出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/01/26 21:26:13」(JST)
| Systematic (IUPAC) name | |
|---|---|
| (1S,2R,4R)-N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine | |
| Clinical data | |
| AHFS/Drugs.com | Consumer Drug Information |
| Legal status |
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| Routes | Oral |
| Pharmacokinetic data | |
| Protein binding | 40% |
| Identifiers | |
| CAS number | 60-40-2 Y |
| ATC code | C02BB01 |
| PubChem | CID 4032 |
| IUPHAR ligand | 3990 |
| DrugBank | DB00657 |
| ChemSpider | 5036243 Y |
| UNII | 6EE945D3OK Y |
| ChEMBL | CHEMBL1398031 N |
| Chemical data | |
| Formula | C11H21N |
| Molecular mass | 167.291 g/mol |
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| N (what is this?) (verify) | |
Mecamylamine (Inversine) is a nonselective and noncompetitive antagonist of nicotinic acetylcholine receptors that was introduced in the 1950s as an antihypertensive drug.[1]
Chemically, it is a secondary aliphatic amine, with a pKaH of 11.2[2]
Mecamylamine has been used as an orally-active ganglionic blocker in treating autonomic dysreflexia and hypertension,[3] but, like most ganglionic blockers, it is more often used now as a research tool.
Mecamylamine is also sometimes used as an anti-addictive drug to help people stop smoking tobacco,[4] and is now more widely used for this application than it is for lowering blood pressure. This effect is thought to be due to its blocking α3β4 nicotinic receptors in the brain. It has also been reported to bring about sustained relief from tics in Tourette's Disorder when a series of more usually used agents had failed [22].
In a recent double-blind, placebo-controlled Phase II trial in Indian patients with major depression, (S)-mecamylamine (TC-5214) appeared to have efficacy as an augmentation therapy. This is the first substantive evidence that shows that compounds where the primary pharmacology is antagonism to neuronal nicotinic receptors will have antidepressant properties.[5][6] TC-5214 is currently in Phase III of clinical development as an add-on treatment and on stage II as a monotherapy treatment for major depression. The first results reported from the Phase III trials showed that TC-5214 failed to meet the primary goal and the trial did not replicate the effects that had been encouraging in the Phase II trial.[7][8] Development is funded by Targacept and AstraZeneca.[9] It did not produce meaningful, beneficial results on patients as measured by changes on the Montgomery-Asberg Depression Rating Scale after eight weeks of treatment as compared with placebo.
(S)-(+)-Mecamylamine dissociates more slowly from α4β2 and α3β4 receptors than does the (R)-(-)-enantiomer.[10]
A large SAR study of mecamylamine and its analogs was reported by a group from Merck in 1962.[11] Another, more recent SAR study was undertaken by Suchocki et al.[12]
A comprehensive review of the pharmacology of mecamylamine was published in 2001.[13]
LD50 for the HCl salt[14] in mice: 21 mg/kg (i.v.); 37 mg/kg (i.p.); 96 mg/kg (p.o.).[15]
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| リンク元 | 「メカミラミン」 |
| 関連記事 | 「hydrochloride」 |