Mifamurtide is a drug against osteosarcoma, a kind of bone cancer mainly affecting children and young adults, which is lethal in about a third of cases.
CAT No: 10-101-165
CAS No:83461-56-7
Synonyms/Alias:83461-56-7;CGP-19835;[(2R)-3-[2-[[(2S)-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoyl]amino]propanoyl]amino]ethoxy-hydroxyphosphoryl]oxy-2-hexadecanoyloxypropyl] hexadecanoate;MTP-cephalin;CHEMBL2111100;CHEBI:135906;Mifamurtide; L-Alaninamide, N-(N-acetylmuramoyl)-L-alanyl-D-a-glutaminyl-N-[(7R)-4-hydroxy-4-oxido-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacos-1-yl]-; L-Alaninamide, N-(N-acetylmuramoyl)-L-alanyl-D-a-glutaminyl-N-[4-hydroxy-10-oxo-7-[(1-oxohexadecyl);N-(N-Acetylmuramoyl)-L-alanyl-D-alpha-glutaminyl-N-[(7R)-4-hydroxy-4-oxido-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacos-1-yl]-L-alaninamide;
Mifamurtide is a synthetic immunomodulatory compound structurally derived from muramyl dipeptide, a naturally occurring component of bacterial cell walls. As a member of the muramyl peptide family, it is characterized by its ability to interact with innate immune receptors and modulate macrophage activity. Mifamurtide's unique biochemical structure and mechanism of action have made it a valuable tool in immunological research, particularly for investigations into host-pathogen interactions, innate immunity, and macrophage signaling pathways. Its utility extends to studies aiming to elucidate the molecular underpinnings of immune activation and inflammatory responses, rendering it a compound of significant interest for both fundamental and applied bioscience research.
Immunology research: Mifamurtide is extensively utilized in experimental immunology to probe the mechanisms underlying innate immune activation. By mimicking pathogen-associated molecular patterns, it serves as a potent agonist for NOD2 and related intracellular pattern recognition receptors. Researchers employ it to dissect the signaling cascades initiated upon recognition of muramyl dipeptide motifs, enabling a deeper understanding of cytokine induction, inflammatory mediator release, and the orchestration of early immune responses. Its defined structure and reproducible activity facilitate controlled studies on immune cell activation dynamics in vitro and ex vivo.
Macrophage activation studies: The compound is a well-established agent for selective activation of macrophages in cell-based assays. Its interaction with mononuclear phagocytes leads to the upregulation of key effector functions such as phagocytosis, reactive oxygen species production, and antigen presentation. Investigators leverage these properties to model the innate immune response to bacterial infection, evaluate the impact of macrophage activation on downstream immunological events, and assess the functional consequences of genetic or pharmacological modulation of macrophage pathways.
Inflammatory signaling investigations: Mifamurtide serves as a standardized stimulus for examining inflammatory signaling networks in diverse cell types. Its ability to trigger NF-κB and MAPK pathways makes it a valuable reagent for delineating the molecular events that drive pro-inflammatory gene expression. Researchers use it to study the kinetics of signal transduction, the interplay between different intracellular pathways, and the regulatory mechanisms that modulate inflammatory output. Such studies are crucial for identifying novel targets for anti-inflammatory intervention and for understanding the basis of immune dysregulation.
Host-pathogen interaction modeling: The compound's structural mimicry of bacterial cell wall fragments allows it to be employed in models of host-pathogen interactions. By simulating the presence of bacterial components, mifamurtide enables controlled investigation of the cellular and molecular responses elicited during infection. This application is particularly relevant for elucidating how innate immune sensors discriminate between self and non-self, how tolerance or hyper-responsiveness develops, and how the immune system orchestrates a coordinated defense against microbial invaders.
Adjuvant mechanism research: Mifamurtide is also used to explore the fundamental principles of adjuvanticity in vaccine development and immunotherapeutic strategies. Its capacity to enhance antigen-specific immune responses via innate immune activation provides a basis for studying how muramyl peptides can potentiate adaptive immunity. Investigators employ it to assess the impact of innate immune priming on antigen presentation, T-cell activation, and the generation of immunological memory, contributing to the rational design of novel adjuvants and immunomodulatory agents for research use.
Mifamurtide, also known as liposomal muramyl tripeptide phosphatidyl ethanolamine (L-MTP-PE), has been approved for the treatment of osteosarcoma in Europe. Mifamurtide's rational drug design employs MTP-PE for macrophage activation in a multilamellar liposome drug carrier, containing the synthetic phospholipids 1-palmitoyl-2-oleoyl phosphatidyl choline (POPC) and 1,2-dioleoyl phosphatidyl serine (OOPS). Although the drug is not cytotoxic towards normal or tumor cells in vitro, immune activation against osteosarcoma lung metastases in vivo accounts for mifamurtide's antiosteosarcoma effects. Phosphatidyl serine-containing lipids signal macrophage cells that have "flipped phosphatidyl serine" to the outer membrane after apoptosis (e.g., after damage of tumor cells from chemotherapy); thus, both mifamurtide's active and inactive ingredients target immune cells in the lungs.
Mifamurtide in osteosarcoma: a practical review.
Mifamurtide (liposomal muramyl tripeptide phosphatidylethanolamine; L-MTP-PE) is a new agent. L-MTP-PE is a nonspecific immunomodulator, which is a synthetic analog of a component of bacterial cell walls. L-MTP-PE activates macrophages and monocytes as a potent activator of immune response in addition to standard chemotherapy. It also improves the overall survival from 70 to 78% and results in a one-third reduction in the risk of death from osteosarcoma.
Mifamurtide for the treatment of nonmetastatic osteosarcoma
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