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
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 |
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 |
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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 |
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Primary | Ubretid Approved UseIt is usually used to treat myasthenia gravis, dysuria due to hypotonic bladder such as neurogenic bladder or after surgery. |
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Primary | Ubretid Approved UseIt is usually used to treat myasthenia gravis, dysuria due to hypotonic bladder such as neurogenic bladder or after surgery. |
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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 |
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Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats. | 2001 Mar |
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[Cholinergic crisis following administration of distigmine bromide: a case report]. | 2002 Jan |
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Rhabdomyolysis caused by distigmine bromide. | 2003 Nov |
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Distigmine bromide induced acute psychotic disorder in a patient with multiple sclerosis. | 2003 Oct |
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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 |
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[A case of acute distigmine bromide intoxication in the therapeutic dosage for treatment of underactive neurogenic bladder]. | 2004 May |
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[Distigmine bromide induced Parkinsonism. A case report]. | 2005 Aug |
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Nocturnal hypersalivation caused by distigmine bromide in a patient with multiple system atrophy. | 2008 |
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[Acute poisoning due to distigmine bromide]. | 2008 Apr |
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[Three cases of cholinergic crisis in which serum distigmine bromide concentrations were measured]. | 2008 Jan |
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Treatment strategy according to findings on pressure-flow study for women with decreased urinary flow rate. | 2009 |
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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 |
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Effect of distigmine bromide on the central cholinergic system. | 2009 Mar |
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Pharmacokinetic and pharmacodynamic analysis of acetylcholinesterase inhibition by distigmine bromide in rats. | 2010 |
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[Bizerine: new anticholinesterase drug with selective gastrointestinal action]. | 2010 Aug |
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[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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:16:24 GMT 2023
by
admin
on
Fri Dec 15 17:16:24 GMT 2023
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Record UNII |
T940307O7B
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QN07AA03
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WHO-ATC |
N07AA03
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17299-00-2
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T940307O7B
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DISTIGMINE
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100000087520
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DTXSID00169484
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927
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C084645
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3551
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3116
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SUB01797MIG
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DB13694
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80756
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |