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
Molecular Formula C149H234N40O47S
Molecular Weight 3369.757
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 29 / 29
E/Z Centers 19
Optical Activity UNSPECIFIED

Approval Year

Unknown
139594
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:58:54 UTC 2023
Edited
by admin
on Fri Dec 15 17:58:54 UTC 2023
Record UNII
5313W10MYT
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
EU-Orphan Drug EU/3/16/1750
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
FDA ORPHAN DRUG 522116
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
NCI_THESAURUS C547
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
Code System Code Type Description
FDA UNII
5313W10MYT
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
PRIMARY
INN
11016
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
PRIMARY
EVMPD
SUB33795
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
PRIMARY
USAN
FG-85
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
PRIMARY
MANUFACTURER PRODUCT INFORMATION
EXENDIN (9-39) AMIDE
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
PRIMARY
NCI_THESAURUS
C133230
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
PRIMARY
DRUG BANK
DB14806
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
PRIMARY
CLINICAL_TRIALS.GOV
EXENDIN (9-39) AMIDE
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
PRIMARY
PUBCHEM
129012199
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
PRIMARY
MERCK INDEX
m5225
Created by admin on Fri Dec 15 17:58:54 UTC 2023 , Edited by admin on Fri Dec 15 17:58:54 UTC 2023
PRIMARY Merck Index
Related Record Type Details
Structure of AVEXITIDE ACETATE
SALT/SOLVATE -> PARENT
GLUCAGON-LIKE PEPTIDE 1 RECEPTOR
TARGET -> INHIBITOR
Related Record Type Details
Structure of AVEXITIDE
ACTIVE MOIETY
Exendin-(9,39) is a competitive antagonist of glucagon-like peptide-1 (GLP-1) at its receptor. However, it is unclear if it has direct and unique effects of its own. We tested the hypothesis that exendin-(9,39) and GLP-1-(9,36)amide have direct effects on hormone secretion and .BETA.-cell function as well as glucose metabolism in healthy subjects. Glucose containing (3-(3)H)glucose was infused to mimic the systemic appearance of glucose after a meal. Saline, GLP-1-(9,36)amide, or exendin-(9,39) at 30 pmol/kg/min (Ex 30) or 300 pmol/kg/min (Ex 300) were infused in random order on separate days. Integrated glucose concentrations were slightly but significantly increased by exendin-(9,39) (365 +/- 43 vs. 383 +/- 35 vs. 492 +/- 49 vs. 337 +/- 50 mmol per 6 h, saline, Ex 30, Ex 300, and GLP-1-(9,36)amide, respectively P = 0.05).
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966