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MedKoo Cat#: 597498 | Name: SHU 9119
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Description:

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

SHU 9119 is an agonist of melanocortin receptor 1 (MC1R) and antagonist of MC4R.

Chemical Structure

SHU 9119
SHU 9119
CAS#168482-23-3

Theoretical Analysis

MedKoo Cat#: 597498

Name: SHU 9119

CAS#: 168482-23-3

Chemical Formula: C54H71N15O9

Exact Mass: 1073.5559

Molecular Weight: 1074.25

Elemental Analysis: C, 60.38; H, 6.66; N, 19.56; O, 13.40

Price and Availability

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1mg USD 450.00
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Related CAS #
No Data
Synonym
Shu 9119; Shu-9119; Shu9119;
IUPAC/Chemical Name
(2S)-N-((3S,6S,E)-3-((4H-imidazol-4-yl)methyl)-14-((2S)-2-((S)-2-((R)-2-amino-3-(naphthalen-2-yl)propanamido)-5-guanidinopentanamido)-3-(indolin-3-yl)propanamido)-2,5,8,15-tetraoxo-1,4,9-triazacyclopentadec-13-en-6-yl)-2-acetamidohexanamide
InChi Key
ORTUTLYEGOSCRP-ATNXLWBUSA-N
InChi Code
InChI=1S/C54H71N15O9/c1-3-4-15-40(63-31(2)70)48(73)68-45-27-46(71)59-21-10-9-17-41(50(75)69-53(78)44(67-52(45)77)26-36-29-58-30-62-36)65-51(76)43(25-35-28-61-39-16-8-7-14-37(35)39)66-49(74)42(18-11-22-60-54(56)57)64-47(72)38(55)24-32-19-20-33-12-5-6-13-34(33)23-32/h5-8,12-14,16-17,19-20,23,29-30,35-36,38,40,42-45,61H,3-4,9-11,15,18,21-22,24-28,55H2,1-2H3,(H,59,71)(H,63,70)(H,64,72)(H,65,76)(H,66,74)(H,67,77)(H,68,73)(H4,56,57,60)(H,69,75,78)/b41-17+/t35?,36?,38-,40+,42+,43+,44+,45+/m1/s1
SMILES Code
CCCC[C@H](NC(C)=O)C(N[C@H]1CC(NCCC/C=C(NC([C@@H](NC([C@@H](NC([C@H](N)Cc(cc2)cc3c2cccc3)=O)CCCNC(N)=N)=O)CC4CNc5ccccc54)=O)\C(NC([C@H](CC6C=NC=N6)NC1=O)=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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
SHU 9119 is a potent melanocortin MC3 and MC4 receptor antagonist (IC50s 0.23 and 0.06 nM, respectively) and a partial MC5 agonist (EC50 = 0.12 nM). SHU 9119 upregulates expression of genes promoting lipogenesis and triglyceride storage (SCD1, LPL, ACCα and FAS), increases triglyceride synthesis, and promotes insulin resistance.
In vitro activity:
To be determined
In vivo activity:
Intracerebroventricular infusion of SHU 9119 increased food intake, body fat, and decreased energy expenditure, mainly by reducing fat oxidation. SHU 9119 also impaired brown adipose tissue activity. Even when pair-fed to the control group, SHU 9119 exhibited these effects, indicating that MC4R inhibition independently impairs BAT activity, suggesting MC4R activation as a potential strategy to enhance BAT function and combat obesity. Reference: J Lipid Res. 2014 Oct;55(10):2022-32. https://pubmed.ncbi.nlm.nih.gov/25016380/
Solvent mg/mL mM comments
Solubility
Water 1.0 0.93
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,074.25 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. Kooijman S, Boon MR, Parlevliet ET, Geerling JJ, van de Pol V, Romijn JA, Havekes LM, Meurs I, Rensen PC. Inhibition of the central melanocortin system decreases brown adipose tissue activity. J Lipid Res. 2014 Oct;55(10):2022-32. doi: 10.1194/jlr.M045989. Epub 2014 Jul 12. PMID: 25016380; PMCID: PMC4173995. 2. Hillebrand JJ, Kas MJ, Scheurink AJ, van Dijk G, Adan RA. AgRP(83-132) and SHU9119 differently affect activity-based anorexia. Eur Neuropsychopharmacol. 2006 Aug;16(6):403-12. doi: 10.1016/j.euroneuro.2005.11.004. Epub 2005 Dec 15. PMID: 16360312.
In vitro protocol:
To be determined
In vivo protocol:
1. Kooijman S, Boon MR, Parlevliet ET, Geerling JJ, van de Pol V, Romijn JA, Havekes LM, Meurs I, Rensen PC. Inhibition of the central melanocortin system decreases brown adipose tissue activity. J Lipid Res. 2014 Oct;55(10):2022-32. doi: 10.1194/jlr.M045989. Epub 2014 Jul 12. PMID: 25016380; PMCID: PMC4173995. 2. Hillebrand JJ, Kas MJ, Scheurink AJ, van Dijk G, Adan RA. AgRP(83-132) and SHU9119 differently affect activity-based anorexia. Eur Neuropsychopharmacol. 2006 Aug;16(6):403-12. doi: 10.1016/j.euroneuro.2005.11.004. Epub 2005 Dec 15. PMID: 16360312.
1: Grieco P, Cai M, Han G, Trivedi D, Campiglia P, Novellino E, Hruby VJ. Further structure-activity studies of lactam derivatives of MT-II and SHU-9119: their activity and selectivity at human melanocortin receptors 3, 4, and 5. Peptides. 2007 Jun;28(6):1191-6. Epub 2007 Mar 1. PubMed PMID: 17482720; PubMed Central PMCID: PMC1955225. 2: Grieco P, Balse-Srinivasan P, Han G, Weinberg D, MacNeil T, Van der Ploeg LH, Hruby VJ. Extensive structure-activity studies of lactam derivatives of MT-II and SHU-9119: their activity and selectivity at human melanocortin receptors 3, 4, and 5. J Pept Res. 2003 Nov;62(5):199-206. PubMed PMID: 14531843. 3: do Carmo JM, da Silva AA, Rushing JS, Hall JE. Activation of the central melanocortin system contributes to the increased arterial pressure in obese Zucker rats. Am J Physiol Regul Integr Comp Physiol. 2012 Mar 1;302(5):R561-7. doi: 10.1152/ajpregu.00392.2011. Epub 2011 Dec 28. PubMed PMID: 22204957; PubMed Central PMCID: PMC3311523. 4: Kabra DG, Pfuhlmann K, García-Cáceres C, Schriever SC, Casquero García V, Kebede AF, Fuente-Martin E, Trivedi C, Heppner K, Uhlenhaut NH, Legutko B, Kabra UD, Gao Y, Yi CX, Quarta C, Clemmensen C, Finan B, Müller TD, Meyer CW, Paez-Pereda M, Stemmer K, Woods SC, Perez-Tilve D, Schneider R, Olson EN, Tschöp MH, Pfluger PT. Hypothalamic leptin action is mediated by histone deacetylase 5. Nat Commun. 2016 Feb 29;7:10782. doi: 10.1038/ncomms10782. PubMed PMID: 26923837; PubMed Central PMCID: PMC4773494. 5: Turcic P, Stambuk N, Konjevoda P, Kelava T, Gabricevic M, Stojkovic R, Aralica G. Modulation of γ2-MSH hepatoprotection by antisense peptides and melanocortin subtype 3 and 4 receptor antagonists. Med Chem. 2015;11(3):286-95. PubMed PMID: 25219927. 6: do Carmo JM, da Silva AA, Rushing JS, Pace B, Hall JE. Differential control of metabolic and cardiovascular functions by melanocortin-4 receptors in proopiomelanocortin neurons. Am J Physiol Regul Integr Comp Physiol. 2013 Aug 15;305(4):R359-68. doi: 10.1152/ajpregu.00518.2012. Epub 2013 Jul 10. PubMed PMID: 23842677; PubMed Central PMCID: PMC3833394. 7: do Carmo JM, da Silva AA, Hall JE. Role of hindbrain melanocortin-4 receptor activity in controlling cardiovascular and metabolic functions in spontaneously hypertensive rats. J Hypertens. 2015 Jun;33(6):1201-6. doi: 10.1097/HJH.0000000000000530. PubMed PMID: 25668357; PubMed Central PMCID: PMC4748968. 8: Shi Z, Brooks VL. Leptin differentially increases sympathetic nerve activity and its baroreflex regulation in female rats: role of oestrogen. J Physiol. 2015 Apr 1;593(7):1633-47. doi: 10.1113/jphysiol.2014.284638. Epub 2014 Dec 22. PubMed PMID: 25398524; PubMed Central PMCID: PMC4386963. 9: Carotenuto A, Merlino F, Cai M, Brancaccio D, Yousif AM, Novellino E, Hruby VJ, Grieco P. Discovery of Novel Potent and Selective Agonists at the Melanocortin-3 Receptor. J Med Chem. 2015 Dec 24;58(24):9773-8. doi: 10.1021/acs.jmedchem.5b01285. Epub 2015 Dec 16. PubMed PMID: 26599352; PubMed Central PMCID: PMC5070805. 10: Zheng H, Patterson LM, Rhodes CJ, Louis GW, Skibicka KP, Grill HJ, Myers MG Jr, Berthoud HR. A potential role for hypothalamomedullary POMC projections in leptin-induced suppression of food intake. Am J Physiol Regul Integr Comp Physiol. 2010 Mar;298(3):R720-8. doi: 10.1152/ajpregu.00619.2009. Epub 2010 Jan 13. PubMed PMID: 20071607; PubMed Central PMCID: PMC2838656. 11: Maranon RO, Lima R, Mathbout M, do Carmo JM, Hall JE, Roman RJ, Reckelhoff JF. Postmenopausal hypertension: role of the sympathetic nervous system in an animal model. Am J Physiol Regul Integr Comp Physiol. 2014 Feb 15;306(4):R248-56. doi: 10.1152/ajpregu.00490.2013. Epub 2013 Dec 31. PubMed PMID: 24381180; PubMed Central PMCID: PMC3921310. 12: Iemolo A, Ferragud A, Cottone P, Sabino V. Pituitary Adenylate Cyclase-Activating Peptide in the Central Amygdala Causes Anorexia and Body Weight Loss via the Melanocortin and the TrkB Systems. Neuropsychopharmacology. 2015 Jul;40(8):1846-55. doi: 10.1038/npp.2015.34. Epub 2015 Feb 4. PubMed PMID: 25649277; PubMed Central PMCID: PMC4839508. 13: Tala SR, Schnell SM, Haskell-Luevano C. Microwave-assisted solid-phase synthesis of side-chain to side-chain lactam-bridge cyclic peptides. Bioorg Med Chem Lett. 2015 Dec 15;25(24):5708-11. doi: 10.1016/j.bmcl.2015.10.095. Epub 2015 Oct 31. PubMed PMID: 26555357; PubMed Central PMCID: PMC4654418. 14: Bassi M, Nakamura NB, Furuya WI, Colombari DS, Menani JV, do Carmo JM, da Silva AA, Hall JE, Colombari E. Activation of the brain melanocortin system is required for leptin-induced modulation of chemorespiratory function. Acta Physiol (Oxf). 2015 Apr;213(4):893-901. doi: 10.1111/apha.12394. Epub 2014 Sep 30. PubMed PMID: 25207799; PubMed Central PMCID: PMC4362918. 15: Xu L, Wang Q, Guo F, Pang M, Sun X, Gao S, Gong Y. Nesfatin-1 signaling in the basom edial amygdala modulates the gastric distension-sensitive neurons discharge and decreases gastric motility via melanocortin 3/4 receptors and modified by the arcuate nucleus. Eur J Pharmacol. 2015 Oct 5;764:164-72. doi: 10.1016/j.ejphar.2015.07.002. Epub 2015 Jul 3. PubMed PMID: 26144374. 16: Shi Z, Cassaglia PA, Gotthardt LC, Brooks VL. Hypothalamic Paraventricular and Arcuate Nuclei Contribute to Elevated Sympathetic Nerve Activity in Pregnant Rats: Roles of Neuropeptide Y and α-Melanocyte-Stimulating Hormone. Hypertension. 2015 Dec;66(6):1191-8. doi: 10.1161/HYPERTENSIONAHA.115.06045. Epub 2015 Oct 19. PubMed PMID: 26483343; PubMed Central PMCID: PMC4824187. 17: Guzmán-Ruiz MA, Ramirez-Corona A, Guerrero-Vargas NN, Sabath E, Ramirez-Plascencia OD, Fuentes-Romero R, León-Mercado LA, Basualdo Sigales M, Escobar C, Buijs RM. Role of the Suprachiasmatic and Arcuate Nuclei in Diurnal Temperature Regulation in the Rat. J Neurosci. 2015 Nov 18;35(46):15419-29. doi: 10.1523/JNEUROSCI.1449-15.2015. PubMed PMID: 26586828. 18: da Silva AA, Kuo JJ, Hall JE. Role of hypothalamic melanocortin 3/4-receptors in mediating chronic cardiovascular, renal, and metabolic actions of leptin. Hypertension. 2004 Jun;43(6):1312-7. Epub 2004 May 3. PubMed PMID: 15123576. 19: Cerritelli S, Hirschberg S, Hill R, Balthasar N, Pickering AE. Activation of Brainstem Pro-opiomelanocortin Neurons Produces Opioidergic Analgesia, Bradycardia and Bradypnoea. PLoS One. 2016 Apr 14;11(4):e0153187. doi: 10.1371/journal.pone.0153187. eCollection 2016. PubMed PMID: 27077912; PubMed Central PMCID: PMC4831707. 20: Iemolo A, Seiglie M, Blasio A, Cottone P, Sabino V. Pituitary adenylate cyclase-activating polypeptide (PACAP) in the central nucleus of the amygdala induces anxiety via melanocortin receptors. Psychopharmacology (Berl). 2016 Sep;233(17):3269-77. doi: 10.1007/s00213-016-4366-y. Epub 2016 Jul 4. PubMed PMID: 27376948; PubMed Central PMCID: PMC4982769.