Methdilazine: Difference between revisions

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{{drugbox
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 462249764
| IUPAC_name = 10-[(1-methylpyrrolidin-3-yl) methyl]- 10''H''-phenothiazine
| IUPAC_name = 10-[(1-methylpyrrolidin-3-yl) methyl]- 10''H''-phenothiazine
| image = Methdilazine.svg
<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|monograph|promethazine-hydrochloride}}
| pregnancy_category = 
| legal_status =
<!--Pharmacokinetic data-->
| bioavailability = 
| metabolism = 
| elimination_half-life = 
| excretion =
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 1982-37-2
| CAS_number = 1982-37-2
| ATC_prefix = R06
| ATC_prefix = R06
| ATC_suffix = AD04
| ATC_suffix = AD04
| ATC_supplemental =
| PubChem = 14677
| PubChem = 14677
| DrugBank = APRD00713
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C=18 | H=20 | N=2 | S=1
| DrugBank = DB00902
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14009
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4Q13LY9Z8X
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04979
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1200959
 
<!--Chemical data-->
| C=18 | H=20 | N=2 | S=1  
| molecular_weight = 296.431 g/mol
| molecular_weight = 296.431 g/mol
| bioavailability =  
| smiles = S2c1ccccc1N(c3c2cccc3)CC4CCN(C)C4
| protein_bound =  
| InChI = 1/C18H20N2S/c1-19-11-10-14(12-19)13-20-15-6-2-4-8-17(15)21-18-9-5-3-7-16(18)20/h2-9,14H,10-13H2,1H3
| metabolism =  
| InChIKey = HTMIBDQKFHUPSX-UHFFFAOYAR
| elimination_half-life =  
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| excretion =
| StdInChI = 1S/C18H20N2S/c1-19-11-10-14(12-19)13-20-15-6-2-4-8-17(15)21-18-9-5-3-7-16(18)20/h2-9,14H,10-13H2,1H3
| pregnancy_US = <!-- A / B / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_category =
| StdInChIKey = HTMIBDQKFHUPSX-UHFFFAOYSA-N
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
| legal_status =  
}}
}}


{{SI}}
'''Methdilazine''' ('''Dilosyn''', '''Tacaryl''') is a [[first-generation antihistamine]] with [[anticholinergic]] properties of the [[phenothiazine]] class.


==Synthesis==
[[File:Methdilazine synthesis.png|thumb|center|700px|Methdilazine synthesis:<ref>L. W. Marsch and R. Peterson, Arzneimittel Forsch., 9, 715 (1959). R. F. Feldkamp and Y. H. Wu,</ref> R. F. Feldkamp and Y. H. Wu; [[Mead Johnson & Company]]; {{US Patent|2,945,855}} (1960).]]


==Overview==
== See also ==
'''Methdilazine''' is an [[antihistamine]].
* [[Phenothiazine]]


==External links==
== References ==
* {{cite journal | author = Rani Basu L, Mazumdar K, Dutta N, Karak P, Dastidar S | title = Antibacterial property of the antipsychotic agent prochlorperazine, and its synergism with methdilazine | journal = Microbiol Res | volume = 160 | issue = 1 | pages = 95–100 | year = 2005 | id = PMID 15782943}}
{{Reflist}}
* {{cite journal | author = Chattopadhyay D, Mukherjee T, Pal P, Saha B, Bhadra R | title = Altered membrane permeability as the basis of bactericidal action of methdilazine | journal = J Antimicrob Chemother | volume = 42 | issue = 1 | pages = 83–6 | year = 1998 | id = PMID 9700532}}
* {{cite journal | author = Rani Basu L, Mazumdar K, Dutta N, Karak P, Dastidar S | title = Antibacterial property of the antipsychotic agent prochlorperazine, and its synergism with methdilazine | journal = Microbiol Res | volume = 160 | issue = 1 | pages = 95–100 | year = 2005 | pmid = 15782943 | doi = 10.1016/j.micres.2004.10.002}}
* {{cite journal | author = Chattopadhyay D, Dastidar S, Chakrabarty A | title = Antimicrobial properties of methdilazine and its synergism with antibiotics and some chemotherapeutic agents | journal = Arzneimittelforschung | volume = 38 | issue = 7 | pages = 869–72 | year = 1988 | id = PMID 2905130}}
* {{cite journal | author = Chattopadhyay D, Mukherjee T, Pal P, Saha B, Bhadra R | title = Altered membrane permeability as the basis of bactericidal action of methdilazine | journal = J Antimicrob Chemother | volume = 42 | issue = 1 | pages = 83–6 | year = 1998 | pmid = 9700532 | doi = 10.1093/jac/42.1.83}}
* {{cite journal | author = Chattopadhyay D, Dastidar S, Chakrabarty A | title = Antimicrobial properties of methdilazine and its synergism with antibiotics and some chemotherapeutic agents | journal = Arzneimittelforschung | volume = 38 | issue = 7 | pages = 869–72 | year = 1988 | pmid = 2905130}}
 
The ring-contracted analog, methdilazine, interestingly enough shows only very weak activity as a tranquilizer; instead, that agent constitutes an important antihistamine.


{{Antihistamines}}
{{Antihistamines}}
{{Cholinergics}}
{{Histaminergics}}
{{Tricyclics}}


[[Category:Antihistamines]]
[[Category:Phenothiazines]]
[[Category:Phenothiazines]]
[[Category:Pyrrolidines]]
[[Category:Pyrrolidines]]
[[Category:H1 receptor antagonists]]




 
{{respiratory-system-drug-stub}}
{{WH}}
{{WikiDoc Sources}}

Revision as of 16:14, 11 April 2015

Methdilazine
File:Methdilazine.svg
Clinical data
AHFS/Drugs.comMonograph
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
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
FormulaC18H20N2S
Molar mass296.431 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Methdilazine (Dilosyn, Tacaryl) is a first-generation antihistamine with anticholinergic properties of the phenothiazine class.

Synthesis

File:Methdilazine synthesis.png
Methdilazine synthesis:[1] R. F. Feldkamp and Y. H. Wu; Mead Johnson & Company; Template:US Patent (1960).

See also

References

  1. ↑ L. W. Marsch and R. Peterson, Arzneimittel Forsch., 9, 715 (1959). R. F. Feldkamp and Y. H. Wu,
  • Rani Basu L, Mazumdar K, Dutta N, Karak P, Dastidar S (2005). "Antibacterial property of the antipsychotic agent prochlorperazine, and its synergism with methdilazine". Microbiol Res. 160 (1): 95–100. doi:10.1016/j.micres.2004.10.002. PMID 15782943.
  • Chattopadhyay D, Mukherjee T, Pal P, Saha B, Bhadra R (1998). "Altered membrane permeability as the basis of bactericidal action of methdilazine". J Antimicrob Chemother. 42 (1): 83–6. doi:10.1093/jac/42.1.83. PMID 9700532.
  • Chattopadhyay D, Dastidar S, Chakrabarty A (1988). "Antimicrobial properties of methdilazine and its synergism with antibiotics and some chemotherapeutic agents". Arzneimittelforschung. 38 (7): 869–72. PMID 2905130.

The ring-contracted analog, methdilazine, interestingly enough shows only very weak activity as a tranquilizer; instead, that agent constitutes an important antihistamine.

Template:Tricyclics


Template:Respiratory-system-drug-stub

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