Details
Stereochemistry | ACHIRAL |
Molecular Formula | C32H52N4O4 |
Molecular Weight | 556.7797 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 2 |
SHOW SMILES / InChI
SMILES
CN(CCCCCCCCCCN(C)C(=O)OC1=CC=CC(=C1)[N+](C)(C)C)C(=O)OC2=CC=CC(=C2)[N+](C)(C)C
InChI
InChIKey=RWZVPVOZTJJMNU-UHFFFAOYSA-N
InChI=1S/C32H52N4O4/c1-33(31(37)39-29-21-17-19-27(25-29)35(3,4)5)23-15-13-11-9-10-12-14-16-24-34(2)32(38)40-30-22-18-20-28(26-30)36(6,7)8/h17-22,25-26H,9-16,23-24H2,1-8H3/q+2
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00944
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00944
Demecarium (HUMORSOL®) is an indirect-acting parasympathomimetic agent, also known as a cholinesterase inhibitor and anticholinesterase. Cholinesterase inhibitors prolong the effect of acetylcholine, which is released at the neuroeffector junction of parasympathetic postganglion nerves, by inactivating the cholinesterases that break it down. Application of demecarium (HUMORSOL®) to the eye produces intense miosis and ciliary muscle contraction due to inhibition of cholinesterase, allowing acetylcholine to accumulate at sites of cholinergic transmission. These effects are accompanied by increased capillary permeability of the ciliary body and iris, increased permeability of the blood-aqueous barrier, and vasodilation. Myopia may be induced or, if present, may be augmented by the increased refractive power of the lens that results from the accommodative effect of the drug. Demecarium (HUMORSOL®) indirectly produces some of the muscarinic and nicotinic effects of acetylcholine as quantities of the latter accumulate.
CNS Activity
Originator
Sources: https://www.google.com/patents/US2789981
Curator's Comment: Schmid, O.; US. Patent 2,789,981; April 23, 1957; assigned to Chemie Linz Ag, Austria.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13920329 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | HUMORSOL Approved UseOpen-angle glaucoma (HUMORSOL® should be used in glaucoma only when shorter-acting miotics have proved inadequate).
Conditions obstructing aqueous outflow, such as synechial formation, that are amenable to miotic therapy.
Following iridectomy.
Accommodative esotropia (accommodative convergent strabismus). Launch Date-3.2849281E11 |
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Palliative | HUMORSOL Approved UseOpen-angle glaucoma (HUMORSOL® should be used in glaucoma only when shorter-acting miotics have proved inadequate).
Conditions obstructing aqueous outflow, such as synechial formation, that are amenable to miotic therapy.
Following iridectomy.
Accommodative esotropia (accommodative convergent strabismus). Launch Date-3.2849281E11 |
PubMed
Title | Date | PubMed |
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Effect of topically applied demecarium bromide and echothiophate iodide on intraocular pressure and pupil size in beagles with normotensive eyes and beagles with inherited glaucoma. | 1993 Feb |
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Effect of topically applied 2% pilocarpine and 0.25% demecarium bromide on blood-aqueous barrier permeability in dogs. | 1994 Dec |
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The effects of topical ocular application of 0.25% demecarium bromide on serum acetylcholinesterase levels in normal dogs. | 2003 Mar |
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Outcomes of nonsurgical management and efficacy of demecarium bromide treatment for primary lens instability in dogs: 34 cases (1990-2004). | 2007 Jul 1 |
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Acute ocular complications from self-administered topical kermes. | 2010 Oct |
Patents
Sample Use Guides
For glaucoma initial therapy with demecarium (HUMORSOL®) place 1 or 2 drops in the glaucomatous eye. The usual dosage can vary from as much as 1 or 2 drops twice a day to as little as 1 or 2 drops twice a week. For treatment of esotropia with demecarium (HUMORSOL®) 1 drop is given daily for 2 weeks, then 1 drop every 2 days for 2 to 3 weeks. In esotropia uncomplicated by amblyopia or anisometropia, demecarium (HUMORSOL®) may be instilled in both eyes, not more than 1 drop at a time every day for 2 to 3 weeks, as too severe a degree of miosis may interfere with vision. Then reduce the dosage to 1 drop every other day for 3 to 4 weeks and reevaluate the patient's status.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14340918
Tetramethoquin and demecarium bromide were compared with physostigmine on the hypogastric guinea-pig nerve-vas deferens preparation. Each drug, in bath concentrations of 1 ug/ml, potentiated the response of the vas deferens to nerve stimulation. Subsequent addition of a higher dose of these agents inhibited the response. With demecarium inhibition occurred with 3 to 5 ug/ml.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C47792
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WHO-VATC |
QS01EB04
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WHO-ATC |
S01EB04
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DB00944
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C100193
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107771
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DTXSID2046965
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100000087729
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ILP8XJ8R5K
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16505-84-3
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801
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SUB01577MIG
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5966
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Demecarium
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C87481
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ILP8XJ8R5K
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)