Distigmine

Distigmine
	Distigmine bromide
Clinical data
Routes of; administration	By mouth, i.m.
ATC code	N07AA03 (WHO) ;
Pharmacokinetic data
Bioavailability	4.65%
Elimination half-life	65 h
Excretion	renal
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	17299-00-2 ; bromide: 15876-67-2 ;
PubChem CID	27522;
ChemSpider	25613 ;
UNII	T940307O7B; bromide: 750F36OP6J ;
KEGG	D01228 ;
ChEBI	CHEBI:31512;
ChEMBL	ChEMBL1098285 ;
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 ; Key:GJHSNEVFXQVOHR-UHFFFAOYSA-L ;
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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.

References

^ ^a ^b ^c "Distigmine" (PDF). The Japanese Pharmacopoeia. Official Monographs (14/I ed.). Tokyo: Yakuji Nippo. Ltd. 2001. p. 599. ISBN 978-4-8408-0672-5.
^ 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" (PDF). Neurourology and Urodynamics. 41 (1): 127–139. doi:10.1002/nau.24839. PMID 34816481. S2CID 244530010.

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[jpdb-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" (PDF). Neurourology and Urodynamics. 41 (1): 127–139. doi:10.1002/nau.24839. PMID 34816481. S2CID 244530010.

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Clinical data
Distigmine bromide
Routes of administration	By mouth, 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	17299-00-2^Y bromide: 15876-67-2^Y
PubChem CID	27522
ChemSpider	25613^Y
UNII	T940307O7B bromide: 750F36OP6J^Y
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)