U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C48H73N11O10S.3C2H4O2
Molecular Weight 1176.382
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EBIRATIDE TRIACETATE

SMILES

CC(O)=O.CC(O)=O.CC(O)=O.CS(=O)(=O)CC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@H](CCCCN)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)NCCCCCCCCN

InChI

InChIKey=SQMYCWHGGFDQSL-ZRJVJLHYSA-N
InChI=1S/C48H73N11O10S.3C2H4O2/c1-70(68,69)27-23-36(51)43(62)55-38(21-22-42(60)61)46(65)59-41(30-35-31-52-32-54-35)48(67)58-40(29-34-18-10-7-11-19-34)47(66)56-37(20-12-14-25-50)45(64)57-39(28-33-16-8-6-9-17-33)44(63)53-26-15-5-3-2-4-13-24-49;3*1-2(3)4/h6-11,16-19,31-32,36-41H,2-5,12-15,20-30,49-51H2,1H3,(H,52,54)(H,53,63)(H,55,62)(H,56,66)(H,57,64)(H,58,67)(H,59,65)(H,60,61);3*1H3,(H,3,4)/t36-,37+,38-,39-,40-,41-;;;/m0.../s1

HIDE SMILES / InChI
Ebiratide (Hoe 427) is a peptide analog of corticotrophin (ACTH 4-9). Ebiratide is endocrinologically inert. Ebiratide is highly lipophilic and has prolonged metabolic stability. Ebiratide exerts neurotrophic properties in vivo. It also was proven to have significant effects on acetylcholine metabolism. It has been investigated in the treatment of Alzheimer's disease.

Approval Year

PubMed

PubMed

TitleDatePubMed
Learning and memory processes of an ACTH4-9 analog (ebiratide; Hoe 427) in mice and rats.
1988 May-Jun

Sample Use Guides

In an acute trial, three different dosages (60, 300, and 600 micrograms) of the endocrinologically inert but behaviorally active corticotropin 4-9 (ACTH4-9) fragment ebiratide were given to three patients with clinically probable Alzheimer's disease and five patients with a major depressive episode who were psychomotor retarded.
Route of Administration: Intravenous
In Vitro Use Guide
The 5-day treatment with ebiratide (10-100 pmol/ml) partially prevented neuronal degeneration that occurred in the cultures in which cells were sparsely plated. Ebiratide (10 pmol/ ml) increased choline acetyltransferase (ChAT) and acetylcholinesterase (AChE) activities up to 1.5 and 1.2 times the respective control values in the sub-confluent cultures.
Name Type Language
EBIRATIDE TRIACETATE
Common Name English
L-PHENYLALANINAMIDE, (2S)-2-AMINO-4-(METHYLSULFONYL)BUTANOYL-L-.ALPHA.-GLUTAMYL-L-HISTIDYL-L-PHENYLALANYL-D-LYSYL-N.ALPHA.-(8-AMINOOCTYL)-, TRIACETATE
Systematic Name English
HOE-427
Code English
Code System Code Type Description
CAS
115994-46-2
Created by admin on Fri Dec 15 16:24:18 GMT 2023 , Edited by admin on Fri Dec 15 16:24:18 GMT 2023
PRIMARY
PUBCHEM
6918102
Created by admin on Fri Dec 15 16:24:18 GMT 2023 , Edited by admin on Fri Dec 15 16:24:18 GMT 2023
PRIMARY
FDA UNII
S4QA804W04
Created by admin on Fri Dec 15 16:24:18 GMT 2023 , Edited by admin on Fri Dec 15 16:24:18 GMT 2023
PRIMARY