BREMELANOTIDE

Synonyms. Bremelanotide; (Ac-Nle4,Asp5,D-Phe7,Lys10)-cyclo-α-MSH (4-10); PT-141; (3S,6S,9R,12S,15S,23S)-15-((N-Acetyl-L-norleucyl)amino)-9-benzyl-6-(3-((diaminomethylidene)amino) propyl)-12-(1H-imidazol-5-ylmethyl)-3-(1H-indol-3-ylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18- hexaa zacyclotricosane-23-carboxylic acid; N-Acetyl-L-2-aminohexanoyl-L-alpha-aspartyl-L-histidyl-D- phenylalanyl-L-arginyl-L-tryptophyl-L-lysine-(2-7)-lactam; Ac-Nle-cyclo(-Asp-His-D-Phe-Arg-Trp-Lys-OH);

BREMELANOTIDE

 

PRODUCT IDENTIFICATION

CAS RN

189691-06-3

EINECS RN

  

FORMULA

C50H68N14O10

MOLE WEIGHT

 1025.16

H.S CODE

  

SMILES

 C1([C@@H](Cc2c[nH]c3c2cccc3)NC([C@H](CCCNC(N)=N)NC (=O)[C@H] (Cc2ccccc2) NC([C@@H](NC([C@@H](CC(=O) NCCCC [C@H](C(O)=O)N1)NC([C@H](CCCC)NC(=O) C)=O)= O)Cc1 cnc[nH]1) =O)=O)=O

CLASSIFICATION

Melanocortin receptor agonist, Aphrodisiac, Erectile dysfunction drug

EXTRA NOTES

 Treatment of sexual dysfunction
A synthetic peptide analogue of alpha-MSH, is an agonist at melanocortin receptors including the MC3R and MC4R, which are expressed primarily in the central nervous system

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

white powder

MELTING POINT

 

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

 

SOLVENT SOLUBILITY  

VAPOR DENSITY

 

log P(octanol-water)

  

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pKa

 

REFRACTIVE INDEX

 

FLASH POINT

 

 

STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents

POLYMERIZATION

Has not been reported

NFPA RATINGS

Health: 0, Flammability:0, Reactivity: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Bremelanotide

Google Scholar Search - Bremelanotide

Drug Information Portal (U.S. National Library of Medicine) - Bremelanotide

PubChem Compound Summary - Bremelanotide

Drug Bank -  Bremelanotide

KEGG (Kyoto Encyclopedia of Genes and Genomes) - Bremelanotide

http://www.ebi.ac.uk/ - Bremelanotide

http://www.ncbi.nlm.nih.gov/ - Bremelanotide

http://toxnet.nlm.nih.gov/
Hazardous Substances Data Bank -  Bremelanotide

http://www.ingentaconnect.com/
In both normal and ED men, treatment with Bremelanotide causes significant increases in erectile activity, in a dose-dependant manner [10]. Clinically and statistically effective doses of the drug (up to 20mg) are safe and well tolerated by both normal and ED patients [12]. Having completed all Phase II trials in men with promising results, Bremelanotide is set to enter Phase III for men in the first half of this year. In women, positive data from a Phase IIa trial and the recent commencement of a Phase IIb trial suggest that entry to Phase III for women may also be on the horizon. If approved, Bremelanotide would be the first FDA-approved synthetic aphrodisiac. This novel therapy could potentially address the substantial need for an effective female sexual dysfunction treatment as well as offer an alternative to traditional PDE inhibition in ED men.

http://www.researchgate.net/
Bremelanotide: The peptide-melanocyte stimulating hormone (MSH) is a product of the proopiomelanocortin pro-hormone. This peptide has long been known to be involved in regulation of energy homeostasis and has been suggested as a target for number medical indications (Hedlund 2004). In the mid-1980s, a group at the University of Arizona synthesized two highly potent MSH analogues (Hadley et al. 1998). One compound, deemed Melanotan I (MTI) was licensed out and further characterised for utility as a tanning drug, given the known role of MSH in pigmentation. A further analogue, Melanotan II (MTII) was developed which was smaller and the hope was that this would aid in its absorption and tissue distribution. The investigator decided to assess for himself whether this second analogue had the tanning capability seen with MTI and proceeded to dose himself. While it is unclear whether he did achieve a tan, what the investigator reports was an “unrelenting” erection lasting 8 hours. Not long after, this compound was licensed out for further development as a sexual dysfunction treatment candidate. PT-141 is the active metabolite of MTII and ultimately became the drug development lead compound and was renamed bremelanotide. Clincal trials in women have demonstrated that bremelanotide increases sexual desire and arousal in women with arousal disorders (Diamond et al. 2004; Diamond et al. 2006; Safarinejad 2008). In one study, using vaginal plethysmography to assess vasocongestion, even though subjective scores were increased over placebo, there was no change in vasocongestion measures as compared to controls, confirming that vaginal vasocongestion is not a suitable method for assessing efficacy of compounds (Diamond et al. 2006). Prior to the discovery and development of bremelanotide, melanocortin receptors were not considered to be of great interest within the sexual medicine field. Since that time, a surge of interest has appeared, and along with it a boost in scientific research investigating the mechanisms involved.

 

 

SALES SPECIFICATION

APPEARANCE

white powder

ASSAY

95.0~105.0% (on Anhydrous, Acetic Acid free basis)

WATER

6.0% max (Karl Fischer)

ACETATE CONTENT

15.0% max (HPLC)

AMINO ACID COMPOSITION

±10% theoretical

INDIVIDUAL IMPURITY

1.0% max (HPLC)

PEPTIDE CONTENT

80% min (by %N)

BACTERIAL ENDOTOXINS

5EU/mg max

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

Not regulated

HAZARD CLASS

  
PACKING GROUP  

 

SAFETY INFORMATION

HAZARD OVERVIEW

May damage fertility or the unborn child. Reproductive hazard

GHS

  

SIGNAL WORD

Danger

PICTOGRAMS

HAZARD STATEMENTS

H360

P STATEMENTS

P201-P308 + P313

EC DIRECTIVES

 

HAZARD CODES

RISK PHRASES

 60

SAFETY PHRASES

 45-53

 

PACKING