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liraglutide

Structure via PubChem · Public domain (PubChem)

EntityQ2526479· pop 30· linked from 256 articles

liraglutide

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Also known as N²⁶-(hexadecanoyl-gamma-glutamyle)-[34-arginine]GLP-1-(7-37)-peptide, N²⁶-(N-hexadecanoyl-L-gamma-glutamyl)-[34-L-arginine]glucagon-like peptide 1-(7-37)-peptide, Arg34Lys26-{N-ε-[γ-Glu(N-α-hexadecanoyl)]}-GLP-1[7-37]

Liraglutide, sold under the brand name Victoza among others, is an anti-diabetic medication used to treat type2 diabetes, and chronic obesity. It is a second-line therapy for diabetes following first-line therapy with metformin. Its effects on long-term health outcomes like heart disease and life expectancy are unclear. It is given by injection under the skin.

Key facts

Drug.C
172
Drug.H
265
Drug.image
Liraglutide cartoon 4APD.png
Drug.image_class
bg-transparent
Drug.image2
Liraglutide ball-and-stick 4APD.png
Drug.image_class2
bg-transparent
Drug.caption
NMR structure of liraglutide. PDB entry
Drug.tradename
Victoza, others
Drug.MedlinePlus
a611003
Drug.DailyMedID
Liraglutide
Drug.pregnancy_AU
B3
Drug.routes_of_administration
Subcutaneous
Drug.ATC_prefix
A10
Drug.ATC_suffix
BJ02
Drug.legal_AU
S4
Drug.legal_CA
Rx-only
Drug.legal_UK
POM
Drug.legal_US
Rx-only

via Wikipedia infobox

Chemical data

Formula
C172H265N43O51
Molecular weight
3751 g/mol
IUPAC name
(2S)-5-[[(5S)-5-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3R)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]propanoyl]amino]-4-carboxybutanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-methylbutanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-4-carboxybutanoyl]amino]acetyl]amino]-5-oxopentanoyl]amino]propanoyl]amino]propanoyl]amino]-6-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-carbamimidamido-1-[[2-[[(2S)-5-carbamimidamido-1-(carboxymethylamino)-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-6-oxohexyl]amino]-2-(hexadecanoylamino)-5-oxopentanoic acid
SMILES
CCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)NCCCC[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)N)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC5=CC=CC=C5)NC(=O)[C@H]([C@@H](C)O)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CC6=CNC=N6)N)C(=O)O
InChIKey
YSDQQAXHVYUZIW-QCIJIYAXSA-N
XLogP
-3.4
Polar surface area
1510 Ų
H-bond donors
54
H-bond acceptors
55
Formal charge
0

via PubChem

Wikidata facts

Mass
3749.949816
Manufacturer
Novo Nordisk
Has use
medication
Show 9 more facts
chemical formula
C₁₇₂H₂₆₅N₄₃O₅₁
World Health Organisation international non-proprietary name
liraglutide
NCI Thesaurus ID
C82239
subject has role
incretins
medical condition treated
glucose intolerance
Commons category
Liraglutide
defined daily dose
1.5
has characteristic
biopharmaceutical
legal status (medicine)
boxed warning
Sources (6)

via Wikidata · CC0

~11 min read

Encyclopedic overview

16 sections
Contents
  • Medical uses
  • Type 2 diabetes
  • Obesity
  • Adverse effects
  • Thyroid cancer
  • Pancreatitis
  • Suicidal behavior and ideation
  • Pharmacodynamics
  • Pharmacokinetics
  • Society and culture
  • Brand names
  • Marketing
  • Controversy
  • History
  • Research
  • References

Liraglutide, sold under the brand name Victoza among others, is an anti-diabetic medication used to treat type2 diabetes, and chronic obesity. It is a second-line therapy for diabetes following first-line therapy with metformin. Its effects on long-term health outcomes like heart disease and life expectancy are unclear. It is given by injection under the skin.

Liraglutide is a glucagon-like peptide-1 receptor agonist (GLP-1 receptor agonist) also known as incretin mimetics. It works by increasing insulin release from the pancreas and decreases excessive glucagon release.

Excerpted from Wikipedia’s “liraglutide” article, available under the CC BY-SA 4.0 licence.

Gallery (3)