Bremelanotide

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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

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CAS_number = 189691-06-3
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PubChem = 6451163
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C=50 | H=68 | N=14 | Co= | I= | Br= | Cl= | F= | O=10 | P= | S= | Se= | Na= | charge=
molecular_weight = 1025.2
smiles = CC(=O)NC(CCCC)C(=O)NC3CC(=O)NCCCCC(NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O) [C@H] (Cc1ccccc1)NC(=O)C(CC2=CNC=N2)NC3=O)CC5=CNc4ccccc45)C(O)=O
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legal_US = Unscheduled
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Bremelanotide (formerly PT-141) is a compound developed for use in treating sexual dysfunction in both men (erectile dysfunction or impotence) and women (sexual arousal disorder). Unlike Viagra and other related medications, it does not act upon the vascular system, but directly increases sexual desire via the nervous system. The development of Bremelanotide for use in treating sexual dysfunction was discontinued in 2008, after concerns were raised over adverse side effects of increased blood pressure.

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.Cite web|url=http://www.cnn.com/HEALTH/men/9906/17/viagra.alternative/|title=Tanning drug may find new life as Viagra alternative|accessdate=2007-09-16|publisher=CNN|year=1999|format=HTML] 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 30, Palatin announced that the U.S. Food and Drug Administration had expressed serious concerns regarding the risk/benefit ratio of bremelanotide with regards to the side effect of increased blood pressure. The FDA stated that they would consider alternate uses for bremelanotide, including as a treatment for individuals who do not respond to more established ED treatments. However, On May 13, 2008, Palatin Technologies announced it "has discontinued development of Bremelanotide for the treatment of male and female sexual dysfunction" however they concurrently announced plans to develop it as a treatment for hemorrhagic shock instead. Cite web|url=http://palatin.com/news/news.asp?param=202|title=Palatin Technologies announces new strategic objectives and reports third quarter 2008 financial results|accessdate=2008-08-21|publisher=Palatin Technologies press release|year=2008|format=HTML] The company additionally announced intentions to focus its attention on another compound, PL-6983, that causes lower blood pressure in animal models. Cite web|url=http://palatin.com/news/news.asp?ID=201|title=Palatin Technologies Announces New Strategic Objectives|accessdate=2008-05-13]

tructure

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). It 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.

References

External links

* [http://www.palatin.com/products/bremelanotide/overview.asp Palatin Technologies] The company that has developed bremelanotide.
* bremelanotide (PT-141) patent (Appl. No.:040547)
* [http://www.pharmcast.com/Patents/Yr2003/Jun2003/061703/6579968_Sexual061703.htm US 6,579,968] bremelanotide (PT-141) patent (Appl. No.:066501)
* [http://www.melanotan.org/ Melanotan.org]
* [http://dx.doi.org/10.1073/pnas.0400491101 Proc. Nat. Acad. Sci 101: 10201 (2004)] A scientific study with female rats.