Glibornuride: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444003955

| ImageFile = Glibornuride.svg

| ImageSize = 250

| IUPACName = ''N''-{[(1''R'',2''R'',3''S'',4''S'')-2-Hydroxybornan-3-yl]carbamoyl}-4-methylbenzene-1-sulfonamide

| SystematicName = ''N''-{[(1''S'',2''S'',3''R'',4''R'')-3-Hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]carbamoyl}-4-methylbenzene-1-sulfonamide

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| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=26944-48-9

| PubChem=33649

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB08962

| SMILES=CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC2C3CCC(C2O)(C3(C)C)C

| InChI = 1/C18H26N2O4S/c1-11-5-7-12(8-6-11)25(23,24)20-16(22)19-14-13-9-10-18(4,15(14)21)17(13,2)3/h5-8,13-15,21H,9-10H2,1-4H3,(H2,19,20,22)/t13-,14+,15+,18+/m1/s1

| InChIKey = RMTYNAPTNBJHQI-LLDVTBCEBZ

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C18H26N2O4S/c1-11-5-7-12(8-6-11)25(23,24)20-16(22)19-14-13-9-10-18(4,15(14)21)17(13,2)3/h5-8,13-15,21H,9-10H2,1-4H3,(H2,19,20,22)/t13-,14+,15+,18+/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = RMTYNAPTNBJHQI-LLDVTBCESA-N

| RTECS =

| MeSHName = C073323

| EINECS = 248-124-6

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 16735831

| Section2 = {{Chembox Properties

| Formula = C₁₈H₂₆N₂O₄S

| MolarMass = 366.48 g/mol

| Appearance =

| Density =

| MeltingPt =

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| Section6 = {{Chembox Pharmacology

| ATCCode_prefix = A10

| ATCCode_suffix = BB04

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| Section7 = {{Chembox Hazards

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| AutoignitionPt =

'''Glibornuride''' ([[International Nonproprietary Name|INN]]) is an [[anti-diabetic drug]] from the group of [[sulfonylurea]]s.<ref>{{cite journal |vauthors=Haupt E, Köberich W, Beyer J, Schöffling K |title=Pharmacodynamic aspects of tolbutamide, glibenclamide, glibornuride and glisoxepide. I. Dose response relations and repeated administration in diabetic subjects |journal=Diabetologia |volume=7 |issue=6 |pages=449–54 |date=December 1971 |pmid=5004178 |doi=10.1007/bf01212061|doi-access=free }}</ref> It is manufactured by [[Meda AB|MEDA Pharma]] and sold in [[Switzerland]] under the brand name '''Glutril'''.<ref>{{cite web|title=Glutril — Drugs.com|url=https://www.drugs.com/international/glutril.html|website=Drugs.com|access-date=12 July 2016}}</ref>

== Synthesis ==

[[File:Glibornuride synthesis.svg|thumb|center|700px|Glibornuride synthesis:<ref>{{Cite journal|doi=10.1007/BF01151769|title=Arylsulfonylureido- und Arylsulfonylamidoacyl-derivate von Oxy- und Oxo-cycloalkanen als potentielle Antidiabetica|journal=Monatshefte für Chemie |volume=100|issue=6|pages=2133|year=1969|last1=Bretschneider|first1=H.|last2=Hohenlohe-Oehringen|first2=K.|last3=Graßmayr|first3=K.}}</ref> See also: {{US patent|3770761}}; eidem, {{US patent|3654357}} (to Hoffmann-La Roche).]]

Gliburnide is an endo-endo derivative made from camphor-3-carboxamide by borohydride reduction (exo approach), followed by [[Hofmann rearrangement]] to [[carbamate]], followed by displacement with sodium tosylamide.

== References ==

{{Oral hypoglycemics and insulin analogs}}

{{Ion channel modulators}}

[[Category:Potassium channel blockers]]

[[Category:Secondary alcohols]]

[[Category:1-(Benzenesulfonyl)-3-cyclohexylureas]]

[[Category:p-Tosyl compounds]]

{{gastrointestinal-drug-stub}}