Metharbital: Difference between revisions

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Metharbital
Clinical data
AHFS/Drugs.com	Monograph
ATC code	N03AA30 (WHO) ;
Identifiers
	IUPAC name 5,5-diethyl-1-methylpyrimidine-2,4,6(1H,3H,5H)-trione;
CAS Number	50-11-3 ;
PubChem CID	4099;
DrugBank	DB00463 ;
ChemSpider	3957 ;
UNII	02OS7K758T;
KEGG	D01382 ;
ChEMBL	ChEMBL450 ;
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	C9H14N2O3
Molar mass	198.219 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C1N(C(=O)NC(=O)C1(CC)CC)C;
	InChI InChI=1S/C9H14N2O3/c1-4-9(5-2)6(12)10-8(14)11(3)7(9)13/h4-5H2,1-3H3,(H,10,12,14) ; Key:FWJKNZONDWOGMI-UHFFFAOYSA-N ;
(verify)

VisualWikitext

Latest revision as of 13:14, 14 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Metharbital was patented in 1905 by Emil Fischer working for Merck.^[1] It was marketed as Gemonil by Abbott Laboratories. It is a barbiturate anticonvulsant, used in the treatment of epilepsy. It has similar properties to phenobarbital.

History

1952 Gemonil was introduced by Abbott Laboratories.
1990 Abbott stopped marketing.

Synthesis

700px[2][3] U.S. Patent 782,742 — 700px^[2]^[3] U.S. Patent 782,742

In an interesting variation on this theme (cf hexobarbital), the bis acid chloride of diethylmalonate (1) is condensed with the O-methyl ether of urea (2, Methyl carbamimidate^[4]) to afford the imino ether of the barbituric acid (3). Heating this ether at 200°C results in O to N migration of the methyl group and formation of metharbital 4.

References

↑ US Patent 782742
↑ A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949).
↑ Template:Cite doi
↑ http://www.chemspider.com/Chemical-Structure.68069.html?rid=81ad3137-afb0-456a-8c9f-d6c73ada4966

The Treatment of Epilepsy 2nd Ed by S. D. Shorvon (Editor), David R. Fish (Editor), Emilio Perucca (Editor), W. Edwin Dodson (Editor). Published by Blackwell 2004. ISBN 0-632-06046-8
The Medical Treatment of Epilepsy by Stanley R Resor. Published by Marcel Dekker (1991). ISBN 0-8247-8549-5.
The Comparative Toxicogenomics Database: Metharbital

Template:GABAAR PAMs

This anticonvulsant-related article is a stub. You can help Wikipedia by expanding it.

[1] US Patent 782742

[2] A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949).

[3] Template:Cite doi

[4] ttp://www.chemspider.com/Chemical-Structure.68069.html?rid=81ad3137-afb0-456a-8c9f-d6c73ada4966

[1]

[2]

[3]

[4]

@@ Line 1: / Line 1: @@
-{{drugbox
+{{Drugbox
-| IUPAC_name = 5,5-diethyl-1-methyl-hexahydropyrimidine-2,4,6-trione
+| verifiedrevid = 459493742
-| image = Metharbital.png
+| IUPAC_name = 5,5-diethyl-1-methylpyrimidine-2,4,6(1''H'',3''H'',5''H'')-trione
+| image = Metharbital Wiki Str.png
 | width = 141
+<!--Clinical data-->
+| tradename =
+| Drugs.com = {{drugs.com|monograph|luminal}}
+| pregnancy_category =
+| legal_status =
+| routes_of_administration =
+<!--Pharmacokinetic data-->
+| bioavailability =
+| protein_bound =
+| metabolism =
+| elimination_half-life =
+<!--Identifiers-->
+| CASNo_Ref = {{cascite|correct|CAS}}
+| CAS_number_Ref = {{cascite|correct|??}}
 | CAS_number = 50-11-3
 | ATC_prefix = N03
 | ATC_suffix = AA30
 | ATC_supplemental =
 | PubChem = 4099
-| DrugBank = APRD00757
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
-| C=9 | H=14 | N=2 | O=3
+ | DrugBank = DB00463
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 3957
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 02OS7K758T
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D01382
+| ChEMBL_Ref = {{ebicite|correct|EBI}}
+| ChEMBL = 450
+<!--Chemical data-->
+| C=9 | H=14 | N=2 | O=3
 | molecular_weight = 198.219 g/mol
-| bioavailability =
+| smiles = O=C1N(C(=O)NC(=O)C1(CC)CC)C
-| protein_bound =
+| InChI = 1/C9H14N2O3/c1-4-9(5-2)6(12)10-8(14)11(3)7(9)13/h4-5H2,1-3H3,(H,10,12,14)
-| metabolism =
+| InChIKey = FWJKNZONDWOGMI-UHFFFAOYAX
-| elimination_half-life =
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
-| pregnancy_category =
+| StdInChI = 1S/C9H14N2O3/c1-4-9(5-2)6(12)10-8(14)11(3)7(9)13/h4-5H2,1-3H3,(H,10,12,14)
-| legal_status =
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
-| routes_of_administration =
+| StdInChIKey = FWJKNZONDWOGMI-UHFFFAOYSA-N
 }}
-'''Metharbital''' was patented in 1905 by [[Hermann Emil Fischer|Emil Fischer]] working for [[Merck KGaA|Merck]]<ref>US Patent 782742</ref>. It was marketed as '''Gemonil''' by [[Abbott Laboratories]]. It is a [[barbiturate]] [[anticonvulsant]], used in the treatment of [[epilepsy]]. It has similar properties to [[phenobarbital]].
+__NOTOC__
+{{SI}}
+{{CMG}}
+== Overview ==
+'''Metharbital''' was patented in 1905 by [[Hermann Emil Fischer|Emil Fischer]] working for [[Merck KGaA|Merck]].<ref>US Patent 782742</ref> It was marketed as '''Gemonil''' by [[Abbott Laboratories]]. It is a [[barbiturate]] [[anticonvulsant]], used in the treatment of [[epilepsy]]. It has similar properties to [[phenobarbital]].
 == History ==
@@ Line 25: / Line 60: @@
 * '''1952''' Gemonil was introduced by Abbott Laboratories.
 * '''1990''' Abbott stopped marketing.
+==Synthesis==
+[[File:Metharbital syn.png|center|700px<ref>A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949).</ref><ref>{{Cite doi|10.1021/ja01104a030}}</ref> {{US patent|782742}}]]
+In an interesting variation on this theme (cf [[hexobarbital]]), the bis acid chloride of [[diethylmalonate]] ('''1''') is condensed with the O-methyl ether of urea ('''2''', Methyl carbamimidate<ref>http://www.chemspider.com/Chemical-Structure.68069.html?rid=81ad3137-afb0-456a-8c9f-d6c73ada4966</ref>) to afford the imino ether of the barbituric acid ('''3'''). Heating this ether at 200°C results in O to N migration of the methyl group and formation of metharbital '''4'''.
 ==References==
+{{Reflist|2}}
 * ''The Treatment of Epilepsy 2nd Ed'' by S. D. Shorvon (Editor), David R. Fish (Editor), Emilio Perucca (Editor), W. Edwin Dodson (Editor). Published by Blackwell 2004. ISBN 0-632-06046-8
 * ''The Medical Treatment of Epilepsy'' by Stanley R Resor. Published by Marcel Dekker (1991). ISBN 0-8247-8549-5.
-* [http://ctd.mdibl.org/voc.go?voc=chem&termUI=metharbital The Comparative Toxicogenomics Database: Metharbital]
+* [http://ctdbase.org/detail.go?type=chem&acc=C084822 The Comparative Toxicogenomics Database: Metharbital]
 <references/>
-{{Barbiturates}}
+{{GABAAR PAMs}}
+[[Category:drug]]
 [[Category:Barbiturates]]
 [[Category:Anticonvulsants]]
+[[Category:Pyrimidinediones]]
+[[Category:Imides]]
+[[Category:GABAA receptor positive allosteric modulators]]
-{{pharma-stub}}
+{{anticonvulsant-stub}}
-{{WikiDoc Sources}}