OXATOMIDE MONOHYDRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H30N4O.H2O
Molecular Weight	444.5686
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=WUVRHFANMRXNRX-UHFFFAOYSA-N

InChI=1S/C27H30N4O.H2O/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);1H2

HIDE SMILES / InChI

Molecular Formula	C27H30N4O
Molecular Weight	426.5533
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 2014
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 2014
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 2014
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 2014
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 2014
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 2014

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
Double-blind multicenter study on the efficacy and tolerability of cetirizine compared with oxatomide in chronic idiopathic urticaria in preschool children.	2001 Jul	11476462
Change in tissue kallikrein level in nasal wash after the administration of oxatomide in patients with nasal allergy.	2001 Mar-Apr	11345148
Preclinical comparison of ebastine and other second generation H1-antihistamines.	2001 Oct	11881966
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
Drug eruption and liver injury caused by terfenadine and oxatomide.	2002 Jul-Aug	12095890
Pranlukast: a review of its use in the management of asthma.	2003	12699401
Evaluation of the effects of anti-pruritic drugs on scratch responses using histamine H1 receptor-deficient mice.	2003 May 30	12787839
West syndrome associated with administration of a histamine H1 antagonist, oxatomide.	2004	15682834
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
Solvent effect on the charge transfer complex of oxatomide with 2,3-dichloro-5,6-dicyanobenzoquinone.	2006 Dec	16488184
Inhibition of angiogenic factor production from murine mast cells by an antiallergic agent (epinastine hydrochloride) in vitro.	2008	18725994
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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:09:07 GMT 2023` Edited by `admin` on `Sat Dec 16 10:09:07 GMT 2023`
Record UNII	AH84KRJ5KM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXATOMIDE MONOHYDRATE

Common Name

English

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

Systematic Name

English

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

Systematic Name

English

Code System Code Type Description

SMS_ID

100000130699