Mecamylamine

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Mecamylamine
Clinical data
Trade namesInversine, Vecamyl
AHFS/Drugs.comConsumer Drug Information
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding40%
Identifiers
  • (1S,2R,4R)-N,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-amine
JSmol)
  • N([C@@]2([C@@H]1CC[C@@H](C1)C2(C)C)C)C
  • InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3/t8-,9+,11+/m0/s1 checkY
  • Key:IMYZQPCYWPFTAG-IQJOONFLSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Mecamylamine (

Turing Pharmaceuticals.[3][4]

Chemically, mecamylamine is a secondary

aliphatic amine, with a pKaH of 11.2[5]

Medical uses

Mecamylamine has been used as an orally-active ganglionic blocker in treating autonomic dysreflexia and hypertension,[6] but, like most ganglionic blockers, it is more often used now as a research tool.

Mecamylamine is also sometimes used as an

nicotinic receptors in the brain. It has also been reported to bring about sustained relief from tics in Tourette syndrome when a series of more usually used agents had failed.[medical citation needed
]

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

Montgomery-Asberg Depression Rating Scale
after eight weeks of treatment as compared with placebo.

Overdose

The LD50 for the HCl salt[13] in mice: 21 mg/kg (i.v.); 37 mg/kg (i.p.); 96 mg/kg (p.o.).[14]

Pharmacology

(S)-(+)-Mecamylamine

α3β4 receptors than does the (R)-(−)-enantiomer.[15]

A large

SAR study was undertaken by Suchocki et al.[17]

A comprehensive review of the pharmacology of mecamylamine was published in 2001.[18]

History

Mecamylamine was brought to market by Merck & Co. in the 1950s; in 1996 Merck sold the asset to Layton Bioscience.[19] In 2002, Targacept acquired it from Layton, intending to repurpose it for CNS conditions.[20] Targacept voluntarily withdrew mecamylamine from the market in 2009

Turing Pharmaceuticals, acquired the rights to mecamylamine from Retrophin.[25]

See also

References

  1. ^ "Mecamylamine". drugs.com. Retrieved May 15, 2015.
  2. S2CID 25690407
    .
  3. ^ "Drug Profile: Mecamylamine - Targacept". AdisInsight. Springer Nature Switzerland AG.
  4. ^ "Drugs@FDA: FDA Approved Drug Products". www.accessdata.fda.gov. Retrieved 2017-10-16.
  5. PMID 13476377
    .
  6. ^ Soine TO (1966). Wilson CO, Gisvold O, Doerge RF (eds.). Textbook of Organic Medicinal and Pharmaceutical Chemistry (5th ed.). Philadelphia: Lippincott. pp. 468–546.
  7. PMID 12080428
    .
  8. PMID 19040552
    .
  9. S2CID 6395092
    .
  10. ^ Carroll J (8 November 2011). "Key AZ/Targacept depression drug flunks first Phase III test". Fiercebiotech.com. Retrieved 2011-11-09.
  11. ^ Hirschler B (8 November 2011). "AstraZeneca, Targacept drug fails depression test". Reuters.
  12. ^ "AstraZeneca Pipeline as of the 27th of January 2011". Retrieved 2011-11-09.
  13. ^ In view of the time period when these data were generated, they presumably refer to the HCl salt of the racemic drug
  14. PMID 13618559
    .
  15. PMID 11303054
    .
  16. PMID 14061006
    .
  17. PMID 2002445
    .
  18. PMID 11354389
    .
  19. PMID 12080428
    .
  20. ^ "Press release: Targacept, Inc. Acquires Marketed Drug To Expand Its CNS Portfolio | Evaluate". Targacept via Evaluate. August 27, 2002.
  21. ^ "Notification letter from Targacept" (PDF). FDA. June 4, 2009.
  22. ^ "Determination That INVERSINE (Mecamylamine Hydrochloride) Tablet and Six Other Drug Products Were Not Withdrawn From Sale for Reasons of Safety or Effectiveness". Federal Register. 28 July 2011.
  23. ^ "Press release: Manchester Announces FDA Approval of Vecamyl". Manchester Pharamceuticals via Evaluate. May 1, 2013.
  24. ^ Fidler B (13 February 2014). "Retrophin Shares Boom Following Manchester Pharma Buyout". Xconomy.
  25. ^ Fidler B (10 August 2015). "Shkreli Leads $90M Round for New Startup, Turing Pharma | Xconomy". Xconomy.
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