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MedKoo Cat#: 328098 | Name: Ipamorelin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ipamorelin, also known as NNC-26-0161, is a a ghrelin mimetic. Ipamorelin counteracts glucocorticoid-induced decrease in bone formation of adult rats. Ipamorelin may ameliorate the symptoms in patients with POI. Ipamorelin accelerates gastric emptying in a rodent model of postoperative ileus through the stimulation of gastric contractility by activating a ghrelin receptor-mediated mechanism involving cholinergic excitatory neurons.

Chemical Structure

Ipamorelin
Ipamorelin
CAS#170851-70-4 (free base)

Theoretical Analysis

MedKoo Cat#: 328098

Name: Ipamorelin

CAS#: 170851-70-4 (free base)

Chemical Formula: C38H49N9O5

Exact Mass: 711.3857

Molecular Weight: 711.87

Elemental Analysis: C, 64.12; H, 6.94; N, 17.71; O, 11.24

Price and Availability

Size Price Availability Quantity
5mg USD 285.00 2 Weeks
25mg USD 650.00 2 Weeks
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Related CAS #
170851-70-4 (free base) Ipamorelin (acetate)
Synonym
Ipamorelin; NNC-26-0161; NNC 26-0161; NNC26-0161; NNC-260161; NNC 260161; NNC260161
IUPAC/Chemical Name
(S)-6-amino-2-((R)-2-((R)-2-((S)-2-(2-amino-2-methylpropanamido)-3-(1H-imidazol-4-yl)propanamido)-3-(naphthalen-2-yl)propanamido)-3-phenylpropanamido)hexanamide
InChi Key
NEHWBYHLYZGBNO-BVEPWEIPSA-N
InChi Code
InChI=1S/C38H49N9O5/c1-38(2,41)37(52)47-32(21-28-22-42-23-43-28)36(51)46-31(20-25-15-16-26-12-6-7-13-27(26)18-25)35(50)45-30(19-24-10-4-3-5-11-24)34(49)44-29(33(40)48)14-8-9-17-39/h3-7,10-13,15-16,18,22-23,29-32H,8-9,14,17,19-21,39,41H2,1-2H3,(H2,40,48)(H,42,43)(H,44,49)(H,45,50)(H,46,51)(H,47,52)/t29-,30+,31+,32-/m0/s1
SMILES Code
NCCCC[C@@H](C(N)=O)NC([C@@H](CC1=CC=CC=C1)NC([C@@H](CC2=CC=C3C=CC=CC3=C2)NC([C@H](CC4=CNC=N4)NC(C(C)(C)N)=O)=O)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ipamorelin, also known as NNC-26-0161, is a a ghrelin mimetic.
In vitro activity:
TBD
In vivo activity:
As illustrated in Figure 3A, rats that received the highest dose of IPAM (ipamorelin) (1 mg/kg i.v.) had a significantly lower number of abdominal contractions at 40 mmHg (p<0.0001) and 60 mmHg (p<0.0001). Administration of the ghrelin antagonist H0900 prevented the anti-nociceptive effects of IPAM (1 mg/kg) as this study observed an effect of pressure (F(3, 48)=146.2, p<0.0001), but not treatment (F(1, 48)=0.3262, p=0.5706) (Figure 3B). Reference: J Exp Pharmacol. 2020 Aug 5;12:267-274. https://pubmed.ncbi.nlm.nih.gov/32801950/

Preparing Stock Solutions

The following data is based on the product molecular weight 711.87 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. N Mohammadi E, Louwies T, Pietra C, Northrup SR, Greenwood-Van Meerveld B. Attenuation of Visceral and Somatic Nociception by Ghrelin Mimetics. J Exp Pharmacol. 2020 Aug 5;12:267-274. doi: 10.2147/JEP.S249747. PMID: 32801950; PMCID: PMC7415447. 2. Greenwood-Van Meerveld B, Tyler K, Mohammadi E, Pietra C. Efficacy of ipamorelin, a ghrelin mimetic, on gastric dysmotility in a rodent model of postoperative ileus. J Exp Pharmacol. 2012 Oct 19;4:149-55. doi: 10.2147/JEP.S35396. PMID: 27186127; PMCID: PMC4863553.
In vitro protocol:
TBD
In vivo protocol:
1. N Mohammadi E, Louwies T, Pietra C, Northrup SR, Greenwood-Van Meerveld B. Attenuation of Visceral and Somatic Nociception by Ghrelin Mimetics. J Exp Pharmacol. 2020 Aug 5;12:267-274. doi: 10.2147/JEP.S249747. PMID: 32801950; PMCID: PMC7415447. 2. Greenwood-Van Meerveld B, Tyler K, Mohammadi E, Pietra C. Efficacy of ipamorelin, a ghrelin mimetic, on gastric dysmotility in a rodent model of postoperative ileus. J Exp Pharmacol. 2012 Oct 19;4:149-55. doi: 10.2147/JEP.S35396. PMID: 27186127; PMCID: PMC4863553.
1: Semenistaya E, Zvereva I, Thomas A, Thevis M, Krotov G, Rodchenkov G. Determination of growth hormone releasing peptides metabolites in human urine after nasal administration of GHRP-1, GHRP-2, GHRP-6, Hexarelin, and Ipamorelin. Drug Test Anal. 2015 Oct;7(10):919-25. doi: 10.1002/dta.1787. PubMed PMID: 25869809. 2: Beck DE, Sweeney WB, McCarter MD; Ipamorelin 201 Study Group.. Prospective, randomized, controlled, proof-of-concept study of the Ghrelin mimetic ipamorelin for the management of postoperative ileus in bowel resection patients. Int J Colorectal Dis. 2014 Dec;29(12):1527-34. doi: 10.1007/s00384-014-2030-8. PubMed PMID: 25331030. 3: Greenwood-Van Meerveld B, Tyler K, Mohammadi E, Pietra C. Efficacy of ipamorelin, a ghrelin mimetic, on gastric dysmotility in a rodent model of postoperative ileus. J Exp Pharmacol. 2012 Oct 19;4:149-55. doi: 10.2147/JEP.S35396. PubMed PMID: 27186127; PubMed Central PMCID: PMC4863553. 4: Venkova K, Mann W, Nelson R, Greenwood-Van Meerveld B. Efficacy of ipamorelin, a novel ghrelin mimetic, in a rodent model of postoperative ileus. J Pharmacol Exp Ther. 2009 Jun;329(3):1110-6. doi: 10.1124/jpet.108.149211. PubMed PMID: 19289567. 5: Adeghate E, Ponery AS. Mechanism of ipamorelin-evoked insulin release from the pancreas of normal and diabetic rats. Neuro Endocrinol Lett. 2004 Dec;25(6):403-6. PubMed PMID: 15665799. 6: Jiménez-Reina L, Cañete R, de la Torre MJ, Bernal G. Influence of chronic treatment with the growth hormone secretagogue Ipamorelin, in young female rats: somatotroph response in vitro. Histol Histopathol. 2002;17(3):707-14. PubMed PMID: 12168778. 7: Andersen NB, Malmlöf K, Johansen PB, Andreassen TT, Ørtoft G, Oxlund H. The growth hormone secretagogue ipamorelin counteracts glucocorticoid-induced decrease in bone formation of adult rats. Growth Horm IGF Res. 2001 Oct;11(5):266-72. PubMed PMID: 11735244. 8: Hansen TK, Ankersen M, Raun K, Hansen BS. Highly potent growth hormone secretagogues: hybrids of NN703 and ipamorelin. Bioorg Med Chem Lett. 2001 Jul 23;11(14):1915-8. PubMed PMID: 11459660. 9: Svensson J, Lall S, Dickson SL, Bengtsson BA, Rømer J, Ahnfelt-Rønne I, Ohlsson C, Jansson JO. The GH secretagogues ipamorelin and GH-releasing peptide-6 increase bone mineral content in adult female rats. J Endocrinol. 2000 Jun;165(3):569-77. PubMed PMID: 10828840. 10: Gobburu JV, Agersø H, Jusko WJ, Ynddal L. Pharmacokinetic-pharmacodynamic modeling of ipamorelin, a growth hormone releasing peptide, in human volunteers. Pharm Res. 1999 Sep;16(9):1412-6. PubMed PMID: 10496658. 11: Johansen PB, Nowak J, Skjaerbaek C, Flyvbjerg A, Andreassen TT, Wilken M, Orskov H. Ipamorelin, a new growth-hormone-releasing peptide, induces longitudinal bone growth in rats. Growth Horm IGF Res. 1999 Apr;9(2):106-13. PubMed PMID: 10373343. 12: Johansen PB, Hansen KT, Andersen JV, Johansen NL. Pharmacokinetic evaluation of ipamorelin and other peptidyl growth hormone secretagogues with emphasis on nasal absorption. Xenobiotica. 1998 Nov;28(11):1083-92. PubMed PMID: 9879640. 13: Raun K, Hansen BS, Johansen NL, Thøgersen H, Madsen K, Ankersen M, Andersen PH. Ipamorelin, the first selective growth hormone secretagogue. Eur J Endocrinol. 1998 Nov;139(5):552-61. PubMed PMID: 9849822. 14: Ankersen M, Johansen NL, Madsen K, Hansen BS, Raun K, Nielsen KK, Thogersen H, Hansen TK, Peschke B, Lau J, Lundt BF, Andersen PH. A new series of highly potent growth hormone-releasing peptides derived from ipamorelin. J Med Chem. 1998 Sep 10;41(19):3699-704. PubMed PMID: 9733495.