OXATOMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H30N4O
Molecular Weight	426.5533
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1NC2=CC=CC=C2N1CCCN3CCN(CC3)C(C4=CC=CC=C4)C5=CC=CC=C5

InChI

InChIKey=BAINIUMDFURPJM-UHFFFAOYSA-N

InChI=1S/C27H30N4O/c32-27-28-24-14-7-8-15-25(24)31(27)17-9-16-29-18-20-30(21-19-29)26(22-10-3-1-4-11-22)23-12-5-2-6-13-23/h1-8,10-15,26H,9,16-21H2,(H,28,32)

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/24474428
Curator's Comment: description was created based on several sources, including, http://www.hindawi.com/journals/jphar/2013/629593/

Oxatomide is a H1-histamine receptor antagonist developed for the treatment of broad spectrum of allergic and other hypersensitivity reactions. The drug is currently marketed in Japan, Taiwan, Italy, Portugal, Indonesia, Argentina, South Africa.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/8753840	Antagonist 2778		6.23 null [pIC50]

Conditions

Condition	Modality	Highest Phase	Product
Chronic urticaria 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7014277	Primary	Approved 8429	TINSET Approved Use Prevention and treatment of allergic diseases: rhinitis, extrinsic asthma (excluding asthma attacks), follicular conjunctivitis, chronic urticaria, atopic dermatitis, food allergies. Launch Date 1.41073921E12
Follicular conjunctivitis 2 Sources: https://farmaci.agenziafarmaco.gov.it/aifa/servlet/PdfDownloadServlet?pdfFileName=footer_000045_025293_RCP.pdf&retry=0&sys=m0b1l3	Primary	Approved 8429	TINSET Approved Use Prevention and treatment of allergic diseases: rhinitis, extrinsic asthma (excluding asthma attacks), follicular conjunctivitis, chronic urticaria, atopic dermatitis, food allergies. Launch Date 1.41073921E12
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12804426	Palliative	Approved 8429	TINSET Approved Use Prevention and treatment of allergic diseases: rhinitis, extrinsic asthma (excluding asthma attacks), follicular conjunctivitis, chronic urticaria, atopic dermatitis, food allergies. Launch Date 1.41073921E12
Perennial allergic rhinitis 47 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1982723	Primary	Approved 8429	TINSET Approved Use Prevention and treatment of allergic diseases: rhinitis, extrinsic asthma (excluding asthma attacks), follicular conjunctivitis, chronic urticaria, atopic dermatitis, food allergies. Launch Date 1.41073921E12
Atopic eczema 2 Sources: https://farmaci.agenziafarmaco.gov.it/aifa/servlet/PdfDownloadServlet?pdfFileName=footer_000045_025293_RCP.pdf&retry=0&sys=m0b1l3	Primary	Approved 8429	TINSET Approved Use Prevention and treatment of allergic diseases: rhinitis, extrinsic asthma (excluding asthma attacks), follicular conjunctivitis, chronic urticaria, atopic dermatitis, food allergies. Launch Date 1.41073921E12
Food allergy 2 Sources: https://farmaci.agenziafarmaco.gov.it/aifa/servlet/PdfDownloadServlet?pdfFileName=footer_000045_025293_RCP.pdf&retry=0&sys=m0b1l3	Primary	Approved 8429	TINSET Approved Use Prevention and treatment of allergic diseases: rhinitis, extrinsic asthma (excluding asthma attacks), follicular conjunctivitis, chronic urticaria, atopic dermatitis, food allergies. Launch Date 1.41073921E12

PubMed

Title	Date	PubMed
Inhibition of mediator release in RBL-2H3 cells by some H1-antagonist derived anti-allergic drugs: relation to lipophilicity and membrane effects.	1995 Feb	7655991
Effect of oxatomide, an antiallergic agent, on QT interval in dogs.	2001	11799844
The role of central histaminergic neuron system as an anticonvulsive mechanism in developing brain.	2001 Nov	11701252
The comparison of the efficacy and safety of cetirizine, oxatomide, ketotifen, and a placebo for the treatment of childhood perennial allergic rhinitis.	2002 Dec	12487225
Gateways to clinical trials.	2002 Jan-Feb	11980386
Oxatomide for stable asthma in adults and children.	2003	12804426
Pranlukast: a review of its use in the management of asthma.	2003	12699401
Enhancement of allergic skin wheal responses in patients with atopic eczema/dermatitis syndrome by playing video games or by a frequently ringing mobile phone.	2003 Jun	12795649
The antiallergic drug oxatomide promotes human eosinophil apoptosis and suppresses IL-5-induced eosinophil survival.	2003 Mar	12642838
Evaluation of the effects of anti-pruritic drugs on scratch responses using histamine H1 receptor-deficient mice.	2003 May 30	12787839
Dietary intake of the flower extracts of German chamomile (Matricaria recutita L.) inhibited compound 48/80-induced itch-scratch responses in mice.	2003 Nov	14692726
[Development of nasal dosage form of oxatomide for rhinitis].	2003 Oct	14685044
Effects of fexofenadine and other antihistamines on components of the allergic response: adhesion molecules.	2003 Oct	14530792
West syndrome associated with administration of a histamine H1 antagonist, oxatomide.	2004	15682834
Cetirizine: a review of its use in allergic disorders.	2004	14977391
Identification of human p450 isoforms involved in the metabolism of the antiallergic drug, oxatomide, and its inhibitory effect on enzyme activity.	2004 May	15133245
The measurement of health-related quality of life (QOL) in paediatric clinical trials: a systematic review.	2004 Nov 22	15555077
Hydroxyzine and metabolites as a source of interference in carbamazepine particle-enhanced turbidimetric inhibition immunoassay (PETINIA).	2005 Aug	16044102
Identification of human P450 isoforms involved in the metabolism of the antiallergic drug, oxatomide, and its kinetic parameters and inhibition constants.	2005 Feb	15684493
Antipruritic effect of the single oral administration of German chamomile flower extract and its combined effect with antiallergic agents in ddY mice.	2005 Oct 3	15964726
Nimesulide-induced fixed drug eruption.	2005 Sep-Oct	16287549
Solvent effect on the charge transfer complex of oxatomide with 2,3-dichloro-5,6-dicyanobenzoquinone.	2006 Dec	16488184
Severe cholinergic urticaria successfully treated with scopolamine butylbromide in addition to antihistamines.	2006 Jul	16716168
[Comparison of clinical efficacy and cost-quality of antihistamines in early treatment for Japanese cedar pollinosis].	2006 May	16883093
Effect of inhibitor of tumor necrosis factor-alpha and oxatomide on immune mediated otitis media.	2006 Sep	16954996
A simple preparation method for mouse eosinophils and their responses to anti-allergic drugs.	2007 Mar	17406808
CINRG pilot trial of oxatomide in steroid-naïve Duchenne muscular dystrophy.	2007 Nov	17459739
Inhibition of angiogenic factor production from murine mast cells by an antiallergic agent (epinastine hydrochloride) in vitro.	2008	18725994
Determination of oxatomide in human plasma by high-performance liquid chromatography-electrospray ionization mass spectrometry.	2008 Jul	18348338
Intact cell binding for in vitro prediction of sedative and non-sedative histamine H1-receptor antagonists based on receptor internalization.	2008 May	18446005
Treatment of allergic rhinitis in infants and children: efficacy and safety of second-generation antihistamines and the leukotriene receptor antagonist montelukast.	2009	19943707
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
An integrative review of systematic reviews related to the management of breathlessness in respiratory illnesses.	2010 Dec 9	21143887
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

Oxatomide should be taken twice daily, after breakfast and after dinner: 30 mg for adults and 0.5 mg/kg for children older tan 1 year.

Route of Administration: Oral

In Vitro Use Guide

The effect of oxatomide on the immunologic release of preformed (histamine and tryptase) and de novo synthesized mediators (leukotriene C4:LTC4 and prostaglandin D2:PGD2) from human basophils and mast cells purified (from 10 to 82%) from human lung parenchyma (HLMC) and skin tissue (HSMC) was studied in vitro. Preincubation (15 min, 37 degrees C) of basophils with oxatomide (10(-7)-10(-5) M) before Der p I antigen or anti-IgE challenge concentration-dependently (10-40%) inhibited the immunologic release of histamine and LTC4. Oxatomide (10(-7)-10(-5) M) also inhibited (10-40%) histamine, tryptase and LTC4 release from HLMC activated by anti-IgE. In addition, oxatomide caused a concentration-dependent inhibition of histamine, tryptase and PGD2 release from HSMC immunologically challenged with a monoclonal antibody against the alpha chain of the high affinity receptor for IgE (anti-Fc epsilon RI) or anti-IgE.

Name

Type

Language

OXATOMIDE

Official Name

English

R 35,443

Code

English

1-[3-[4-(Diphenylmethyl)-1-piperazinyl]propyl]-2-benzimidazolinone

Systematic Name

English

OXATOMIDE [MI]

Common Name

English

R-35443

Code

English

OXATOMIDE [USAN]

Common Name

English

DASTEN

Brand Name

English

CELTECT

Brand Name

English

Oxatomide [WHO-DD]

Common Name

English

NSC-309710

Code

English

OXATOMIDE [JAN]

Common Name

English

2H-BENZIMIDAZOL-2-ONE, 1-(3-(4-(DIPHENYLMETHYL)-1-PIPERAZINYL)PROPYL)-1,3-DIHYDRO-

Systematic Name

English

OXATOMIDE [MART.]

Common Name

English

TINSET

Brand Name

English

oxatomide [INN]

Common Name

English

COBIONA

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QR06AE06