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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

11 - Combustible Solids

wgk_germany

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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P Fedorocko et al.
Neoplasma, 50(3), 176-184 (2003-08-26)
The anti-tumor effects of i.p. administered cyclooxygenase inhibitor - diclofenac and i.v. administered liposomal muramyl tripeptide phosphatidylethanolamine (MTP-PE) were investigated using a s.c. growing murine fibrosarcoma tumor. Tumor growth was assessed by measuring tumor volumes and survival of the mice.
Kanji Mori et al.
Expert review of anticancer therapy, 8(2), 151-159 (2008-02-19)
Osteosarcoma is the most common form of primary malignant bone tumor. The use of chemotherapy drugs with many side effects, including high-dose methotrexate, doxorubicin, cisplatin and ifosfamide, has greatly improved osteosarcoma survival compared with surgery alone. However, for 20 years
Prescrire international, 20(115), 89-89 (2011-06-09)
The standard treatment for children and young adults with osteosarcoma consists of surgery, preceded and followed by methotrexate-based chemotherapy. Mifamurtide is an immunostimulant derived from a bacterial cell wall component. It is authorised in the European Union as an adjunct
L L Worth et al.
Hematology/oncology clinics of North America, 15(4), 723-740 (2001-10-26)
Biologic response modifiers are becoming an important addition to surgery, chemotherapy, and radiotherapy in the management of cancer. As this field of research grows and expands, more biologic response modifiers will be incorporated into therapeutic regimens. By stimulating the immune
Alexander J Chou et al.
Cancer, 115(22), 5339-5348 (2009-07-29)
The addition of liposomal muramyl tripeptide phosphatidylethanolamine (MTP-PE) to chemotherapy has been shown to improve overall survival in patients with nonmetastatic osteosarcoma (OS). The authors report the results of addition of liposomal MTP-PE to chemotherapy for patients with metastatic OS.
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