関: loratadine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/12 12:21:04」(JST)

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Loratadine (INN) is a second-generation^[1] H₁ histamine antagonist drug used to treat allergies. In structure, it is closely related to tricyclic antidepressants, such as imipramine, and is distantly related to the atypical antipsychotic quetiapine.^[2]

Loratadine is marketed by Schering-Plough^{[needs update]} under several trade names (e.g., Claritin) and also by Shionogi in Japan. It is available as a generic drug and is marketed for its nonsedating properties. In a version named Claritin-D or Clarinase, it is combined with pseudoephedrine, a decongestant; this makes it useful for colds, as well as allergies but adds potential side effects of insomnia, anxiety, and nervousness.

History

Schering-Plough developed loratadine as part of a quest for a potential blockbuster drug: a nonsedating antihistamine. However, by the time Schering submitted the drug to the U.S. Food and Drug Administration (FDA) for approval, the agency had already approved a competitor's nonsedating antihistamine, terfenadine (trade name Seldane), and, therefore, put loratadine on a lower priority.^[3]

Loratadine was approved by the FDA in 1993.^[3] The drug continued to be available only by prescription in the U.S. until it went off patent in 2002.^{[citation needed]} It was then subsequently approved for over-the-counter sales. Once it became an unpatented over-the-counter drug, the price dropped significantly.

Schering also developed desloratadine (Clarinex), which is an active metabolite of loratadine.

Indications

Loratadine is indicated for the symptomatic relief of allergy such as hay fever (allergic rhinitis), urticaria (hives), chronic idiopathic urticaria,^[4] and other skin allergies.^[5] For allergic rhinitis (hay fever), loratadine is effective for both nasal and eye symptoms: sneezing, runny nose, itchy or burning eyes. Loratadine could be also used to treat mild to moderate pain from headaches.^{[citation needed]}

Similarly to cetirizine, loratadine attenuates the itching associated with Kimura's disease.^[6]

Forms

An example of a loratadine 10-mg tablet (Rx)

The drug is available in many different forms, such as: tablets, oral suspension, and syrup,^[5] and in combination with pseudoephedrine.^[7] Also available are quick-dissolving tablets, which are marketed as being faster to get into one's circulatory system, but require special handling to avoid degrading in the package.

Cautions and contraindications

Patients with severe hepatic (liver) disorders may need to start with a lower dose. No dose adaptation is necessary for elderly or renally (kidney) impaired patients.^[5]^[8]

Loratadine is usually compatible with breast-feeding (classified category L-2 by the American Academy of Pediatrics).^[9] In the U.S., it is classified as category B in pregnancy, meaning animal reproduction studies have failed to demonstrate a risk to the fetus, and no adequate and well-controlled studies in pregnant women have been conducted.^[10]

Adverse effects

As a "nonsedating" antihistamine, loratadine causes less (but still significant, in some cases) sedation and psychomotor retardation than the older antihistamines because it penetrates the blood/brain barrier to a smaller extent. Although drowsiness is rare at the common 10-mg dose, patients should, nevertheless, be advised that it can occur and may affect performance of skilled tasks (e.g., driving). Patients who do experience drowsiness while taking loratadine should avoid the use of alcohol, as it can cause excessive drowsiness. Otherwise, loratadine and alcohol are unlikely to cause problems. Nevertheless, it would be in the patient's best interest to take caution when combining alcohol and any medication.^[11]

Other possible side effects include headache and antimuscarinic effects such as urinary retention, dry mouth, blurred vision, and gastrointestinal disturbances.^[5]^[8]

Mechanism of action

Loratadine is a tricyclic antihistamine, which acts as a selective inverse agonist of peripheral histamine H₁-receptors.^[8] Histamine is responsible for many features of allergic reactions.

Pharmacokinetics

Loratadine is given orally, is well absorbed from the gastrointestinal tract, and has rapid first-pass hepatic metabolism; it is metabolized by isoenzymes of the cytochrome P450 system, including CYP3A4, CYP2D6, and, to a lesser extent, several others.^[12]^[13] Loratadine is almost totally (97–99%) bound to plasma proteins. Its metabolite desloratadine, which is largely responsible for the antihistaminergic effects, binds to plasma proteins by 73–76%.^[5]

Loratadine's peak effect occurs after one to two hours, and its biological half-life is on average 8 hours (range 3 to 20 hours) with desloratadine's half-life being 27 hours (range 9 to 92 hours), accounting for its long-lasting effect.^[14] About 40% is excreted as conjugated metabolites into the urine, and a similar amount is excreted into the feces. Traces of unmetabolised loratadine can be found in the urine.^[5]

Interactions

Substances that act as inhibitors of the CYP3A4 enzyme such as ketoconazole, erythromycin, cimetidine, and furanocoumarin derivatives (found in grapefruit) lead to increased plasma levels of loratadine. This had clinically significant effects in controlled trials of higher-than-usual doses of loratadine (20 mg).^{[citation needed]}

Antihistamines should be discontinued about 48 hr prior to skin allergy tests, since these drugs may prevent or diminish otherwise-positive reactions to dermal activity indicators.

Availability

Loratadine is available under many brand names and dosage forms worldwide.^[15] In the US, in an unprecedented action, in 1998 the insurance company Wellpoint petitioned the FDA to allow loratadine and two other antihistamines to be made available over the counter (OTC) while it was still under patent; the FDA granted the request, which was not binding on manufacturers.^[16] In the US, Schering-Plough made loratadine available OTC in 2002.^[16] Loratadine is available in many countries OTC.^[17]

References

^ Holdcroft, C. (1993). "Terfenadine, astemizole and loratadine: Second generation antihistamines". The Nurse practitioner 18 (11): 13–14. doi:10.1097/00006205-199311000-00005. PMID 8278087. edit
^ Kay GG, Harris AG (July 1999). "Loratadine: a nonsedating antihistamine. Review of its effects on cognition, psychomotor performance, mood and sedation". Clinical and experimental allergy: journal of the British Society for Allergy and Clinical Immunology. 29 Suppl 3: 147–50. doi:10.1046/j.1365-2222.1999.0290s3147.x. PMID 10444229.
^ ^a ^b Hall, Stephen S. (2001-03-11). "The Claritin Effect; Prescription for Profit". The New York Times. Retrieved 2010-06-28.
^ Pons-Guiraud, A; Nekam, K; Lahovsky, J; Costa, A; Piacentini, A (2006). "Emedastine difumarate versus loratadine in chronic idiopathic urticaria: A randomized, double-blind, controlled European multicentre clinical trial". European journal of dermatology : EJD 16 (6): 649–54. PMID 17229605. edit
^ ^a ^b ^c ^d ^e ^f Jasek, W, ed. (2007). Austria-Codex (in German) 1 (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. pp. 1768–71. ISBN 978-3-85200-181-4.
^ Ueda, T; Arai, S; Amoh, Y; Katsuoka, K (2011). "Kimura's disease treated with suplatast tosilate and loratadine". European journal of dermatology : EJD 21 (6): 1020–1. doi:10.1684/ejd.2011.1539 (inactive 2015-05-04). PMID 21914581. edit
^ Jasek, W, ed. (2007). Austria-Codex (in German) 1 (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. pp. 1731–34. ISBN 978-3-85200-181-4.
^ ^a ^b ^c Mutschler, Ernst; Gerd Geisslinger; Heyo K. Kroemer; Monika Schäfer-Korting (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 456–461. ISBN 3-8047-1763-2.
^ Committee on Drugs (1 September 2001). "Transfer of drugs and other chemicals into human milk". Pediatrics 108 (3): 776–89. PMID 11533352.
^ See, Sharon (November 15, 2003). "Desloratadine for Allergic Rhinitis". American Family Physician.
^ Kristi Monson, PharmD. "Claritin and Alcohol". emedtv.com.
^ Nelson, Wendel L. (2002). "Antihistamines and related antiallergic and antiulcer agents". In Williams, David H.; Foye, William O.; Lemke, Thomas L. Foye's principles of medicinal chemistry. Hagerstown, MD: Lippincott Williams & Wilkins. p. 805. ISBN 0-683-30737-1. Retrieved on 1 December 2009 through Google Book Search.
^ Ghosal A, Gupta S, Ramanathan R et al. (August 2009). "Metabolism of loratadine and further characterization of its in vitro metabolites". Drug Metab Lett 3 (3): 162–70. doi:10.2174/187231209789352067. PMID 19702548.
^ Affrime, M; Gupta, S; Banfield, C; Cohen, A (2002). "A pharmacokinetic profile of desloratadine in healthy adults, including elderly". Clinical pharmacokinetics. 41 Suppl 1: 13–9. PMID 12169042. edit
^ drugs.com Loratadine at drugs.com international listings Page accessed April 11, 2015]
^ ^a ^b Cohen JP et al. Switching prescription drugs to over the counter. BMJ. 2005 Jan 1;330(7481):39-41. PMID 15626806 PMC 539854
^ Association of the European Self-Medication Industry Database. Loratadine OTC regulation Page accessed April 11, 2015

External links

Loratadine—MedlinePlus Drug Information, U.S. National Library of Medicine, National Institutes of Health
Claritin (loratadine) drug description—RxList (Internet Drug Index)
U.S. National Library of Medicine: Drug Information Portal - Loratadine
Claritin.ph—Claritin Philippines Website

UpToDate Contents

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English Journal

Pharmaceutical evaluation and dynamic vapor sorption studies of fast dissolving intraoral films of Loratadine.

Arya A, Sharma V, Pathak K.SourceDepartment of Pharmaceutics, Rajiv Academy for Pharmacy , Mathura, Uttar Pradesh , India.
Pharmaceutical development and technology.Pharm Dev Technol.2013 Nov-Dec;18(6):1329-38. doi: 10.3109/10837450.2012.685659. Epub 2012 Jun 5.
The aim of the study was to develop intraoral films (IOFs) of loratadine and to assess the storage conditions by dynamic vapour sorption studies. The excipient selection was guided by drug excipient compatibility studies and the incompatibility of loratadine with dibutylphathalate and Tween20 was co
PMID 22663089

Spectroscopic behavior of loratadine and desloratadine in different aqueous media conditions studied by means of TD-DFT calculations.

Brasca R, Romero MA, Goicoechea HC, Kelterer AM, Fabian WM.SourceLaboratorio de Desarrollo Analítico y Quimiometría (LADAQ), Cátedra de Química Analítica I, Facultad de Bioquímica y Ciencias Biológicas, Universidad Nacional del Litoral-CONICET, Ciudad Universitaria, S3000ZAA Santa Fe, Argentina; Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Av. Rivadavia 1917, C1033AAJ Capital Federal, Argentina. Electronic address: rbrasca@fiq.unl.edu.ar.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2013 Nov;115:250-8. doi: 10.1016/j.saa.2013.06.037. Epub 2013 Jun 19.
In this study, we explained the influence of the stepwise protonation of two antihistaminic drugs on their experimental absorption spectra. We demonstrated the capability of the TD-CAM-B3LYP method, combined with a polarizable continuum model, to produce good performance for the calculated spectra.
PMID 23835058

Robust analysis of the hydrophobic basic analytes loratadine and desloratadine in pharmaceutical preparations and biological fluids by sweeping-cyclodextrin-modified micellar electrokinetic chromatography.

El-Awady M, Belal F, Pyell U.SourceDepartment of Chemistry, University of Marburg, Hans-Meerwein-Straße, D-35032, Marburg, Germany; Mansoura University, Faculty of Pharmacy, Analytical Chemistry Department, 35516, Mansoura, Egypt.
Journal of chromatography. A.J Chromatogr A.2013 Sep 27;1309:64-75. doi: 10.1016/j.chroma.2013.08.020. Epub 2013 Aug 9.
The analysis of hydrophobic basic analytes by micellar electrokinetic chromatography (MEKC) is usually challenging because of the tendency of these analytes to be adsorbed onto the inner capillary wall in addition to the difficulty to separate these compounds as they exhibit extremely high retention
PMID 23953618

Japanese Journal

〓痒性皮膚疾患に対するロラタジン口腔内速溶錠(クラリチン^【○!R】レディタブ^【○!R】錠)の服用性及び有用性の検討 : 患者主体の評価を中心に

窪田泰夫,森上徹也,森上純子,松岡由恵,中井浩三,横井郁美,丹生名都子,宮本泉,松田保史,米田耕造
西日本皮膚科 = The Nishinihon journal of dermatology 69(6), 653-659, 2007-12-01
NAID 10026636749

ロラタジン口腔内速溶錠(クラリチン^【○!R】レディタブ^【○!R】錠)の使用感ならびに有用性の検討

古江増隆,今福信一
西日本皮膚科 = The Nishinihon journal of dermatology 68(2), 195-198, 2006-04-01
NAID 10018350901

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「ロラタジン」

Loratadine
Systematic (IUPAC) name
	Ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate
Clinical data
Trade names	Claritin
AHFS/Drugs.com	monograph
MedlinePlus	a697038
Pregnancy; category	AU: B1; US: B (No risk in non-human studies);
Legal status	CA: OTC; UK: General sales list (GSL, OTC); US: OTC;
Routes of; administration	oral
Pharmacokinetic data
Bioavailability	almost 100%
Protein binding	97–99%
Metabolism	Hepatic (CYP2D6- and 3A4-mediated)
Half-life	8 hours, active metabolite desloratadine 27 hours
Excretion	40% as conjugated metabolites into urine; Similar amount into the feces
Identifiers
CAS Registry Number	79794-75-5
ATC code	R06AX13
PubChem	CID: 3957
DrugBank	DB00455
ChemSpider	3820
UNII	7AJO3BO7QN
KEGG	D00364
ChEMBL	CHEMBL998
Chemical data
Formula	C22H23ClN2O2
Molecular mass	382.88 g/mol
	SMILES O=C(OCC)N4CC/C(=C2/c1ccc(Cl)cc1CCc3cccnc23)CC4;
	InChI InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3 ; Key:JCCNYMKQOSZNPW-UHFFFAOYSA-N ;
(what is this?) (verify)

　　[★]

英: loratadine
商: クラリチン Claritin
同: Claritin, Alavert, Dimetapp

[1] Holdcroft, C. (1993). "Terfenadine, astemizole and loratadine: Second generation antihistamines". The Nurse practitioner 18 (11): 13–14. doi:10.1097/00006205-199311000-00005. PMID 8278087. edit

[pmid10444229-2] Kay GG, Harris AG (July 1999). "Loratadine: a nonsedating antihistamine. Review of its effects on cognition, psychomotor performance, mood and sedation". Clinical and experimental allergy: journal of the British Society for Allergy and Clinical Immunology. 29 Suppl 3: 147–50. doi:10.1046/j.1365-2222.1999.0290s3147.x. PMID 10444229.

[NYTimes-3] Hall, Stephen S. (2001-03-11). "The Claritin Effect; Prescription for Profit". The New York Times. Retrieved 2010-06-28.

[4] Pons-Guiraud, A; Nekam, K; Lahovsky, J; Costa, A; Piacentini, A (2006). "Emedastine difumarate versus loratadine in chronic idiopathic urticaria: A randomized, double-blind, controlled European multicentre clinical trial". European journal of dermatology : EJD 16 (6): 649–54. PMID 17229605. edit

[Austria-Codex-5] ^ ^a ^b ^c ^d ^e ^f Jasek, W, ed. (2007). Austria-Codex (in German) 1 (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. pp. 1768–71. ISBN 978-3-85200-181-4.

[6] Ueda, T; Arai, S; Amoh, Y; Katsuoka, K (2011). "Kimura's disease treated with suplatast tosilate and loratadine". European journal of dermatology : EJD 21 (6): 1020–1. doi:10.1684/ejd.2011.1539 (inactive 2015-05-04). PMID 21914581. edit

[7] Jasek, W, ed. (2007). Austria-Codex (in German) 1 (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. pp. 1731–34. ISBN 978-3-85200-181-4.

[Mutschler-8] Mutschler, Ernst; Gerd Geisslinger; Heyo K. Kroemer; Monika Schäfer-Korting (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 456–461. ISBN 3-8047-1763-2.

[9] Committee on Drugs (1 September 2001). "Transfer of drugs and other chemicals into human milk". Pediatrics 108 (3): 776–89. PMID 11533352.

[10] See, Sharon (November 15, 2003). "Desloratadine for Allergic Rhinitis". American Family Physician.

[11] Kristi Monson, PharmD. "Claritin and Alcohol". emedtv.com.

[Foye-12] Nelson, Wendel L. (2002). "Antihistamines and related antiallergic and antiulcer agents". In Williams, David H.; Foye, William O.; Lemke, Thomas L. Foye's principles of medicinal chemistry. Hagerstown, MD: Lippincott Williams & Wilkins. p. 805. ISBN 0-683-30737-1. Retrieved on 1 December 2009 through Google Book Search.

[13] Ghosal A, Gupta S, Ramanathan R et al. (August 2009). "Metabolism of loratadine and further characterization of its in vitro metabolites". Drug Metab Lett 3 (3): 162–70. doi:10.2174/187231209789352067. PMID 19702548.

[14] Affrime, M; Gupta, S; Banfield, C; Cohen, A (2002). "A pharmacokinetic profile of desloratadine in healthy adults, including elderly". Clinical pharmacokinetics. 41 Suppl 1: 13–9. PMID 12169042. edit

[15] rugs.com Loratadine at drugs.com international listings Page accessed April 11, 2015]

[Cohen-16] Cohen JP et al. Switching prescription drugs to over the counter. BMJ. 2005 Jan 1;330(7481):39-41. PMID 15626806 PMC 539854

[17] Association of the European Self-Medication Industry Database. Loratadine OTC regulation Page accessed April 11, 2015

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Claritin