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SML0195

Sigma-Aldrich

Mifamurtide

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill) :
C59H109N6O19P
Numéro CAS:
83461-56-7
Poids moléculaire :
1237.50
Code UNSPSC :
12352200
ID de substance PubChem :
329825220
Nomenclature NACRES :
NA.77

Essai

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

water: 2 mg/mL, clear (warmed)

Auteur

Novartis

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

ZVLWUMPAHCEZAW-KRNLDFAISA-N

Application

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

Actions biochimiques/physiologiques

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.
Synthetic, lipophilic analog of muramyl dipeptide. Immunostimulant promoting cancer cell destruction via in vivo macrophage activation. Antineoplastic immunomodulator.

Caractéristiques et avantages

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
014M4728V
113M4759V
111M4724V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

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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
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
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
N O Macková et al.
Physiological research, 51(5), 511-521 (2002-12-10)
The effects of liposomal muramyl tripeptide phosphatidylethanolamine (MTP-PE/MLV, radioprotective immunomodulator; 10 mg/kg) and indomethacin (INDO, inhibitor of prostaglandin production; 2 mg/kg) on post-irradiation recovery of hematopoietic functions in mice were investigated. Two agents with distinct radioprotective mechanisms were administered alone
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
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