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Ipamorelin acetate (NNC26-0161 acetate )

Alias: NNC-26-0161; NNC 26-0161; Ipamorelin; 170851-70-4; NNC-26-0,161; Y9M3S784Z6; Aib-His-D-2-Nal-D-Phe-Lys-NH2; NNC26-0161; NNC-260161; NNC 260161; NNC260161.
Cat No.:V22633 Purity: ≥98%
Ipamorelin (NNC-26-0161) is a a novel and potent ghrelin mimetic peptide compound that counteracts glucocorticoid-induced decrease in bone formation of adult rats.
Ipamorelin acetate (NNC26-0161 acetate )
Ipamorelin acetate (NNC26-0161 acetate ) Chemical Structure CAS No.: 170851-70-4
Product category: New12
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: =99.41%

Purity: =99.7%

Product Description
Ipamorelin (NNC-26-0161) is a a novel and potent ghrelin mimetic peptide compound that 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.
Ipamorelin (NNC-26-0161) is a pentapeptide growth hormone secretagogue (GHS) and a selective agonist of the ghrelin/growth hormone secretagogue receptor (GHS-R1a). It has the amino acid sequence Aib-His-D-2-Nal-D-Phe-Lys-NH2. Ipamorelin mimics ghrelin and binds to the ghrelin receptor (GHSR) in the brain, selectively stimulating the release of growth hormone (GH) from the pituitary gland. It induces longitudinal bone growth in rats.
Biological Activity I Assay Protocols (From Reference)
Targets
Ghrelin receptor (or GH secretagogue receptor, GHSR)
Ipamorelin targets the ghrelin receptor, also known as the growth hormone secretagogue receptor (GHS-R1a). It is a selective agonist of the GHS receptor. It binds to COS-7 cells expressing GHS-R1a with a Ki of 63.4 nM. By activating this receptor, it stimulates the release of growth hormone from the pituitary gland.
ln Vitro
Ipamorelin is a pentapeptide (Aib-His-D-2-Nal-D-Phe-Lys-NH2) and a ghrelin mimetic with growth hormone (GH) releasing activity. Ipamorelin mimics ghrelin and binds to the ghrelin receptor (or GH secretagogue receptor, GHSR) in the brain, thereby selectively stimulating the release of GH from the pituitary gland. This results in increased plasma GH levels, which would affect many biological processes. Besides its presence in the brain, GHSR can also be found in the gastrointestinal tract, heart, lung, liver, kidney, pancreas, adipose tissue and immune cells. Unlike other GH releasing peptides, ipamorelin only stimulates GH release in a manner very similar to that of growth hormone releasing hormone.
Ipamorelin is a potent and selective agonist of the ghrelin receptor. It binds to COS-7 cells expressing GHS-R1a with a Ki of 63.4 nM. It stimulates GH release via a GHRP-like receptor. Its activity has been confirmed in various in vitro binding and functional assays. It induces longitudinal bone growth in rats.
ln Vivo
IPAMORELIN is a Protein drug with a maximum clinical trial phase of II and has 1 investigational indication.
Ipamorelin is a growth hormone secretagogue that stimulates the release of growth hormone in vivo. It induces longitudinal bone growth in rats. It has been investigated for the treatment of ileus and gastrointestinal dysmotility. Its ability to stimulate GH release makes it a potential therapeutic agent for growth hormone deficiency and other conditions.
Enzyme Assay
The primary in vitro assay for Ipamorelin is a radioligand binding assay using cells expressing GHS-R1a. The compound's ability to displace a labeled ligand is measured to determine its Ki value. Functional assays measure its ability to stimulate GH release from pituitary cells in culture.
Cell Assay
Cellular assays for Ipamorelin involve treating cells expressing GHS-R1a, such as COS-7 cells, with the compound and measuring its effects on receptor-mediated signaling. Its ability to stimulate GH release can be assessed in primary pituitary cell cultures by measuring GH levels in the culture supernatant.
Animal Protocol
In vivo animal experiments for Ipamorelin have been conducted in rats to assess its effects on growth hormone release and bone growth. The compound is administered, and its effects on serum GH levels and longitudinal bone growth are measured. Its effects on gastrointestinal motility have also been investigated.
ADME/Pharmacokinetics
Ipamorelin has a molecular weight of 711.89 g/mol and a molecular formula of C38H49N9O5. It is a pentapeptide growth hormone secretagogue. It is typically used as a research reagent. Its purity is typically ≥98%. The compound is also known as NNC-26-0161.
Toxicity/Toxicokinetics
The toxicological profile of Ipamorelin is not extensively detailed in the provided sources. As a research compound, it is not intended for human use. Standard safety precautions should be followed when handling. Its safety would need to be established through preclinical studies if it were to be developed for therapeutic applications.
References
[1]. 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.
Additional Infomation
Iparrelin has been investigated for the treatment of intestinal obstruction. Iparrelin is a pentapeptide (Aib-His-D-2-Nal-D-Phe-Lys-NH2), a growth hormone-releasing peptide analog with growth hormone (GH)-releasing activity. Iparrelin mimics GH-releasing peptide and binds to the GH-releasing peptide receptor (or growth hormone secretagogue receptor, GHSR) in the brain, thereby selectively stimulating the pituitary gland to release growth hormone. This leads to elevated plasma growth hormone levels, which in turn affect many biological processes. Besides the brain, GHSR is also found in the gastrointestinal tract, heart, lungs, liver, kidneys, pancreas, adipose tissue, and immune cells. Unlike other GH-releasing peptides, iparelin stimulates growth hormone release in a manner very similar to GH-releasing hormone.
Ipamorelin (NNC-26-0161) is a pentapeptide growth hormone secretagogue and selective agonist of the ghrelin receptor. It stimulates the release of growth hormone from the pituitary gland and induces longitudinal bone growth in rats. It has been investigated for the treatment of ileus and gastrointestinal dysmotility. It is available from various chemical suppliers for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C38H49N9O5
Molecular Weight
711.8530
Exact Mass
711.385
Elemental Analysis
C, 64.12; H, 6.94; N, 17.71; O, 11.24
CAS #
170851-70-4
PubChem CID
9831659
Sequence
Aib-His-D-2-Nal-D-Phe-Lys-NH2; H-Aib-His-D-2Nal-D-Phe-Lys-NH2; alpha-methyl-alanyl-L-histidyl-3-(2-naphthyl)-D-alanyl-D-phenylalanyl-L-lysinamide
SequenceShortening
XHXFK
Appearance
Powder
Density
1.3±0.1 g/cm3
Boiling Point
1185.5±65.0 °C at 760 mmHg
Flash Point
670.7±34.3 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.624
LogP
1.72
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
19
Heavy Atom Count
52
Complexity
1200
Defined Atom Stereocenter Count
4
SMILES
O=C(C([H])(C([H])([H])C1C([H])=C([H])C2=C([H])C([H])=C([H])C([H])=C2C=1[H])N([H])C(C([H])(C([H])([H])C1=C([H])N=C([H])N1[H])N([H])C(C(C([H])([H])[H])(C([H])([H])[H])N([H])[H])=O)=O)N([H])C([H])(C(N([H])C([H])(C(N([H])[H])=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H])=O)C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H]
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
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
Synonyms
NNC-26-0161; NNC 26-0161; Ipamorelin; 170851-70-4; NNC-26-0,161; Y9M3S784Z6; Aib-His-D-2-Nal-D-Phe-Lys-NH2; NNC26-0161; NNC-260161; NNC 260161; NNC260161.
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.4048 mL 7.0240 mL 14.0479 mL
5 mM 0.2810 mL 1.4048 mL 2.8096 mL
10 mM 0.1405 mL 0.7024 mL 1.4048 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
Safety and Efficacy of Ipamorelin Compared to Placebo for the Recovery of Gastrointestinal Function
CTID: NCT01280344
Phase: Phase 2
Status: Completed
Date: 2017-04-13
Safety and Efficacy of Ipamorelin for Management of Post-Operative Ileus
CTID: NCT00672074
Phase: Phase 2
Status: Completed
Date: 2017-04-14
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