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Details

Stereochemistry ACHIRAL
Molecular Formula C22H32N4O4.2Br
Molecular Weight 576.322
Optical Activity NONE
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=C[N+](C)=CC=C1)C(=O)OC2=C[N+](C)=CC=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

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H32N4O4
Molecular Weight 416.5139
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: 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

Targets

Targets

Primary TargetPharmacologyConditionPotency
45.0 nM [IC50]
Target ID: Muscarinic receptors (rat)
0.36 µM [Ki]
Target ID: Nicotinic receptors (rat)
22.9 µM [Ki]
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
[Cholinergic crisis following administration of distigmine bromide: a case report].
2002 Jan
Distigmine bromide induced acute psychotic disorder in a patient with multiple sclerosis.
2003 Oct
[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
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
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
Effect of distigmine bromide on the central cholinergic system.
2009 Mar
Pharmacokinetic and pharmacodynamic analysis of acetylcholinesterase inhibition by distigmine bromide in rats.
2010
[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. 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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:07:05 GMT 2023
Edited
by admin
on Fri Dec 15 15:07:05 GMT 2023
Record UNII
750F36OP6J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DISTIGMINE BROMIDE
INN   MART.   MI   WHO-DD  
INN  
Official 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
Distigmine bromide [WHO-DD]
Common 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 Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
Code System Code Type Description
SMS_ID
100000081078
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY
CAS
15876-67-2
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY
INN
764
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY
ChEMBL
CHEMBL1199307
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY
MERCK INDEX
m4675
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID60935985
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY
PUBCHEM
27522
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY
ECHA (EC/EINECS)
240-013-0
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY
FDA UNII
750F36OP6J
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY
CHEBI
31512
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY
NCI_THESAURUS
C87487
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY
EVMPD
SUB06323MIG
Created by admin on Fri Dec 15 15:07:05 GMT 2023 , Edited by admin on Fri Dec 15 15:07:05 GMT 2023
PRIMARY
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ACTIVE MOIETY