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Substance Name: Exenatide [USAN:INN:BAN:JAN]
RN: 141758-74-9
UNII: 9P1872D4OL
InChIKey: HTQBXNHDCUEHJF-XWLPCZSASA-N

Note

  • Isolated from the venom of the lizard Heloderma suspectum; increases pancreatic acinar cAMP; identical to exendin-3 except that Gly(2)-Glu(3) replaces Ser(2)-Asp(3); exenatide is a synthetic version of exendin-4; has antidiabetic and antiobesity activities; binds to GLP-1 receptor as GLP-1 agonist.

Molecular Formula

  • C184-H282-N50-O60-S

Molecular Weight

  • 4186.6078
 

Classification Codes

  • Antidiabetic
  • GLP-1 Receptor Agonist
  • Hormone Antagonists
  • Hormones
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Hypoglycemic Agents
  • Incretins

Names and Synonyms

Name of Substance

  • Exenatide
  • Exenatide [USAN:INN:BAN:JAN]

Synonyms

  • AC 2993
  • AC 2993A
  • AC-2993
  • AC002993
  • AC2993
  • AC2993A
  • Bydureon
  • Bydureon Pen
  • Byetta
  • DA 3091
  • Exenatide
  • Exenatide Synthetic
  • Exendin 4
  • HSDB 7789
  • ITCA 650
  • LY 2148568
  • LY2148568
  • PT302
  • UNII-9P1872D4OL

Systematic Names

  • Exendin 3 (Heloderma horridum), 2-glycine-3-L-glutamic acid-
  • Exendin 4 (Heloderma suspectum)
  • L-Serinamide, L-histidylglycyl-L-alpha-glutamylglycyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-alpha-aspartyl-L-leucyl-L-seryl-L-lysyl-L-glutaminyl-L-methionyl-L-alpha-glutamyl-L-alpha-glutamyl-L-alpha-glutamyl-L-alanyl-L-valyl-L-arginyl-L-leucyl-L-phenylalanyl-L-isoleucyl-L-alpha-glutamyl-L-tryptophyl-L-leucyl-L-lysyl-L-asparaginylglycylglycyl-L-prolyl-L-seryl-L-serylglycyl-L-alanyl-L-prolyl-L-prolyl-L-prolyl-

Registry Numbers

CAS Registry Number

  • 141758-74-9

FDA UNII

  • 9P1872D4OL

Other Registry Numbers

  • 141732-76-5
  • 286014-72-0
  • 335149-21-8

System Generated Number

  • 0141758749

Structure Descriptors

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

InChIKey

HTQBXNHDCUEHJF-XWLPCZSASA-N

Smiles

CC[C@H](C)[C@H](NC(=O)[C@H](Cc1ccccc1)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(=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](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)[C@@H](N)Cc3c[nH]cn3)[C@@H](C)O)[C@@H](C)O)C(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc4c[nH]c5ccccc45)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)N6CCC[C@H]6C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N7CCC[C@H]7C(=O)N8CCC[C@H]8C(=O)N9CCC[C@H]9C(=O)N[C@@H](CO)C(=O)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
monkey LD subcutaneous > 5mg/kg (5mg/kg)   Toxicologist. Vol. 48, Pg. 324, 1999.
rat LD subcutaneous > 30mg/kg (30mg/kg)   Toxicologist. Vol. 48, Pg. 324, 1999.