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Details

Stereochemistry ABSOLUTE
Molecular Formula C46H56N12O6.3C2H4O2
Molecular Weight 1053.1695
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Hexapeptide-2 acetate

SMILES

CC(O)=O.CC(O)=O.CC(O)=O.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=XGWOPQAMQAZCJE-SLBOMMQWSA-N
InChI=1S/C46H56N12O6.3C2H4O2/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;3*1-2(3)4/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);3*1H3,(H,3,4)/t27-,34-,37-,38+,39+,40-;;;/m0.../s1

HIDE SMILES / InChI

Molecular Formula C46H56N12O6
Molecular Weight 873.0136
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C2H4O2
Molecular Weight 60.052
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment: GHRP-6 mimics ghrelin-induced stimulation of food intake and suppression of locomotor activity in goldfish.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.5 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:50:24 UTC 2023
Edited
by admin
on Fri Dec 15 15:50:24 UTC 2023
Record UNII
USP2MY0E7I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Hexapeptide-2 acetate
Common Name English
L-Lysinamide, L-histidyl-D-tryptophyl-L-alanyl-L-tryptophyl-D-phenylalanyl-, triacetate
Systematic Name English
Growth hormone releasing hexapeptide acetate
Common Name English
HIS-D-TRP-ALA-TRP-D-PHE-LYS-NH2 ACETATE
Systematic Name English
GHRP-6 (acetate)
Common Name English
SKF-110679 ACETATE
Common Name English
SKF-110679 ACETATE HYDRATE
Common Name English
Code System Code Type Description
PUBCHEM
72941687
Created by admin on Fri Dec 15 15:50:24 UTC 2023 , Edited by admin on Fri Dec 15 15:50:24 UTC 2023
PRIMARY
CAS
145177-42-0
Created by admin on Fri Dec 15 15:50:24 UTC 2023 , Edited by admin on Fri Dec 15 15:50:24 UTC 2023
PRIMARY
FDA UNII
USP2MY0E7I
Created by admin on Fri Dec 15 15:50:24 UTC 2023 , Edited by admin on Fri Dec 15 15:50:24 UTC 2023
PRIMARY
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ACTIVE MOIETY