Exenatide free base | CAS#141758-74-9 | diabetes mellitus type 2

MedKoo Cat#: 333199 | Name: Exenatide free base

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Description:

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

Exenatide is a medication used to treat diabetes mellitus type 2. Exenatide binds to the intact human Glucagon-like peptide-1 receptor (GLP-1R) in a similar way to the human peptide glucagon-like peptide-1 (GLP-1); exenatide bears a 50% amino acid homology to GLP-1 and it has a longer half-life in vivo. It is used together with diet, exercise, and potentially other antidiabetic medication. It is a less preferred treatment option after metformin and sulfonylureas.

Chemical Structure

Exenatide free base

CAS#141758-74-9 (free base)

Theoretical Analysis

MedKoo Cat#: 333199

Name: Exenatide free base

CAS#: 141758-74-9 (free base)

Chemical Formula: C184H282N50O60S

Exact Mass: 4184.0273

Molecular Weight: 4186.63

Elemental Analysis: C, 52.79; H, 6.79; N, 16.73; O, 22.93; S, 0.77

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 450.00	2 Weeks
100mg	USD 950.00	2 Weeks

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Related CAS #

141758-74-9 (free base) 141732-76-5 (acetate)

Synonym

Exenatide; Exendin 4; Exendin-4; exenatidum

IUPAC/Chemical Name

L-Serinamide, L-histidylglycyl-L-alpha-glutamylglycyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-alpha-aspartyl-L-leucyl-L-seryl-L-lysyl-L-glutaminyl-L-methionyl-L-alpha-glutamyl-L-alpha-glutamyl-L-alpha-glutamyl-L-alanyl-L-valyl-L-arginyl-L-leucyl-L-phenylalanyl-L-isoleucyl-L-alpha-glutamyl-L-tryptophyl-L-leucyl-L-lysyl-L-asparaginylglycylglycyl-L-prolyl-L-seryl-L-serylglycyl-L-alanyl-L-prolyl-L-prolyl-L-prolyl-

InChi Key

HTQBXNHDCUEHJF-XWLPCZSASA-N

InChi Code

InChI=1S/C184H282N50O60S/c1-16-94(10)147(178(289)213-114(52-58-144(257)258)163(274)218-121(73-101-77-195-105-39-24-23-38-103(101)105)168(279)215-116(68-90(2)3)165(276)205-107(41-26-28-61-186)158(269)219-122(75-134(189)243)154(265)198-79-135(244)196-83-139(248)231-63-30-43-129(231)175(286)225-127(87-238)174(285)223-125(85-236)155(266)200-80-136(245)202-96(12)181(292)233-65-32-45-131(233)183(294)234-66-33-46-132(234)182(293)232-64-31-44-130(232)176(287)222-124(84-235)150(190)261)229-170(281)119(71-99-34-19-17-20-35-99)217-166(277)117(69-91(4)5)214-159(270)108(42-29-62-194-184(191)192)212-177(288)146(93(8)9)228-151(262)95(11)203-156(267)111(49-55-141(251)252)208-161(272)112(50-56-142(253)254)209-162(273)113(51-57-143(255)256)210-164(275)115(59-67-295-15)211-160(271)110(47-53-133(188)242)207-157(268)106(40-25-27-60-185)206-172(283)126(86-237)224-167(278)118(70-92(6)7)216-169(280)123(76-145(259)260)220-173(284)128(88-239)226-180(291)149(98(14)241)230-171(282)120(72-100-36-21-18-22-37-100)221-179(290)148(97(13)240)227-138(247)82-199-153(264)109(48-54-140(249)250)204-137(246)81-197-152(263)104(187)74-102-78-193-89-201-102/h17-24,34-39,77-78,89-98,104,106-132,146-149,195,235-241H,16,25-33,40-76,79-88,185-187H2,1-15H3,(H2,188,242)(H2,189,243)(H2,190,261)(H,193,201)(H,196,244)(H,197,263)(H,198,265)(H,199,264)(H,200,266)(H,202,245)(H,203,267)(H,204,246)(H,205,276)(H,206,283)(H,207,268)(H,208,272)(H,209,273)(H,210,275)(H,211,271)(H,212,288)(H,213,289)(H,214,270)(H,215,279)(H,216,280)(H,217,277)(H,218,274)(H,219,269)(H,220,284)(H,221,290)(H,222,287)(H,223,285)(H,224,278)(H,225,286)(H,226,291)(H,227,247)(H,228,262)(H,229,281)(H,230,282)(H,249,250)(H,251,252)(H,253,254)(H,255,256)(H,257,258)(H,259,260)(H4,191,192,194)/t94-,95-,96-,97+,98+,104-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,146-,147-,148-,149-/m0/s1

SMILES Code

OC[C@@H](C(N)=O)NC([C@H]1N(C([C@H]2N(C([C@H]3N(C([C@H](C)NC(CNC([C@H](CO)NC([C@H](CO)NC([C@H]4N(C(CNC(CNC([C@H](CC(N)=O)NC([C@H](CCCCN)NC([C@H](CC(C)C)NC([C@H](CC5=CNC6=C5C=CC=C6)NC([C@H](CCC(O)=O)NC([C@H]([C@@H](C)CC)NC([C@H](CC7=CC=CC=C7)NC([C@H](CC(C)C)NC([C@H](CCCNC(N)=N)NC([C@H](C(C)C)NC([C@H](C)NC([C@H](CCC(O)=O)NC([C@H](CCC(O)=O)NC([C@H](CCC(O)=O)NC([C@H](CCSC)NC([C@H](CCC(N)=O)NC([C@H](CCCCN)NC([C@H](CO)NC([C@H](CC(C)C)NC([C@H](CC(O)=O)NC([C@H](CO)NC([C@H]([C@H](O)C)NC([C@H](CC8=CC=CC=C8)NC([C@H]([C@H](O)C)NC(CNC([C@H](CCC(O)=O)NC(CNC([C@H](CC9=CNC=N9)N)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)CCC4)=O)=O)=O)=O)=O)CCC3)=O)CCC2)=O)CCC1)=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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Exendin-4 (Exenatide), a 39 amino acid peptide, is a long-acting glucagon-like peptide-1 receptor agonist with an IC50 of 3.22 nM.

In vitro activity:

In contrast to the control group, HG markedly increased TNF-α, IL-1β and IL-6 expression (Fig. 2). Significantly, inhibitory effects on these pro-inflammatory factors were observed when hRVECs were treated with both exenatide and HG (Fig. 2), which indicated a possible protective effect of exenatide against the inflammatory response. In addition, S1P, an agonist of S1PR2, counteracted the inhibition of inflammation mediators by exenatide. These data implied that exenatide could decrease the inflammatory response induced by HG through regulation of S1PR2 protein activity. Reference: Adv Clin Exp Med. 2021 May;30(5):555-561. https://pubmed.ncbi.nlm.nih.gov/33984196/

In vivo activity:

Exenatide treatment improved the impaired memory of SD rats and increased CaMKII content in hippocampus There was no difference in MDA and GSH levels among groups. Exenatide treatment also diminished locomotor activity in OFT. In conclusion, treatment with exenatide, at least in part, prevented from these cognitive and behavioral changes possibly through normalizing CaMKII levels in the hippocampus. Reference: Brain Res Bull. 2021 Sep;174:194-202. https://pubmed.ncbi.nlm.nih.gov/34146656/

	Solvent	mg/mL	mM
Solubility
	DMSO	32.0	7.64
	Water	50.0	11.94

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 4,186.63 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.

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. Yang Y, Zhao Q. Exenatide regulates inflammation and the production of reactive oxygen species via inhibition of S1PR2 synthesis. Adv Clin Exp Med. 2021 May;30(5):555-561. doi: 10.17219/acem/133483. PMID: 33984196. 2. Liu Y, Wang DW, Wang D, Duan BH, Kuang HY. Exenatide Attenuates Non-Alcoholic Steatohepatitis by Inhibiting the Pyroptosis Signaling Pathway. Front Endocrinol (Lausanne). 2021 Apr 19;12:663039. doi: 10.3389/fendo.2021.663039. PMID: 33953700; PMCID: PMC8092357. 3. Turan I, Sayan Ozacmak H, Ozacmak VH, Ergenc M, Bayraktaroğlu T. The effects of glucagon-like peptide 1 receptor agonist (exenatide) on memory impairment, and anxiety- and depression-like behavior induced by REM sleep deprivation. Brain Res Bull. 2021 Sep;174:194-202. doi: 10.1016/j.brainresbull.2021.06.011. Epub 2021 Jun 17. PMID: 34146656. 4. Zhao L, Zhang X, Feng J, Xiao Z, Liu Y, Long H, Chen X, Tang W. [Exenatide promotes cholesterol efflux in pancreatic tissue of obese diabetic rats]. Nan Fang Yi Ke Da Xue Xue Bao. 2021 Mar 25;41(3):370-375. Chinese. doi: 10.12122/j.issn.1673-4254.2021.03.08. PMID: 33849827; PMCID: PMC8075781.

In vitro protocol:

In vivo protocol:

1. Turan I, Sayan Ozacmak H, Ozacmak VH, Ergenc M, Bayraktaroğlu T. The effects of glucagon-like peptide 1 receptor agonist (exenatide) on memory impairment, and anxiety- and depression-like behavior induced by REM sleep deprivation. Brain Res Bull. 2021 Sep;174:194-202. doi: 10.1016/j.brainresbull.2021.06.011. Epub 2021 Jun 17. PMID: 34146656. 2. Zhao L, Zhang X, Feng J, Xiao Z, Liu Y, Long H, Chen X, Tang W. [Exenatide promotes cholesterol efflux in pancreatic tissue of obese diabetic rats]. Nan Fang Yi Ke Da Xue Xue Bao. 2021 Mar 25;41(3):370-375. Chinese. doi: 10.12122/j.issn.1673-4254.2021.03.08. PMID: 33849827; PMCID: PMC8075781.

1: Xu Q, Zhang X, Li T, Shao S. Exenatide regulates Th17/Treg balance via PI3K/Akt/FoxO1 pathway in db/db mice. Mol Med. 2022 Dec 3;28(1):144. doi: 10.1186/s10020-022-00574-6. PMID: 36463128; PMCID: PMC9719171. 2: Kalra S, Saboo B. Exenatide implant therapy in diabetes. J Pak Med Assoc. 2018 Oct;68(10):1538-1540. PMID: 30317359. 3: Mullins RJ, Mustapic M, Chia CW, Carlson O, Gulyani S, Tran J, Li Y, Mattson MP, Resnick S, Egan JM, Greig NH, Kapogiannis D. A Pilot Study of Exenatide Actions in Alzheimer's Disease. Curr Alzheimer Res. 2019;16(8):741-752. doi: 10.2174/1567205016666190913155950. PMID: 31518224; PMCID: PMC7476877. 4: Bradley DP, Kulstad R, Schoeller DA. Exenatide and weight loss. Nutrition. 2010 Mar;26(3):243-9. doi: 10.1016/j.nut.2009.07.008. PMID: 20152707. 5: Retnakaran R, Ye C, Emery A, Kramer CK, Zinman B. The metabolic effects of adding exenatide to basal insulin therapy when targeting remission in early type 2 diabetes in a randomized clinical trial. Nat Commun. 2022 Oct 16;13(1):6109. doi: 10.1038/s41467-022-33867-9. PMID: 36244997; PMCID: PMC9573864. 6: Ma RL, Deng Y, Wang YF, Zhu SY, Ding XS, Sun AJ. Short-term combined treatment with exenatide and metformin for overweight/obese women with polycystic ovary syndrome. Chin Med J (Engl). 2021 Nov 3;134(23):2882-2889. doi: 10.1097/CM9.0000000000001712. PMID: 34732660; PMCID: PMC8667970. 7: Eid TJ, Kaur M, Kaur R. Exenatide ER-induced eosinophilia. Am J Health Syst Pharm. 2020 Jun 23;77(13):1006-1007. doi: 10.1093/ajhp/zxaa105. PMID: 32470112. 8: Yoo BK, Triller DM, Yoo DJ. Exenatide: a new option for the treatment of type 2 diabetes. Ann Pharmacother. 2006 Oct;40(10):1777-84. doi: 10.1345/aph.1H060. Epub 2006 Sep 19. PMID: 16985091. 9: van der Aart-van der Beek AB, Apperloo E, Jongs N, Rouw DB, Sjöström CD, Friedli I, Johansson L, van Raalte DH, Hoogenberg K, Heerspink HJL. Albuminuria- lowering effect of dapagliflozin, exenatide, and their combination in patients with type 2 diabetes: A randomized cross-over clinical study. Diabetes Obes Metab. 2023 Jun;25(6):1758-1768. doi: 10.1111/dom.15033. Epub 2023 Mar 13. PMID: 36843215. 10: van Ruiten CC, Smits MM, Kok MD, Serné EH, van Raalte DH, Kramer MHH, Nieuwdorp M, IJzerman RG. Mechanisms underlying the blood pressure lowering effects of dapagliflozin, exenatide, and their combination in people with type 2 diabetes: a secondary analysis of a randomized trial. Cardiovasc Diabetol. 2022 Apr 28;21(1):63. doi: 10.1186/s12933-022-01492-x. PMID: 35484607; PMCID: PMC9052512. 11: Zhu CS, Kwan EA, Williams GM, Lewin-Smith M, Lincoln MS, Lee AJ. Exenatide- induced granulomatous panniculitis associated with poly(d,l-lactide-co- glycolide). J Cutan Pathol. 2022 May;49(5):496-499. doi: 10.1111/cup.14193. Epub 2022 Jan 6. PMID: 34954842. 12: Liu Y, Wang DW, Wang D, Duan BH, Kuang HY. Exenatide Attenuates Non- Alcoholic Steatohepatitis by Inhibiting the Pyroptosis Signaling Pathway. Front Endocrinol (Lausanne). 2021 Apr 19;12:663039. doi: 10.3389/fendo.2021.663039. PMID: 33953700; PMCID: PMC8092357. 13: Heimbürger SM, Brønden A, Johansen NJ, Dejgaard TF, Vilsbøll T, Knop FK. The efficacy and safety of exenatide once weekly in patients with type 2 diabetes. Expert Opin Pharmacother. 2019 Apr;20(5):501-510. doi: 10.1080/14656566.2019.1571040. Epub 2019 Feb 7. PMID: 30730773. 14: Guo X, Zhou Z, Lyu X, Xu H, Zhu H, Pan H, Wang L, Yang H, Gong F. The Antiobesity Effect and Safety of GLP-1 Receptor Agonist in Overweight/Obese Patients Without Diabetes: A Systematic Review and Meta-Analysis. Horm Metab Res. 2022 Jul;54(7):458-471. doi: 10.1055/a-1844-1176. Epub 2022 May 5. PMID: 35512849. 15: Siamashvili M, Davis SN. Update on the effects of GLP-1 receptor agonists for the treatment of polycystic ovary syndrome. Expert Rev Clin Pharmacol. 2021 Sep;14(9):1081-1089. doi: 10.1080/17512433.2021.1933433. Epub 2021 May 27. PMID: 34015974. 16: Li J, Chen H, Lou J, Bao G, Wu C, Lou Z, Wang X, Ding J, Li Z, Xiao J, Xu H, Gao W, Zhou K. Exenatide improves random-pattern skin flap survival via TFE3 mediated autophagy augment. J Cell Physiol. 2021 May;236(5):3641-3659. doi: 10.1002/jcp.30102. Epub 2020 Oct 12. PMID: 33044023. 17: Mulvaney CA, Duarte GS, Handley J, Evans DJ, Menon S, Wyse R, Emsley HC. GLP-1 receptor agonists for Parkinson's disease. Cochrane Database Syst Rev. 2020 Jul 23;7(7):CD012990. doi: 10.1002/14651858.CD012990.pub2. PMID: 32700772; PMCID: PMC7390475. 18: Bai C, Wang Y, Niu Z, Guan Y, Huang J, Nian X, Zuo F, Zhao J, Kazumi T, Wu B. Exenatide improves hepatocyte insulin resistance induced by different regional adipose tissue. Front Endocrinol (Lausanne). 2022 Sep 29;13:1012904. doi: 10.3389/fendo.2022.1012904. PMID: 36246878; PMCID: PMC9558273. 19: Ye ZR, Yan CQ, Liao N, Wen SH. The Effectiveness and Safety of Exenatide Versus Metformin in Patients with Polycystic Ovary Syndrome: A Meta-Analysis of Randomized Controlled Trials. Reprod Sci. 2023 Aug;30(8):2349-2361. doi: 10.1007/s43032-023-01222-y. Epub 2023 Mar 31. PMID: 37002532; PMCID: PMC10354168. 20: Guyton J, Jeon M, Brooks A. Glucagon-like peptide 1 receptor agonists in type 1 diabetes mellitus. Am J Health Syst Pharm. 2019 Oct 15;76(21):1739-1748. doi: 10.1093/ajhp/zxz179. PMID: 31612934.