Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C59H108N6O19P.Na.H2O |
Molecular Weight | 1277.4964 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Na+].CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCCNC(=O)[C@H](C)NC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](NC(C)=O)C=O)C(N)=O)OC(=O)CCCCCCCCCCCCCCC
InChI
InChIKey=NGIYLSFJGRLEMI-MHTUOZSYSA-M
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/t43-,44-,45+,47+,48+,49-,50+,54+,55+;;/m0../s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20481644Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6965228 | https://www.ncbi.nlm.nih.gov/pubmed/2302725 | https://www.ncbi.nlm.nih.gov/pubmed/10851426
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20481644
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6965228 | https://www.ncbi.nlm.nih.gov/pubmed/2302725 | https://www.ncbi.nlm.nih.gov/pubmed/10851426
Mifamurtide (liposomal muramyl tripeptide phosphatidylethanolamine; trade name Mepact) is an immunomodulator with antitumor effects that appear to be mediated via activation of monocytes and macrophages. After intravenous administration, mifamurtide is selectively phagocytosed by monocytes and macrophages. Cytosolic Mifamurtide specifically interacts with nucleotide-binding oligomerization domain 2 (NOD2) receptor that induces nuclear factor (NF)-kB activation and is implicated in innate immune defense. Activation of monocyte-mediated tumoricidal function was observed following in vivo treatment with mifamurtide in phase I/II clinical trials. Intravenous administration of mifamurtide inhibited tumor growth and increased survival in rodent models of lung and liver metastasis. In a large, randomized, open-label, multicenter, phase III trial, the addition of adjuvant (postoperative) mifamurtide to three- or four-drug combination chemotherapy (doxorubicin, cisplatin, and high-dose methotrexate with, or without, ifosfamide) was associated with a statistically significant improvement in overall survival in patients with newly diagnosed, high-grade, non-metastatic, resectable osteosarcoma. The pattern of outcome was generally similar in a small cohort of patients with metastatic disease who were enrolled in this trial. Mifamurtide is generally well tolerated; adverse events attributed to administration of the drug include chills, fever, headache, nausea, and myalgias. In the EU, mifamurtide is indicated in children, adolescents, and young adults for the treatment of high-grade, resectable, non-metastatic osteosarcoma after macroscopically complete surgical resection; it is administered by intravenous infusion in conjunction with postoperative multiagent chemotherapy. In the US, mifamurtide is currently an investigational agent that holds orphan drug status for the treatment of osteosarcoma.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6965228
Curator's Comment: Mifamurtide [N-acetylmuramyl-L-alanyl-D-isoglutamyl-L-alanyl-2- (l',2'-dipalmitoyl-sn-glycero-3'-phosphoryl)-ethylamide] was the gift of Ciba-Geigy Ltd, Basel, Switzerland.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL612578 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20481644 |
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Target ID: CHEMBL613301 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20481644 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Mepact Approved UseMepact is indicated in children, adolescents and young adults for the treatment of high-grade resectable non-metastatic osteosarcoma after macroscopically complete surgical resection. It is used in combination with postoperative multi-agent chemotherapy. Safety and efficacy have been assessed in studies of patients two to 30 years of age at initial diagnosis. |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20481644
2 mg/m2 infused intravenously over 1 hour twice weekly (at least 3 days apart) for 12 weeks, followed by 2 mg/m2 once weekly for an additional 24 weeks, for a total of 48 infusions in 36 weeks
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2302725
Monocytes (10^5) of 14 healthy donors and 24 cancer patients were used for activity evaluation. Monocytes were incubated for 24 h in medium with or without 500 nmol/ml liposome-encapsulated Mifamurtide. Then, the monocytes were washed and incubated with 10^4 labeled A375 melanoma cells. The assays were terminated 72 h later. The percentage cytotoxicities of untreated monocytes and tumor cells were compared.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
L03AX15
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WHO-VATC |
QL03AX15
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FDA ORPHAN DRUG |
143401
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NCI_THESAURUS |
C2139
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EMA ASSESSMENT REPORTS |
MEPACT(AUTHORIZED OSTEOSARCOMA)
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EU-Orphan Drug |
EU/3/16/1700
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2960
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m7535
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1LM890Q4FY
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838853-48-8
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C037144
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CHEMBL2111100
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Mifamurtide
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RR-112
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C1394
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8274
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100000183846
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123133557
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DB13615
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ACTIVE MOIETY
SUBSTANCE RECORD