U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats.
2001 Mar
Effects of TAK-802, a novel acetylcholinesterase inhibitor, and various cholinomimetics on the urodynamic characteristics in anesthetized guinea pigs.
2004 Jun 28
[Distigmine bromide induced Parkinsonism. A case report].
2005 Aug
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
Pharmacokinetic and pharmacodynamic analysis of acetylcholinesterase inhibition by distigmine bromide in rats.
2010
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 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
WHO-ATC N07AA03
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
Code System Code Type Description
CAS
17299-00-2
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY
FDA UNII
T940307O7B
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY
WIKIPEDIA
DISTIGMINE
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY
SMS_ID
100000087520
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID00169484
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY
DRUG CENTRAL
927
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY
MESH
C084645
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY
RXCUI
3551
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY RxNorm
PUBCHEM
3116
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY
EVMPD
SUB01797MIG
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY
DRUG BANK
DB13694
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY
CHEBI
80756
Created by admin on Fri Dec 15 17:16:24 GMT 2023 , Edited by admin on Fri Dec 15 17:16:24 GMT 2023
PRIMARY