TETRAPEPTIDE-15

Possibly Marketed Outside US

First approved in 2012

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H37N5O5
Molecular Weight	571.6667
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CC1=CC=C(O)C=C1)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](CC4=CC=CC=C4)C(N)=O

InChI

InChIKey=XIJHWXXXIMEHKW-LJWNLINESA-N

InChI=1S/C32H37N5O5/c33-25(18-23-13-15-24(38)16-14-23)32(42)37-17-7-12-28(37)31(41)36-27(20-22-10-5-2-6-11-22)30(40)35-26(29(34)39)19-21-8-3-1-4-9-21/h1-6,8-11,13-16,25-28,38H,7,12,17-20,33H2,(H2,34,39)(H,35,40)(H,36,41)/t25-,26-,27-,28-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C32H37N5O5
Molecular Weight	571.6667
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24084000 | https://www.ncbi.nlm.nih.gov/pubmed/19932695 | https://www.ncbi.nlm.nih.gov/pubmed/18374539

Tetrapeptide-15 (Endomorphin-2) is an endogenous agonist at μ-opioid receptors (μORs) in the spinal cord; it exhibits antinociceptive/analgesic, immunosuppressive, and pro-angiogenic activities. Endomorphin-2 increases pain thresholds in animal models of thermal pain and inhibits the formation of antibodies in other cellular models. In HUVECs, this peptide stimulates proliferation, migration, adhesion, and tube formation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 231 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9087409 \| https://www.ncbi.nlm.nih.gov/pubmed/26005537 \| https://www.ncbi.nlm.nih.gov/pubmed/10510460	Agonist 2752		0.69 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25794206 https://www.ncbi.nlm.nih.gov/pubmed/23119108 https://www.ncbi.nlm.nih.gov/pubmed/18567517	Primary	Preclinical	Unknown Approved Use Unknown
Cough 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12706478	Primary	Preclinical	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16636106	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Spinal endomorphin 2 antinociception and the mechanisms that produce it are both sex- and stage of estrus cycle-dependent in rats.	2013-11	24084000
The stimulative effects of endogenous opioids on endothelial cell proliferation, migration and angiogenesis in vitro.	2010-02-25	19932695
Endomorphin 1 and endomorphin 2 suppress in vitro antibody formation at ultra-low concentrations: anti-peptide antibodies but not opioid antagonists block the activity.	2008-08	18374539
The antitussive effects of endomorphin-1 and endomorphin-2 in mice.	2003-04-25	12706478

Patents

Sample Use Guides

In Vivo Use Guide

Endomorphin-2, at doses of 3, 10 and 30 ug, i.c.v., dose-dependently inhibited the number of capsaicin-induced coughs.

Route of Administration: Other

In Vitro Use Guide

Endomorphin-2 (100 uM) produced a significant inhibition, of both the frequency (-22.8%) and the amplitude (-30.5%) of the spontaneous IPSCs in rat cardiac vagal neurons.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:42:32 GMT 2025` Edited by `admin` on `Mon Mar 31 23:42:32 GMT 2025`
Record UNII	3PH5M0466G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENDOMORPHIN 2

Preferred Name

English

TETRAPEPTIDE-15

Official Name

English

TYR-PRO-PHE-PHE-NH2

Common Name

English

L-TYROSYL-L-PROLYL-L-PHENYLALANYL-L-PHENYLALANINAMIDE

Systematic Name

English

L-TYROSYL-L-PROLYL-L-PHENYLALANYL-L-PHENYLALANINAMIDE, (-)-

Systematic Name

English

L-PHENYLALANINAMIDE, L-TYROSYL-L-PROLYL-L-PHENYLALANYL-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID70415506