LGM Pharma

Liraglutide

CAS No: 204656-20-2

Liraglutide

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Product Details:

CAS No: 204656-20-2
Synonyms: Arg34Lys26-(N-epsilon-(gamma-Glu(N-alpha-hexadecanoyl)))-GLP-1(7-37), Liraglutida, Liraglutida [INN-Spanish], Liraglutide, Liraglutidum, Liraglutidum [INN-Latin], N(sup 26)-(Hexadecanoyl-gamma-glutamyle)-(34-arginine)GLP-1-(7-37)-peptide, NN 2211, NN-2211, NN2211, NNC 90-1170, UNII-839I73S42A, Victoza
ATC code: A10BX07
Molecular Weight: 3751.2 g/mol
Chemical Formula: C172-H265-N43-O51
Assay/Purity: Typically NLT 98%
IUPAC Name: L-histidyl-L-alanyl-L-α-glutamylglycyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-α-aspartyl-L-valyl-L-seryl-L-seryl-L-tyrosyl-L-leucyl-L-α-glutamylglycyl-L-glutaminyl-L-alanyl-L-alanyl-N6-[N-(1-oxohexadecyl)-L-γ-glutamyl]-L-lysyl-L-α-glutamyl-L-phenylalanyl-L-isoleucyl-L-alanyl-L-tryptophyl-L-leucyl-L-valyl-L-arginylglycyl-L-arginyl-glycine
SMILES: C(CCC)CCCCCCCCCCCC(N[C,H](C(=O)NCCCC[C,H](NC([C,,H](NC([C,,H](NC([C,,H](NC(CNC([C,,H](NC([C,,H](NC([C,,H](NC([C,,H](NC([C,,H](NC([C,,H](NC([C,,H](NC([C,,H](NC([C,,H](NC([C,,H](NC([C,,H](NC(CNC([C,,H](NC([C,,H](NC([C,,H](N)Cc1cnc[nH]1)=O)C)=O)CCC(=O)O)=O)=O)[C,H](O)C)=O)Cc1ccccc1)=O)[C,H](O)C)=O)CO)=O)CC(=O)O)=O)C(C)C)=O)CO)=O)CO)=O)Cc1ccc(cc1)O)=O)CC(C)C)=O)CCC(=O)O)=O)=O)CCC(=O)N)=O)C)=O)C)=O)C(N[C,H](C(N[C,H](C(N[C,H](C(N[C,H](C(N[C,H](C(N[C,H](C(N[C,H](C(N[C,H](C(NCC(N[C,H](C(NCC(O)=O)=O)CCCNC(N)=N)=O)=O)CCCNC(N)=N)=O)C(C)C)=O)CC(C)C)=O)Cc1c[nH]c2c1cccc2)=O)C)=O)[C,,H](C)CC)=O)Cc1ccccc1)=O)CCC(=O)O)=O)CCC(=O)O)=O
InChl: nChI=1S/C172H265N43O51/c1-18-20-21-22-23-24-25-26-27-28-29-30-37-53-128(223)193-112(59-64-132(227)228)148(244)180-68-41-40-50-111(154(250)199-116(62-67-135(233)234)155(251)204-120(73-100-44-33-31-34-45-100)160(256)214-140(93(11)19-2)168(264)192-97(15)146(242)201-122(76-103-79-183-108-49-39-38-48-106(103)108)158(254)203-118(72-90(5)6)159(255)212-138(91(7)8)166(262)200-110(52-43-70-182-172(177)178)150(246)184-81-129(224)194-109(51-42-69-181-171(175)176)149(245)187-84-137(237)238)196-144(240)95(13)189-143(239)94(12)191-153(249)115(58-63-127(174)222)195-130(225)82-185-152(248)114(61-66-134(231)232)198-156(252)117(71-89(3)4)202-157(253)119(75-102-54-56-105(221)57-55-102)205-163(259)124(85-216)208-165(261)126(87-218)209-167(263)139(92(9)10)213-162(258)123(78-136(235)236)206-164(260)125(86-217)210-170(266)142(99(17)220)215-161(257)121(74-101-46-35-32-36-47-101)207-169(265)141(98(16)219)211-131(226)83-186-151(247)113(60-65-133(229)230)197-145(241)96(14)190-147(243)107(173)77-104-80-179-88-188-104/h31-36,38-39,44-49,54-57,79-80,88-99,107,109-126,138-142,183,216-221H,18-30,37,40-43,50-53,58-78,81-87,173H2,1-17H3,(H2,174,222)(H,179,188)(H,180,244)(H,184,246)(H,185,248)(H,186,247)(H,187,245)(H,189,239)(H,190,243)(H,191,249)(H,192,264)(H,193,223)(H,194,224)(H,195,225)(H,196,240)(H,197,241)(H,198,252)(H,199,250)(H,200,262)(H,201,242)(H,202,253)(H,203,254)(H,204,251)(H,205,259)(H,206,260)(H,207,265)(H,208,261)(H,209,263)(H,210,266)(H,211,226)(H,212,255)(H,213,258)(H,214,256)(H,215,257)(H,227,228)(H,229,230)(H,231,232)(H,233,234)(H,235,236)(H,237,238)(H4,175,176,181)(H4,177,178,182)/t93-,94-,95-,96-,97-,98+,99+,107-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,138-,139-,140-,141-,142-/m0/s1

Additional Details: [+]

Indication:

For use in/treatment of diabetes mellitus type 2.

Pharmacodynamics:

Liraglutide is a once-daily GLP-1 derivative for the treatment of type 2 diabetes. GLP-1, in its natural form, is short-lived in the body (the half-life after subcutaneous injection is approximately one hour), so it is not very useful as a therapeutic agent. However, liraglutide has a half-life after subcutaneous injection of 11–15 hours, making it suitable for once-daily dosing. The prolonged action of liraglutide is achieved by attaching a fatty acid molecule at one position of the GLP-1 molecule, enabling it to bind to albumin within the subcutaneous tissue and bloodstream. The active GLP-1 is then released from albumin at a slow, consistent rate. Binding with albumin also results in slower degradation and reduced elimination of liraglutide from the circulation by the kidneys compared to GLP-1.

Mode of Action:

Liraglutide is an acylated GLP-1 (Glucagon-Like Peptide-1) receptor agonist. Liraglutide upregulates intracellular cAMP resulting in the release of insulin given elevated blood glucose concentrations. Glucagon secretion is also decreased in a glucose-dependent fashion by liraglutide.

Metabolism:

During the initial 24 hours following administration of a single [3H]-liraglutide dose to healthy subjects, the major component in plasma was intact liraglutide. Liraglutide is endogenously metabolized in a similar manner to large proteins without a specific organ as a major route of elimination.

Toxicity:

In a clinical trial, one patient with type 2 diabetes experienced a single overdose of Victoza 17.4 mg subcutaneous (10 times the maximum recommended dose). Effects of the overdose included severe nausea and vomiting requiring hospitalization. No hypoglycemia was reported. The patient recovered without complications. In the event of overdosage, appropriate supportive treatment should be initiated according to the patient’s clinical signs and symptoms. RISK OF THYROID C-CELL TUMORS

General Reference:

  1. Russell-Jones D: Molecular, pharmacological and clinical aspects of liraglutide, a once-daily human GLP-1 analogue. Mol Cell Endocrinol. 2009 Jan 15;297(1-2):137-40. Epub 2008 Nov 25. Pubmed
  2. Vilsboll T: Liraglutide: a new treatment for type 2 diabetes. Drugs Today (Barc). 2009 Feb;45(2):101-13. Pubmed
  3. http://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=15776
  4. Malm-Erjefalt M, Bjornsdottir I, Vanggaard J, Helleberg H, Larsen U, Oosterhuis B, van Lier JJ, Zdravkovic M, Olsen AK: Metabolism and excretion of the once-daily human glucagon-like peptide-1 analog liraglutide in healthy male subjects and its in vitro degradation by dipeptidyl peptidase IV and neutral endopeptidase. Drug Metab Dispos. 2010 Nov;38(11):1944-53. doi: 10.1124/dmd.110.034066. Epub 2010 Aug 13. Pubmed


Liraglutide News:

  • As of 2015 one-third of adults in the United States are estimated to be classified as obese.
  • As the only available injectable treatment for obesity, Liraglutide (Saxenda) achieved an FDA approval in late 2014.
  • Approximately 49 percent of the patients who received Liraglutide as Saxenda lost at least 5 percent of their body weight.
  • On June 17, 2013 Endocrine Today reported at the ENDO 2013 meeting that Liraglutide demonstrated success as a weight loss treatment.
  • Combined with the antidiabetic drug Metformin, Liraglutide was administered on a short term basis to women with polycystic ovary syndrome who were considered obese.
  • Of the female participants in this study who received the combination of both Liraglutide and Metformin 22 percent of these women lost more than 5 percent of their body weight.

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