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gosteganan   Click here for help

GtoPdb Ligand ID: 14105

Synonyms: HPRP-A1 | PL-18
Compound class: Peptide
Comment: Gosteganan is the INN (included in WHO INN proposed list 133, 10th July 2025; formerly PL-18) for a broad-spectrum antimicrobial peptide derived from the N-terminus of the Helicobacter pylori ribosomal protein L1 (RpL1). Gosteganan demonstrates antibacterial activity against both against Gram-negative and Gram-positive bacteria and also has antifungal activity [2]. It is claimed in patent WO2012142855A1 (ProteLight Pharma) [1].
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](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CC1=CC=CC=C1)C(=O)N[C@H](CO)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CC2=CNC3=C2C=CC=C3)C(=O)N[C@H](CC(=O)N)C(=O)N[C@H](CC4=CNC5=C4C=CC=C5)C(=O)N[C@H](CCCCN)C(=O)N)NC(=O)[C@@H](CCCCN)NC(=O)[C@@H](CCCCN)NC(=O)[C@@H](CC6=CC=CC=C6)NC(=O)C
Isomeric SMILES C([C@H](C(N[C@@H](C(N[C@H](CC=1C=2C(NC1)=CC=CC2)C(N[C@H](CCCCN)C(N)=O)=O)=O)CC(N)=O)=O)NC([C@H](NC([C@H](NC([C@H](NC([C@@H](CC3=CC=CC=C3)NC([C@H](NC([C@H](NC([C@H](NC([C@H](NC([C@H](NC([C@H](NC([C@@H](CC4=CC=CC=C4)NC(C)=O)=O)CCCCN)=O)CCCCN)=O)CC(C)C)=O)CCCCN)=O)CCCCN)=O)CC(C)C)=O)=O)CO)=O)CCCCN)=O)CC(C)C)=O)C=5C=6C(NC5)=CC=CC6
InChI InChI=1S/C103H159N25O18/c1-61(2)50-79(121-92(135)76(41-21-27-47-107)117-91(134)75(40-20-26-46-106)119-98(141)82(114-64(7)130)53-65-30-10-8-11-31-65)95(138)118-74(39-19-25-45-105)90(133)116-77(42-22-28-48-108)93(136)122-80(51-62(3)4)96(139)124-83(54-66-32-12-9-13-33-66)99(142)128-87(60-129)103(146)120-78(43-23-29-49-109)94(137)123-81(52-63(5)6)97(140)125-85(56-68-59-113-72-37-17-15-35-70(68)72)101(144)127-86(57-88(110)131)102(145)126-84(55-67-58-112-71-36-16-14-34-69(67)71)100(143)115-73(89(111)132)38-18-24-44-104/h8-17,30-37,58-59,61-63,73-87,112-113,129H,18-29,38-57,60,104-109H2,1-7H3,(H2,110,131)(H2,111,132)(H,114,130)(H,115,143)(H,116,133)(H,117,134)(H,118,138)(H,119,141)(H,120,146)(H,121,135)(H,122,136)(H,123,137)(H,124,139)(H,125,140)(H,126,145)(H,127,144)(H,128,142)/t73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-/m1/s1
InChI Key MQLNDKCRPLFISR-XNXSXEKGSA-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/)
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Summary of Clinical Use Click here for help
Gosteganan is being developed as a treatment for bacterial vaginosis using suppository administration. A Phase 1 study (NCT05340790) to evaluate the safety, tolerability and pharmacokinetics of gosteganan in healthy subjects has begun recruitment.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT05340790 First in Human Study in Healthy Volunteers of Antimicrobial Peptide PL-18 Vaginal Suppositories Phase 1 Interventional Protelight Pharmaceuticals Australia PTY LTD