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Details

Stereochemistry ABSOLUTE
Molecular Formula C46H56N12O6
Molecular Weight 873.0136
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SKF-110679

SMILES

C[C@H](NC(=O)[C@@H](CC1=CNC2=C1C=CC=C2)NC(=O)[C@@H](N)CC3=CN=CN3)C(=O)N[C@@H](CC4=CNC5=C4C=CC=C5)C(=O)N[C@H](CC6=CC=CC=C6)C(=O)N[C@@H](CCCCN)C(N)=O

InChI

InChIKey=WZHKXNSOCOQYQX-FUAFALNISA-N
InChI=1S/C46H56N12O6/c1-27(54-44(62)39(20-29-23-51-35-15-7-5-13-32(29)35)57-43(61)34(48)22-31-25-50-26-53-31)42(60)56-40(21-30-24-52-36-16-8-6-14-33(30)36)46(64)58-38(19-28-11-3-2-4-12-28)45(63)55-37(41(49)59)17-9-10-18-47/h2-8,11-16,23-27,34,37-40,51-52H,9-10,17-22,47-48H2,1H3,(H2,49,59)(H,50,53)(H,54,62)(H,55,63)(H,56,60)(H,57,61)(H,58,64)/t27-,34-,37-,38+,39+,40-/m0/s1

HIDE SMILES / InChI

Description

Growth hormone releasing hexapeptide (GHRP-6) is a synthetic met-enkephalin analog that induces the release of growth hormone in vivo through binding of the ghrelin receptor. GHRP-6 increases proliferation in astrocytes through a mechanism that involves PI3K/Akt signaling. GHRP-6 also inhibits development of restraint stress-induced gastric lesions and reverses ovariectomy-induced effects on serum glucose and insulin levels. Additionally, GHRP-6 decreases locomotor activity and increases food intake in vivo. Essentially a synthetic version of ghrelin analogue, GHRP-6 (like GHRP-2) stimulates the release of an endogenous growth hormone (GH) within the somatotropes of the anterior pituitary in the animal and human body. Specifically, GHRP-6 will increase the number of somatotropes in a GH pulse by limiting the amount of somatostatin present, while standard GHRH increases the amplitude at which the pituitary cells pulse. Unlike ghrelin, GHRP-6 is not specifically used to increase appetite, but it may have secondary actions that impact hypothalamic neurons. These effects last for approximately an hour after the initial application, which mimics the natural application of GH, and consists of an eight hour circulation period. In studies GHRP-6 has shown biological actions similar to the naturally occurring hunger stimulating peptide ghrelin. Its main use is to promote food intake by stimulating hunger and aid in energy metabolism. It can be used in the treatment of GH deficiency as well as cachexia, eating disorders and obesity. GHRP-6 is a synthetic met-enkephalin (a naturally occurring opioid growth factor) analog. GHRP-6 contains D-amino acids that are entirely synthetic, lacks opioid activity, and shares no sequence relation with GHRH. It has also been shown that GHRP-6 can lead to re-stimulation of the natural production of HGH. Studies have shown that GHRP-6 increases the secretion of IGF-1 (InsulinLike Growth Factor 1) by the liver, which is speculated to be a required component in the anabolic mechanisms leading to the action of HGH. It also appears that GHRP-6 has positive implications for the central nervous system, as ghrelin is known to protect neurons.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.5 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Primary
PubMed

PubMed

TitleDatePubMed
On the in vitro and in vivo activity of a new synthetic hexapeptide that acts on the pituitary to specifically release growth hormone.
1984 May
Molecular analysis of rat pituitary and hypothalamic growth hormone secretagogue receptors.
1997 Apr
Nonpeptide and peptide growth hormone secretagogues act both as ghrelin receptor agonist and as positive or negative allosteric modulators of ghrelin signaling.
2005 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Six patients with endogenous hypercortisolism, nine with exogenous glucocorticoid excess and 10 normal controls were submitted to three tests, in random order, with GHRH (100 ug), GHRP-6 (ug/ kg) or GHRP+GHRP-6, in the same doses, i.v., on separate days.
Route of Administration: Intravenous
In Vitro Use Guide
In vitro the minimum and maximum active dosages ranged from 1-10 ng/ml in the pituitary incubate assay.
Name Type Language
SKF-110679
Common Name English
GROWTH HORMONE RELEASING HEXAPEPTIDE
Preferred Name English
U-75799E
Code English
GROWTH HORMONE-RELEASING PEPTIDE 6
Common Name English
L-LYSINAMIDE, L-HISTIDYL-D-TRYPTOPHYL-L-ALANYL-L-TRYPTOPHYL-D-PHENYLALANYL-
Common Name English
HIS-D-TRP-ALA-TRP-D-PHE-LYS NH2
Common Name English
GHRP-6
Common Name English
SK&F-110679
Code English
HIS-D-TRP-ALA-TRP-D-PHE-LYS-NH2
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 46190
Created by admin on Tue Oct 22 12:09:43 UTC 2019 , Edited by admin on Tue Oct 22 12:09:43 UTC 2019
Code System Code Type Description
MESH
C041048
Created by admin on Tue Oct 22 12:09:43 UTC 2019 , Edited by admin on Tue Oct 22 12:09:43 UTC 2019
PRIMARY
CAS
87616-84-0
Created by admin on Tue Oct 22 12:09:43 UTC 2019 , Edited by admin on Tue Oct 22 12:09:43 UTC 2019
PRIMARY
PUBCHEM
9919153
Created by admin on Tue Oct 22 12:09:43 UTC 2019 , Edited by admin on Tue Oct 22 12:09:43 UTC 2019
PRIMARY
WIKIPEDIA
GHRP-6
Created by admin on Tue Oct 22 12:09:43 UTC 2019 , Edited by admin on Tue Oct 22 12:09:43 UTC 2019
PRIMARY