Semaglutide

Semaglutide
Structure of Semaglutide
Experimentally determined structure of semaglutide while complexed with the GLP-1 receptor. PDB: 7KI0​
Clinical data
Pronunciation/sɛmˈæɡlʊtaɪd/ sem-AG-luu-tyde or /ˌsɛməˈɡluːtaɪd/ SEM-ə-GLOO-tyde
Trade namesOzempic, Rybelsus, Wegovy, others
AHFS/Drugs.comMonograph
MedlinePlusa618008
License data
Pregnancy
category
Routes of
administration		Subcutaneous, oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability89%
MetabolismProteolysis
Elimination half-life7 days
Duration of action63.6 h
ExcretionUrine and feces
Identifiers
  • 18-[[(1R)-4-[2-[2-[2-[2-[2-[2-[[(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-[[2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-2-methylpropanoyl]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-oxoethoxy]ethoxy]ethylamino]-2-oxoethoxy]ethoxy]ethylamino]-1-carboxy-4-oxobutyl]amino]-18-oxooctadecanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ECHA InfoCard100.219.541 Edit this at Wikidata
Chemical and physical data
FormulaC187H291N45O59
Molar mass4113.641 g·mol−1
  • CCC(C)C(C(=O)NC(C)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CCCNC(=N)N)C(=O)NCC(=O)NC(CCCNC(=N)N)C(=O)NCC(=O)O)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CCC(=O)O)NC(=O)C(CCCCNC(=O)COCCOCCNC(=O)COCCOCCNC(=O)CCC(C(=O)O)NC(=O)CCCCCCCCCCCCCCCCC(=O)O)NC(=O)C(C)NC(=O)C(C)NC(=O)C(CCC(=O)N)NC(=O)CNC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(C(C)C)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(CC5=CC=CC=C5)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(CCC(=O)O)NC(=O)C(C)(C)NC(=O)C(CC6=CN=CN6)N
  • InChI=1S/C187H291N45O59/c1-18-105(10)154(180(282)208-108(13)159(261)216-133(86-114-89-200-119-50-40-39-49-117(114)119)170(272)218-129(82-102(4)5)171(273)228-152(103(6)7)178(280)215-121(53-44-72-199-186(192)193)162(264)201-91-141(242)209-120(52-43-71-198-185(190)191)161(263)204-94-151(257)258)230-172(274)131(83-111-45-33-31-34-46-111)219-167(269)126(64-69-149(253)254)214-166(268)122(51-41-42-70-195-144(245)98-290-79-78-289-76-74-197-145(246)99-291-80-77-288-75-73-196-139(240)66-61-127(183(285)286)211-140(241)54-37-29-27-25-23-21-19-20-22-24-26-28-30-38-55-146(247)248)212-158(260)107(12)206-157(259)106(11)207-165(267)125(60-65-138(189)239)210-142(243)92-202-163(265)123(62-67-147(249)250)213-168(270)128(81-101(2)3)217-169(271)130(85-113-56-58-116(238)59-57-113)220-175(277)135(95-233)223-177(279)137(97-235)224-179(281)153(104(8)9)229-174(276)134(88-150(255)256)221-176(278)136(96-234)225-182(284)156(110(15)237)231-173(275)132(84-112-47-35-32-36-48-112)222-181(283)155(109(14)236)227-143(244)93-203-164(266)124(63-68-148(251)252)226-184(287)187(16,17)232-160(262)118(188)87-115-90-194-100-205-115/h31-36,39-40,45-50,56-59,89-90,100-110,118,120-137,152-156,200,233-238H,18-30,37-38,41-44,51-55,60-88,91-99,188H2,1-17H3,(H2,189,239)(H,194,205)(H,195,245)(H,196,240)(H,197,246)(H,201,264)(H,202,265)(H,203,266)(H,204,263)(H,206,259)(H,207,267)(H,208,282)(H,209,242)(H,210,243)(H,211,241)(H,212,260)(H,213,270)(H,214,268)(H,215,280)(H,216,261)(H,217,271)(H,218,272)(H,219,269)(H,220,277)(H,221,278)(H,222,283)(H,223,279)(H,224,281)(H,225,284)(H,226,287)(H,227,244)(H,228,273)(H,229,276)(H,230,274)(H,231,275)(H,232,262)(H,247,248)(H,249,250)(H,251,252)(H,253,254)(H,255,256)(H,257,258)(H,285,286)(H4,190,191,198)(H4,192,193,199)/t105-,106-,107-,108-,109+,110+,118-,120-,121-,122-,123-,124-,125-,126-,127+,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,152-,153-,154-,155-,156-/m0/s1
  • Key:DLSWIYLPEUIQAV-CCUURXOWSA-N checkY[pubchem]

Semaglutide is an antidiabetic medication used for the treatment of type 2 diabetes and an anti-obesity medication used for long-term weight management.[19][20][21] It is a peptide similar to the hormone glucagon-like peptide-1 (GLP-1), modified with a side chain.[22][23] It can be administered by subcutaneous injection or taken orally.[24][13][14][15] It is sold under the brand names Ozempic[13] and Rybelsus[14] for diabetes, and under the brand name Wegovy for weight loss.[15]

Semaglutide is a glucagon-like peptide-1 receptor agonist.[13][14][15] The most common side effects include nausea, vomiting, diarrhea, abdominal pain, and constipation.[13][16][17][18][25]

It was approved for medical use in the US in 2017.[13][26] In 2022, it was the 48th most commonly prescribed medication in the United States, with more than 13 million prescriptions.[27][28]

  1. ^ a b Cite error: The named reference AusPAR: Semaglutide was invoked but never defined (see the help page).
  2. ^ a b "Rybelsus APMDS". Therapeutic Goods Administration (TGA). 22 February 2022. Retrieved 23 February 2022.
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ Cite error: The named reference TGA Ozempic was invoked but never defined (see the help page).
  5. ^ "Summary for ARTG Entry: 346198 Rybelsus semaglutide 3 mg tablet blister pack". Therapeutic Goods Administration (TGA). Archived from the original on 24 February 2022. Retrieved 23 February 2022.
  6. ^ "Wegovy (Novo Nordisk Pharmaceuticals Pty Ltd)". Therapeutic Goods Administration (TGA). 7 October 2022. Archived from the original on 14 April 2023. Retrieved 7 April 2023.
  7. ^ Product Monograph Including Patient Medication Information – Ozempic semaglutide injection (PDF) (Report). Novo-Nordisk Canada. 21 August 2020 [Initial approval 4 January 2018]. Archived (PDF) from the original on 7 June 2021. Retrieved 6 June 2021.
  8. ^ Product Monograph Including Patient Medication Information – Rybelsus semaglutide tablets (PDF) (Report). Novo-Nordisk Canada. 30 March 2020. Archived (PDF) from the original on 14 December 2021. Retrieved 6 June 2021.
  9. ^ "Regulatory Decision Summary – Rybelsus". Health Canada. 23 October 2014. Archived from the original on 5 June 2022. Retrieved 4 June 2022.
  10. ^ "Drug and medical device highlights 2018: Helping you maintain and improve your health". Health Canada. 14 October 2020. Archived from the original on 17 April 2024. Retrieved 17 April 2024.
  11. ^ "Ozempic 0.25 mg solution for injection in pre-filled pen – Summary of Product Characteristics (SmPC)". (emc). 9 April 2021. Archived from the original on 6 June 2021. Retrieved 6 June 2021.
  12. ^ "Rybelsus – Summary of Product Characteristics (SmPC)". (emc). 25 November 2020. Archived from the original on 6 June 2021. Retrieved 6 June 2021.
  13. ^ a b c d e f Cite error: The named reference Ozempic FDA label was invoked but never defined (see the help page).
  14. ^ a b c d Cite error: The named reference Rybelsus FDA label was invoked but never defined (see the help page).
  15. ^ a b c d Cite error: The named reference Wegovy FDA label was invoked but never defined (see the help page).
  16. ^ a b Cite error: The named reference Ozempic EPAR was invoked but never defined (see the help page).
  17. ^ a b Cite error: The named reference Rybelsus EPAR was invoked but never defined (see the help page).
  18. ^ a b Cite error: The named reference Wegovy EPAR was invoked but never defined (see the help page).
  19. ^ Singh G, Krauthamer M, Bjalme-Evans M (January 2022). "Wegovy (semaglutide): a new weight loss drug for chronic weight management". Journal of Investigative Medicine. 70 (1): 5–13. doi:10.1136/jim-2021-001952. PMC 8717485. PMID 34706925.
  20. ^ Phillips A, Clements JN (February 2022). "Clinical review of subcutaneous semaglutide for obesity". Journal of Clinical Pharmacy and Therapeutics. 47 (2): 184–193. doi:10.1111/jcpt.13574. PMID 34964141. S2CID 245538758.
  21. ^ Amaro A, Sugimoto D, Wharton S (January 2022). "Efficacy and safety of semaglutide for weight management: evidence from the STEP program". Postgraduate Medicine. 134 (sup1): 5–17. doi:10.1080/00325481.2022.2147326. PMID 36691309. S2CID 256192982.
  22. ^ Cite error: The named reference doggrell was invoked but never defined (see the help page).
  23. ^ Cite error: The named reference goldenberg was invoked but never defined (see the help page).
  24. ^ Hughes S, Neumiller JJ (January 2020). "Oral Semaglutide". Clinical Diabetes. 38 (1): 109–111. doi:10.2337/cd19-0079. PMC 6969659. PMID 31975761.
  25. ^ "Ozempic Drug Trial Snapshot". U.S. Food and Drug Administration (FDA). 5 December 2017. Archived from the original on 31 December 2023. Retrieved 31 December 2023. Public Domain This article incorporates text from this source, which is in the public domain.
  26. ^ Cite error: The named reference Ozempic FDA approval was invoked but never defined (see the help page).
  27. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  28. ^ "Semaglutide Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.