Details of the Drug

General Information of Drug (ID: DMVWHTG)

Drug Name
Afamelanotide
Synonyms [Nle4,dPhe7]alpha-MSH; alpha-NDP-MSH; NDP-MSH
Indication
Disease Entry ICD 11 Status REF
Erythropoietic porphyrias 5C58.12 Approved [1]
Erythropoietic protoporphyria 5C58.12 Approved [2]
Vitiligo ED63.0 Phase 2 [3]
ATC Code
D02BB02: Afamelanotide
D02BB: Protectives against UV-radiation for systemic use
D02B: PROTECTIVES AGAINST UV-RADIATION
D02: EMOLLIENTS AND PROTECTIVES
D: DERMATOLOGICALS
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 5 Molecular Weight (mw) 1646.8
Logarithm of the Partition Coefficient (xlogp) -3.5
Rotatable Bond Count (rotbonds) 51
Hydrogen Bond Donor Count (hbonddonor) 23
Hydrogen Bond Acceptor Count (hbondacc) 22
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 138.9 +/- 42.6 mcgh/L [4]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 3.7 +/- 1.3 mcg/L [4]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 36 h [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 30 minutes [4]
Metabolism
The drug is metabolized via serum and proteolytic enzyme [5]
Vd
The volume of distribution (Vd) of drug is 0.54 L/kg [5]
Chemical Identifiers
Formula
C78H111N21O19
IUPAC Name
(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-5-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-6-amino-1-[(2S)-2-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-2-oxoethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Canonical SMILES
CCCC[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N5CCC[C@H]5C(=O)N[C@@H](C(C)C)C(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CC6=CC=C(C=C6)O)NC(=O)[C@H](CO)NC(=O)C
InChI
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
InChIKey
UAHFGYDRQSXQEB-LEBBXHLNSA-N
Cross-matching ID
PubChem CID
16197727
ChEBI ID
CHEMBL441738
CAS Number
75921-69-6
TTD ID
D0V2OX
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Melanocortin receptor 1 (MC1R) TT0MV2T MSHR_HUMAN Modulator [1]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Erythropoietic porphyrias
ICD Disease Classification 5C58.12
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Melanocortin receptor 1 (MC1R) DTT MC1R 1.44E-06 0.41 2.15
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
2 Afamelanotide FDA Label
3 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4 EMA Approved Drugs: Afamelanotide
5 Ghosal A, Chowdhury SK, Tong W, Hapangama N, Yuan Y, Su AD, Zbaida S: Identification of human liver cytochrome P450 enzymes responsible for the metabolism of lonafarnib (Sarasar). Drug Metab Dispos. 2006 Apr;34(4):628-35. doi: 10.1124/dmd.105.007906. Epub 2006 Jan 27.