| 词条 | Oxatomide |
| 释义 |
| Verifiedfields = changed | verifiedrevid = 462266871 | IUPAC_name = 13-[4-(diphenylmethyl)piperazin-1-yl]propyl1,3-dihydro-2H-benzimidazol-2-one | image = Oxatomide.png | width = 250px | tradename = Tinset, others | Drugs.com = {{drugs.com|international|oxatomide}} | pregnancy_category = | legal_status = Rx-only | routes_of_administration = By mouth | bioavailability = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 60607-34-3 | ATC_prefix = R06 | ATC_suffix = AE06 | PubChem = 4615 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4454 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = J31IL9Z2EE | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D01773 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 13828 | synonyms = KW-4354; McN-JR 35443; R-35443 | C=27 | H=30 | N=4 | O=1 | molecular_weight = 426.553 g/mol | SMILES = O=C2Nc1ccccc1N2CCCN5CCN(C(c3ccccc3)c4ccccc4)CC5 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = BAINIUMDFURPJM-UHFFFAOYSA-N }}Oxatomide, sold under the brand name Tinset among others, is a first-generation antihistamine of the diphenylmethylpiperazine family which is marketed in Europe, Japan, and a number of other countries.[1][2][3][4] It was discovered at Janssen Pharmaceutica in 1975.[5] Oxatomide lacks any anticholinergic effects.[2] In addition to its H1 receptor antagonism, it also possesses antiserotonergic activity similarly to hydroxyzine.[2] It was patented in 1976 and came into medical use in 1981.[6] ChemistrySynthesisReaction of 2-Benzimidazolinone with isopropenyl acetate leads to the singly protected imidazolone derivative (2). Alkylation of this with 3-chloro-1-bromopropane affords the functionalized derivative (3). Alkylation of the monobenzhydryl derivative of piperazine (4) with 3 gives oxatomide (5), after hydrolytic removal of the protecting group. References1. ^{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA912|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=912–}} {{Antihistamines}}{{Navboxes2. ^1 2 {{cite journal |vauthors=Ohmori K, Ishii H, Nito M, Shuto K, Nakamizo N | title = [Pharmacological studies on oxatomide (KW-4354). (7) Antagonistic effects on chemical mediators] | language = Japanese | journal = Nippon Yakurigaku Zasshi. Folia Pharmacologica Japonica | volume = 81 | issue = 5 | pages = 399–409 |date=May 1983 | pmid = 6138301 | doi = 10.1254/fpj.81.399| url = }} 3. ^{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA768|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=768–}} 4. ^https://www.drugs.com/international/oxatomide.html 5. ^{{cite book|author=Harry Schwartz|title=Breakthrough: the discovery of modern medicines at Janssen|url=https://books.google.com/books?id=hwhtAAAAMAAJ|date=August 1989|publisher=Skyline Pub. Group|isbn=978-1-56019-100-1|page=149}} 6. ^{{cite book |last1=Fischer |first1=Jnos |last2=Ganellin |first2=C. Robin |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=548 |url=https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA548 |language=en}} 7. ^J. Vandenberk et al., {{Cite patent|DE|2714437}}; eidem, {{US patent|4250176}} (1977, 1981 both to Janssen). | title = Pharmacodynamics | titlestyle = background:#ccccff | list1 ={{Histamine receptor modulators}}{{Serotonin receptor modulators}}{{Xenobiotic-sensing receptor modulators}} }}{{Respiratory-system-drug-stub}} 7 : Benzimidazoles|Belgian inventions|H1 receptor antagonists|Janssen Pharmaceutica|Lactams|Piperazines|Ureas |
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