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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Clinical efficacy of distigmine bromide in the treatment of patients with underactive detrusor. | 2004 |
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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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Effects of TAK-802, a novel acetylcholinesterase inhibitor, on distension-induced rhythmic bladder contractions in rats and guinea pigs. | 2004 Feb 6 |
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[Distigmine bromide induced Parkinsonism. A case report]. | 2005 Aug |
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Ubretid (distigmine bromide) taken to treat urinary retention prolongs the effect of suxamethonium. | 2008 |
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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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[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.
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C47792
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ACTIVE MOIETY
SUBSTANCE RECORD