Azatadine: Difference between revisions

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{{drugbox
{{Drugbox
| verifiedrevid = 477164914
| IUPAC_name = 11-(1-methylpiperidin-4-ylidene)-6,11-dihydro-<br>5''H''-benzo[5,6]cyclohepta[1,2-b]pyridine
| IUPAC_name = 11-(1-methylpiperidin-4-ylidene)-6,11-dihydro-<br>5''H''-benzo[5,6]cyclohepta[1,2-b]pyridine
| image =
| image =Azatadine.png
 
<!--Clinical data-->
| tradename = Optimine
| Drugs.com = {{drugs.com|CONS|azatadine}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = B
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = Rx-only
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 3964-81-6
| CAS_number = 3964-81-6
| ATC_prefix = R06
| ATC_prefix = R06
| ATC_suffix = AX09
| ATC_suffix = AX09
| ATC_supplemental =
| PubChem = 19861
| PubChem = 19861
| DrugBank = APRD00810
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C=20 | H=22 | N=2
| DrugBank = DB00719
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 18709
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 94Z39NID6C
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07482
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2946
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 946
 
<!--Chemical data-->
| C=20 | H=22 | N=2  
| molecular_weight = 290.402 g/mol
| molecular_weight = 290.402 g/mol
| bioavailability =  
| smiles = n4c3\C(=C1/CCN(C)CC1)c2ccccc2CCc3ccc4
| protein_bound =  
| InChI = 1/C20H22N2/c1-22-13-10-16(11-14-22)19-18-7-3-2-5-15(18)8-9-17-6-4-12-21-20(17)19/h2-7,12H,8-11,13-14H2,1H3
| metabolism =  
| InChIKey = SEBMTIQKRHYNIT-UHFFFAOYAF
| elimination_half-life =  
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| excretion =
| StdInChI = 1S/C20H22N2/c1-22-13-10-16(11-14-22)19-18-7-3-2-5-15(18)8-9-17-6-4-12-21-20(17)19/h2-7,12H,8-11,13-14H2,1H3
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_US = <!-- A / B / C / D / X -->
| StdInChIKey = SEBMTIQKRHYNIT-UHFFFAOYSA-N
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
| legal_status =  
| routes_of_administration =  
}}
}}


{{SI}}
'''Azatadine''' ('''Optimine''') is a [[first-generation antihistamine]] and [[anticholinergic]] that was launched [[Schering-Plough]] in 1973.<ref>{{cite pmid|8795241}}</ref><ref>{{cite pmid|1982614}}</ref><ref>{{cite pmid|1968324}}</ref>
 
It was patented in 1967.<ref>Azatadine, Villani, F. J.; Caldwell, W. {{US patent|3326924}} (1967).</ref>
 
*It is a predecessor to [[loratidine]], albeit lacking the chlorine atom. Also, it is N-methyl instead of carboethoxyamido.


== See also ==


==Overview==
* [[Benzocycloheptenes]]
'''Azatadine''' is an [[antihistamine]].


==External links==
== References ==
* {{cite journal | author = Zhang D, Hansen E, Deck J, Heinze T, Sutherland J, Cerniglia C | title = Fungal biotransformation of the antihistamine azatadine by Cunninghamella elegans. | journal = Appl Environ Microbiol | volume = 62 | issue = 9 | pages = 3477-9 | year = 1996 | id = PMID 8795241}}
{{Reflist|2}}
* {{cite journal | author = Katelaris C | title = Comparative effects of loratadine and azatadine in the treatment of seasonal allergic rhinitis. | journal = Asian Pac J Allergy Immunol | volume = 8 | issue = 2 | pages = 103-7 | year = 1990 | id = PMID 1982614}}
* {{cite journal | author = Small P, Barrett D, Biskin N | title = Effects of azatadine, terfenadine, and astemizole on allergen-induced nasal provocation. | journal = Ann Allergy | volume = 64 | issue = 2 Pt 1 | pages = 129-31 | year = 1990 | id = PMID 1968324}}


{{Antihistamines}}
{{Antihistamines}}
{{Cholinergics}}
{{Histaminergics}}
{{Tricyclics}}
[[Category:Piperidines]]
[[Category:Benzocycloheptapyridines]]
[[Category:H1 receptor antagonists]]
[[Category:Drug]]


[[Category:Antihistamines]]




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{{respiratory-system-drug-stub}}

Revision as of 12:54, 13 April 2015

Azatadine
Clinical data
Trade namesOptimine
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • US: B (No risk in non-human studies)
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
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
FormulaC20H22N2
Molar mass290.402 g/mol
3D model (JSmol)
  (verify)

Azatadine (Optimine) is a first-generation antihistamine and anticholinergic that was launched Schering-Plough in 1973.[1][2][3]

It was patented in 1967.[4]

  • It is a predecessor to loratidine, albeit lacking the chlorine atom. Also, it is N-methyl instead of carboethoxyamido.

See also

References

  1. ↑ PMID 8795241 (PMID 8795241)
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  2. ↑ PMID 1982614 (PMID 1982614)
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  3. ↑ PMID 1968324 (PMID 1968324)
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  4. ↑ Azatadine, Villani, F. J.; Caldwell, W. U.S. Patent 3,326,924 (1967).

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