Bremelanotide

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Bremelanotide
Systematic (IUPAC) name
(3R,6R,9S,12R,15R,23R)-15-{[(2R)-2-

Acetamidohexanoyl]amino}-9-benzyl- 6-(3-carbamimidamidopropyl)-12- (1H-imidazol-5-ylmethyl)-3-(1H-indol- 3-ylmethyl)-2,5,8,11,14,17-hexaoxo- 1,4,7,10,13,18-hexaazacyclotricosane -23-carboxylic acid
Identifiers
CAS number 189691-06-3
ATC code  ?
PubChem 6451163
Chemical data
Formula C50H68N14O10 
Mol. mass 1025.2
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?
Legal status

?(US)
Routes  ?

Bremelanotide (formerly PT-141) is the generic term for a new medication for use in treating sexual dysfunction in men (erectile dysfunction or impotence) as well as sexual dysfunction in women (sexual arousal disorder). It is the only known synthetic aphrodisiac. Unlike Viagra and other related medications, it does not act upon the vascular system, but directly increases sexual desire. Bremelanotide is a spray introduced nasally.

Contents

[edit] Development

Originally, the peptide Melanotan II that bremelanotide was developed from was tested as a sunless tanning agent. In initial testing, Melanotan II did induce tanning but additionally caused sexual arousal and spontaneous erections as unexpected side effects in nine out of the ten original male volunteer test subjects.[1] In clinical studies, bremelanotide was shown to be effective in treating male sexual and erectile dysfunction as well as female sexual dysfunction.

A Phase III clinical trial was scheduled to begin in the first half of 2007, but was delayed until August 2007. On August 30th, Palatin announced that the FDA had expressed serious concerns regarding the benefit/risk ratio of bremelanotide with regards to the side effect of increased blood pressure. The FDA also stated that they would consider alternate uses for bremelanotide, including as a treatment for individuals who do not respond to more established ED treatments.


On May 13, 2008 Palatin Technologies announced it "has discontinued development of Bremelanotide for the treatment of male and female sexual dysfunction".

However it is also "advancing new Palatin compound PL-6983, which in animal models causes significantly lower increases in blood pressure than seen with Bremelanotide, into Phase 1 clinical studies for treatment of male and female sexual dysfunction." [2]

[edit] Structure

Bremelanotide is a cyclic hepta-peptide lactam analog of alpha-melanocyte-stimulating hormone (alpha-MSH) that activates the melanocortin receptors MC3-R and MC4-R in the central nervous system. It has the amino acid sequence Ac-Nle-cyclo[Asp-His-D-Phe-Arg-Trp-Lys]-OH or cyclo-[Nle4, Asp5, D-Phe7, Lys10]alpha-MSH-(4-10). PT-141 is a metabolite of Melanotan II that lacks the C-terminal amide function. Its molecular formula is C50H68N14O10 with a molecular weight of 1025.2.

[edit] References

  1. ^ Tanning drug may find new life as Viagra alternative (HTML). CNN (1999). Retrieved on 2007-09-16.
  2. ^ Palatin Technologies Announces New Strategic Objectives. Retrieved on 2008-05-13.

[edit] External links