Distigmine

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 443699749

| IUPAC_name = (1-methylpyridin-1-ium-3-yl) N-methyl-N-{6-[methyl-
(1-methylpyridin-1-ium-3-yl)oxycarbonylamino]
hexyl}carbamate dibromide

| image = Distigmine bromide.svg

| width = 250

| caption = Distigmine bromide

| tradename =

| pregnancy_AU =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = By mouth, i.m.

| bioavailability = 4.65% {{cite book | chapter = Distigmine | title = The Japanese Pharmacopoeia | edition = 14/I | series = Official Monographs | publisher = Yakuji Nippo. Ltd. | location = Tokyo | date = 2001 | isbn = 978-4-8408-0672-5 | chapter-url = https://www.pmda.go.jp/files/000152719.pdf | page = 599 }}

| protein_bound =

| metabolism =

| elimination_half-life = 65 h

| excretion = renal

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 17299-00-2

| ATC_prefix = N07

| ATC_suffix = AA03

| PubChem = 27522

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 25613

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D01228

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = T940307O7B

| ChEBI = 31512

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1098285

| index2_label = bromide

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 15876-67-2

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 750F36OP6J

| C=22 | H=32 | Br=2 | N=4 | O=4

| smiles = [Br-].[Br-].O=C(Oc1ccc[n+](c1)C)N(CCCCCCN(C(=O)Oc2ccc[n+](c2)C)C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C22H32N4O4.2BrH/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;2*1H/q+2;;/p-2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GJHSNEVFXQVOHR-UHFFFAOYSA-L

}}

Distigmine (as distigmine bromide) is a parasympathomimetic. Distigmine is similar to pyridostigmine and neostigmine but has a longer duration of action. It is available as tablets on prescription only. It is commonly used to treat various conditions, including myasthenia gravis and underactive bladder.{{cite journal | vauthors = Moro C, Phelps C, Veer V, Clark J, Glasziou P, Tikkinen KA, Scott AM | title = The effectiveness of parasympathomimetics for treating underactive bladder: A systematic review and meta-analysis | journal = Neurourology and Urodynamics | date = November 2021 | volume = 41 | issue = 1 | pages = 127–139 | pmid = 34816481 | doi = 10.1002/nau.24839 | s2cid = 244530010 | url = https://pure.bond.edu.au/ws/files/118955227/AM_The_effectiveness_of_parasympathomimetics_for_treating.pdf }} 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.