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SML0195

Sigma-Aldrich

Mifamurtide

≥98% (HPLC)

Synonym(s):

CGP-19835, MTP-PE, MTP-cephalin, Muramyl tripeptide phosphatidylethanolamine, N-(N-Acetylmuramoyl)-L-alanyl-D-α-glutaminyl-N-[(7R)-4-hydroxy-4-oxido-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacos-1-yl]-L-alaninamide

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About This Item

Empirical Formula (Hill Notation):
C59H109N6O19P
CAS Number:
83461-56-7
Molecular Weight:
1237.50
UNSPSC Code:
12352200
PubChem Substance ID:
329825220
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

water: 2 mg/mL, clear (warmed)

originator

Novartis

storage temp.

−20°C

SMILES string

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

1S/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)/t43-,44-,45+,47+,48+,49-,50+,54+,55+/m0/s1

InChI key

ZVLWUMPAHCEZAW-KRNLDFAISA-N

Application

Mifamurtide may be used in immunological and cancer-related cell signaling studies.

Biochem/physiol Actions

Mifamurtide (Muramyl tripeptide phosphatidylethanolamine; MTP-cephalin; MTP-PE) is a synthetic, lipophilic analog of muramyl dipeptide. It acts as an immunostimulant promoting cancer cell destruction via in vivo macrophage activation.
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.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Karthik Venkatakrishnan et al.
European journal of clinical pharmacology, 68(10), 1347-1355 (2012-03-31)
This study evaluated the pharmacokinetics (PK), pharmacodynamics (PD), safety/tolerability, and cardiac safety of liposomal muramyl tripeptide phosphatidyl-ethanolamine [mifamurtide (L-MTP-PE)] in healthy adults. L-MTP-PE 4 mg was administered intravenously over 30 min. Study participants were monitored from 24 h preinfusion until 72 h postinfusion. Blood
Prospectively planned analysis of data from a phase III study of liposomal muramyltripeptide phosphatidylethanolamine in the treatment of osteosarcoma.
Jean-Loup Romet-Lemonne et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 23(26), 6437-6438 (2005-09-13)
Kosei Ando et al.
Expert opinion on pharmacotherapy, 12(2), 285-292 (2011-01-14)
The standard treatment for osteosarcoma requires both macroscopic surgical wide resection and postoperative multi-drug chemotherapy in neoadjuvant and adjuvant settings. However, the 5-year event-free survival has remained at a plateau of 60-70% of patients with nonmetastatic osteosarcoma for more than
R M Durham et al.
The Journal of surgical research, 76(2), 179-184 (1998-08-12)
Muramlytripeptide phosphatidylethanolamine (MTP) stimulates synthesis of cytokines by hepatic Kupffer cells. We have shown in a perfused rat liver model that secondary ischemia/reperfusion (I/R) downregulates tumor necrosis factor alpha (TNF-alpha) expression after Escherichia coli (EC) bacteremia. Here, we tested the
A Nardin et al.
Current cancer drug targets, 6(2), 123-133 (2006-03-15)
About one third of osteosarcoma patients develop lung metastasis refractory to chemotherapy. Recent studies indicate that biological response modifiers activating the patient's immune system may help controlling minimal residual disease via pathways distinct from those used by cytotoxic drugs, and
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