clinical data Trade names … Wikipedia
Beclometasone dipropionate — Systematic (IUPAC) name (8S,9R,10S,11S,13S,14S,16S,17R) 9 chloro 11 hydroxy 10,13,16 trimethyl 3 oxo 17 [2 (propionyloxy)acetyl] 6,7,8,9,10,11,12,13,14,15,16,17 dodecahydro 3H cyclo … Wikipedia
Flunisolide — Systematic (IUPAC) name (1S,2S,4R,8S,9S,11S,12S,13R,19S) 19 fluoro 11 hydroxy 8 (2 hydroxyacetyl) 6,6,9,13 tetramethyl 5,7 dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa 14,17 dien 16 one … Wikipedia
Ciclesonide — Systematic (IUPAC) name 2 [(1S, 2S, 4R, 8S, 9S,11S, 12S, 13R) 6 cyclohexyl 11 hydroxy 9, 13 dimethyl 16 oxo 5, 7 dioxapentacyclo [10.8.0.02,9.04, 8.013,18] icosa 14, 17 dien 8 yl] 2 oxoethyl 2 … Wikipedia

Academic Dictionaries and Encyclopedias

Mometasone furoate

Contents

Uses, administration, and pharmacodynamics

Availability

References

External links

Look at other dictionaries:

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Academic Dictionaries and Encyclopedias

Wikipedia

Mometasone furoate

Contents

Uses, administration, and pharmacodynamics

Availability

References

External links

Look at other dictionaries:

Share the article and excerpts

Direct link