Identification

Summary

Lixisenatide is a GLP-1 receptor agonist used for the management of type 2 diabetes mellitus.

Brand Names
Adlyxin Starter Kit, Adlyxine, Lyxumia, Soliqua
Generic Name
Lixisenatide
DrugBank Accession Number
DB09265
Background

Lixisenatide is a glucagon-like peptide-1 (GLP-1) receptor agonist used in the treatment of type 2 diabetes mellitus (T2DM). It is sold under the brand name Adlyxin by Sanofi-Aventis. Adlyxin recieved FDA approval July 28, 2016 3.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 4858.56
Monoisotopic: 4855.544321891
Chemical Formula
C215H347N61O65S
Synonyms
  • des-38-proline-exendine-4 (Heloderma suspectum)-(1-39)-peptidylpenta-L-lysyl-L-lysinamide
  • DesPro38Exendin-4(1-39)-Lys6-NH2
  • Lixisenatida
  • Lixisénatide
  • Lixisenatide
External IDs
  • AQVE-10010
  • AVE 0010
  • AVE0010
  • ZP 10
  • ZP10A peptide

Pharmacology

Indication

For use as an antihyperglycemic agent in the treatment of T2DM Label.

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Lixisenatide acts as an agonist at the GLP-1 receptor. In the pancreas, this agonism results in increased glucose-stimulated insulin exocytosis by beta islet cells. This produces a reduction in blood glucose due to increased glucose uptake by tissues 1. GLP-1 receptor activation in the GI tract results in delayed gastric emptying which is thought to mediate the effects of lixisenatide on postprandial blood glucose.

Mechanism of action

The activation of the GLP-1 receptor by lixisenatide results in the activation of adenylyl cyclase [19193]. This increases the concentration of cyclic adenosine monophosphate in the cell leading to the activation of protein kinase A (PKA) as well as Epac1 and Epac2. PKA, Epac1, and Epac2 are involved the in release of Ca2+ from the endoplasmic reticulum which is known as the "amplification" pathway which increases insulin release when the triggering pathway is activated. By activating this amplification pathway lixisenatide increases glucose stimulated insulin secretion.

TargetActionsOrganism
AGlucagon-like peptide 1 receptor
agonist
Humans
Absorption

tmax of 1-3.5h when administered subcutaneously Label.

Volume of distribution

100L Label

Protein binding

55% bound to plasma proteins 4.

Metabolism

Assumed to undergo proteolytic degradation Label.

Route of elimination

Assumed to be proteolytic degradation and excretion in urine Label.

Half-life

3h Label

Clearance

35L/h Label

Adverse Effects
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Toxicity

Thyroid C-cell adenomas occurred in rats when exposed to >15 times human exposure of 20mcg/day Label. Overdose is associated with GI side effects typical of GLP-1 receptor agonists.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Lixisenatide which could result in a higher serum level.
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Lixisenatide.
AcebutololThe therapeutic efficacy of Lixisenatide can be increased when used in combination with Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Lixisenatide which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Lixisenatide which could result in a higher serum level.
AcenocoumarolLixisenatide can cause a decrease in the absorption of Acenocoumarol resulting in a reduced serum concentration and potentially a decrease in efficacy.
AcetaminophenAcetaminophen may decrease the excretion rate of Lixisenatide which could result in a higher serum level.
AcetazolamideThe therapeutic efficacy of Lixisenatide can be increased when used in combination with Acetazolamide.
AcetohexamideLixisenatide may increase the hypoglycemic activities of Acetohexamide.
Acetyl sulfisoxazoleThe therapeutic efficacy of Lixisenatide can be increased when used in combination with Acetyl sulfisoxazole.
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Food Interactions
  • Take at the same time every day.
  • Take before a meal. Take lixisenatide within one hour before the first meal of the day.

Products

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dosage, form, labeller, route of administration, and marketing period.
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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AdlyxinInjection, solution100 ug/1mLSubcutaneoussanofi-aventis U.S. LLC2016-07-27Not applicableUS flag
AdlyxineSolution20 mcg / actSubcutaneousSanofi Aventis2017-09-12Not applicableCanada flag
AdlyxineSolution10 mcg / actSubcutaneousSanofi Aventis2017-09-12Not applicableCanada flag
LyxumiaInjection, solution10 μgSubcutaneousSanofi Aventis Groupe2016-09-08Not applicableEU flag
LyxumiaInjection, solution20 μgSubcutaneousSanofi Aventis Groupe2016-09-08Not applicableEU flag
LyxumiaInjection, solution20 μgSubcutaneousSanofi Aventis Groupe2016-09-08Not applicableEU flag
LyxumiaInjection, solution20 μgSubcutaneousSanofi Aventis Groupe2016-09-08Not applicableEU flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AdlyxinLixisenatide (50 ug/1mL) + Lixisenatide (100 ug/1mL)Subcutaneoussanofi-aventis U.S. LLC2016-07-27Not applicableUS flag
AdlyxinLixisenatide (50 ug/1mL) + Lixisenatide (100 ug/1mL)Subcutaneoussanofi-aventis U.S. LLC2016-07-27Not applicableUS flag
AdlyxineLixisenatide (0.05 mg / mL) + Lixisenatide (0.1 mg / mL)Kit; SolutionSubcutaneousSanofi Aventis2017-09-122018-10-08Canada flag
AdlyxineLixisenatide (0.05 mg / mL) + Lixisenatide (0.1 mg / mL)Kit; SolutionSubcutaneousSanofi Aventis2017-09-122018-10-08Canada flag
LYXUMIA SOLUTION FOR INJECTION IN PRE-FILLED PEN 10MCG AND 20MCG (50mcg/mL and 100mcg/mL)Lixisenatide (0.05 mg/mL) + Lixisenatide (0.1 mg/mL)Injection, solutionSubcutaneousSANOFI-AVENTIS SINGAPORE PTE. LTD.2014-10-30Not applicable
LYXUMIA SOLUTION FOR INJECTION IN PRE-FILLED PEN 10MCG AND 20MCG (50mcg/mL and 100mcg/mL)Lixisenatide (0.05 mg/mL) + Lixisenatide (0.1 mg/mL)Injection, solutionSubcutaneousSANOFI-AVENTIS SINGAPORE PTE. LTD.2014-10-30Not applicable
SoliquaLixisenatide (33 mcg / mL) + Insulin glargine (100 unit / mL)SolutionSubcutaneousSanofi Aventis2018-09-12Not applicableCanada flag
Soliqua 100/33Lixisenatide (33 ug/1mL) + Insulin glargine (100 U/1mL)Injection, solutionSubcutaneoussanofi-aventis U.S. LLC2016-11-21Not applicableUS flag
SOLİQUA SOLOSTAR 100 U/ML + 33 MCG/ML SC ENJEKSİYONLUK ÇÖZELTİ İÇEREN KULLANIMA HAZIR KALEM, 3 KALEMLixisenatide (33 mcg/mL) + Insulin glargine (100 U/mL)Injection, solutionSubcutaneousSANOFİ SAĞLIK ÜRÜNLERİ LTD. ŞTİ.2020-08-14Not applicableTurkey flag
SOLİQUA SOLOSTAR 100 U/ML + 33 MCG/ML SC ENJEKSİYONLUK ÇÖZELTİ İÇEREN KULLANIMA HAZIR KALEM, 5 KALEMLixisenatide (33 mcg/mL) + Insulin glargine (100 U/mL)Injection, solutionSubcutaneousSANOFİ SAĞLIK ÜRÜNLERİ LTD. ŞTİ.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
A10AE54 — Insulin glargine and lixisenatideA10BJ03 — Lixisenatide
Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
74O62BB01U
CAS number
320367-13-3
InChI Key
XVVOERDUTLJJHN-IAEQDCLQSA-N
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
IUPAC Name
(4S)-4-[({[(1S,2R)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[({2-[(2S)-2-{[(1S)-1-{[(1S)-1-[({[(2S)-1-[(2S)-2-[(2S)-2-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-carbamoylpentyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}-2-hydroxyethyl]carbamoyl}pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)methyl]carbamoyl}-2-carbamoylethyl]carbamoyl}pentyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-carboxypropyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}-3-methylbutyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}pentyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-carboxyethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}methyl)carbamoyl]-4-{2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]acetamido}butanoic acid
SMILES
CC[C@H](C)[C@H](NC(=O)[C@H](CC1=CC=CC=C1)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(N)=O)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](CC1=CC=CC=C1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](N)CC1=CNC=N1)[C@@H](C)O)[C@@H](C)O)C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=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(N)=O

References

General References
  1. Lorenz M, Pfeiffer C, Steinstrasser A, Becker RH, Rutten H, Ruus P, Horowitz M: Effects of lixisenatide once daily on gastric emptying in type 2 diabetes--relationship to postprandial glycemia. Regul Pept. 2013 Aug 10;185:1-8. doi: 10.1016/j.regpep.2013.04.001. Epub 2013 May 9. [Article]
  2. Doyle ME, Egan JM: Mechanisms of action of glucagon-like peptide 1 in the pancreas. Pharmacol Ther. 2007 Mar;113(3):546-93. Epub 2006 Dec 28. [Article]
  3. Adlyxin FDA Approval Announcement [Link]
  4. EMA Lixisenatide Assessment [Link]
KEGG Drug
D09729
PubChem Compound
131704317
PubChem Substance
310265161
ChemSpider
17295846
RxNav
1440051
ChEBI
85662
ChEMBL
CHEMBL2108336
Wikipedia
Lixisenatide
FDA label
Download (1.13 MB)
MSDS
Download (80 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceType 2 Diabetes Mellitus1
4CompletedTreatmentDiabetes Mellitus / Diabetic Kidney Disease (DKD) / Diabetic Nephropathy / Glucagon-Like Peptide 11
4CompletedTreatmentDiabetes / Type 2 Diabetes Mellitus1
4CompletedTreatmentType 2 Diabetes Mellitus3
4RecruitingTreatmentType 2 Diabetes Mellitus1
4TerminatedTreatmentType 2 Diabetes Mellitus1
4Unknown StatusTreatmentType 2 Diabetes Mellitus1
3CompletedTreatmentAcute Coronary Syndrome (ACS)1
3CompletedTreatmentType 2 Diabetes Mellitus30
3TerminatedTreatmentType 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionSubcutaneous100 ug/1mL
Kit; solutionSubcutaneous
SolutionSubcutaneous10 mcg / act
SolutionSubcutaneous20 mcg / act
Injection
Injection, solutionParenteral; Subcutaneous10 MICROGRAMMI
Injection, solutionParenteral; Subcutaneous20 MICROGRAMMI
Injection, solutionSubcutaneous10 μg
Injection, solutionSubcutaneous20 μg
SolutionSubcutaneous0.15 mg/3ml
SolutionSubcutaneous0.3 mg/3ml
Injection, solution
Injection, solutionSubcutaneous10 mcg/0.2ml
Injection, solutionSubcutaneous20 mcg/0.2ml
Injection, solutionSubcutaneous50 mcg/mL
Injection, solutionSubcutaneous0.05 mg/mL
Injection, solutionSubcutaneous100 mcg/mL
SolutionSubcutaneous0.05 mg
SolutionSubcutaneous0.1 mg
Injection, solution
SolutionSubcutaneous
Injection, solutionSubcutaneous
Injection, solutionSubcutaneous100 units/ml
Injection, solutionCutaneous; Parenteral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US9011391No2015-04-212024-03-26US flag
US9233211No2016-01-122024-03-02US flag
US8603044No2013-12-102024-03-02US flag
US8512297No2013-08-202024-09-15US flag
US8679069No2014-03-252025-04-12US flag
US8992486No2015-03-312024-06-05US flag
US8556864No2013-10-152024-03-03US flag
US7918833Yes2011-04-052028-03-23US flag
US9561331No2017-02-072024-08-28US flag
US9623189No2017-04-182024-08-19US flag
US9610409No2017-04-042024-03-02US flag
US9526844No2016-12-272024-03-02US flag
US9604008No2017-03-282024-03-02US flag
US9533105No2017-01-032024-08-17US flag
US9408979No2016-08-092024-03-02US flag
US9604009No2017-03-282024-08-16US flag
US9072836No2015-07-072032-03-15US flag
US9084853No2015-07-212031-10-05US flag
US8882721No2014-11-112031-06-28US flag
US9511193No2016-12-062032-01-19US flag
USRE45313No2014-12-302020-07-12US flag
US8475414No2013-07-022030-12-28US flag
US9308329No2016-04-122030-12-28US flag
US8915888No2014-12-232030-06-08US flag
US9408893No2016-08-092032-08-27US flag
US9526764No2016-12-272029-10-09US flag
US9707176No2017-07-182030-11-11US flag
US9775954No2017-10-032024-03-02US flag
US9827379No2017-11-282024-03-02US flag
US9821032No2017-11-212032-05-09US flag
US9855388No2018-01-022029-04-24US flag
US9440029No2016-09-132032-01-30US flag
US9950039No2018-04-242035-12-10US flag
US9981013No2018-05-292030-08-30US flag
US9717852No2017-08-012033-04-08US flag
US10028910No2018-07-242030-11-11US flag
US10029011No2018-07-242032-08-02US flag
US10117909No2018-11-062029-10-09US flag
US10201663No2019-02-122034-03-10US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP-33ChemAxon
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)11.89ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count78ChemAxon
Hydrogen Donor Count70ChemAxon
Polar Surface Area2060.16 Å2ChemAxon
Rotatable Bond Count169ChemAxon
Refractivity1221.37 m3·mol-1ChemAxon
Polarizability505.8 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Transmembrane signaling receptor activity
Specific Function
This is a receptor for glucagon-like peptide 1. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name
GLP1R
Uniprot ID
P43220
Uniprot Name
Glucagon-like peptide 1 receptor
Molecular Weight
53025.22 Da
References
  1. Nadkarni P, Chepurny OG, Holz GG: Regulation of glucose homeostasis by GLP-1. Prog Mol Biol Transl Sci. 2014;121:23-65. doi: 10.1016/B978-0-12-800101-1.00002-8. [Article]
  2. Lorenz M, Lawson F, Owens D, Raccah D, Roy-Duval C, Lehmann A, Perfetti R, Blonde L: Differential effects of glucagon-like peptide-1 receptor agonists on heart rate. Cardiovasc Diabetol. 2017 Jan 13;16(1):6. doi: 10.1186/s12933-016-0490-6. [Article]
  3. Gallwitz B: Novel Therapeutic Approaches in Diabetes. Endocr Dev. 2016;31:43-56. doi: 10.1159/000439372. Epub 2016 Jan 19. [Article]
  4. Htike ZZ, Zaccardi F, Papamargaritis D, Webb DR, Khunti K, Davies MJ: Efficacy and safety of glucagon-like peptide-1 receptor agonists in type 2 diabetes: A systematic review and mixed-treatment comparison analysis. Diabetes Obes Metab. 2017 Apr;19(4):524-536. doi: 10.1111/dom.12849. Epub 2017 Feb 17. [Article]

Drug created at October 27, 2015 21:41 / Updated at May 28, 2022 06:24