lixisenatide   Click here for help

GtoPdb Ligand ID: 7387

Synonyms: Adlyxin® | AVE-0010 | Lyxumia®
Approved drug
lixisenatide is an approved drug (EMA (2013), FDA (2016))
Compound class: Peptide
Comment: Lixisenatide is a GLP-1 peptide mimetic. The sequence for this drug differs from native GLP-1 as depicted in [7], and is largely based on the sequence of exendin-4 from the Gila monster (Heloderma suspectum). Lixisenatide is licensed as a once-daily mealtime GLP-1 receptor agonist administered by sub-cuteneous injection.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

lixisenatide is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NCCCCC(C(=O)NC(C(=O)NCC(=O)NCC(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)N1CCCC1C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)CCCCN)CCCCN)CCCCN)CCCCN)CCCCN)CCCCN)CO)C)CO)CO)CC(=O)N)NC(=O)C(NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(NC(=O)C(C(CC)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(C)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(NC(=O)C(C(O)C)NC(=O)CNC(=O)C(NC(=O)CNC(=O)C(Cc1[nH]cnc1)N)CCC(=O)O)Cc1ccccc1)CO)CC(=O)O)CC(C)C)CO)CCCCN)CCC(=O)N)CCSC)CCC(=O)O)CCC(=O)O)CCC(=O)O)C)CCCNC(=N)N)CC(C)C)Cc1ccccc1)CCC(=O)O)CC(C)C
Isomeric SMILES NCCCC[C@@H](C(=O)N[C@H](C(=O)NCC(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCCCN)CCCCN)CCCCN)CCCCN)CCCCN)CCCCN)CO)C)CO)CO)CC(=O)N)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)CNC(=O)[C@@H](NC(=O)CNC(=O)[C@H](Cc1[nH]cnc1)N)CCC(=O)O)Cc1ccccc1)CO)CC(=O)O)CC(C)C)CO)CCCCN)CCC(=O)N)CCSC)CCC(=O)O)CCC(=O)O)CCC(=O)O)C)CCCNC(=N)N)CC(C)C)Cc1ccccc1)CCC(=O)O)CC(C)C
InChI 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
InChI Key XVVOERDUTLJJHN-IAEQDCLQSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Athauda D, Maclagan K, Skene SS, Bajwa-Joseph M, Letchford D, Chowdhury K, Hibbert S, Budnik N, Zampedri L, Dickson J et al.. (2017)
Exenatide once weekly versus placebo in Parkinson's disease: a randomised, double-blind, placebo-controlled trial.
Lancet, 390 (10103): 1664-1675. [PMID:28781108]
2. Aviles-Olmos I, Dickson J, Kefalopoulou Z, Djamshidian A, Ell P, Soderlund T, Whitton P, Wyse R, Isaacs T, Lees A et al.. (2013)
Exenatide and the treatment of patients with Parkinson's disease.
J Clin Invest, 123 (6): 2730-6. [PMID:23728174]
3. Ferrannini E, Niemoeller E, Dex T, Servera S, Mari A. (2022)
Fixed-ratio combination of insulin glargine plus lixisenatide (iGlarLixi) improves ß-cell function in people with type 2 diabetes.
Diabetes Obes Metab, 24 (6): 1159-1165. [PMID:35257461]
4. Meissner WG, Remy P, Giordana C, Maltête D, Derkinderen P, Houéto JL, Anheim M, Benatru I, Boraud T, Brefel-Courbon C et al.. (2024)
Trial of Lixisenatide in Early Parkinson's Disease.
N Engl J Med, 390 (13): 1176-1185. [PMID:38598572]
5. Meissner WG, Remy P, Giordana C, Maltete D, Derkinderen P, Houéto JL, Anheim M, Benatru I, Boraud T, Brefel-Courbon C et al.. (2024)
Trial of Lixisenatide in Early Parkinson’s Disease.
New England Journal of Medicine, 390 (13). DOI: 10.1056/NEJMoa2312323
6. Pagano G, Taylor KI, Anzures Cabrera J, Simuni T, Marek K, Postuma RB, Pavese N, Stocchi F, Brockmann K, Svoboda H et al.. (2024)
Prasinezumab slows motor progression in rapidly progressing early-stage Parkinson's disease.
Nat Med, 30 (4): 1096-1103. [PMID:38622249]
7. Werner U, Haschke G, Herling AW, Kramer W. (2010)
Pharmacological profile of lixisenatide: A new GLP-1 receptor agonist for the treatment of type 2 diabetes.
Regul Pept, 164 (2-3): 58-64. [PMID:20570597]