Afamelanotide acetate | CAS# 1566590-77-9 (acetate)

MedKoo Cat#: 413388 | Name: Afamelanotide acetate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Afamelanotide acetate is a synthetic α-melanocyte stimulating hormone analog and first-in-class melanocortin-1 receptor agonist that is approved in the EU for the prevention of phototoxicity in adults with erythropoietic protoporphyria.

Chemical Structure

Afamelanotide acetate

CAS#1566590-77-9 (acetate)

Theoretical Analysis

MedKoo Cat#: 413388

Name: Afamelanotide acetate

CAS#: 1566590-77-9 (acetate)

Chemical Formula: C84H123N21O25

Exact Mass: 1825.8999

Molecular Weight: 1827.03

Elemental Analysis: C, 55.22; H, 6.79; N, 16.10; O, 21.89

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 Weeks
25mg	USD 1,250.00	2 Weeks

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Related CAS #

1566590-77-9 (acetate) 75921-69-6 (free base)

Synonym

Afamelanotide acetate; CUV 1647; CUV-1647; CUV1647

IUPAC/Chemical Name

(4S,7S,10R,13S,16S,22S)-7-((1H-imidazol-4-yl)methyl)-16-((1H-indol-3-yl)methyl)-26-amino-22-((S)-2-(((S)-1-amino-3-methyl-1-oxobutan-2-yl)carbamoyl)pyrrolidine-1-carbonyl)-10-benzyl-4-((2S,5S,8S,11S)-2-butyl-8-(4-hydroxybenzyl)-5,11-bis(hydroxymethyl)-4,7,10,13-tetraoxo-3,6,9,12-tetraazatetradecanamido)-13-(3-guanidinopropyl)-5,8,11,14,17,20-hexaoxo-6,9,12,15,18,21-hexaazahexacosanoic acid compound with acetic acid (1:3)

InChi Key

VHLLBJXKNRAYGM-BHHWPIKXSA-N

InChi Code

1S/C78H111N21O19.3C2H4O2/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;3*1-2(3)4/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);3*1H3,(H,3,4)/t52-,53-,54-,55-,56+,57-,58-,59-,60-,61-,62-,65-;;;/m0.../s1

SMILES Code

CCCC[C@@H](C(N[C@H](C(N[C@H](C(N[C@@H](C(N[C@H](C(N[C@H](C(NCC(N[C@H](C(N1CCC[C@H]1C(N[C@H](C(N)=O)C(C)C)=O)=O)CCCCN)=O)=O)Cc(c[nH]2)c3c2cccc3)=O)CCCNC(N)=N)=O)Cc4ccccc4)=O)Cc5nc[nH]c5)=O)CCC(O)=O)=O)NC([C@@H](NC([C@@H](NC([C@@H](NC(C)=O)CO)=O)Cc6ccc(O)cc6)=O)CO)=O.CC(O)=O.CC(O)=O.CC(O)=O

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

>2 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).

HS Tariff Code

2934.99.9001

More Info

Afamelanotide differs from endogenous α-melanocyte stimulating hormone at the fourth and seventh amino acid residues, increasing its resistance to immediate degradation and increasing its binding time to melanocortin-1 receptor. Afamelanotide is mimic the pharmacological activity of α-melanocyte stimulating hormone by binding to the melanocortin-1 receptor on melanocytes and activating the synthesis of eumelanin. Eumelanin provides photoprotection through mechanisms including, but not limited to, the absorption and scattering of visible and UV light and antioxidant activity. Afamelanotide increases eumelanin density in healthy volunteers and patients with erythropoietic protoporphyria. In healthy, fair-skinned volunteers, a significant increase in melanin density and skin darkening in both sun-exposed and non-sun-exposed sites was seen with subcutaneous injections of afamelanotide. The most common afamelanotide adverse events included headache and nausea. Common adverse effects include back pain, upper respiratory tract infections, decreased appetite, migraine, and dizziness.

Instruction

View handling instruction

	Solvent	mg/mL	mM	comments
Solubility
	Soluble in DMSO	0.0	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,827.03 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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. PMID: 31753192. 2: Searle T, Al-Niaimi F, Ali FR. Vitiligo: an update on systemic treatments. Clin Exp Dermatol. 2021 Mar;46(2):248-258. doi: 10.1111/ced.14435. Epub 2020 Dec 22. PMID: 33350506. 3: Karagaiah P, Valle Y, Sigova J, Zerbinati N, Vojvodic P, Parsad D, Schwartz RA, Grabbe S, Goldust M, Lotti T. Emerging drugs for the treatment of vitiligo. Expert Opin Emerg Drugs. 2020 Mar;25(1):7-24. doi: 10.1080/14728214.2020.1712358. Epub 2020 Feb 3. PMID: 31958256. 4: Wensink D, Wagenmakers MAEM, Langendonk JG. Afamelanotide for prevention of phototoxicity in erythropoietic protoporphyria. Expert Rev Clin Pharmacol. 2021 Feb;14(2):151-160. doi: 10.1080/17512433.2021.1879638. PMID: 33507118. 5: Wu J, Cotliar R. Afamelanotide: An Orphan Drug with Potential for Broad Dermatologic Applications. J Drugs Dermatol. 2021 Mar 1;20(3):290-294. doi: 10.36849/JDD.5526. PMID: 33683075. 6: 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. PMID: 26979527. 7: 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. PMID: 30859308. 8: 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. PMID: 26132941; PMCID: PMC4780255. 9: 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. PMID: 28063031. 10: Minder EI. Afamelanotide, an agonistic analog of α-melanocyte-stimulating hormone, in dermal phototoxicity of erythropoietic protoporphyria. Expert Opin Investig Drugs. 2010 Dec;19(12):1591-602. doi: 10.1517/13543784.2010.535515. Epub 2010 Nov 13. PMID: 21073357. 11: 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. PMID: 28003770; PMCID: PMC5161401. 12: Minder EI, Schneider-Yin X. Afamelanotide (CUV1647) in dermal phototoxicity of erythropoietic protoporphyria. Expert Rev Clin Pharmacol. 2015 Jan;8(1):43-53. doi: 10.1586/17512433.2014.956089. Epub 2014 Dec 3. PMID: 25470471. 13: Balwani M. Erythropoietic Protoporphyria and X-Linked Protoporphyria: pathophysiology, genetics, clinical manifestations, and management. Mol Genet Metab. 2019 Nov;128(3):298-303. doi: 10.1016/j.ymgme.2019.01.020. Epub 2019 Jan 24. PMID: 30704898; PMCID: PMC6656624. 14: Grimes PE, Hamzavi I, Lebwohl M, Ortonne JP, Lim HW. The efficacy of afamelanotide and narrowband UV-B phototherapy for repigmentation of vitiligo. JAMA Dermatol. 2013 Jan;149(1):68-73. doi: 10.1001/2013.jamadermatol.386. PMID: 23407924. 15: McNeil MM, Nahhas AF, Braunberger TL, Hamzavi IH. Afamelanotide in the Treatment of Dermatologic Disease. Skin Therapy Lett. 2018 Nov;23(6):6-10. PMID: 30517779. 16: de Baat C, Phoa KH, Zweers PGMA, Bolling MC, Rozema FR, Vissink A. Serie: Medicamenten en mondzorg. Hyperpigmentatie van de orale slijmvliezen door afamelanotide [Medicaments and oral healthcare. Hyperpigmentation of oral soft tissues due to afamelanotide]. Ned Tijdschr Tandheelkd. 2020 Apr;127(4):237-243. Dutch. doi: 10.5177/ntvt.2020.04.19115. PMID: 32459219. 17: Fabrikant J, Touloei K, Brown SM. A review and update on melanocyte stimulating hormone therapy: afamelanotide. J Drugs Dermatol. 2013 Jul 1;12(7):775-9. PMID: 23884489. 18: Minder AE, Schneider-Yin X, Zulewski H, Minder CE, Minder EI. Afamelanotide Is Associated with Dose-Dependent Protective Effect from Liver Damage Related to Erythropoietic Protoporphyria. Life (Basel). 2023 Apr 21;13(4):1066. doi: 10.3390/life13041066. PMID: 37109595; PMCID: PMC10143433. 19: Lim HW, Grimes PE, Agbai O, Hamzavi I, Henderson M, Haddican M, Linkner RV, Lebwohl M. Afamelanotide and narrowband UV-B phototherapy for the treatment of vitiligo: a randomized multicenter trial. JAMA Dermatol. 2015 Jan;151(1):42-50. doi: 10.1001/jamadermatol.2014.1875. PMID: 25230094. 20: Wensink D, Wagenmakers MAEM, Barman-Aksözen J, Friesema ECH, Wilson JHP, van Rosmalen J, Langendonk JG. Association of Afamelanotide With Improved Outcomes in Patients With Erythropoietic Protoporphyria in Clinical Practice. JAMA Dermatol. 2020 May 1;156(5):570-575. doi: 10.1001/jamadermatol.2020.0352. PMID: 32186677; PMCID: PMC7081144.