AFAMELANOTIDE

Synonyms. Afamelanotide; 4-Nle-7-phe-alpha-msh; (Nle(4)-dphe(7))alpha-melanocyte-stimulating hormone; (Nle4,D-Phe7)-alpha-MSH; (Nle4-D-Phe7)-alpha-Melanocyte-stimulating hormone; 4-Nle-7-phe-alpha-msh; 4-Norleucine-7-D-phenylalanine-alpha-melanocyte-stimulating ormone; 4-Norleucyl-7-phenylalanine-alpha-msh; 4-L-Norleucine-7-D-phenylalanine-alpha-melanotropin; 4-Norleucyl-7-phenylalanine-alpha-msh; Ndp-msh; Melanotan-1; Melanotan I; Other RN: 103088-28-4, 162112-36-9, 272781-22-3

AFAMELANOTIDE

 

PRODUCT IDENTIFICATION

CAS RN

75921-69-6

EINECS RN

  

FORMULA

 C78H111N21O19

MOLE WEIGHT

 1646.85

H.S CODE

 2924.19.8000

SMILES

 N1(CCC[C@H]1C(=O)N[C@@H](C(C)C)C(N)=O)C([C@@H](NC(CNC([C @H](Cc1 c[nH] c2ccccc12)NC(=O)[C@H](CCCNC(N)=N)NC([C@H](NC(= O)[C@H](C c1cnc [nH]1)NC(=O) [C@H](CCC(O)=O)NC([C@@H](NC([C@ @H]( NC([C@H] (Cc1ccc(cc1)O)NC(=O)[C@H](CO)NC(C)= O)=O)CO) =O) CCCC)=O)Cc1ccccc1) =O) =O)=O)CCCCN)=O

CLASSIFICATION

 Affinity label, Anticarcinogenic, Antineoplastic, Indicator

EXTRA NOTES

 alpha-Melanocyte Stimulating Hormone (alpha-MSH)

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

powder

MELTING POINT

 

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

 

SOLVENT SOLUBILITY  

VAPOR DENSITY

 

log P(octanol-water)

  

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pH

 

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: 2,Flammability:1, Reactivity: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Afamelanotide

Google Scholar Search - Afamelanotide

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

PubChem Compound Summary - Afamelanotide

Drug Bank -  Afamelanotide

KEGG (Kyoto Encyclopedia of Genes and Genomes) - Afamelanotide

http://www.ebi.ac.uk/ - Afamelanotide

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

http://melanotan.org/
Melanotan-1 ([Nle4, D-Phe7]α-MSH - under its generic name "afamelanotide") was approved on May 5, 2010 by the Italian Medicines Agency (AIFA - Agenzia Italiana del Farmaco) as a medication for those afflicted with the orphan disease erythropoietic protoporphyria (EPP). The drug is used to induce photoprotective dermal eumelanin pigmentation and thereby reduce the effects of painful, burning dermal photosensitivity caused by the disease. This marks the first time ever that a governmental health regulatory agency has given approval for this drug for usage in human medicinal therapy. For EPP treatment the drug will be marketed under the trade name "Scenesse"® a registered brand name trademark of Clinuvel Pharmaceuticals Ltd. (formerly EpiTan Ltd.).

http://www.cancerresearchuk.org/
Afamelanotide is a drug currently being developed by an Australian company called Clinuvel. Afamelanotide is also called SCENESSE. It is being developed as a skin implant that is given by injection. Afamelanotide is a man made (synthetic) form of a naturally occurring hormone called alpha melanocyte stimulating hormone (a-MSH). This hormone stimulates cells called melanocytes. Melanocytes lie in the deeper layers of the outer part of the skin (the epidermis). These are the cells that become cancerous in melanoma. Melanocytes make the pigment melanin when the skin is exposed to sunlight. The melanin then moves into surrounding skin cells to help protect them against the sun's rays. Melanin makes fair skinned people tan in the sun. Melanocytes are more active in darker skinned people. So dark skinned people have more protection against skin cancer than fair skinned people. Afamelanotide can produce darkening of the skin by stimulating the melanocytes to make more melanin. The aim of the development of afamelanotide is to produce a drug that can help to protect people with certain medical conditions. These conditions make their skin more prone to burning and damage when exposed to the sun. Although the results of early phase trials seem to show that afamelanotide may be a useful drug for people at very high risk of UV damage, the research is still at an early stage. We need results from much larger clinical trials before we know if this drug is effective and safe for medical use, and it isn’t currently licensed in the UK.

 

SALES SPECIFICATION

APPEARANCE

white powder

PURITY

98.0 min (on Anhydrous basis)

WATER

10.0% max (Karl Fischer)

TRIFLUOROACETATE

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 known

HAZARD CLASS

  
PACKING GROUP  

 

SAFETY INFORMATION

HAZARD OVERVIEW

Avoid contact and inhalation. May causes eye irritation. May causes skin irritation. May cause gastrointestinal irritation. May causes respiratory tract irritation
HAZARD CODES

 

RISK PHRASES

  

SAFETY PHRASES

22-24/25

 

PACKING