Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H32N4O4.2Br |
Molecular Weight | 576.322 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Br-].[Br-].CN(CCCCCCN(C)C(=O)OC1=C[N+](C)=CC=C1)C(=O)OC2=C[N+](C)=CC=C2
InChI
InChIKey=GJHSNEVFXQVOHR-UHFFFAOYSA-L
InChI=1S/C22H32N4O4.2BrH/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;2*1H/q+2;;/p-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 |
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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 |
---|---|---|
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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Effects of TAK-802, a novel acetylcholinesterase inhibitor, and various cholinomimetics on the urodynamic characteristics in anesthetized guinea pigs. | 2004 Jun 28 |
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Ubretid (distigmine bromide) taken to treat urinary retention prolongs the effect of suxamethonium. | 2008 |
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[Acute poisoning due to distigmine bromide]. | 2008 Apr |
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[Treatment approach to congenital myasthenic syndrome in a patient with acetylcholine receptor deficiency]. | 2009 Jan |
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Effect of distigmine bromide on the central cholinergic system. | 2009 Mar |
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.
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C47792
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ACTIVE MOIETY
SUBSTANCE RECORD