MODIMELANOTIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C113H181N33O25S
Molecular Weight	2433.917
Optical Activity	UNSPECIFIED
Defined Stereocenters	18 / 18
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)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=C4C=CC=C5)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=WHRVKPBBRZHWTN-ZHHKRVSMSA-N

InChI=1S/C113H181N33O25S/c1-66(2)94(95(121)154)145-111(170)91-38-25-54-146(91)112(171)84(36-16-23-52-120)130-92(151)62-127-96(155)87(58-70-60-126-74-29-9-8-28-73(70)74)141-102(161)81(37-24-53-125-113(122)123)136-106(165)85(56-68-26-6-5-7-27-68)139-108(167)88(59-71-61-124-65-128-71)142-104(163)82(43-44-93(152)153)137-105(164)83(45-55-172-4)138-109(168)89(63-147)144-107(166)86(57-69-39-41-72(150)42-40-69)140-110(169)90(64-148)143-103(162)80(35-15-22-51-119)135-101(160)79(34-14-21-50-118)134-100(159)78(33-13-20-49-117)133-99(158)77(32-12-19-48-116)132-98(157)76(31-11-18-47-115)131-97(156)75(129-67(3)149)30-10-17-46-114/h5-9,26-29,39-42,60-61,65-66,75-91,94,126,147-148,150H,10-25,30-38,43-59,62-64,114-120H2,1-4H3,(H2,121,154)(H,124,128)(H,127,155)(H,129,149)(H,130,151)(H,131,156)(H,132,157)(H,133,158)(H,134,159)(H,135,160)(H,136,165)(H,137,164)(H,138,168)(H,139,167)(H,140,169)(H,141,161)(H,142,163)(H,143,162)(H,144,166)(H,145,170)(H,152,153)(H4,122,123,125)/t75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,94-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C113H181N33O25S
Molecular Weight	2433.917
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	18 / 18
E/Z Centers	12
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27543797 | https://www.ncbi.nlm.nih.gov/pubmed/28601936 | https://www.ncbi.nlm.nih.gov/pubmed/7786004

Modimelanotide is a melanocortinergic peptide drug derived from α-melanocyte-stimulating hormone (α-MSH) which was under development for the treatment of acute kidney injury. Modimelanotide had promising preclinical data, and a Phase II trial in patients undergoing cardiopulmonary bypass surgery showed a reduced incidence of acute kidney injury in subjects that received Modimelanotide. However, a Phase IIb, multicenter study of Modimelanotide in patients with chronic kidney disease who underwent cardiopulmonary bypass surgery failed to show a significant reduction in the incidence of acute kidney injury in subjects who received the drug, both by serum creatinine measurements and by novel biomarkers of tubular injury.

Originator

Approval Year

PubMed

Title	Date	PubMed
ABT-719 for the Prevention of Acute Kidney Injury in Patients Undergoing High-Risk Cardiac Surgery: A Randomized Phase 2b Clinical Trial.	2016 Aug 20	27543797

Patents

Sample Use Guides

In Vivo Use Guide

800, 1600, or 2100 μg/kg

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:00:12 GMT 2023` Edited by `admin` on `Sat Dec 16 11:00:12 GMT 2023`
Record UNII	96C1EBE9CG
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MODIMELANOTIDE

Official Name

English

ABT-719

Code

English

Modimelanotide [WHO-DD]

Common Name

English

modimelanotide [INN]

Common Name

English

AP-214

Code

English

L-VALINAMIDE, N2-ACETYL-L-LYSYL-L-LYSYL-L-LYSYL-L-LYSYL-L-LYSYL-L-LYSYL-L-SERYL-L-TYROSYL-L-SERYL-L-METHIONYL-L-.ALPHA.-GLUTAMYL-L-HISTIDYL-L-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYLGLYCYL-L-LYSYL-L-PROLYL-

Systematic Name

English

ZP-1480

Code

English

ACETYLHEXA-L-LYSYL(HUMAN MELANOTROPIN ALPHA (ALPHA-MSH)) MELANOCORTIN RECEPTOR AGONIST

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL3545104