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Details

Stereochemistry ACHIRAL
Molecular Formula C22H32N4O4
Molecular Weight 416.5139
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of DISTIGMINE

SMILES

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

InChI

InChIKey=AHZBEVXBKNYXPU-UHFFFAOYSA-N
InChI=1S/C22H32N4O4/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/q+2

HIDE SMILES / InChI

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
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
Clinical efficacy of distigmine bromide in the treatment of patients with underactive detrusor.
2004
[A case of acute distigmine bromide intoxication in the therapeutic dosage for treatment of underactive neurogenic bladder].
2004 May
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
Nocturnal hypersalivation caused by distigmine bromide in a patient with multiple system atrophy.
2008
[Acute poisoning due to distigmine bromide].
2008 Apr
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.
Name Type Language
DISTIGMINE
WHO-DD  
Common Name English
PYRIDINIUM, 3,3'-(1,6-HEXANEDIYLBIS((METHYLIMINO)CARBONYLOXY))BIS(1-METHYL-
Common Name English
Distigmine [WHO-DD]
Common Name English
DISTIGMINE CATION
Common Name English
DISTIGMINE ION
Common Name English
Classification Tree Code System Code
WHO-VATC QN07AA03
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
WHO-ATC N07AA03
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
Code System Code Type Description
CAS
17299-00-2
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
PRIMARY
FDA UNII
T940307O7B
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
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WIKIPEDIA
DISTIGMINE
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
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SMS_ID
100000087520
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID00169484
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
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DRUG CENTRAL
927
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
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MESH
C084645
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
PRIMARY
RXCUI
3551
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
PRIMARY RxNorm
PUBCHEM
3116
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
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EVMPD
SUB01797MIG
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
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DRUG BANK
DB13694
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
PRIMARY
CHEBI
80756
Created by admin on Fri Dec 15 17:16:24 UTC 2023 , Edited by admin on Fri Dec 15 17:16:24 UTC 2023
PRIMARY