AFAMELANOTIDE ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C78H111N21O19.3C2H4O2
Molecular Weight	1827.0044
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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](CC2=CNC=N2)C(=O)N[C@H](CC3=CC=CC=C3)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC4=CNC5=CC=CC=C45)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N6CCC[C@H]6C(=O)N[C@@H](C(C)C)C(N)=O

InChI

InChIKey=VHLLBJXKNRAYGM-BHHWPIKXSA-N

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

HIDE SMILES / InChI

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C78H111N21O19
Molecular Weight	1646.8483
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26979527 | https://www.ncbi.nlm.nih.gov/pubmed/26132941 | https://www.ncbi.nlm.nih.gov/pubmed/28063031

Afamelanotide (SCENESSE) 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. 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.

Approval Year

C_max

Value	Dose	Co-administered	Analyte	Population
3.7 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210797s000lbl.pdf	16 mg single, subcutaneous dose: 16 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		AFAMELANOTIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
138.9 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210797s000lbl.pdf	16 mg single, subcutaneous dose: 16 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		AFAMELANOTIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
15 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210797s000lbl.pdf	16 mg single, subcutaneous dose: 16 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		AFAMELANOTIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 110		CYP 74

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 150	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210797Orig1s000OtherR.pdf#page=70 Page: 70.0	unlikely
CYP 150	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210797Orig1s000OtherR.pdf#page=70 Page: 70.0	unlikely

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210797Orig1s000OtherR.pdf#page=69 Page: 35.0

Sourcing

Vendor/Aggregator	ID	URL
Ambinter	Amb19930648	http://www.ambinter.com/reference/19930648
AN PharmaTech	AN-37109
Chemieliva Pharmaceutical Co., Ltd	PBCM0816867
ChemMol	49423239	http://www.chemmol.com/chemmol/49423239.html
eNovation Chemicals	D680237	https://www.enovationchem.com/ProductDetails.asp?ProductID=D680237
iChemical	EBD23779	http://www.ichemical.com/chemicals/cas-75921-69-6
MuseChem	P000195	https://www.musechem.com/product/P000195.html
Parchem	29363	http://www.parchem.com/chemical-supplier-distributor/Melanotan-019363.aspx
PubChem	16197727	https://pubchem.ncbi.nlm.nih.gov/compound/16197727

PubMed

Title	Date	PubMed
Substituted NDP-MSH peptides paired with mutant melanocortin-4 receptors demonstrate the role of transmembrane 6 in receptor activation.	2007-09-18	17713970
The role of melanocortins in body weight regulation: opportunities for the treatment of obesity.	2002-04-12	12007532
Molecular determinants of ligand binding to the human melanocortin-4 receptor.	2000-12-05	11101306
Pharmacologic response of a controlled-release PLGA formulation for the alpha-melanocyte stimulating hormone analog, Melanotan-I.	2000-05	10888312
Characterization of melanocortin receptor ligands on cloned brain melanocortin receptors and on grooming behavior in the rat.	1999-08-13	10493100
Skin pigmentation and pharmacokinetics of melanotan-I in humans.	1997-04	9113347
Proopiomelanocortin processing in the pituitary, central nervous system, and peripheral tissues.	1988-02	3286233
4-Norleucine, 7-D-phenylalanine-alpha-melanocyte-stimulating hormone: a highly potent alpha-melanotropin with ultralong biological activity.	1980-10	6777774

Sample Use Guides

In Vivo Use Guide

Afamelanotide is supplied in a biodegradable, controlled-release implant containing 16 mg of the active drug, which is to be administered subcutaneously in the area above the suprailiac crest using a 14-gauge catheter with needle

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:25:48 GMT 2025` Edited by `admin` on `Mon Mar 31 21:25:48 GMT 2025`
Record UNII	1XCC161YKC
Record Status	`FAILED`
Record Version

Download

Name

Type

Language

AFAMELANOTIDE ACETATE

Official Name

English

SCENESSE

Preferred Name

English

CUV1647 ACETATE

Code

English

AC-SER-TYR-SER-NLE-GLU-HIS-D-PHE-ARG-TRP-GLY-LYS-PRO-VAL-NH2.3 HOAC

Common Name

English

A-MELANOTROPIN, 4(NLE)-7(D-PHE)

Common Name

English

CUV-1647 ACETATE

Code

English

AFAMELANOTIDE ACETATE [USAN]

Common Name

English

AFAMELANOTIDE TRIACETATE

Common Name

English

Afamelanotide acetate [WHO-DD]

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/08/541