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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
[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
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
[A case of acute distigmine bromide intoxication in the therapeutic dosage for treatment of underactive neurogenic bladder].
2004 May
[Distigmine bromide improves chronic intestinal pseudo-obstruction in a case of MELAS].
2007 Apr
Ubretid (distigmine bromide) taken to treat urinary retention prolongs the effect of suxamethonium.
2008
Nocturnal hypersalivation caused by distigmine bromide in a patient with multiple system atrophy.
2008
[Three cases of cholinergic crisis in which serum distigmine bromide concentrations were measured].
2008 Jan
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
Effect of distigmine bromide on the central cholinergic system.
2009 Mar
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
[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
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
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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
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WIKIPEDIA
DISTIGMINE
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SMS_ID
100000087520
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EPA CompTox
DTXSID00169484
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DRUG CENTRAL
927
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MESH
C084645
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RXCUI
3551
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PRIMARY RxNorm
PUBCHEM
3116
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EVMPD
SUB01797MIG
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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
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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
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