U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H32N4O4.2Br
Molecular Weight 576.322
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DISTIGMINE BROMIDE

SMILES

[Br-].[Br-].CN(CCCCCCN(C)C(=O)OC1=CC=C[N+](C)=C1)C(=O)OC2=CC=C[N+](C)=C2

InChI

InChIKey=GJHSNEVFXQVOHR-UHFFFAOYSA-L
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

HIDE SMILES / InChI

Description

Distigmine is an acetylcholinesterase (AChE) inhibitor. Distigmine shows direct binding to muscarinic receptors in the rat bladder, and repeated oral administration of distigmine causes downregulation of muscarinic receptors in the rat bladder. The observed direct interaction of distigmine with the bladder muscarinic receptors may partly contribute to the therapeutic and/or side effects seen in the treatment of detrusor underactivity. It is usually used to treat myasthenia gravis, dysuria due to hypotonic bladder such as neurogenic bladder or after surgery. Common side effects are: nausea/vomiting, abdominal pain, diarrhea, increased salivation, hypersecretion in respiratory tract, sweating, bradycardia, miosis, difficulty in breathing. 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.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
[Bizerine: new anticholinesterase drug with selective gastrointestinal action].
2010 Aug
Patents

Sample Use Guides

In Vivo Use Guide
For dysuria due to hypotonic bladder such as neurogenic bladder or after surgery, for adults, take 1 tablet (5 mg of the active ingredient) daily. For myasthenia gravis, for adults, take 1-4 tablet(s) (5-20 mg of the active ingredient) daily in 1-4 divided dose(s). Start with 1 tablet (5 mg) daily, and the dose should be adjusted according to symptoms.
Route of Administration: Oral
In Vitro Use Guide
Distigmine (30 nM—10 uM) inhibited specific [3H]oxotremorine-M binding in the bladder, submaxillary gland and cerebral cortex of rats in a concentration-dependent manner. The Ki values for distigmine did not differ significantly among tissues.
Name Type Language
DISTIGMINE BROMIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
DISTIGMINE BROMIDE [WHO-DD]
Common Name English
PYRIDINIUM, 3,3'-(1,6-HEXANEDIYLBIS((METHYLIMINO)CARBONYL)OXY)BIS(1-METHYL-, BROMIDE (1:2)
Common Name English
DISTIGMINE DIBROMIDE
Code English
BC-51
Code English
HEXAMARIUM BROMIDE
Common Name English
DISTIGMINE BROMIDE [INN]
Common Name English
3,3'-(1,6-HEXANEDIYLBIS((METHYLIMINO)CARBONYL)OXY)BIS(1-METHYLPYRIDINIUM)DIBROMIDE
Common Name English
DISTIGMINE BROMIDE [JAN]
Common Name English
HEXAMETHYLENEBIS(N-METHYLCARBAMINOYL-1-METHYL-3-HYDROXYPYRIDINIUM BROMIDE)
Common Name English
UBRITIL
Brand Name English
UBRETID
Brand Name English
3-HYDROXY-1-METHYLPYRIDINIUM BROMIDE HEXAMETHYLENEBIS-(N-METHYLCARBAMATE)
Systematic Name English
DISTIGMINE BROMIDE [MART.]
Common Name English
DISTIGMINE BROMIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47792
Created by admin on Tue Oct 22 05:42:18 UTC 2019 , Edited by admin on Tue Oct 22 05:42:18 UTC 2019
Code System Code Type Description
CAS
15876-67-2
Created by admin on Tue Oct 22 05:42:18 UTC 2019 , Edited by admin on Tue Oct 22 05:42:18 UTC 2019
PRIMARY
INN
764
Created by admin on Tue Oct 22 05:42:18 UTC 2019 , Edited by admin on Tue Oct 22 05:42:18 UTC 2019
PRIMARY
ChEMBL
CHEMBL1199307
Created by admin on Tue Oct 22 05:42:18 UTC 2019 , Edited by admin on Tue Oct 22 05:42:18 UTC 2019
PRIMARY
MERCK INDEX
M4675
Created by admin on Tue Oct 22 05:42:18 UTC 2019 , Edited by admin on Tue Oct 22 05:42:18 UTC 2019
PRIMARY Merck Index
PUBCHEM
27522
Created by admin on Tue Oct 22 05:42:18 UTC 2019 , Edited by admin on Tue Oct 22 05:42:18 UTC 2019
PRIMARY
ECHA (EC/EINECS)
240-013-0
Created by admin on Tue Oct 22 05:42:18 UTC 2019 , Edited by admin on Tue Oct 22 05:42:18 UTC 2019
PRIMARY
NCI_THESAURUS
C87487
Created by admin on Tue Oct 22 05:42:18 UTC 2019 , Edited by admin on Tue Oct 22 05:42:18 UTC 2019
PRIMARY
EVMPD
SUB06323MIG
Created by admin on Tue Oct 22 05:42:18 UTC 2019 , Edited by admin on Tue Oct 22 05:42:18 UTC 2019
PRIMARY