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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
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
Clinical efficacy of distigmine bromide in the treatment of patients with underactive detrusor.
2004
Effects of TAK-802, a novel acetylcholinesterase inhibitor, on distension-induced rhythmic bladder contractions in rats and guinea pigs.
2004 Feb 6
Effects of TAK-802, a novel acetylcholinesterase inhibitor, and various cholinomimetics on the urodynamic characteristics in anesthetized guinea pigs.
2004 Jun 28
[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
Effects of the selective acetylcholinesterase inhibitor TAK-802 on the voiding behavior and bladder mass increase in rats with partial bladder outlet obstruction.
2005 Sep
Ubretid (distigmine bromide) taken to treat urinary retention prolongs the effect of suxamethonium.
2008
Treatment strategy according to findings on pressure-flow study for women with decreased urinary flow rate.
2009
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
[Treatment approach to congenital myasthenic syndrome in a patient with acetylcholine receptor deficiency].
2009 Jan
Pharmacokinetic and pharmacodynamic analysis of acetylcholinesterase inhibition by distigmine bromide in rats.
2010
Demonstration of muscarinic and nicotinic receptor binding activities of distigmine to treat detrusor underactivity.
2010
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 17:16:24 GMT 2023
Edited
by admin
on Fri Dec 15 17:16:24 GMT 2023
Record UNII
T940307O7B
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
Structure of DISTIGMINE BROMIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of DISTIGMINE
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