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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.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 45.0 nM [IC50]
Muscarinic receptors (rat)
2
Target ID: Muscarinic receptors (rat)
Binding Agent
1064
 0.36 µM [Ki]
Nicotinic receptors (rat)
2
Target ID: Nicotinic receptors (rat)
Binding Agent
1064
 22.9 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Ubretid

Approved Use

It is usually used to treat myasthenia gravis, dysuria due to hypotonic bladder such as neurogenic bladder or after surgery.
Primary
Approved
8429
Ubretid

Approved Use

It is usually used to treat myasthenia gravis, dysuria due to hypotonic bladder such as neurogenic bladder or after surgery.
Primary
Approved
8429
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
[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
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
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
Demonstration of muscarinic and nicotinic receptor binding activities of distigmine to treat detrusor underactivity.
2010
[Establishing indicators for diagnosis of cholinergic crisis].
2010 Oct
Patents

Patents

EP2356984A1
2
US7122198
3

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:07:05 UTC 2023
Edited
by admin
on Fri Dec 15 15:07:05 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
Code System Code Type Description
SMS_ID
100000081078
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY
CAS
15876-67-2
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY
INN
764
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY
ChEMBL
CHEMBL1199307
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY
MERCK INDEX
m4675
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID60935985
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY
PUBCHEM
27522
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY
ECHA (EC/EINECS)
240-013-0
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY
FDA UNII
750F36OP6J
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY
CHEBI
31512
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY
NCI_THESAURUS
C87487
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY
EVMPD
SUB06323MIG
Created by admin on Fri Dec 15 15:07:05 UTC 2023 , Edited by admin on Fri Dec 15 15:07:05 UTC 2023
PRIMARY
Related Record Type Details
Structure of DISTIGMINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DISTIGMINE
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