Meprobamat

Meprobamat
(IUPAC) ime
	[2-(carbamoyloxymethyl)-2-methyl-pentyl] carbamate
Klinički podaci
AHFS/Drugs.com	Monografija
MedlinePlus	a682077
Identifikatori
CAS broj	57-53-4
ATC kod	N05BC01
PubChem	4064
DrugBank	DB00371
ChemSpider	3924
UNII	9I7LNY769Q
KEGG	D00376
ChEMBL	CHEMBL979
Hemijski podaci
Formula	C9H18N2O4
Mol. masa	218.250 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C9H18N2O4/c1-3-4-9(2,5-14-7(10)12)6-15-8(11)13/h3-6H2,1-2H3,(H2,10,12)(H2,11,13) ; Key: NPPQSCRMBWNHMW-UHFFFAOYSA-N
Fizički podaci
Gustina	1.229 g/cm³
Tačka topljenja	105–106 °C (221–223 °F)
Tačka ključanja	200 °C (392 °F) to 210 °C (410 °F)
Farmakokinetički podaci
Bioraspoloživost	?
Metabolizam	Hepatic
Poluvreme eliminacije	10 hours
Izlučivanje	Renal
Farmakoinformacioni podaci
Trudnoća	D(US)
Pravni status	Samo na recept (S4) (AU) Schedule IV (SAD)
Način primene	Oral

Meprobamat (Miltown, Equanil, Meprospan) karbamatni je derivat koji se koristi kao anksiolitički lek. On se svojevremeno bio jedan od najšire korišćenih anksiolitika, ali je u velikoj meri zamenjen benzodiazepinima, zbog nihovog šireg terapeutskog indeksa (niže toksičnosti) i manje učestalosti znatnih nuspojava.^[6]

Hemija

Meprobamat, 2-metil-2-propil-1,3-propandiol dikarbamat se sintetiše reakcijom 2-metilvaleraldehida sa dva molekula formaldehida i naknadnom transformacijom rezultirajućeg 2-metil-2-propilpropan-1,3-diola u dikarbamat putem sukcesivnih reakcija sa fosgenom i amonijakom.^[7]^[8]^[9]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Keith Parker; Laurence Brunton; Goodman, Louis Sanford; Lazo, John S.; Gilman, Alfred (2006). Goodman & Gilman's The Pharmacological Basis of Therapeutics (11 izd.). New York: McGraw-Hill. ISBN 0-07-142280-3.
↑ F.M. Berger, B.J. Ludwig, U.S. Patent 2.724.720 (1955).
↑ F.A. Fries, K. Moenkemeyer, CH 373026 (1963).
↑ Ludwig, B. J.; Piech, E. C. (1951). „Some Anticonvulsant Agents Derived from 1,3-Propanediols”. Journal of the American Chemical Society 73: 5779. DOI:10.1021/ja01156a086.

Spoljašnje veze

	Portal Medicina
	Portal Hemija

List of psychotropic substances under international control Arhivirano 2012-08-31 na Wayback Machine-u.
The Comparative Toxicogenomics Database: Meprobamate.
RxList.com - Meprobamate Arhivirano 2005-04-26 na Wayback Machine-u

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[6] Keith Parker; Laurence Brunton; Goodman, Louis Sanford; Lazo, John S.; Gilman, Alfred (2006). Goodman & Gilman's The Pharmacological Basis of Therapeutics (11 izd.). New York: McGraw-Hill. ISBN 0-07-142280-3.

[7] F.M. Berger, B.J. Ludwig, U.S. Patent 2.724.720 (1955).

[8] F.A. Fries, K. Moenkemeyer, CH 373026 (1963).

[9] Ludwig, B. J.; Piech, E. C. (1951). „Some Anticonvulsant Agents Derived from 1,3-Propanediols”. Journal of the American Chemical Society 73: 5779. DOI:10.1021/ja01156a086.

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