Distigmine
Distigmine (as distigmine bromide) is a parasympathomimetic that inhibit cholinesterases. Distigmine is similar to pyridostigmine and neostigmine but has a longer duration of action. It is available as tablets on prescription only. Distigmine has a greater risk of causing cholinergic crisis because of accumulation of the drug being more likely than with neostigmine or pyridostigmine and so distigmine is rarely used as a treatment for myasthenia gravis, unlike pyridostigmine and neostigmine.
General
Type : Carbamate, Drug, Pyridine
Chemical_Nomenclature : (1-methylpyridin-1-ium-3-yl) N-methyl-N-[6-[methyl-(1-methylpyridin-1-ium-3-yl)oxycarbonylamino]hexyl]carbamate
Canonical SMILES : C[N+]1=CC=CC(=C1)OC(=O)N(C)CCCCCCN(C)C(=O)OC2=C[N+](=CC=C2)C
InChI : InChI=1S\/C22H32N4O4\/c1-23-13-9-11-19(17-23)29-21(27)25(3)15-7-5-6-8-16-26(4)22(28)30-20-12-10-14-24(2)18-20\/h9-14,17-18H,5-8,15-16H2,1-4H3\/q+2
InChIKey : AHZBEVXBKNYXPU-UHFFFAOYSA-N
Other name(s) : UNII-T940307O7B || CHEBI:80756 || AC1L1F7E || CHEMBL1199307 || SCHEMBL16674116 || Distigmine bromide || Hexamarium
MW : 416.52
Formula : C22H32N4O4+2
CAS_number : 17299-00-2
PubChem : 3116
UniChem : AHZBEVXBKNYXPU-UHFFFAOYSA-N
Wikipedia : Distigmine
Target
Families : Distigmine ligand of proteins in family
BCHE
References (17)
| Title : Distigmine Bromide Produces Sustained Potentiation of Guinea-Pig Urinary Bladder Motility by Inhibiting Cholinesterase Activity - Obara_2017_Biol.Pharm.Bull_40_807 |
| Author(s) : Obara K , Chino D , Tanaka Y |
| Ref : Biol Pharm Bull , 40 :807 , 2017 |
| Abstract : |
| PubMedSearch : Obara_2017_Biol.Pharm.Bull_40_807 |
| PubMedID: 28566624 |
| Title : The Long-Lasting Enhancing Effect of Distigmine on Acetylcholine-Induced Contraction of Guinea Pig Detrusor Smooth Muscle Correlates with Its Anticholinesterase Activity - Obara_2017_Biol.Pharm.Bull_40_1092 |
| Author(s) : Obara K , Ogawa T , Chino D , Tanaka Y |
| Ref : Biol Pharm Bull , 40 :1092 , 2017 |
| Abstract : |
| PubMedSearch : Obara_2017_Biol.Pharm.Bull_40_1092 |
| PubMedID: 28674252 |
| Title : Effect of distigmine on the contractile response of guinea pig urinary bladder to electrical field stimulation - Obara_2017_Eur.J.Pharmacol_809_209 |
| Author(s) : Obara K , Kobayashi Y , Chino D , Tanaka Y |
| Ref : European Journal of Pharmacology , 809 :209 , 2017 |
| Abstract : |
| PubMedSearch : Obara_2017_Eur.J.Pharmacol_809_209 |
| PubMedID: 28511871 |
| Title : Long-Lasting Inhibitory Effects of Distigmine on Recombinant Human Acetylcholinesterase Activity - Obara_2017_Biol.Pharm.Bull_40_1739 |
| Author(s) : Obara K , Chino D , Tanaka Y |
| Ref : Biol Pharm Bull , 40 :1739 , 2017 |
| Abstract : |
| PubMedSearch : Obara_2017_Biol.Pharm.Bull_40_1739 |
| PubMedID: 28966245 |
| Title : [Bowel obstruction-induced cholinergic crisis with progressive respiratory failure following distigmine bromide treatment] - Kobayashi_2016_Chudoku.Kenkyu_29_26 |
| Author(s) : Kobayashi K , Sekiguchi H , Sato N , Hirose Y |
| Ref : Chudoku Kenkyu , 29 :26 , 2016 |
| Abstract : |
| PubMedSearch : Kobayashi_2016_Chudoku.Kenkyu_29_26 |
| PubMedID: 27255021 |
| Title : Effects of Silodosin, an alpha-Adrenoceptor Antagonist, and Distigmine, an Acetylcholinesterase Inhibitor, and Their Combined Effects on Impaired Voiding Function in Zucker Diabetic Fatty Rats - Tatemichi_2015_Pharmacology_95_285 |
| Author(s) : Tatemichi S , Tsuchioka K , Yonekubo S , Maruyama K , Kobayashi M |
| Ref : Pharmacology , 95 :285 , 2015 |
| Abstract : |
| PubMedSearch : Tatemichi_2015_Pharmacology_95_285 |
| PubMedID: 26023044 |
| Title : Effects of bethanechol chloride and distigmine bromide on postvoiding residual volume in patients with underactive bladder - Izumi_2014_Minerva.Urol.Nefrol_66_241 |
| Author(s) : Izumi K , Maolake A , Maeda Y , Shigehara K , Namiki M |
| Ref : Minerva Urol Nefrol , 66 :241 , 2014 |
| Abstract : |
| PubMedSearch : Izumi_2014_Minerva.Urol.Nefrol_66_241 |
| PubMedID: 25531193 |
| Title : Effect of distigmine combined with propiverine on bladder activity in rats with spinal cord injury - Sugaya_2012_Int.J.Urol_19_480 |
| Author(s) : Sugaya K , Nishijima S , Kadekawa K , Ashitomi K , Yamamoto H |
| Ref : Int J Urol , 19 :480 , 2012 |
| Abstract : |
| PubMedSearch : Sugaya_2012_Int.J.Urol_19_480 |
| PubMedID: 22221137 |
| Title : Marked hydronephrosis and hydroureter after distigmine therapy in an adult male patient with paraplegia due to spinal cord injury: a case report - Vaidyanathan_2009_Cases.J_2_7333 |
| Author(s) : Vaidyanathan S , Mansour P , Soni BM , Hughes PL , Singh G , Oo T |
| Ref : Cases J , 2 :7333 , 2009 |
| Abstract : |
| PubMedSearch : Vaidyanathan_2009_Cases.J_2_7333 |
| PubMedID: 19918519 |
| Title : Effect of distigmine bromide on the central cholinergic system - Nakayama_2009_J.Psychopharmacol_23_190 |
| Author(s) : Nakayama K , Katsu H , Kitazumi K |
| Ref : J Psychopharmacol , 23 :190 , 2009 |
| Abstract : |
| PubMedSearch : Nakayama_2009_J.Psychopharmacol_23_190 |
| PubMedID: 18515453 |
| Title : Nocturnal hypersalivation caused by distigmine bromide in a patient with multiple system atrophy - |
| Author(s) : Suzuki K , Miyamoto T , Miyamoto M , Hirata K |
| Ref : Intern Med , 47 :983 , 2008 |
| PubMedID: 18480587 |
| Title : [A case of acute distigmine bromide intoxication in the therapeutic dosage for treatment of underactive neurogenic bladder] - Tada_2004_No.To.Shinkei_56_415 |
| Author(s) : Tada M , Fujita N , Umeda M , Koike H , Nagai H |
| Ref : No To Shinkei , 56 :415 , 2004 |
| Abstract : |
| PubMedSearch : Tada_2004_No.To.Shinkei_56_415 |
| PubMedID: 15279199 |
| Title : [Cholinergic crisis following administration of distigmine bromide: a case report] - Yamanaka_2002_Hinyokika.Kiyo_48_21 |
| Author(s) : Yamanaka S , Fujita I , Murota T , Kawakita M , Matsuda T |
| Ref : Hinyokika Kiyo , 48 :21 , 2002 |
| Abstract : |
| PubMedSearch : Yamanaka_2002_Hinyokika.Kiyo_48_21 |
| PubMedID: 11868380 |
| Title : Absolute bioavailability, pharmacokinetics, renal and biliary clearance of distigmine after a single oral dose in comparison to i.v. administration of 14C-distigmine-bromide in healthy volunteers - Vree_1999_Int.J.Clin.Pharmacol.Ther_37_393 |
| Author(s) : Vree TB , Waitzinger J , Hammermaier A , Radhofer-Welte S |
| Ref : Int J Clinical Pharmacology & Therapeutics , 37 :393 , 1999 |
| Abstract : |
| PubMedSearch : Vree_1999_Int.J.Clin.Pharmacol.Ther_37_393 |
| PubMedID: 10475142 |
| Title : [Relationship between cholinergic symptoms caused by distigmine and the activities of serum AChE and BChE] - Koga_1997_Nihon.Shinkei.Seishin.Yakurigaku.Zasshi_17_143 |
| Author(s) : Koga M , Miyata H , Tsuno N , Nakayama K , Ushijima S , Tanaka Y , Hiraga Y , Kobayashi N |
| Ref : Nihon Shinkei Seishin Yakurigaku Zasshi , 17 :143 , 1997 |
| Abstract : |
| PubMedSearch : Koga_1997_Nihon.Shinkei.Seishin.Yakurigaku.Zasshi_17_143 |
| PubMedID: 9278940 |
| Title : Inhibition of acetylcholinesterase by distigmine bromide (Ubretid) - Breuel_1993_Int.J.Clin.Pharmacol.Ther.Toxicol_31_230 |
| Author(s) : Breuel HP , Bohn-Olszewsky W , Engelsen SJ , Samhaber EM , Niklaus H |
| Ref : International Journal of Clinical Pharmacology, Therapy, & Toxicology , 31 :230 , 1993 |
| Abstract : |
| PubMedSearch : Breuel_1993_Int.J.Clin.Pharmacol.Ther.Toxicol_31_230 |
| PubMedID: 8100221 |