83461-56-7 Usage
Description
N-Acetylmuramyl-alanyl-isoglutaminyl-alanyl-sn-glycero-3-phosphoethanolamine is a complex molecule that plays a crucial role in the structure and function of bacterial cell walls. It is a component of peptidoglycan, a polymer that forms the rigid layer of the cell wall, providing protection and maintaining cell shape. This molecule is also involved in cell division and communication processes in bacteria.
Used in Pharmaceutical Industry:
N-Acetylmuramyl-alanyl-isoglutaminyl-alanyl-sn-glycero-3-phosphoethanolamine is used as a drug candidate for the development of novel antibiotics targeting bacterial cell wall synthesis. Its unique structure and function make it a promising target for the design of new antimicrobial agents that can overcome the growing problem of antibiotic resistance.
Used in Research Applications:
N-Acetylmuramyl-alanyl-isoglutaminyl-alanyl-sn-glycero-3-phosphoethanolamine is used as a research tool for studying the molecular mechanisms of bacterial cell wall synthesis, cell division, and communication. It can be employed in various experimental setups, such as in vitro assays and animal models, to investigate the role of this molecule in bacterial physiology and pathogenesis.
Used in Osteosarcoma Treatment:
N-Acetylmuramyl-alanyl-isoglutaminyl-alanyl-sn-glycero-3-phosphoethanolamine is used as a component of Mifamurtide, a drug approved for the treatment of osteosarcoma, a type of bone cancer. Mifamurtide is believed to enhance the immune response against cancer cells, leading to improved outcomes for patients with this aggressive malignancy.
Used in Immunological and Cancer-Related Cell Signaling Studies:
N-Acetylmuramyl-alanyl-isoglutaminyl-alanyl-sn-glycero-3-phosphoethanolamine is used as a research compound for investigating the immunological and cell signaling pathways involved in cancer development and progression. Its role in modulating immune responses and cell communication can provide valuable insights into the molecular mechanisms underlying cancer growth and metastasis, potentially leading to the discovery of new therapeutic targets and strategies.
Biochem/physiol Actions
Mifamurtide is an immunomodulator and regulates the activation of monocytes and macrophages. Mifamurtide upregulates the secretion of pro-inflammatory cytokines such as TNF-α, IL-1, IL-8, nitric oxide and prostaglandins E2 and D2. It has anti-tumor effects in children and young adults with high-grade osteosarcoma.
Mechanism of action
Being a
phospholipid, mifamurtide accumulates in the lipid bilayer of the liposomes upon infusion. After
application of the liposomal infusion, the drug is cleared from the plasma within minutes. However, it is
concentrated in lung, liver, spleen, nasopharynx and thyroid, and the terminal half-life is 18 hours,
which is longer than the natural substance.
Clinical Use
Mifamurtide is an anticancer agent for the treatment of osteosarcoma, the most common primary
malignancy of bone tissue mainly affecting children and adolescents. The drug was invented by
Ciba-Geigy (now Novartis) in the early 1980s and the agent was subsequently licensed to Jenner
Biotherapies in the 1990s. IDM Pharma bought the rights to the drug from Jenner in April 2003.In March 2009, mifamurtide was approved in the 27 European Union member states plus Iceland,
Liechtenstein and Norway via a centralized marketing authorization. After the approval, IDM Pharma
was acquired by Takeda, which began launching mifamurtide, as Mepact ?, in February 2010.
Mifamurtide, a fully synthetic lipophilic derivative of muramyl dipeptide (MDP), is muramyl tripeptide
phosphatidylethanolamine (MTP-PE), which is formulated as a liposomal infusion.
Synthesis
Two synthetic routes have been reported, and
the scheme describes the more process-amenable route. Commercially available 1,2-dipalmitoyl-snglycero-
3-phosphoethanolamine (110) was coupled with N-Boc-L-alanine (111) by means of Nhydroxysuccinimide
(112), DCC in DMF to give amide 113, which was followed by hydrogenolysis of
the CBZ group to give the corresponding L-alanyl-phosphoric acid 114. Next, commercially available
N-acetylmuramoyl-L-alanyl-D-isoglutamine (115) was subjected to hydroxybenzotriazole (HOBT) and
DIC in DMF to provide the corresponding succinimide ester 116 which was condensed with compound
114 to provide mifamurtide (IX). No yields were provided for these transformations.
Drug interactions
Potentially hazardous interactions with other drugs
Analgesics: avoid with high dose NSAIDs.
Ciclosporin: avoid concomitant use.
Corticosteroids: avoid concomitant use.
Tacrolimus: avoid concomitant use.
Metabolism
The cells of the reticuloendothelial system clear
mifamurtide liposomes by phagocytosis.
Check Digit Verification of cas no
The CAS Registry Mumber 83461-56-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,3,4,6 and 1 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 83461-56:
(7*8)+(6*3)+(5*4)+(4*6)+(3*1)+(2*5)+(1*6)=137
137 % 10 = 7
So 83461-56-7 is a valid CAS Registry Number.
InChI:InChI=1/C59H109N6O19P/c1-7-9-11-13-15-17-19-21-23-25-27-29-31-33-52(71)80-41-47(84-53(72)34-32-30-28-26-24-22-20-18-16-14-12-10-8-2)42-82-85(78,79)81-38-37-61-57(75)43(3)62-51(70)36-35-48(56(60)74)65-58(76)44(4)63-59(77)45(5)83-55(54(73)50(69)40-67)49(39-66)64-46(6)68/h39,43-45,47-50,54-55,67,69,73H,7-38,40-42H2,1-6H3,(H2,60,74)(H,61,75)(H,62,70)(H,63,77)(H,64,68)(H,65,76)(H,78,79)
