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
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
DescriptionCurator'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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL220 |
45.0 nM [IC50] | ||
Target ID: Muscarinic receptors (rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20410601 |
0.36 µM [Ki] | ||
Target ID: Nicotinic receptors (rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20410601 |
22.9 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Ubretid Approved UseIt is usually used to treat myasthenia gravis, dysuria due to hypotonic bladder such as neurogenic bladder or after surgery. |
|||
Primary | Ubretid Approved UseIt is usually used to treat myasthenia gravis, dysuria due to hypotonic bladder such as neurogenic bladder or after surgery. |
|||
Primary | Ubretid Approved UseIt is usually used to treat myasthenia gravis, dysuria due to hypotonic bladder such as neurogenic bladder or after surgery. |
PubMed
Title | Date | PubMed |
---|---|---|
[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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20410601
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 | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)