Mifamurtide

DRACPC ID  DRACPC0011

Active Ingredients   Mifamurtide

Description  A liposomal formulation containing a muramyl dipeptide (MDP) analogue with potential immunomodulatory and antineoplastic activities. Muramyl tripeptide phosphatidylethanolamine (MTP-PE), a derivative of the mycobacterial cell wall component MDP, activates both monocytes and macrophages. Activated macrophages secrete cytokines and induce the recruitment and activation of other immune cells, which may result in indirect tumoricidal effects. Liposomal encapsulation of MTP-PE prolongs its half-life and enhances tissue targeting.

Synonyms  CGP 19835A Lipid; Junovan; L-Alaninamide, 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)-, Monosodium Salt, Hydrate; L-MTP-PE; Mepact; MTP-PE Liposome; muramyl tripeptide phosphatidylethanolamine; Muramyl Tripeptide Phosphatidylethanolamine Liposome; MuramylNAc-Ala-isoGln-Lys-tripeptide-PE; Mifamurtide

Type  Small Molecule

Disease  Osteosarcoma 

Classification

  

Immunomodulator Peptide and derivative MDP derivative

Structure Information


Molecular Formula  C59H108N6O19P.Na.H2O

Molecular Weight  1277.5

Active Sequence  Not available

Sequence Length  Not available

Modification  Not available

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  sodium;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]ethyl 2,3-di(hexadecanoyloxy)propyl phosphate;hydrate

InChI  InChI=1S/C59H109N6O19P.Na.H2O/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);;1H2/q;+1;/p-1

InChI_Key NGIYLSFJGRLEMI-UHFFFAOYSA-M

SMILES  CCCCCCCCCCCCCCCC(OCC(OC(CCCCCCCCCCCCCCC)=O)COP([O-])(OCCNC(C(NC(CCC(NC(C(NC(C(OC(C(O)C(O)CO)C(NC(C)=O)C=O)C)=O)C)=O)C(N)=O)=O)C)=O)=O)=O.[H]O[H].[Na+]

External Codes


PubChem CID  123133557

DrugBank Accession Number  DB13615

NCI Thesaurus Code  C1394  

UNII  1LM890Q4FY   GSRS

CAS  838853-48-8



Drug approval


Drug indication
    Indicated in children, adolescents and young adults for the treatment of high-grade, resectable, non-metastatic osteosarcoma after macroscopically complete surgical resection, typically in combination with post-operative multi-agent chemotherapy.

Drug Name Strength Dosage Form/Route Company Marketing Status Drug ID Approval year
Mepact 4 mg Powder; Intravenous Takeda France Sas Prescription EMEA/H/C/000802 2009

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT03643133 Multicentre, Randomised, Phase 2 Trial of Mifamurtide Combined With Post-operative Chemotherapy for Newly Diagnosed High Risk Osteosarcoma Patients (Metastatic Osteosarcoma at Diagnosis or Localised Disease With Poor Histological Response) Osteosarcoma Phase 2 Treatment
NCT00631631 Liposomal Muramyl Tripeptide Phosphatidyl Ethanolamine (L-MTP-PE) for High-risk Osteosarcoma Osteosarcoma Treatment
NCT02441309 A Mechanistic Study Of Mifamurtide (MTP-PE) In Patients With Metastatic And/Or Recurrent Osteosarcoma Osteosarcoma Phase 2 Treatment
NCT01459484 ABCB1/P-glycoprotein Expression as Biologic Stratification Factor for Patients With Non Metastatic Osteosarcoma - Prospective Study (ISG/OS-2) Osteosarcoma Phase 2 Treatment
NCT04062721 Feasibility and Safety of Local Immunomodulation Combined With Radiofrequency Ablation for Unresectable Colorectal Liver Metastases: A Monocentric Phase I Trial Unresectable Colorectal Liver Metastases Phase 1 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





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