Rupatadine: Difference between revisions

Jump to navigation Jump to search
VisualWikitext
No edit summary
 
No edit summary
 
(3 intermediate revisions by 2 users not shown)
Line 1: Line 1:
{{drugbox
{{Drugbox
| IUPAC_name       = 8-chloro-6,11-dihydro-11-(1-((5-methyl-3-pyridyl)methyl)-<br>4-piperidylidene)-5''H''-benzo(5,6)cyclohepta(1,2-b)pyridine
| Verifiedfields = changed
| image             =
| Watchedfields = changed
| CAS_number        = 158876-82-5
| verifiedrevid = 464384578
| ATC_prefix        = R06
| IUPAC_name = 8-Chloro-6,11-dihydro-11-[1-[(5-methyl-3-pyridinyl)methyl]-4-piperidinylidene]-5''H''-benzo[5,6]cyclohepta[1,2-b]pyridine fumarate
| ATC_suffix        = AX28
| image =Rupatadine.png
| PubChem          = 133017
 
| DrugBank          =  
<!--Clinical data-->
| C = 26 | H = 26 | Cl = 1 | N = 3
| tradename = Rupafin, Alergoliber, Rinialer, Pafinur, Rupax, Ralif
| molecular_weight = 415.958 g/mol
| Drugs.com = {{drugs.com|international|rupatadine}}
| bioavailability   =  
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| protein_bound     = 99%
| pregnancy_US = <!-- A / B            / C / D / X -->
| metabolism       = [[Liver|Hepatic]], [[Cytochrome P450|CYP]]-mediated
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC                  / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = Prescription drug
| routes_of_administration = Oral
 
<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound = 98–99%
| metabolism = [[Liver|Hepatic]], [[Cytochrome P450|CYP]]-mediated
| elimination_half-life = 5.9 hours
| elimination_half-life = 5.9 hours
| excretion         = Fecal (60.9%) and [[kidney|renal]] (34.6%)
| excretion = 34.6% urine, 60.9% faeces
| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
 
| pregnancy_US      = <!-- A / B            / C / D / X -->
<!--Identifiers-->
| pregnancy_category=   
| CAS_number_Ref = {{cascite|changed|??}}
| legal_AU          = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| CAS_number = 158876-82-5
| legal_CA          =  <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
| CAS_supplemental = (free base)<br />{{CAS|182349-12-8}} ([[fumarate]])
| legal_UK          = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| ATC_prefix = R06
| legal_US          =  <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| ATC_suffix = AX28
| legal_status      =  
| PubChem = 133017
| routes_of_administration = Oral
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =   
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 117388
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2AE8M83G3E
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 91397
 
<!--Chemical data-->
| C=26 | H=26 | Cl=1 | N=3
| molecular_weight = 415.958 g/mol
| smiles = Clc1cc5c(cc1)\C(=C3/CCN(Cc2cncc(c2)C)CC3)c4ncccc4CC5
| InChI = 1/C26H26ClN3/c1-18-13-19(16-28-15-18)17-30-11-8-20(9-12-30)25-24-7-6-23(27)14-22(24)5-4-21-3-2-10-29-26(21)25/h2-3,6-7,10,13-16H,4-5,8-9,11-12,17H2,1H3
| InChIKey = WUZYKBABMWJHDL-UHFFFAOYAE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C26H26ClN3/c1-18-13-19(16-28-15-18)17-30-11-8-20(9-12-30)25-24-7-6-23(27)14-22(24)5-4-21-3-2-10-29-26(21)25/h2-3,6-7,10,13-16H,4-5,8-9,11-12,17H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WUZYKBABMWJHDL-UHFFFAOYSA-N
}}
}}
__Notoc__
{{SI}}
{{CMG}}
==Overview==
'''Rupatadine''' is a second generation [[antihistamine]] and [[Platelet-activating factor|PAF]] antagonist used to treat allergies. It was discovered and developed by J. [[Uriach y Cia]], S. A.<ref>Patents: {{Patent|EP|577957}}, {{Patent|US|5407941}}, {{Patent|US|5476856}}</ref> and is marketed under several trade names such as '''Rupafin''', '''Alergoliber''', '''Rinialer''', '''Pafinur''', '''Rupax''' and '''Ralif'''.
== Therapeutic indications approved ==
Rupatadine fumarate has been approved for the treatment of allergic rhinitis and chronic urticaria in adults and children over 12 years. The [[defined daily dose]] (DDD) is 10&nbsp;mg orally.
=== Available form ===
Rupatadine is available as round, light salmon coloured tablets containing 10&nbsp;mg of rupatadine (as fumarate) to be administered orally, once a day.


==Overview==
== Side effects ==
'''Rupatadine''' is a new selective [[histamine]] [[histamine H1 receptor|H<sub>1</sub> receptor]] and [[platelet-activating factor]] (PAF) antagonist. Ruptatadine is marketed by Panacea-Biotech under the trade name '''Ralif'''.  Ralif is approved for the treatment of [[allergic rhinitis]].
Rupatadine is a non-sedating antihistamine. However, as in other non sedating second-generation antihistamines, the most common side effects in controlled clinical studies were [[somnolence]], [[headache]]s and [[fatigue (medical)|fatigue]].
 
== Mechanism of action ==
Rupatadine is a second generation, non-[[sedating]], long-acting histamine antagonist with selective peripheral H<sub>1</sub> receptor antagonist activity. It further blocks the receptors of the platelet-activating factor (PAF) according to in vitro and in vivo studies.<ref>{{cite pmid|8996188}}</ref>
 
Rupatadine possesses anti-allergic properties such as the inhibition of the [[degranulation]] of [[mast cell]]s induced by immunological and non-immunological stimuli, and inhibition of the release of [[cytokine]]s, particularly of the [[Tumor necrosis factors|TNF]] in human mast cells and [[monocyte]]s.<ref name="picardo">{{cite pmid|17020424}}</ref>
 
== Pharmacokinetics ==
Rupatadine has several [[active metabolite]]s such as [[desloratadine]], 3-hydroxydesloratadine, 6-hydroxydesloratadine and 5-hydroxydesloratadine.
 
== History ==
Rupatadine discovery, pre-clinical and clinical development was performed by J. Uriach y Cia, S. A., a Spanish pharmaceutical company. It was launched in 2003 in Spain by J. Uriach y Cia, S. A., with the brand name of Rupafin.  The registration of the product is approved in 23 countries from the EU, 8 Central American countries, Brazil, Argentina, Chile, Turkey and 14 African countries.


==External links==
== Efficacy in humans ==
*[http://www.panacea-biotec.com/products/ralif.htm Product information]
The efficacy of rupatadine as treatment for [[allergic rhinitis]] (AR) and [[chronic idiopathic urticaria]] (CIU) has been investigated in adults and adolescents (aged over 12 years) in several controlled studies, showing a rapid onset of action and a good safety profile even in prolonged treatment periods of a year.<ref name="picardo" /><ref>{{cite pmid|17335300}}</ref><ref>{{cite pmid|18339040}}</ref>


[[Category:H1 receptor antagonists]]
== References ==
{{Reflist|2}}


{{Antihistamines}}
{{Antihistamines}}
[[es:Rupatadina]]
{{Histaminergics}}
{{SIB}}
{{Tricyclics}}


{{WH}}
[[Category:Drug]]
 
[[Category:H1 receptor antagonists]]
{{WS}}
[[Category:Pyridines]]
[[Category:Piperidines]]
[[Category:Organochlorides]]
[[Category:Benzocycloheptapyridines]]

Latest revision as of 15:36, 9 April 2015

Rupatadine
Clinical data
Trade namesRupafin, Alergoliber, Rinialer, Pafinur, Rupax, Ralif
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • Prescription drug
Pharmacokinetic data
Protein binding98–99%
MetabolismHepatic, CYP-mediated
Elimination half-life5.9 hours
Excretion34.6% urine, 60.9% faeces
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC26H26ClN3
Molar mass415.958 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

WikiDoc Resources for Rupatadine

Articles

Most recent articles on Rupatadine

Most cited articles on Rupatadine

Review articles on Rupatadine

Articles on Rupatadine in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Rupatadine

Images of Rupatadine

Photos of Rupatadine

Podcasts & MP3s on Rupatadine

Videos on Rupatadine

Evidence Based Medicine

Cochrane Collaboration on Rupatadine

Bandolier on Rupatadine

TRIP on Rupatadine

Clinical Trials

Ongoing Trials on Rupatadine at Clinical Trials.gov

Trial results on Rupatadine

Clinical Trials on Rupatadine at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Rupatadine

NICE Guidance on Rupatadine

NHS PRODIGY Guidance

FDA on Rupatadine

CDC on Rupatadine

Books

Books on Rupatadine

News

Rupatadine in the news

Be alerted to news on Rupatadine

News trends on Rupatadine

Commentary

Blogs on Rupatadine

Definitions

Definitions of Rupatadine

Patient Resources / Community

Patient resources on Rupatadine

Discussion groups on Rupatadine

Patient Handouts on Rupatadine

Directions to Hospitals Treating Rupatadine

Risk calculators and risk factors for Rupatadine

Healthcare Provider Resources

Symptoms of Rupatadine

Causes & Risk Factors for Rupatadine

Diagnostic studies for Rupatadine

Treatment of Rupatadine

Continuing Medical Education (CME)

CME Programs on Rupatadine

International

Rupatadine en Espanol

Rupatadine en Francais

Business

Rupatadine in the Marketplace

Patents on Rupatadine

Experimental / Informatics

List of terms related to Rupatadine

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Rupatadine is a second generation antihistamine and PAF antagonist used to treat allergies. It was discovered and developed by J. Uriach y Cia, S. A.[1] and is marketed under several trade names such as Rupafin, Alergoliber, Rinialer, Pafinur, Rupax and Ralif.

Therapeutic indications approved

Rupatadine fumarate has been approved for the treatment of allergic rhinitis and chronic urticaria in adults and children over 12 years. The defined daily dose (DDD) is 10 mg orally.

Available form

Rupatadine is available as round, light salmon coloured tablets containing 10 mg of rupatadine (as fumarate) to be administered orally, once a day.

Side effects

Rupatadine is a non-sedating antihistamine. However, as in other non sedating second-generation antihistamines, the most common side effects in controlled clinical studies were somnolence, headaches and fatigue.

Mechanism of action

Rupatadine is a second generation, non-sedating, long-acting histamine antagonist with selective peripheral H1 receptor antagonist activity. It further blocks the receptors of the platelet-activating factor (PAF) according to in vitro and in vivo studies.[2]

Rupatadine possesses anti-allergic properties such as the inhibition of the degranulation of mast cells induced by immunological and non-immunological stimuli, and inhibition of the release of cytokines, particularly of the TNF in human mast cells and monocytes.[3]

Pharmacokinetics

Rupatadine has several active metabolites such as desloratadine, 3-hydroxydesloratadine, 6-hydroxydesloratadine and 5-hydroxydesloratadine.

History

Rupatadine discovery, pre-clinical and clinical development was performed by J. Uriach y Cia, S. A., a Spanish pharmaceutical company. It was launched in 2003 in Spain by J. Uriach y Cia, S. A., with the brand name of Rupafin. The registration of the product is approved in 23 countries from the EU, 8 Central American countries, Brazil, Argentina, Chile, Turkey and 14 African countries.

Efficacy in humans

The efficacy of rupatadine as treatment for allergic rhinitis (AR) and chronic idiopathic urticaria (CIU) has been investigated in adults and adolescents (aged over 12 years) in several controlled studies, showing a rapid onset of action and a good safety profile even in prolonged treatment periods of a year.[3][4][5]

References

  1. ↑ Patents: Template:Patent, Template:Patent, Template:Patent
  2. ↑ PMID 8996188 (PMID 8996188)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  3. ↑ 3.0 3.1 PMID 17020424 (PMID 17020424)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  4. ↑ PMID 17335300 (PMID 17335300)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  5. ↑ PMID 18339040 (PMID 18339040)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand

Template:Tricyclics

Retrieved from "https://www.wikidoc.org/index.php?title=Rupatadine&oldid=1085352"