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fulipiftide   Click here for help

GtoPdb Ligand ID: 14377

Synonyms: BR 21001 | BR21001 | BRM-421 | BRM421 | PSP 29-mer
Compound class: Peptide
Comment: Fulipiftide (BRM421; BRIM Biotechnology) is a synthetic analogue of pigment epithelium-derived factor (PEDF). The peptide induces regenerative effects (via ERK2 and STAT3 signalling) and has anti-inflammatory activity. It has been used in the study of tendon repair [3], but has been repurposed for dry eye disease [4] where it is reported to stimulate corneal limbal stem cell proliferation/differentiation and increase mucin secretion from goblet cells. Like full-length PEDF, fulipiftide may act through patatin-like phospholipase domain-containing protein 2 (PNPLA2), which is involved in mitogenic signalling in human embryonic and neural stem cells, and other progenitor cells [1-2,5].
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@H](C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H]2CCCN2C(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC3=CC=C(C=C3)O)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)C
Isomeric SMILES C(N[C@H](C(N[C@H](C(N[C@@H](CC1=CN=CN1)C(NCC(N[C@@H]([C@@H](C)O)C(N)=O)=O)=O)=O)[C@H](CC)C)=O)CC(O)=O)(=O)[C@H]2N(C([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](CC3=CC=C(O)C=C3)NC([C@H](CC4=CC=C(O)C=C4)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](CC5=CN=CN5)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC(CNC([C@@H](NC([C@@H](NC(C)=O)CO)=O)CC(C)C)=O)=O)C)=O)CCC(O)=O)=O)CCC(N)=O)=O)CCCNC(=N)N)=O)[C@@H](C)O)=O)CCC(O)=O)=O)CO)=O)[C@H](CC)C)=O)[C@H](CC)C)=O)=O)CCCNC(=N)N)=O)C)=O)CC(C)C)=O)=O)=O)CC(O)=O)=O)CC(C)C)=O)[C@H](CC)C)=O)CO)=O)CO)=O)CCC2
InChI InChI=1S/C144H227N41O47/c1-20-69(11)110(137(227)174-94(52-80-56-151-64-157-80)120(210)156-59-105(197)179-114(75(17)190)116(146)206)181-132(222)97(55-109(204)205)173-136(226)102-29-26-46-185(102)142(232)101(63-189)178-134(224)99(61-187)177-139(229)111(70(12)21-2)180-131(221)91(49-68(9)10)169-130(220)96(54-108(202)203)172-128(218)93(51-79-32-36-83(194)37-33-79)171-127(217)92(50-78-30-34-82(193)35-31-78)170-126(216)90(48-67(7)8)167-118(208)74(16)160-121(211)84(27-24-44-153-143(147)148)164-129(219)95(53-81-57-152-65-158-81)175-138(228)112(71(13)22-3)183-140(230)113(72(14)23-4)182-135(225)100(62-188)176-124(214)88(40-43-107(200)201)166-141(231)115(76(18)191)184-125(215)85(28-25-45-154-144(149)150)163-122(212)86(38-41-103(145)195)165-123(213)87(39-42-106(198)199)162-117(207)73(15)159-104(196)58-155-119(209)89(47-66(5)6)168-133(223)98(60-186)161-77(19)192/h30-37,56-57,64-76,84-102,110-115,186-191,193-194H,20-29,38-55,58-63H2,1-19H3,(H2,145,195)(H2,146,206)(H,151,157)(H,152,158)(H,155,209)(H,156,210)(H,159,196)(H,160,211)(H,161,192)(H,162,207)(H,163,212)(H,164,219)(H,165,213)(H,166,231)(H,167,208)(H,168,223)(H,169,220)(H,170,216)(H,171,217)(H,172,218)(H,173,226)(H,174,227)(H,175,228)(H,176,214)(H,177,229)(H,178,224)(H,179,197)(H,180,221)(H,181,222)(H,182,225)(H,183,230)(H,184,215)(H,198,199)(H,200,201)(H,202,203)(H,204,205)(H4,147,148,153)(H4,149,150,154)/t69-,70-,71-,72-,73-,74-,75+,76+,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,110-,111-,112-,113-,114-,115-/m0/s1
InChI Key WKXNKQZYGSNBDJ-VGQQASIRSA-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
An opthalmic solution containing fulipiftide (BRM421) was progressed as a clinical candidate for the treatment of dry eye disease (Keratoconjunctivitis Sicca). The FDA granted orphan designation for the treatment of the degenerative corneal disease neurotrophic keratitis in late 2022.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03066219 Safety and Efficacy of BRM421 for Dry Eye Syndrome Phase 2 Interventional BRIM Biotechnology Inc.
NCT04343287 Safety and Efficacy of BRM421 for Dry Eye Syndrome Treatment Phase 2/Phase 3 Interventional BRIM Biotechnology Inc.
NCT05695781 Assessment of the Safety and Efficacy of BRM421 Ophthalmic Solutions in Dry Eye Subjects. Phase 3 Interventional BRIM Biotechnology Inc.
NCT07078955 A Dose Regimen Study of BRM421 Ophthalmic Solution in Patients With Dry Eye Disease Phase 2 Interventional BRIM Biotechnology Inc.