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 |
|---|---|---|---|
Target ID: CHEMBL220 |
45.0 nM [IC50] | ||
Target ID: Muscarinic receptors (rat) |
0.36 µM [Ki] | ||
Target ID: Nicotinic receptors (rat) |
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. |
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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 |
|---|---|---|
| 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 |
|
| Effects of TAK-802, a novel acetylcholinesterase inhibitor, on distension-induced rhythmic bladder contractions in rats and guinea pigs. | 2004 Feb 6 |
|
| [Distigmine bromide induced Parkinsonism. A case report]. | 2005 Aug |
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| Effects of the selective acetylcholinesterase inhibitor TAK-802 on the voiding behavior and bladder mass increase in rats with partial bladder outlet obstruction. | 2005 Sep |
|
| [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 |
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| Nocturnal hypersalivation caused by distigmine bromide in a patient with multiple system atrophy. | 2008 |
|
| [Acute poisoning due to distigmine bromide]. | 2008 Apr |
|
| [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 |
|
| 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 |
|
| [Treatment approach to congenital myasthenic syndrome in a patient with acetylcholine receptor deficiency]. | 2009 Jan |
|
| Effect of distigmine bromide on the central cholinergic system. | 2009 Mar |
|
| Pharmacokinetic and pharmacodynamic analysis of acetylcholinesterase inhibition by distigmine bromide in rats. | 2010 |
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| 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
| Substance Class |
Chemical
Created
by
admin
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| Record UNII |
T940307O7B
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| Record Status |
Validated (UNII)
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QN07AA03
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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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C084645
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3116
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SUB01797MIG
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DB13694
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80756
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ACTIVE MOIETY |
