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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=CC=C[N+](C)=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.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.4 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DISTIGMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
228.4 μg × h/L
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DISTIGMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
69.5 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DISTIGMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
83.2%
DISTIGMINE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
10 mg 2 times / day multiple, oral
Recommended
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Disc. AE: Rhabdomyolysis...
AEs leading to
discontinuation/dose reduction:
Rhabdomyolysis
Sources:
10 mg 2 times / day multiple, oral
Recommended
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Other AEs: Cholinergic crisis...
Other AEs:
Cholinergic crisis (grade 5)
Sources:
10 mg 2 times / day multiple, oral
Recommended
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Disc. AE: Parkinsonism...
AEs leading to
discontinuation/dose reduction:
Parkinsonism
Sources:
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Disc. AE: Psychotic disorder...
AEs leading to
discontinuation/dose reduction:
Psychotic disorder
Sources:
0.5 mg 1 times / day multiple, intramuscular
Studied dose
Dose: 0.5 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 0.5 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Disc. AE: Diarrhoea...
AEs leading to
discontinuation/dose reduction:
Diarrhoea (6.5%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Rhabdomyolysis Disc. AE
10 mg 2 times / day multiple, oral
Recommended
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Cholinergic crisis grade 5
10 mg 2 times / day multiple, oral
Recommended
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Parkinsonism Disc. AE
10 mg 2 times / day multiple, oral
Recommended
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Psychotic disorder Disc. AE
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Diarrhoea 6.5%
Disc. AE
0.5 mg 1 times / day multiple, intramuscular
Studied dose
Dose: 0.5 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 0.5 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Symptomatic and urodynamic improvement by oral distigmine bromide in poor voiders after transurethral resection of the prostate.
2001 Feb
Effects of TAK-802, a novel acetylcholinesterase inhibitor, on distension-induced rhythmic bladder contractions in rats and guinea pigs.
2004 Feb 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
[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. 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
DISTIGMINE CATION
Preferred Name English
PYRIDINIUM, 3,3'-(1,6-HEXANEDIYLBIS((METHYLIMINO)CARBONYLOXY))BIS(1-METHYL-
Common Name English
Distigmine [WHO-DD]
Common Name English
DISTIGMINE ION
Common Name English
Classification Tree Code System Code
WHO-VATC QN07AA03
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
WHO-ATC N07AA03
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
Code System Code Type Description
CAS
17299-00-2
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY
FDA UNII
T940307O7B
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY
WIKIPEDIA
DISTIGMINE
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY
SMS_ID
100000087520
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID00169484
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY
DRUG CENTRAL
927
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY
MESH
C084645
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY
RXCUI
3551
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY RxNorm
PUBCHEM
3116
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY
EVMPD
SUB01797MIG
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY
DRUG BANK
DB13694
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY
CHEBI
80756
Created by admin on Mon Mar 31 18:43:24 GMT 2025 , Edited by admin on Mon Mar 31 18:43:24 GMT 2025
PRIMARY