GHRP-6

{{Short description|Chemical compound}}

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| Verifiedfields = changed

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| verifiedrevid = 428750426

| IUPAC_name = L-histidyl-D-tryptophyl-L-alanyl-L-tryptophyl-D-phenylalanyl-L-Lysinamide

| image = GHRP-6.png

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| bioavailability = Oral: <1.0%{{cite journal| author=Hartman ML, Farello G, Pezzoli SS, Thorner MO| title=Oral administration of growth hormone (GH)-releasing peptide stimulates GH secretion in normal men. | journal=J Clin Endocrinol Metab | year= 1992 | volume= 74 | issue= 6 | pages= 1378–84 | pmid=1592884 | doi=10.1210/jcem.74.6.1592884 | pmc= | url=https://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=1592884 }}

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| elimination_half-life = 2.5 hours{{cite journal | vauthors = Cabrales A, Gil J, Fernández E, Valenzuela C, Hernández F, García I, Hernández A, Besada V, Reyes O, Padrón G, Berlanga J, Guillén G, González LJ | title = Pharmacokinetic study of Growth Hormone-Releasing Peptide 6 (GHRP-6) in nine male healthy volunteers | journal = European Journal of Pharmaceutical Sciences | volume = 48 | issue = 1–2 | pages = 40–46 | date = January 2013 | pmid = 23099431 | doi = 10.1016/j.ejps.2012.10.006 }}

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 87616-84-0

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| UNII = 4H7N4I6X6A

| ATC_prefix = None

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| PubChem = 5486806

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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 26333269

| C=46 | H=56 | N=12 | O=6

| smiles = C[C@@H](C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@H](Cc3ccccc3)C(=O)N[C@@H](CCCCN)C(=O)N)NC(=O)[C@@H](Cc4c[nH]c5c4cccc5)NC(=O)[C@H](Cc6c[nH]cn6)N

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = WZHKXNSOCOQYQX-FUAFALNISA-N

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Growth hormone-releasing peptide 6 (GHRP-6) (developmental code name SKF-110679), also known as growth hormone-releasing hexapeptide, is one of several synthetic met-enkephalin analogues that include unnatural D-amino acids, were developed for their growth hormone-releasing activity and are called growth hormone secretagogues. They lack opioid activity but are potent stimulators of growth hormone (GH) release. These secretagogues are distinct from growth hormone releasing hormone (GHRH) in that they share no sequence relation and derive their function through activation of a completely different receptor. This receptor was originally called the growth hormone secretagogue receptor (GHSR), but due to subsequent discoveries, the hormone ghrelin is now considered the receptor's natural endogenous ligand, and it has been renamed as the ghrelin receptor. Therefore, these GHSR agonists act as synthetic ghrelin mimetics.

It has been discovered that when GHRP-6 and insulin are administered simultaneously, GH response to GHRP-6 is increased (1). However, the consumption of carbohydrates and/or dietary fats, around the administration window of GH secretagogues significantly blunts the GH release. A recent study in normal mice showed significant differences in body composition, muscle growth, glucose metabolism, memory and cardiac function in the mice being administered the GHRP-6 (2). There are still many questions regarding this fairly new compound.

See also

References

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Further reading

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  • {{cite journal | vauthors = Korbonits M, Goldstone AP, Gueorguiev M, Grossman AB | title = Ghrelin--a hormone with multiple functions | journal = Frontiers in Neuroendocrinology | volume = 25 | issue = 1 | pages = 27–68 | date = April 2004 | pmid = 15183037 | doi = 10.1016/j.yfrne.2004.03.002 | s2cid = 24821233 }}
  • {{cite journal | vauthors = Peñalva A, Carballo A, Pombo M, Casanueva FF, Dieguez C | title = Effect of growth hormone (GH)-releasing hormone (GHRH), atropine, pyridostigmine, or hypoglycemia on GHRP-6-induced GH secretion in man | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 76 | issue = 1 | pages = 168–171 | date = January 1993 | pmid = 8421084 | doi = 10.1210/jcem.76.1.8421084 }}
  • {{cite journal | vauthors = Camanni F, Ghigo E, Arvat E | title = Growth hormone-releasing peptides and their analogs | journal = Frontiers in Neuroendocrinology | volume = 19 | issue = 1 | pages = 47–72 | date = January 1998 | pmid = 9465289 | doi = 10.1006/frne.1997.0158 | s2cid = 31400577 }}
  • {{cite journal | vauthors = Adeghate E, Ponery AS | title = Ghrelin stimulates insulin secretion from the pancreas of normal and diabetic rats | journal = Journal of Neuroendocrinology | volume = 14 | issue = 7 | pages = 555–560 | date = July 2002 | pmid = 12121492 | doi = 10.1046/j.1365-2826.2002.00811.x | s2cid = 26490804 }}
  • {{cite journal | vauthors = McGirr R, McFarland MS, McTavish J, Luyt LG, Dhanvantari S | title = Design and characterization of a fluorescent ghrelin analog for imaging the growth hormone secretagogue receptor 1a | journal = Regulatory Peptides | volume = 172 | issue = 1–3 | pages = 69–76 | date = December 2011 | pmid = 21893106 | doi = 10.1016/j.regpep.2011.08.011 | s2cid = 8213917 }}
  • {{cite web | vauthors = Koh B, Hardie M | date = 2013 | title = We need an advocate against ASADA's power in doping control. | url = https://theconversation.edu.au/we-need-an-advocate-against-asadas-power-in-doping-control-12119 | work = The Conversation }}

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{{GH/IGF-1 axis signaling modulators}}

Category:Ghrelin receptor agonists

Category:Growth hormone secretagogues

Category:Hexapeptides

Category:World Anti-Doping Agency prohibited substances

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