Afamelanotide free base
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MedKoo CAT#: 330224

CAS#: 75921-69-6 (free base)

Description: Afamelanotide, also known as CUV1647, is a Melanocortin receptor agonist. Afamelanotide is a synthetic peptide and analogue of α-melanocyte stimulating hormone used to prevent skin damage from the sun in people with erythropoietic protoporphyria .It is under development in other skin disorders in several jurisdictions. It causes skin to turn darker by causing the skin to make more melanin.


Price and Availability

Size
Price

1mg
USD 265
Size
Price

Size
Price

Afamelanotide, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 330224
Name: Afamelanotide free base
CAS#: 75921-69-6 (free base)
Chemical Formula: C78H111N21O19
Exact Mass: 1645.8365
Molecular Weight: 1646.874
Elemental Analysis: C, 56.89; H, 6.79; N, 17.86; O, 18.46


Related CAS #: 1566590-77-9 (acetate)   75921-69-6 (free base)    

Synonym: Afamelanotide; CUV1647; CUV-1647; CUV 1647; MBJ 05; MBJ-05; MBJ05; Melanotan I; Melanotan-1; MT-1 (Nlefmsh); Ndp-msh; 4-Norleucyl-7-phenylalanine-alpha-msh

IUPAC/Chemical Name: The amino acid sequence is Ac-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2

InChi Key: UAHFGYDRQSXQEB-PWPYQVNISA-N

InChi Code: InChI=1S/C78H111N21O19/c1-5-6-19-52(91-75(116)61(41-101)97-72(113)57(34-46-24-26-49(103)27-25-46)94-74(115)60(40-100)88-44(4)102)68(109)92-54(28-29-64(105)106)70(111)96-59(36-48-38-83-42-87-48)73(114)93-56(33-45-16-8-7-9-17-45)71(112)90-53(22-14-31-84-78(81)82)69(110)95-58(35-47-37-85-51-20-11-10-18-50(47)51)67(108)86-39-63(104)89-55(21-12-13-30-79)77(118)99-32-15-23-62(99)76(117)98-65(43(2)3)66(80)107/h7-11,16-18,20,24-27,37-38,42-43,52-62,65,85,100-101,103H,5-6,12-15,19,21-23,28-36,39-41,79H2,1-4H3,(H2,80,107)(H,83,87)(H,86,108)(H,88,102)(H,89,104)(H,90,112)(H,91,116)(H,92,109)(H,93,114)(H,94,115)(H,95,110)(H,96,111)(H,97,113)(H,98,117)(H,105,106)(H4,81,82,84)/t52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,65-/m0/s1

SMILES Code: CCCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(C)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(N)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.90.01


Additional Information

Sequences: SYSXEHFRWGKPV
(Modifications: Ser-1 = N-terminal Ac, X = Nle, Phe-7 = D-Phe, Val-13 = C-terminal amide)


References

1: Zubair R, Hamzavi IH. Phototherapy for Vitiligo. Dermatol Clin. 2020 Jan;38(1):55-62. doi: 10.1016/j.det.2019.08.005. Epub 2019 Oct 18. Review. PubMed PMID: 31753192.

2: Cong TX, Hao D, Wen X, Li XH, He G, Jiang X. From pathogenesis of acne vulgaris to anti-acne agents. Arch Dermatol Res. 2019 Jul;311(5):337-349. doi: 10.1007/s00403-019-01908-x. Epub 2019 Mar 11. Review. PubMed PMID: 30859308.

3: Zubair R, Lyons AB, Vellaichamy G, Peacock A, Hamzavi I. What's New in Pigmentary Disorders. Dermatol Clin. 2019 Apr;37(2):175-181. doi: 10.1016/j.det.2018.12.008. Epub 2019 Feb 16. Review. PubMed PMID: 30850040.

4: Balwani M. Erythropoietic Protoporphyria and X-Linked Protoporphyria: pathophysiology, genetics, clinical manifestations, and management. Mol Genet Metab. 2019 Jan 24. pii: S1096-7192(18)30641-3. doi: 10.1016/j.ymgme.2019.01.020. [Epub ahead of print] Review. PubMed PMID: 30704898; PubMed Central PMCID: PMC6656624.

5: McNeil MM, Nahhas AF, Braunberger TL, Hamzavi IH. Afamelanotide in the Treatment of Dermatologic Disease. Skin Therapy Lett. 2018 Nov;23(6):6-10. PubMed PMID: 30517779.

6: Stölzel U, Kubisch I, Stauch T. [Porphyrias-what is verified?]. Internist (Berl). 2018 Dec;59(12):1239-1248. doi: 10.1007/s00108-018-0509-z. Review. German. PubMed PMID: 30328490.

7: Dawe R. An overview of the cutaneous porphyrias. F1000Res. 2017 Oct 30;6:1906. doi: 10.12688/f1000research.10101.1. eCollection 2017. Review. PubMed PMID: 29152226; PubMed Central PMCID: PMC5664971.

8: Meurer M, Ceric-Dehdari P. [Systemic treatment of vitiligo : Balance and current developments]. Hautarzt. 2017 Nov;68(11):876-884. doi: 10.1007/s00105-017-4065-6. Review. German. PubMed PMID: 29030646.

9: Balwani M, Bloomer J, Desnick R; Porphyrias Consortium of the NIH-Sponsored Rare Diseases Clinical Research Network. Erythropoietic Protoporphyria, Autosomal Recessive. 2012 Sep 27 [updated 2017 Sep 7]. In: Adam MP, Ardinger HH, Pagon RA, Wallace SE, Bean LJH, Stephens K, Amemiya A, editors. GeneReviews® [Internet]. Seattle (WA): University of Washington, Seattle; 1993-2019. Available from http://www.ncbi.nlm.nih.gov/books/NBK100826/ PubMed PMID: 23016163.

10: Rodrigues M, Ezzedine K, Hamzavi I, Pandya AG, Harris JE; Vitiligo Working Group. Current and emerging treatments for vitiligo. J Am Acad Dermatol. 2017 Jul;77(1):17-29. doi: 10.1016/j.jaad.2016.11.010. Review. PubMed PMID: 28619557.

11: Passeron T. Medical and Maintenance Treatments for Vitiligo. Dermatol Clin. 2017 Apr;35(2):163-170. doi: 10.1016/j.det.2016.11.007. Review. PubMed PMID: 28317526.

12: Habbema L, Halk AB, Neumann M, Bergman W. Risks of unregulated use of alpha-melanocyte-stimulating hormone analogues: a review. Int J Dermatol. 2017 Oct;56(10):975-980. doi: 10.1111/ijd.13585. Epub 2017 Mar 7. Review. PubMed PMID: 28266027.

13: Minder EI, Barman-Aksoezen J, Schneider-Yin X. Pharmacokinetics and Pharmacodynamics of Afamelanotide and its Clinical Use in Treating Dermatologic Disorders. Clin Pharmacokinet. 2017 Aug;56(8):815-823. doi: 10.1007/s40262-016-0501-5. Review. PubMed PMID: 28063031.

14: Lim HW, Arellano-Mendoza MI, Stengel F. Current challenges in photoprotection. J Am Acad Dermatol. 2017 Mar;76(3S1):S91-S99. doi: 10.1016/j.jaad.2016.09.040. Epub 2016 Dec 27. PubMed PMID: 28038886.

15: Lane AM, McKay JT, Bonkovsky HL. Advances in the management of erythropoietic protoporphyria - role of afamelanotide. Appl Clin Genet. 2016 Dec 12;9:179-189. doi: 10.2147/TACG.S122030. eCollection 2016. Review. PubMed PMID: 28003770; PubMed Central PMCID: PMC5161401.

16: Farahnik B, Blattner CM, Mortazie MB, Perry BM, Lear W, Elston DM. Interventional treatments for Hailey-Hailey disease. J Am Acad Dermatol. 2017 Mar;76(3):551-558.e3. doi: 10.1016/j.jaad.2016.08.039. Epub 2016 Oct 13. Review. PubMed PMID: 27745906.

17: Kim ES, Garnock-Jones KP. Afamelanotide: A Review in Erythropoietic Protoporphyria. Am J Clin Dermatol. 2016 Apr;17(2):179-85. doi: 10.1007/s40257-016-0184-6. Review. PubMed PMID: 26979527.

18: Urbanski U, Frank J, Neumann NJ. [Erythropoietic protoporphyria : Clinical manifestations, diagnosis and new therapeutic possibilities]. Hautarzt. 2016 Mar;67(3):211-5. doi: 10.1007/s00105-015-3733-7. Review. German. PubMed PMID: 26669872.

19: Langendonk JG, Balwani M, Anderson KE, Bonkovsky HL, Anstey AV, Bissell DM, Bloomer J, Edwards C, Neumann NJ, Parker C, Phillips JD, Lim HW, Hamzavi I, Deybach JC, Kauppinen R, Rhodes LE, Frank J, Murphy GM, Karstens FPJ, Sijbrands EJG, de Rooij FWM, Lebwohl M, Naik H, Goding CR, Wilson JHP, Desnick RJ. Afamelanotide for Erythropoietic Protoporphyria. N Engl J Med. 2015 Jul 2;373(1):48-59. doi: 10.1056/NEJMoa1411481. PubMed PMID: 26132941; PubMed Central PMCID: PMC4780255.

20: Luger TA, Böhm M. An α-MSH analog in erythropoietic protoporphyria. J Invest Dermatol. 2015 Apr;135(4):929-931. doi: 10.1038/jid.2015.16. PubMed PMID: 25785940.