Exenatide

Exenatide
Single conformer of the solution NMR structure of exenatide. PDB: 7MLL​
Clinical data
Pronunciation/ɛɡzˈɛnətaɪd/ ⓘ
Trade namesByetta, Bydureon, Bydureon BCise, others
AHFS/Drugs.comMonograph
MedlinePlusa605034
License data
Pregnancy
category
  • AU: C
Routes of
administration		Subcutaneous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)[1][2]
  • US: ℞-only[3][4][5]
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityN/A
Metabolismproteolysis
Elimination half-life2.4 h
ExcretionKidney
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.212.123
Chemical and physical data
FormulaC184H282N50O60S
Molar mass4186.63 g·mol−1
3D model (JSmol)
SMILES
  • [H]/N=C(\N)/NCCC[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc2c[nH]c3c2cccc3)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N)C(=O)NCC(=O)NCC(=O)N4CCC[C@H]4C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N5CCC[C@H]5C(=O)N6CCC[C@H]6C(=O)N7CCC[C@H]7C(=O)N[C@@H](CO)C(=O)N)NC(=O)[C@H](C(C)C)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(=O)N)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]([C@@H](C)O)NC(=O)[C@H](Cc8ccccc8)NC(=O)[C@H]([C@@H](C)O)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)[C@H](Cc9cnc[nH]9)N
InChI
  • InChI=1S/C184H282N50O60S/c1-16-94(10)147(178(289)213-114(52-58-144(257)258)163(274)218-121(73-101-77-195-105-39-24-23-38-103(101)105)168(279)215-116(68-90(2)3)165(276)205-107(41-26-28-61-186)158(269)219-122(75-134(189)243)154(265)198-79-135(244)196-83-139(248)231-63-30-43-129(231)175(286)225-127(87-238)174(285)223-125(85-236)155(266)200-80-136(245)202-96(12)181(292)233-65-32-45-131(233)183(294)234-66-33-46-132(234)182(293)232-64-31-44-130(232)176(287)222-124(84-235)150(190)261)229-170(281)119(71-99-34-19-17-20-35-99)217-166(277)117(69-91(4)5)214-159(270)108(42-29-62-194-184(191)192)212-177(288)146(93(8)9)228-151(262)95(11)203-156(267)111(49-55-141(251)252)208-161(272)112(50-56-142(253)254)209-162(273)113(51-57-143(255)256)210-164(275)115(59-67-295-15)211-160(271)110(47-53-133(188)242)207-157(268)106(40-25-27-60-185)206-172(283)126(86-237)224-167(278)118(70-92(6)7)216-169(280)123(76-145(259)260)220-173(284)128(88-239)226-180(291)149(98(14)241)230-171(282)120(72-100-36-21-18-22-37-100)221-179(290)148(97(13)240)227-138(247)82-199-153(264)109(48-54-140(249)250)204-137(246)81-197-152(263)104(187)74-102-78-193-89-201-102/h17-24,34-39,77-78,89-98,104,106-132,146-149,195,235-241H,16,25-33,40-76,79-88,185-187H2,1-15H3,(H2,188,242)(H2,189,243)(H2,190,261)(H,193,201)(H,196,244)(H,197,263)(H,198,265)(H,199,264)(H,200,266)(H,202,245)(H,203,267)(H,204,246)(H,205,276)(H,206,283)(H,207,268)(H,208,272)(H,209,273)(H,210,275)(H,211,271)(H,212,288)(H,213,289)(H,214,270)(H,215,279)(H,216,280)(H,217,277)(H,218,274)(H,219,269)(H,220,284)(H,221,290)(H,222,287)(H,223,285)(H,224,278)(H,225,286)(H,226,291)(H,227,247)(H,228,262)(H,229,281)(H,230,282)(H,249,250)(H,251,252)(H,253,254)(H,255,256)(H,257,258)(H,259,260)(H4,191,192,194)/t94-,95-,96-,97+,98+,104-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,146-,147-,148-,149-/m0/s1 N
  • Key:HTQBXNHDCUEHJF-XWLPCZSASA-N N
 NY (what is this?)  (verify)

Exenatide, sold under the brand name Byetta among others, is a medication used to treat type 2 diabetes.[6] It is used together with diet, exercise, and potentially other antidiabetic medication.[6] It is a treatment option after metformin and sulfonylureas.[7] It is given by injection under the skin.[6]

Common side effects include low blood sugar, nausea, dizziness, abdominal pain, and pain at the site of injection.[6] Other serious side effects may include medullary thyroid cancer, angioedema, pancreatitis, and kidney injury.[6] Use in pregnancy and breastfeeding is of unclear safety.[8] Exenatide is a glucagon-like peptide-1 receptor agonist (GLP-1 receptor agonist) also known as incretin mimetics.[6] It works by increasing insulin release from the pancreas and decreases excessive glucagon release.[6]

Exenatide was approved for medical use in the United States in 2005.[6] In 2019, it was the 312th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[9]

  1. ^ Cite error: The named reference UKByettalabel was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference UKBydureonlabel was invoked but never defined (see the help page).
  3. ^ "Bydureon- exenatide injection, suspension, extended release Bydureon- exenatide kit". DailyMed. 28 February 2020. Retrieved 2 December 2020.
  4. ^ "Bydureon BCise- exenatide injection, suspension, extended release". DailyMed. 28 February 2020. Retrieved 2 December 2020.
  5. ^ "Byetta- exenatide injection". DailyMed. 28 February 2020. Retrieved 2 December 2020.
  6. ^ a b c d e f g h "Exenatide Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 22 March 2019.
  7. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 684–685. ISBN 978-0-85711-338-2.
  8. ^ "Exenatide Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved 3 March 2019.
  9. ^ "Exenatide - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
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