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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

Molecular Formula BrH
Molecular Weight 80.9115
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H32N4O4
Molecular Weight 416.5147
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

TargetsConditions

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
Symptomatic and urodynamic improvement by oral distigmine bromide in poor voiders after transurethral resection of the prostate.
2001 Feb
Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats.
2001 Mar
[Cholinergic crisis following administration of distigmine bromide: a case report].
2002 Jan
Rhabdomyolysis caused by distigmine bromide.
2003 Nov
Distigmine bromide induced acute psychotic disorder in a patient with multiple sclerosis.
2003 Oct
Clinical efficacy of distigmine bromide in the treatment of patients with underactive detrusor.
2004
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
Effects of TAK-802, a novel acetylcholinesterase inhibitor, on distension-induced rhythmic bladder contractions in rats and guinea pigs.
2004 Feb 6
Effects of TAK-802, a novel acetylcholinesterase inhibitor, and various cholinomimetics on the urodynamic characteristics in anesthetized guinea pigs.
2004 Jun 28
[A case of acute distigmine bromide intoxication in the therapeutic dosage for treatment of underactive neurogenic bladder].
2004 May
[Distigmine bromide induced Parkinsonism. A case report].
2005 Aug
Differential effects of TAK-802, a selective acetylcholinesterase inhibitor, and carbamate acetylcholinesterase inhibitors on contraction of the detrusor smooth muscle of the guinea pig.
2005 Nov 12
Effects of the selective acetylcholinesterase inhibitor TAK-802 on the voiding behavior and bladder mass increase in rats with partial bladder outlet obstruction.
2005 Sep
[Distigmine bromide improves chronic intestinal pseudo-obstruction in a case of MELAS].
2007 Apr
Ubretid (distigmine bromide) taken to treat urinary retention prolongs the effect of suxamethonium.
2008
Nocturnal hypersalivation caused by distigmine bromide in a patient with multiple system atrophy.
2008
[Acute poisoning due to distigmine bromide].
2008 Apr
[Three cases of cholinergic crisis in which serum distigmine bromide concentrations were measured].
2008 Jan
Treatment strategy according to findings on pressure-flow study for women with decreased urinary flow rate.
2009
Marked hydronephrosis and hydroureter after distigmine therapy in an adult male patient with paraplegia due to spinal cord injury: a case report.
2009 Aug 6
[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
Pharmacokinetic and pharmacodynamic analysis of acetylcholinesterase inhibition by distigmine bromide in rats.
2010
Demonstration of muscarinic and nicotinic receptor binding activities of distigmine to treat detrusor underactivity.
2010
[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
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:44:31 UTC 2021
Edited
by admin
on Sat Jun 26 12:44:31 UTC 2021
Record UNII
750F36OP6J
Record Status Validated (UNII)
Record Version
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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
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ACTIVE MOIETY