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trofinetide   Click here for help

GtoPdb Ligand ID: 12482

Synonyms: ACP-2566 | analogue 4 [PMID: 15837309] | Daybue® | glycyl-alpha-methyl-L-prolyl-L-glutamic acid | NNZ-2566 | NNZ2566
Approved drug
trofinetide is an approved drug (FDA (2023))
Compound class: Peptide
Comment: Trofinetide (NNZ-2566), a synthetic analogue of the amino‐terminal tripeptide of insulin-like growth factor 1 (IGF-1; GPE). It was developed as a neuroprotective agent, for potential application in neurodegenerative diseases of the central nervous system, and traumatic brain injury.
The endogenous glycine-proline-glutamate tripeptide (GPE, Glypromate) is present in the brain [7], and it has been demonstrated to partially reverse core symptoms in Mecp2-deficient mice that are a model of human Rett syndrome [8]. Trofinetide has been modified to offer a longer half-life than GPE.

trofinetide is commercially available from our sponsors

2D Structure
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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.

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SMILES / InChI / InChIKey
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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/)

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Canonical SMILES C[C@]1(CCCN1C(=O)CN)C(=O)N[C@@H](CCC(=O)O)C(=O)O
Isomeric SMILES C[C@]1(CCCN1C(=O)CN)C(=O)N[C@@H](CCC(=O)O)C(=O)O
InChI InChI=1S/C13H21N3O6/c1-13(5-2-6-16(13)9(17)7-14)12(22)15-8(11(20)21)3-4-10(18)19/h8H,2-7,14H2,1H3,(H,15,22)(H,18,19)(H,20,21)/t8-,13-/m0/s1
InChI Key BUSXWGRAOZQTEY-SDBXPKJASA-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/)
Classification Click here for help
Compound class Peptide
Approved drug? Yes. US FDA (2023)
IUPAC Name Click here for help
(2S)-2-[[(2S)-1-(2-aminoacetyl)-2-methylpyrrolidine-2-carbonyl]amino]pentanedioic acid
International Nonproprietary Names Click here for help
INN number INN
10076 trofinetide
Synonyms Click here for help
ACP-2566 | analogue 4 [PMID: 15837309] | Daybue® | glycyl-alpha-methyl-L-prolyl-L-glutamic acid | NNZ-2566 | NNZ2566
Database Links Click here for help
CAS Registry No. 853400-76-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL197084
DrugBank Ligand DB06045
GtoPdb PubChem SID 479821272
PubChem CID 11318905
Search Google for chemical match using the InChIKey BUSXWGRAOZQTEY-SDBXPKJASA-N
Search Google for chemicals with the same backbone BUSXWGRAOZQTEY
Search PubMed clinical trials trofinetide
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UniChem Compound Search for chemical match using the InChIKey BUSXWGRAOZQTEY-SDBXPKJASA-N
UniChem Connectivity Search for chemical match using the InChIKey BUSXWGRAOZQTEY-SDBXPKJASA-N

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

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MedChemExpress
Trofinetide (links to external site)
Cat. No. HY-16757