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Details

Stereochemistry ACHIRAL
Molecular Formula C22H32N4O4.2Br
Molecular Weight 576.3218
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DISTIGMINE BROMIDE

SMILES

C[n+]1cccc(c1)OC(=O)N(C)CCCCCCN(C)C(=O)Oc2ccc[n+](C)c2.[Br-].[Br-]

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
Curator's Comment:: http://www.medicines.org.uk/emc/PIL.3897.latest.pdf | http://www.torii.co.jp/iyakuDB/data/if/if_ubr_t.pdf

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ubretid

Approved Use

It is usually used to treat myasthenia gravis, dysuria due to hypotonic bladder such as neurogenic bladder or after surgery.
Primary
Ubretid

Approved Use

It is usually used to treat myasthenia gravis, dysuria due to hypotonic bladder such as neurogenic bladder or after surgery.
Primary
Ubretid

Approved Use

It is usually used to treat myasthenia gravis, dysuria due to hypotonic bladder such as neurogenic bladder or after surgery.
PubMed

PubMed

TitleDatePubMed
Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats.
2001 Mar
Rhabdomyolysis caused by distigmine bromide.
2003 Nov
Combination of a cholinergic drug and an alpha-blocker is more effective than monotherapy for the treatment of voiding difficulty in patients with underactive detrusor.
2004 Feb
[Distigmine bromide improves chronic intestinal pseudo-obstruction in a case of MELAS].
2007 Apr
Nocturnal hypersalivation caused by distigmine bromide in a patient with multiple system atrophy.
2008
[Acute poisoning due to distigmine bromide].
2008 Apr
[Treatment approach to congenital myasthenic syndrome in a patient with acetylcholine receptor deficiency].
2009 Jan
Effect of distigmine bromide on the central cholinergic system.
2009 Mar
[Bizerine: new anticholinesterase drug with selective gastrointestinal action].
2010 Aug
[Establishing indicators for diagnosis of cholinergic crisis].
2010 Oct
Patents

Sample Use Guides

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.
Route of Administration: Oral
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
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 Sat Jun 26 12:44:31 UTC 2021 , Edited by admin on Sat Jun 26 12:44:31 UTC 2021
Code System Code Type Description
CAS
15876-67-2
Created by admin on Sat Jun 26 12:44:31 UTC 2021 , Edited by admin on Sat Jun 26 12:44:31 UTC 2021
PRIMARY
INN
764
Created by admin on Sat Jun 26 12:44:31 UTC 2021 , Edited by admin on Sat Jun 26 12:44:31 UTC 2021
PRIMARY
ChEMBL
CHEMBL1199307
Created by admin on Sat Jun 26 12:44:31 UTC 2021 , Edited by admin on Sat Jun 26 12:44:31 UTC 2021
PRIMARY
MERCK INDEX
M4675
Created by admin on Sat Jun 26 12:44:31 UTC 2021 , Edited by admin on Sat Jun 26 12:44:31 UTC 2021
PRIMARY Merck Index
PUBCHEM
27522
Created by admin on Sat Jun 26 12:44:31 UTC 2021 , Edited by admin on Sat Jun 26 12:44:31 UTC 2021
PRIMARY
ECHA (EC/EINECS)
240-013-0
Created by admin on Sat Jun 26 12:44:31 UTC 2021 , Edited by admin on Sat Jun 26 12:44:31 UTC 2021
PRIMARY
FDA UNII
750F36OP6J
Created by admin on Sat Jun 26 12:44:31 UTC 2021 , Edited by admin on Sat Jun 26 12:44:31 UTC 2021
PRIMARY
NCI_THESAURUS
C87487
Created by admin on Sat Jun 26 12:44:31 UTC 2021 , Edited by admin on Sat Jun 26 12:44:31 UTC 2021
PRIMARY
EVMPD
SUB06323MIG
Created by admin on Sat Jun 26 12:44:31 UTC 2021 , Edited by admin on Sat Jun 26 12:44:31 UTC 2021
PRIMARY