Lixisenatide | CAS# 320367-13-3 | GLP-1 receptor agonist

MedKoo Cat#: 413581 | Name: Lixisenatide

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Description:

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

Lixisenatide is a once-daily injectable GLP-1 receptor agonist for the treatment of type 2 diabetes. It is a synthetic glucagon-like peptide 1 (GLP-1) receptor agonist; binds GLP-1 receptor; has antidiabetic effects in mice; amino acid sequence is H-HGEGTFTSDLSKQMEEEAVRLFIEWLKNGGPSSGAPPSK KKKKK-NH2 (ZP10A).

Chemical Structure

Lixisenatide

CAS#320367-13-3 (free base)

Theoretical Analysis

MedKoo Cat#: 413581

Name: Lixisenatide

CAS#: 320367-13-3 (free base)

Chemical Formula: C215H347N61O65S

Exact Mass: 4855.5443

Molecular Weight: 4858.56

Elemental Analysis: C, 53.15; H, 7.20; N, 17.59; O, 21.40; S, 0.66

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 500.00	2 Weeks
10mg	USD 950.00	2 Weeks

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Related CAS #

320367-13-3 (free base) 1997361-87-1 (acetate)

Synonym

Lixisenatide; AVE0010; AVE-0010; AVE 0010

IUPAC/Chemical Name

Des-38-proline-exendine-4 (Heloderma suspectum)-(1-39)-peptidylpenta-L-lysyl-L-lysinamide

InChi Key

XVVOERDUTLJJHN-IAEQDCLQSA-N

InChi Code

InChI=1S/C215H347N61O65S/c1-16-115(10)173(210(337)256-141(68-74-170(299)300)194(321)261-148(94-122-98-232-126-50-24-23-49-124(122)126)199(326)258-143(89-111(2)3)196(323)247-134(58-32-40-83-223)189(316)262-149(96-160(226)285)180(307)235-100-161(286)233-104-165(290)274-85-42-60-156(274)207(334)267-154(108-280)206(333)265-151(105-277)181(308)237-101-162(287)239-117(12)213(340)276-87-44-62-158(276)214(341)275-86-43-61-157(275)208(335)268-153(107-279)204(331)249-132(56-30-38-81-221)187(314)246-131(55-29-37-80-220)186(313)245-130(54-28-36-79-219)185(312)244-129(53-27-35-78-218)184(311)243-128(52-26-34-77-217)183(310)242-127(176(227)303)51-25-33-76-216)272-201(328)146(92-120-45-19-17-20-46-120)260-197(324)144(90-112(4)5)257-190(317)135(59-41-84-231-215(228)229)255-209(336)172(114(8)9)271-177(304)116(11)240-182(309)138(65-71-167(293)294)251-192(319)139(66-72-168(295)296)252-193(320)140(67-73-169(297)298)253-195(322)142(75-88-342-15)254-191(318)137(63-69-159(225)284)250-188(315)133(57-31-39-82-222)248-203(330)152(106-278)266-198(325)145(91-113(6)7)259-200(327)150(97-171(301)302)263-205(332)155(109-281)269-212(339)175(119(14)283)273-202(329)147(93-121-47-21-18-22-48-121)264-211(338)174(118(13)282)270-164(289)103-236-179(306)136(64-70-166(291)292)241-163(288)102-234-178(305)125(224)95-123-99-230-110-238-123/h17-24,45-50,98-99,110-119,125,127-158,172-175,232,277-283H,16,25-44,51-97,100-109,216-224H2,1-15H3,(H2,225,284)(H2,226,285)(H2,227,303)(H,230,238)(H,233,286)(H,234,305)(H,235,307)(H,236,306)(H,237,308)(H,239,287)(H,240,309)(H,241,288)(H,242,310)(H,243,311)(H,244,312)(H,245,313)(H,246,314)(H,247,323)(H,248,330)(H,249,331)(H,250,315)(H,251,319)(H,252,320)(H,253,322)(H,254,318)(H,255,336)(H,256,337)(H,257,317)(H,258,326)(H,259,327)(H,260,324)(H,261,321)(H,262,316)(H,263,332)(H,264,338)(H,265,333)(H,266,325)(H,267,334)(H,268,335)(H,269,339)(H,270,289)(H,271,304)(H,272,328)(H,273,329)(H,291,292)(H,293,294)(H,295,296)(H,297,298)(H,299,300)(H,301,302)(H4,228,229,231)/t115-,116-,117-,118+,119+,125-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,152-,153-,154-,155-,156-,157-,158-,172-,173-,174-,175-/m0/s1

SMILES Code

CC[C@H](C)[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)[C@@H](N)Cc3c[nH]cn3)[C@@H](C)O)[C@@H](C)O)C(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc4c[nH]c5ccccc45)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N)C(=O)NCC(=O)NCC(=O)N6CCC[C@H]6C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N7CCC[C@H]7C(=O)N8CCC[C@H]8C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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:

Lixisenatide is a glucagon-like peptide-1 (GLP-1) receptor agonist that can be used in the treatment of type 2 diabetes mellitus (T2DM).

In vitro activity:

Lixisenatide attenuated LPS-induced oxidative stress by reducing reactive oxygen species (ROS) production and nicotinamide adenine dinucleotide phosphate (NADPH) oxidases-1 (NOX-1) expression in MAC-T MECs. Additionally, lixisenatide inhibited LPS-induced expression and secretion of tumor necrosis factor-α (TNF-α), interleukin 6 (IL-6), and interleukin 1β (IL-1β). Reference: Chem Res Toxicol. 2020 Apr 20;33(4):982-987. https://pubmed.ncbi.nlm.nih.gov/32191445/

In vivo activity:

Eight-week-old male Sprague-Dawley rats were divided into lixisenatide (LIX, n = 10), traumatic control (T-CON, n = 10), and normal control (n = 5) groups. he LIX group showed significantly lower mRNA levels of interleukin 1 beta (IL-1β), tumor necrosis factor-alpha (TNF-α), thioredoxin interacting protein (TXNIP), and glial fibrillary acidic protein (GFAP) than the T-CON group. Also, the LIX group exhibited decreased TXNIP and GFAP expression compared with the T-CON group, and similar expression to the normal control group, according to Western blot analysis. Reference: Eur J Pharmacol. 2022 Oct 15;933:175269. https://pubmed.ncbi.nlm.nih.gov/36103932/

	Solvent	mg/mL	mM	comments
Solubility
	Water	103.0	21.20

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 4,858.56 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. Li P, Liu Q, Zhang T, Guo W, Qiao W, Deng M. Protective Effects of Lixisenatide against Lipopolysaccharide-Induced Inflammation Response in MAC-T Bovine Mammary Epithelial Cells: A Therapeutic Implication in Mastitis. Chem Res Toxicol. 2020 Apr 20;33(4):982-987. doi: 10.1021/acs.chemrestox.9b00524. Epub 2020 Mar 19. PMID: 32191445. 2. Du X, Zhang H, Zhang W, Wang Q, Wang W, Ge G, Bai J, Guo X, Zhang Y, Jiang X, Gu J, Xu Y, Geng D. The protective effects of lixisenatide against inflammatory response in human rheumatoid arthritis fibroblast-like synoviocytes. Int Immunopharmacol. 2019 Oct;75:105732. doi: 10.1016/j.intimp.2019.105732. Epub 2019 Jul 20. PMID: 31336333. 3. Chung YW, Lee JY, Ju HH, Choi JA. Anti-inflammatory effect of glucagon-like Peptide-1 receptor agonist on the neurosensory retina in an acute optic nerve injury rat model. Eur J Pharmacol. 2022 Oct 15;933:175269. doi: 10.1016/j.ejphar.2022.175269. Epub 2022 Sep 11. PMID: 36103932. 4. Ren G, Xue P, Wu B, Yang F, Wu X. Intranasal treatment of lixisenatide attenuated emotional and olfactory symptoms via CREB-mediated adult neurogenesis in mouse depression model. Aging (Albany NY). 2021 Jan 10;13(3):3898-3908. doi: 10.18632/aging.202358. Epub 2021 Jan 10. PMID: 33461175; PMCID: PMC7906191.

In vitro protocol:

In vivo protocol:

1. Chung YW, Lee JY, Ju HH, Choi JA. Anti-inflammatory effect of glucagon-like Peptide-1 receptor agonist on the neurosensory retina in an acute optic nerve injury rat model. Eur J Pharmacol. 2022 Oct 15;933:175269. doi: 10.1016/j.ejphar.2022.175269. Epub 2022 Sep 11. PMID: 36103932. 2. Ren G, Xue P, Wu B, Yang F, Wu X. Intranasal treatment of lixisenatide attenuated emotional and olfactory symptoms via CREB-mediated adult neurogenesis in mouse depression model. Aging (Albany NY). 2021 Jan 10;13(3):3898-3908. doi: 10.18632/aging.202358. Epub 2021 Jan 10. PMID: 33461175; PMCID: PMC7906191.

1: Pfeffer MA, Claggett B, Diaz R, Dickstein K, Gerstein HC, Køber LV, Lawson FC, Ping L, Wei X, Lewis EF, Maggioni AP, McMurray JJ, Probstfield JL, Riddle MC, Solomon SD, Tardif JC; ELIXA Investigators. Lixisenatide in Patients with Type 2 Diabetes and Acute Coronary Syndrome. N Engl J Med. 2015 Dec 3;373(23):2247-57. doi: 10.1056/NEJMoa1509225. PMID: 26630143. 2: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Lixisenatide. 2019 Apr 10. PMID: 31643608. 3: Lixisenatide for type 2 diabetes. Med Lett Drugs Ther. 2017 Jan 30;59(1513):19-21. PMID: 28118649. 4: Baker DE, Levien TL. Lixisenatide. Hosp Pharm. 2017 Jan;52(1):65-80. doi: 10.1310/hpj5201-65. PMID: 28179743; PMCID: PMC5278917. 5: Muskiet MHA, Tonneijck L, Huang Y, Liu M, Saremi A, Heerspink HJL, van Raalte DH. Lixisenatide and renal outcomes in patients with type 2 diabetes and acute coronary syndrome: an exploratory analysis of the ELIXA randomised, placebo- controlled trial. Lancet Diabetes Endocrinol. 2018 Nov;6(11):859-869. doi: 10.1016/S2213-8587(18)30268-7. Epub 2018 Oct 3. PMID: 30292589. 6: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Lixisenatide. 2018 Dec 3. PMID: 30000034. 7: McCarty D, Coleman M, Boland CL. Lixisenatide: A New Daily GLP-1 Agonist for Type 2 Diabetes Management. Ann Pharmacother. 2017 May;51(5):401-409. doi: 10.1177/1060028017689878. Epub 2017 Jan 29. PMID: 28133970. 8: Whyte MB, Shojaee-Moradie F, Sharaf SE, Jackson NC, Fielding B, Hovorka R, Mendis J, Russell-Jones D, Umpleby AM. Lixisenatide Reduces Chylomicron Triacylglycerol by Increased Clearance. J Clin Endocrinol Metab. 2019 Feb 1;104(2):359-368. doi: 10.1210/jc.2018-01176. PMID: 30215735; PMCID: PMC6300412. 9: Cai X, Gao X, Yang W, Ji L. Comparison between insulin degludec/liraglutide treatment and insulin glargine/lixisenatide treatment in type 2 diabetes: a systematic review and meta-analysis. Expert Opin Pharmacother. 2017 Dec;18(17):1789-1798. doi: 10.1080/14656566.2017.1400011. Epub 2017 Nov 5. PMID: 29090600. 10: Rosenstock J, Aronson R, Grunberger G, Hanefeld M, Piatti P, Serusclat P, Cheng X, Zhou T, Niemoeller E, Souhami E, Davies M; LixiLan-O Trial Investigators. Benefits of LixiLan, a Titratable Fixed-Ratio Combination of Insulin Glargine Plus Lixisenatide, Versus Insulin Glargine and Lixisenatide Monocomponents in Type 2 Diabetes Inadequately Controlled on Oral Agents: The LixiLan-O Randomized Trial. Diabetes Care. 2016 Nov;39(11):2026-2035. doi: 10.2337/dc16-0917. Epub 2016 Aug 15. Erratum in: Diabetes Care. 2017 Jun;40(6):809. PMID: 27527848.