Afamelanotide acetateProduct ingredient for Afamelanotide
- Name
- Afamelanotide acetate
- Drug Entry
- Afamelanotide
Afamelanotide is a first-in-class, synthetic, 13-amino acid peptide analogue of the endogenous alpha melanocyte-stimulating hormone (α-MSH).4 It differs structurally from its endogenous counterpart by only two amino acids - these structural differences improve biological efficacy by imparting a greater affinity for its target and a longer biological half-life.2,3 Afamelanotide is currently the only approved drug therapy used in the management of erythropoietic protoporphyria, having received approval in the EU in December 20147 and subsequent FDA approval in October 2019.5 Despite its relatively recent approval, afamelanotide has been available for use as an orphan drug in both the US and EU since 2008.8,9
- Accession Number
- DBSALT003139
- Structure
Structure for Afamelanotide acetate (DBSALT003139)
- Synonyms
- Afamelanotide acetate / Afamelanotide triacetate
- External IDs
- CUV1647 acetate
- UNII
- 1XCC161YKC
- CAS Number
- 1566590-77-9
- Weight
- Average: 1827.03
Monoisotopic: 1825.899898545 - Chemical Formula
- C84H123N21O25
- InChI Key
- VHLLBJXKNRAYGM-BHHWPIKXSA-N
- InChI
- InChI=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
- IUPAC Name
- (4S)-4-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1S)-1-[({[(2S)-6-amino-1-[(2S)-2-{[(1S)-1-carbamoyl-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]carbamoyl}methyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido]hexanamido]butanoic acid; tris(acetic acid)
- SMILES
- CC(O)=O.CC(O)=O.CC(O)=O.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=CC=CC=C12)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(N)=O
- External Links
- ChemSpider
- 81367588
- Wikipedia
- Afamelanotide
- Predicted Properties
Property Value Source logP -7.8 Chemaxon pKa (Strongest Acidic) 3.47 Chemaxon pKa (Strongest Basic) 11.58 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 24 Chemaxon Hydrogen Donor Count 23 Chemaxon Polar Surface Area 642.98 Å2 Chemaxon Rotatable Bond Count 50 Chemaxon Refractivity 433.79 m3·mol-1 Chemaxon Polarizability 170.86 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon