reltecimod   Click here for help

GtoPdb Ligand ID: 13721

Synonyms: AB 103 | AB103 | p2TA
Compound class: Peptide
Comment: Reltecimod is a mimetic peptide that prevents binding of bacterial superantigens to the host target of CD28 [1]. It entered clinical development as an immunomodulating agent, with the aim of reducing the acute inflammatory response observed in patients with necrotizing soft tissue infections (NSTIs) that can lead to organ failure [2-3].
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 CC(C)C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](C)C(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@@H]2CCCN2C(=O)[C@H](CO)NC(=O)[C@@H](C)N
Isomeric SMILES C[C@H](C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](C)C(=O)O)N
InChI InChI=1S/C46H72N10O15S/c1-22(2)18-30(52-39(63)29(15-17-72-8)50-43(67)34-10-9-16-56(34)45(69)33(21-57)54-37(61)24(5)47)42(66)55-36(23(3)4)44(68)48-25(6)38(62)51-31(19-27-11-13-28(58)14-12-27)41(65)53-32(20-35(59)60)40(64)49-26(7)46(70)71/h11-14,22-26,29-34,36,57-58H,9-10,15-21,47H2,1-8H3,(H,48,68)(H,49,64)(H,50,67)(H,51,62)(H,52,63)(H,53,65)(H,54,61)(H,55,66)(H,59,60)(H,70,71)/t24-,25+,26-,29+,30+,31+,32+,33+,34+,36+/m1/s1
InChI Key VRNHFZYMPDKTBS-WYUJEMNCSA-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. Arad G, Levy R, Nasie I, Hillman D, Rotfogel Z, Barash U, Supper E, Shpilka T, Minis A, Kaempfer R. (2011)
Binding of superantigen toxins into the CD28 homodimer interface is essential for induction of cytokine genes that mediate lethal shock.
PLoS Biol, 9 (9): e1001149. [PMID:21931534]
2. Bulger EM, Maier RV, Sperry J, Joshi M, Henry S, Moore FA, Moldawer LL, Demetriades D, Talving P, Schreiber M et al.. (2014)
A Novel Drug for Treatment of Necrotizing Soft-Tissue Infections: A Randomized Clinical Trial.
JAMA Surg, 149 (6): 528-36. [PMID:24740134]
3. Bulger EM, May AK, Robinson BRH, Evans DC, Henry S, Green JM, Toschlog E, Sperry JL, Fagenholz P, Martin ND et al.. (2020)
A Novel Immune Modulator for Patients With Necrotizing Soft Tissue Infections (NSTI): Results of a Multicenter, Phase 3 Randomized Controlled Trial of Reltecimod (AB 103).
Ann Surg, 272 (3): 469-478. [PMID:32657946]
4. Ramachandran G, Tulapurkar ME, Harris KM, Arad G, Shirvan A, Shemesh R, Detolla LJ, Benazzi C, Opal SM, Kaempfer R et al.. (2013)
A peptide antagonist of CD28 signaling attenuates toxic shock and necrotizing soft-tissue infection induced by Streptococcus pyogenes.
J Infect Dis, 207 (12): 1869-77. [PMID:23493729]