U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C149H234N40O47S
Molecular Weight 3369.757
Optical Activity UNSPECIFIED
Defined Stereocenters 29 / 29
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AVEXITIDE

SMILES

[H][C@](NC(=O)[C@H](CC1=CC=CC=C1)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(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC2=CNC3=CC=CC=C23)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)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(N)=O

InChI

InChIKey=WSEVKKHALHSUMB-RYVRVIGHSA-N
InChI=1S/C149H234N40O47S/c1-14-78(10)120(185-139(227)98(62-81-29-16-15-17-30-81)177-136(224)97(61-76(6)7)175-129(217)88(35-24-53-158-149(156)157)172-144(232)119(77(8)9)184-122(210)79(11)164-126(214)90(41-46-114(199)200)168-131(219)91(42-47-115(201)202)169-132(220)92(43-48-116(203)204)170-134(222)94(50-58-237-13)171-130(218)89(40-45-109(153)194)167-127(215)86(33-20-22-51-150)166-140(228)103(72-192)182-137(225)95(59-74(2)3)174-123(211)84(152)64-118(207)208)145(233)173-93(44-49-117(205)206)133(221)178-99(63-82-66-159-85-32-19-18-31-83(82)85)138(226)176-96(60-75(4)5)135(223)165-87(34-21-23-52-151)128(216)179-100(65-110(154)195)124(212)161-67-111(196)160-69-113(198)186-54-25-36-105(186)142(230)183-104(73-193)141(229)181-102(71-191)125(213)162-68-112(197)163-80(12)146(234)188-56-27-38-107(188)148(236)189-57-28-39-108(189)147(235)187-55-26-37-106(187)143(231)180-101(70-190)121(155)209/h15-19,29-32,66,74-80,84,86-108,119-120,159,190-193H,14,20-28,33-65,67-73,150-152H2,1-13H3,(H2,153,194)(H2,154,195)(H2,155,209)(H,160,196)(H,161,212)(H,162,213)(H,163,197)(H,164,214)(H,165,223)(H,166,228)(H,167,215)(H,168,219)(H,169,220)(H,170,222)(H,171,218)(H,172,232)(H,173,233)(H,174,211)(H,175,217)(H,176,226)(H,177,224)(H,178,221)(H,179,216)(H,180,231)(H,181,229)(H,182,225)(H,183,230)(H,184,210)(H,185,227)(H,199,200)(H,201,202)(H,203,204)(H,205,206)(H,207,208)(H4,156,157,158)/t78-,79-,80-,84-,86-,87-,88-,89+,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,119-,120-/m0/s1

HIDE SMILES / InChI

Approval Year

Unknown
139594
Name Type Language
AVEXITIDE
USAN   INN  
Official Name English
avexitide [INN]
Common Name English
9-39-EXENDIN 4 (HELODERMA SUSPECTUM)
Common Name English
L-SERINAMIDE, 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-
Systematic Name English
EXENDIN 3 (HELODERMA HORRIDUM HORRIDUM (MEXICAN BEADED LIZARD)) (9-39)-PEPTIDE 39-AMIDE: L-.ALPHA.-ASPARTYL-L-LEUCYL-L-SERYL-L-LYSYL-L-GLUTAMINYL-LMETHIONYL-L-.ALPHA.-GLUTAMYL-L-.ALPHA.-GLUTAMYL-L-.ALPHA.-GLUTAMYL-L-ALANYL-L-VALYL-L-ARGINYL-L-LEUCYL-L-PH
Systematic Name English
EXENDIN (9-39) AMIDE
Common Name English
ASP-LEU-SER-LYS-GLN-MET-GLU-GLU-GLU-ALA-VAL-ARG-LEU-PHE-LLE-GLU-TRP-LEU-LYS-ASN-GIY-GIY-PRO-SER-SER-GIY-ALA-PRO-PRO-PRO-SER-NH2
Common Name English
AVEXITIDE [USAN]
Common Name English
EXENDIN (9-39) [MI]
Common Name English
EXENDIN (9-39)
MI  
Common Name English
EXENDIN-3 (9-39) AMIDE
Common Name English
EXENDIN(9-39)AMIDE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 321310
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
EU-Orphan Drug EU/3/16/1750
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
FDA ORPHAN DRUG 522116
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
NCI_THESAURUS C547
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
Code System Code Type Description
FDA UNII
5313W10MYT
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY
INN
11016
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY
EVMPD
SUB33795
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY
USAN
FG-85
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY
MANUFACTURER PRODUCT INFORMATION
EXENDIN (9-39) AMIDE
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY Biological Activity: Potent and selective GLP-1 receptor antagonist (Kd = 1.7 nM at cloned human GLP-1 receptors). Inhibits cAMP production and insulin release induced by GLP-1 (7-36), exendin-3 (IC50 = 20 nM) and exendin-4. Blocks the inhibitory effect of GLP-1 on food intake in rats.
CAS
133514-43-9
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY
NCI_THESAURUS
C133230
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY
DRUG BANK
DB14806
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY
CLINICAL_TRIALS.GOV
EXENDIN (9-39) AMIDE
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY Official Title: Effect of GLP-1 on Glucose Metabolism in Healthy Subjects and Patients With T2DM. Part 1: A Pilot Study to Assess the Efficacy of Exendin(9-39)Amide as a GLP-1 Receptor Antagonist in Healthy SubjectsDetailed Description: Exendin(9-39) has been shown a specific and reversible antagonist at the human GLP-1 receptor in vivo. In initial validation studies intravenous exendin(9-39) dose-dependently reduced the insulinotropic action of intravenous GLP-1. The maximal dose of 300 pmol/kg/min used in these studies was sufficient to reduce GLP-1 stimulated insulin plasma levels by about 83%. However, to quantify the contribution of incretin hormones to the incretin effect as stated above a nearly complete inhibition of the GLP-1 action is necessary.Therefore the purpose of this pilot study is to characterize the dose-response characteristics of exendin(9-39) more completely and to find a dosage which inhibits the insulinotropic action of GLP-1 by at least 95%.
EPA CompTox
DTXSID00158156
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY
PUBCHEM
129012199
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY
MERCK INDEX
m5225
Created by admin on Fri Dec 15 17:58:54 GMT 2023 , Edited by admin on Fri Dec 15 17:58:54 GMT 2023
PRIMARY Merck Index
ACTIVE MOIETY
Structure of AVEXITIDE
SALT/SOLVATE (PARENT)
Structure of AVEXITIDE ACETATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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