CIBINETIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C51H84N16O21
Molecular Weight	1257.3073
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(O)=O

InChI

InChIKey=WZTIQQBMSJTRBR-WYKNNRPVSA-N

InChI=1S/C51H84N16O21/c1-22(2)17-30(47(84)65-32(19-36(53)71)48(85)66-33(20-68)49(86)67-34(21-69)50(87)88)63-40(77)24(5)57-41(78)25(7-6-16-56-51(54)55)59-43(80)29(11-15-39(75)76)62-46(83)31(18-23(3)4)64-45(82)27(8-12-35(52)70)60-44(81)28(10-14-38(73)74)61-42(79)26-9-13-37(72)58-26/h22-34,68-69H,6-21H2,1-5H3,(H2,52,70)(H2,53,71)(H,57,78)(H,58,72)(H,59,80)(H,60,81)(H,61,79)(H,62,83)(H,63,77)(H,64,82)(H,65,84)(H,66,85)(H,67,86)(H,73,74)(H,75,76)(H,87,88)(H4,54,55,56)/t24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26431906 | https://www.ncbi.nlm.nih.gov/pubmed/28475703 | https://www.ncbi.nlm.nih.gov/pubmed/30876881 | https://www.ncbi.nlm.nih.gov/pubmed/29223734

Cibinetide (ARA 290; helix B surface peptide) is a novel potent and selective peptide agonist of innate repair receptor (IRR) with anti-inflammatory and tissue-protective activities. IRR activation promotes tissue protection and repair in a wide variety of preclinical models, including diabetic wound healing, diabetic neuropathy, and ischemic retinopathy. In a mouse model of diabetic small nerve fiber loss, daily administration of Cibinetide reversed neuronal dystrophy. Cibinetide administration significantly improved re-epithelization, angiogenesis, and wound healing strength in a mouse model of diabetic wounds. In clinical studies, Cibinetide administration has shown significantly increased small nerve fiber abundance, reduced neuropathic symptoms and promoted nerve fiber repair in patients with sarcoidosis or diabetes-related nerve fiber loss.

Originator

Approval Year

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

1, 4, or 8 mg cibinetide or placebo daily for 28 days

Route of Administration: Other

Name

Type

Language

CIBINETIDE

Official Name

English

L-SERINE, 5-OXO-L-PROLYL-L-.ALPHA.-GLUTAMYL-L-GLUTAMINYL-L-LEUCYL-L-.ALPHA.-GLUTAMYL-L-ARGINYL-L-ALANYL-L-LEUCYL-L-ASPARAGINYL-L-SERYL-

Systematic Name

English

PYR-GLU-GLN-LEU-GLU-ARG-ALA-LEU-ASN-SER-SER-OH

Common Name

English

ARA-290

Code

English

PH-BSP

Common Name

English

PHBSP

Common Name

English

L-PYR-L-GLU-L-GLN-L-LEU-L-GLU-L-ARG-L-ALA-L-LEU-L-ASN-L-SER-L-SER

Common Name

English

ARA290

Code

English

Cibinetide [WHO-DD]

Common Name

English

ARA 290

Code

English

L-PYROGLUTAMYL-L-GLUTAMYL-L-GLUTAMINYL-L-IEUCYL-L-GLUTAMYL-L-ARGINYL-L-ALANYL-L-LEUCYL-L-ASPARAGINYL-L-SERYL-L-SERINE

Systematic Name

English

CIBINETIDE [USAN]

Common Name

English

L-PYROGLUTAMYL-L-GLUTAMYL-L-GLUTAMINYL-L-LEUCYL-L-GLUTAMYL-L-ARGINYL-L-ALANYL-L-LEUCYL-L-ASPARAGINYL-L-SERYL-L-SERINE

Systematic Name

English

cibinetide [INN]

Common Name

English

PGLU-GLU-GLN-LEU-GLU-ARG-ALA-LEU-ASN-SER-SER

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/16/1721