teduglutide   Click here for help

GtoPdb Ligand ID: 7049

Synonyms: ALX-0600 | Gattex® | GLP2-2G | Revestive®
Approved drug Immunopharmacology Ligand
teduglutide is an approved drug (FDA and EMA (2012))
Compound class: Peptide
Comment: Teduglutide is a glucagon-like peptide-2 (GLP-2) analogue in which position 2 amino acid alanine is replaced by glycine, increasing the peptide's resistance to proteolytic cleavage by dipeptidyl peptidase-4 (DPP-4) [2]. The chemical structure shown here was generated using the SMILES from PubChem CID 16139605. The intestinotrophic effects of GLP-2 (e.g. promotion of intestinal growth, reduced epithelial cell apoptosis and inflammation) has led to the development of GLP-2 analogues like teduglutide for the treatment of GI disorders such as short bowel syndrome and inflammatory bowel diseases.

teduglutide is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CC(=O)O)[C@H](O)C)[C@H](CC)C)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)CNC(=O)[C@H](Cc1[nH]cnc1)N)CC(=O)O)CO)Cc1ccccc1)CO)CC(=O)O)CCC(=O)O)CCSC)CC(=O)N)CC(C)C)CC(=O)O)CC(=O)N)CC(C)C)C)C)CCCNC(=N)N)CC(=O)O)Cc1ccccc1)CC(=O)N)CC(C)C)CCC(=O)N
Isomeric SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(=O)O)C(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](Cc1cnc[nH]1)N
InChI InChI=1S/C164H252N44O55S/c1-21-77(11)126(156(255)187-95(44-46-114(167)214)141(240)206-130(83(17)211)160(259)186-93(42-33-34-49-165)140(239)202-129(80(14)24-4)159(258)208-131(84(18)212)161(260)200-111(163(262)263)66-125(230)231)203-151(250)100(54-76(9)10)189-145(244)103(57-88-67-175-92-41-32-31-40-90(88)92)192-147(246)105(60-116(169)216)199-157(256)127(78(12)22-2)204-152(251)102(56-87-38-29-26-30-39-87)190-149(248)109(64-123(226)227)195-137(236)94(43-35-50-174-164(171)172)183-134(233)82(16)179-133(232)81(15)180-142(241)98(52-74(5)6)188-146(245)104(59-115(168)215)194-150(249)110(65-124(228)229)196-143(242)99(53-75(7)8)198-158(257)128(79(13)23-3)205-162(261)132(85(19)213)207-153(252)106(61-117(170)217)193-139(238)97(48-51-264-20)185-138(237)96(45-47-120(220)221)184-148(247)108(63-122(224)225)197-155(254)113(72-210)201-144(243)101(55-86-36-27-25-28-37-86)191-154(253)112(71-209)182-119(219)70-177-136(235)107(62-121(222)223)181-118(218)69-176-135(234)91(166)58-89-68-173-73-178-89/h25-32,36-41,67-68,73-85,91,93-113,126-132,175,209-213H,21-24,33-35,42-66,69-72,165-166H2,1-20H3,(H2,167,214)(H2,168,215)(H2,169,216)(H2,170,217)(H,173,178)(H,176,234)(H,177,235)(H,179,232)(H,180,241)(H,181,218)(H,182,219)(H,183,233)(H,184,247)(H,185,237)(H,186,259)(H,187,255)(H,188,245)(H,189,244)(H,190,248)(H,191,253)(H,192,246)(H,193,238)(H,194,249)(H,195,236)(H,196,242)(H,197,254)(H,198,257)(H,199,256)(H,200,260)(H,201,243)(H,202,239)(H,203,250)(H,204,251)(H,205,261)(H,206,240)(H,207,252)(H,208,258)(H,220,221)(H,222,223)(H,224,225)(H,226,227)(H,228,229)(H,230,231)(H,262,263)(H4,171,172,174)/t77-,78-,79-,80-,81-,82-,83+,84+,85+,91-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,126-,127-,128-,129-,130-,131-,132-/m0/s1
InChI Key CILIXQOJUNDIDU-ASQIGDHWSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Blonski W, Buchner AM, Aberra F, Lichtenstein G. (2013)
Teduglutide in Crohn's disease.
Expert Opin Biol Ther, 13 (8): 1207-14. [PMID:23834252]
2. Jeppesen PB. (2012)
Teduglutide, a novel glucagon-like peptide 2 analog, in the treatment of patients with short bowel syndrome.
Therap Adv Gastroenterol, 5 (3): 159-71. [PMID:22570676]
3. Kochar B, Long MD, Shelton E, Young L, Farraye FA, Yajnik V, Herfarth H. (2017)
Safety and Efficacy of Teduglutide (Gattex) in Patients With Crohn's Disease and Need for Parenteral Support Due to Short Bowel Syndrome-associated Intestinal Failure.
J Clin Gastroenterol, 51 (6): 508-511. [PMID:27433811]
4. McKeage K. (2015)
Teduglutide: a guide to its use in short bowel syndrome.
Clin Drug Investig, 35 (5): 335-40. [PMID:25859983]
5. Yazbeck R. (2010)
Teduglutide, a glucagon-like peptide-2 analog for the treatment of gastrointestinal diseases, including short bowel syndrome.
Curr Opin Mol Ther, 12 (6): 798-809. [PMID:21154171]