Distigmine

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.[2] 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.

Distigmine
Distigmine bromide
Clinical data
Routes of
administration		By mouth, i.m.
ATC code
Pharmacokinetic data
Bioavailability4.65% [1]
Elimination half-life65 h [1]
Excretionrenal [1]
Identifiers
IUPAC name
  • (1-methylpyridin-1-ium-3-yl) N-methyl-N-{6-[methyl-
    (1-methylpyridin-1-ium-3-yl)oxycarbonylamino]
    hexyl}carbamate dibromide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.036.360
Chemical and physical data
FormulaC22H32Br2N4O4
Molar mass576.330 g·mol−1
3D model (JSmol)
SMILES
  • [Br-].[Br-].O=C(Oc1ccc[n+](c1)C)N(CCCCCCN(C(=O)Oc2ccc[n+](c2)C)C)C
InChI
  • InChI=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 Y
  • Key:GJHSNEVFXQVOHR-UHFFFAOYSA-L Y
 NY (what is this?)  (verify)

References
  1. "Distigmine" (PDF). The Japanese Pharmacopoeia. Official Monographs (14/I ed.). Tokyo: Yakuji Nippo. Ltd. 2001. p. 599. ISBN 978-4-8408-0672-5.
  2. Moro C, Phelps C, Veer V, Clark J, Glasziou P, Tikkinen KA, Scott AM (November 2021). "The effectiveness of parasympathomimetics for treating underactive bladder: A systematic review and meta-analysis". Neurourology and Urodynamics. 41 (1): 127–139. doi:10.1002/nau.24839. PMID 34816481. S2CID 244530010.
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