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. 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	oral, i.m.
ATC code	N07AA03 (WHO)
Pharmacokinetic data
Bioavailability	4.65% [1]
Elimination half-life	65 h [1]
Excretion	renal [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	15876-67-2^Y
PubChem CID	27522
ChemSpider	25613^Y
UNII	T940307O7B
KEGG	D01228^N
ChEBI	CHEBI:31512
ChEMBL	ChEMBL1098285^Y
CompTox Dashboard (EPA)	DTXSID60935985
ECHA InfoCard	100.036.360
Chemical and physical data
Formula	C22H32Br2N4O4
Molar mass	576.330 g·mol^−1
3D model (JSmol)	Interactive image
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. The Japanese Pharmacopoeia, Edition 14/I: Official Monographs, Yakuji Nippo. Ltd., Tokyo (2001), ISBN 978-4840806725, Page 599.