Metopimazine: Difference between revisions
m (Protected "Metopimazine": Protecting pages from unwanted edits ([edit=sysop] (indefinite) [move=sysop] (indefinite))) |
No edit summary |
||
(One intermediate revision by the same user not shown) | |||
Line 1: | Line 1: | ||
{{ | {{Drugbox | ||
| IUPAC_name | | Verifiedfields = changed | ||
| image | | verifiedrevid = 462251895 | ||
| IUPAC_name = 1-(3-[2-(methylsulfonyl)-10''H''-phenothiazin-10-yl]propyl)piperidine-4-carboxamide | |||
| | | image = Metopimazine.png | ||
| | |||
<!--Clinical data--> | |||
| tradename = | |||
| Drugs.com = {{drugs.com|international|metopimazine}} | |||
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | |||
| | | pregnancy_US = <!-- A / B / C / D / X --> | ||
| pregnancy_category = | |||
| | | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | ||
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | |||
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | |||
| pregnancy_AU | | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | ||
| pregnancy_US | | legal_status = | ||
| pregnancy_category= | | routes_of_administration = | ||
| legal_AU | |||
| legal_CA | <!--Pharmacokinetic data--> | ||
| legal_UK | | bioavailability = | ||
| legal_US | | protein_bound = | ||
| legal_status | | metabolism = | ||
| routes_of_administration = | | elimination_half-life = | ||
| excretion = | |||
<!--Identifiers--> | |||
| CAS_number_Ref = {{cascite|changed|??}} | |||
| CAS_number = 14008-44-7 | |||
| ATC_prefix = A04 | |||
| ATC_suffix = AD05 | |||
| PubChem = 26388 | |||
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | |||
| DrugBank = | |||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| ChemSpiderID = 24584 | |||
| UNII_Ref = {{fdacite|correct|FDA}} | |||
| UNII = 238S75V9AV | |||
| ChEMBL_Ref = {{ebicite|correct|EBI}} | |||
| ChEMBL = 398615 | |||
<!--Chemical data--> | |||
| C=22 | H=27 | N=3 | O=3 | S=2 | |||
| molecular_weight = 445.6 g/mol | |||
| smiles = O=S(=O)(c2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCC(C(=O)N)CC4)C | |||
| InChI = 1/C22H27N3O3S2/c1-30(27,28)17-7-8-21-19(15-17)25(18-5-2-3-6-20(18)29-21)12-4-11-24-13-9-16(10-14-24)22(23)26/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26) | |||
| InChIKey = BQDBKDMTIJBJLA-UHFFFAOYAM | |||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | |||
| StdInChI = 1S/C22H27N3O3S2/c1-30(27,28)17-7-8-21-19(15-17)25(18-5-2-3-6-20(18)29-21)12-4-11-24-13-9-16(10-14-24)22(23)26/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26) | |||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | |||
| StdInChIKey = BQDBKDMTIJBJLA-UHFFFAOYSA-N | |||
}} | }} | ||
__NOTOC__ | |||
{{SI}} | |||
{{CMG}} | |||
==Overview== | |||
'''Metopimazine''' ([[International Nonproprietary Name|INN]]) is a [[phenothiazine]] [[antiemetic]]. | '''Metopimazine''' ([[International Nonproprietary Name|INN]]) is a [[phenothiazine]] [[antiemetic]]. | ||
== | ==Synthesis== | ||
[[File:Metopimazine_synthesis.svg.png|700px|thumb|center| Metopimazine synthesis:Jacob, R. M.; Robert, J. G.; {{Patent|DE|1092476}} (1959).]] | |||
The reduced basicity of phenothiazine nitrogen requires that even acylation proceed via the anion. The amide ('''2''') from the methyl thioether ('''2''') can be prepared, for example, by sequential reaction with [[sodium amide]] and [[acetic anhydride]]. Oxidation of that intermediate with [[peracid]] proceeds preferentially on the more electron-rich alkyl thioether to give the [[sulfone]]; this affords the [[phenothiazine]] ('''3''') on hydrolysis of the amide. Complex side chains are most conveniently incorporated in a stepwise fashion. The first step in the present sequence involves reaction of ('''3''') as its anion with 1-bromo-3-chloropropane to give ('''4'''). The use of that halide with alkylate piperidine-4-carboxamide ('''5''') affords the [[antipsychotic]] agent [[metopimazine]] ('''6'''). | |||
{{ | ==References== | ||
{{Reflist|2}} | |||
{{Antiemetics and antinauseants}} | {{Antiemetics and antinauseants}} | ||
Line 37: | Line 72: | ||
[[Category:Antiemetics]] | [[Category:Antiemetics]] | ||
[[Category:Phenothiazines]] | [[Category:Phenothiazines]] | ||
[[Category: | [[Category:Sulfones]] | ||
[[Category:Piperidines]] | |||
[[Category:Amides]] | |||
[[Category:Drug]] |
Latest revision as of 12:42, 10 April 2015
Clinical data | |
---|---|
AHFS/Drugs.com | International Drug Names |
ATC code | |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
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 | |
Formula | C22H27N3O3S2 |
Molar mass | 445.6 g/mol |
3D model (JSmol) | |
| |
| |
(what is this?) (verify) |
WikiDoc Resources for Metopimazine |
Articles |
---|
Most recent articles on Metopimazine Most cited articles on Metopimazine |
Media |
Powerpoint slides on Metopimazine |
Evidence Based Medicine |
Clinical Trials |
Ongoing Trials on Metopimazine at Clinical Trials.gov Clinical Trials on Metopimazine at Google
|
Guidelines / Policies / Govt |
US National Guidelines Clearinghouse on Metopimazine
|
Books |
News |
Commentary |
Definitions |
Patient Resources / Community |
Patient resources on Metopimazine Discussion groups on Metopimazine Patient Handouts on Metopimazine Directions to Hospitals Treating Metopimazine Risk calculators and risk factors for Metopimazine
|
Healthcare Provider Resources |
Causes & Risk Factors for Metopimazine |
Continuing Medical Education (CME) |
International |
|
Business |
Experimental / Informatics |
Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]
Overview
Metopimazine (INN) is a phenothiazine antiemetic.
Synthesis
The reduced basicity of phenothiazine nitrogen requires that even acylation proceed via the anion. The amide (2) from the methyl thioether (2) can be prepared, for example, by sequential reaction with sodium amide and acetic anhydride. Oxidation of that intermediate with peracid proceeds preferentially on the more electron-rich alkyl thioether to give the sulfone; this affords the phenothiazine (3) on hydrolysis of the amide. Complex side chains are most conveniently incorporated in a stepwise fashion. The first step in the present sequence involves reaction of (3) as its anion with 1-bromo-3-chloropropane to give (4). The use of that halide with alkylate piperidine-4-carboxamide (5) affords the antipsychotic agent metopimazine (6).
References
- Pages with script errors
- Template:drugs.com link with non-standard subpage
- Articles with changed CASNo identifier
- E number from Wikidata
- ECHA InfoCard ID from Wikidata
- Chemical articles with unknown parameter in Infobox drug
- Chemical pages without DrugBank identifier
- Articles without KEGG source
- Drugs with no legal status
- Drugboxes which contain changes to verified fields
- Antiemetics
- Phenothiazines
- Sulfones
- Piperidines
- Amides
- Drug