Mifamurtide

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 201860

CAS#: 83461-56-7 (free acid)

Description: Mifamurtide is 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. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Chemical Structure

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Mifamurtide
CAS# 83461-56-7 (free acid)

Theoretical Analysis

MedKoo Cat#: 201860
Name: Mifamurtide
CAS#: 83461-56-7 (free acid)
Chemical Formula: C59H109N6O19P
Exact Mass: 1236.74851
Molecular Weight: 1237.5
Elemental Analysis: C, 57.26; H, 8.88; N, 6.79; O, 24.56; P, 2.50

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 83461-56-7 (free acid)   90825-43-7 (sodium)   838853-48-8 (sodium hydrate)    

Synonym: CGP 19835A Lipid; muramyl tripeptide phosphatidylethanolamine liposome. US brand name: JUNOVAN. Foreign brand name: MEPACT. Abbreviations: LMTPPE. MTPPE Liposome .

IUPAC/Chemical Name: 2-[[(2S)-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,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 phosphoric acid

InChi Key: JMUHBNWAORSSBD-ZXSMYVEWSA-N

InChi Code: InChI=1S/C59H109N6O19P/c1-7-9-11-13-15-17-19-21-23-25-27-29-31-33-50(69)79-40-46(83-51(70)34-32-30-28-26-24-22-20-18-16-14-12-10-8-2)41-81-85(77,78)80-38-37-61-56(73)42(3)62-49(68)36-35-47(55(60)72)65-57(74)43(4)63-58(75)44(5)82-54-52(64-45(6)67)59(76)84-48(39-66)53(54)71/h42-44,46-48,52-54,59,66,71,76H,7-41H2,1-6H3,(H2,60,72)(H,61,73)(H,62,68)(H,63,75)(H,64,67)(H,65,74)(H,77,78)/t42-,43-,44+,46?,47+,48+,52+,53?,54+,59+/m0/s1

SMILES Code: O=P(OCCNC([C@@H](NC(CC[C@@H](NC([C@@H](NC([C@H](O[C@@H]1[C@@H](NC(C)=O)[C@H](O)O[C@H](CO)C1O)C)=O)C)=O)C(N)=O)=O)C)=O)(O)OCC(OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 1237.5 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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 1: Song HJ, Lee JA, Han E, Lee EK. Lifetime effectiveness of mifamurtide addition to chemotherapy in nonmetastatic and metastatic osteosarcoma: a Markov process model analysis. Tumour Biol. 2015 Apr 3. [Epub ahead of print] PubMed PMID: 25835978.

2: Brosa M, García del Muro X, Mora J, Villacampa A, Pozo-Rubio T, Cubells L, Montoto C. Orphan drugs revisited: cost-effectiveness analysis of the addition of mifamurtide to the conventional treatment of osteosarcoma. Expert Rev Pharmacoecon Outcomes Res. 2015 Apr;15(2):331-40. doi: 10.1586/14737167.2015.972378. Epub 2014 Oct 29. PubMed PMID: 25354299.

3: Song HJ, Lee EK, Lee JA, Kim HL, Jang KW. The addition of mifamurtide to chemotherapy improves lifetime effectiveness in children with osteosarcoma: a Markov model analysis. Tumour Biol. 2014 Sep;35(9):8771-9. doi: 10.1007/s13277-014-2139-y. Epub 2014 May 30. PubMed PMID: 24874050.

4: Johal S, Ralston S, Knight C. Mifamurtide for high-grade, resectable, nonmetastatic osteosarcoma following surgical resection: a cost-effectiveness analysis. Value Health. 2013 Dec;16(8):1123-32. doi: 10.1016/j.jval.2013.08.2294. Epub 2013 Oct 3. PubMed PMID: 24326165.

5: Li Y, Plesescu M, Prakash SR. Synthesis of isotopically labeled versions of L-MTP-PE (mifamurtide) and MDP. J Labelled Comp Radiopharm. 2013 Jul-Aug;56(9-10):475-9. doi: 10.1002/jlcr.3078. Epub 2013 Jul 9. PubMed PMID: 24285524.

6: Venkatakrishnan K, Liu Y, Noe D, Mertz J, Bargfrede M, Marbury T, Farbakhsh K, Oliva C, Milton A. Pharmacokinetics and pharmacodynamics of liposomal mifamurtide in adult volunteers with mild or moderate hepatic impairment. Br J Clin Pharmacol. 2014 Jun;77(6):998-1010. doi: 10.1111/bcp.12261. PubMed PMID: 24134216; PubMed Central PMCID: PMC4093925.

7: Venkatakrishnan K, Liu Y, Noe D, Mertz J, Bargfrede M, Marbury T, Farbakhsh K, Oliva C, Milton A. Pharmacokinetics and pharmacodynamics of liposomal mifamurtide in adult volunteers with mild or moderate renal impairment. Br J Clin Pharmacol. 2014 Jun;77(6):986-97. doi: 10.1111/bcp.12260. PubMed PMID: 24134181; PubMed Central PMCID: PMC4093924.

8: Anderson PM, Meyers P, Kleinerman E, Venkatakrishnan K, Hughes DP, Herzog C, Huh W, Sutphin R, Vyas YM, Shen V, Warwick A, Yeager N, Oliva C, Wang B, Liu Y, Chou A. Mifamurtide in metastatic and recurrent osteosarcoma: a patient access study with pharmacokinetic, pharmacodynamic, and safety assessments. Pediatr Blood Cancer. 2014 Feb;61(2):238-44. doi: 10.1002/pbc.24686. Epub 2013 Aug 31. PubMed PMID: 23997016.

9: Venkatakrishnan K, Kramer WG, Synold TW, Goodman DB, Sides E 3rd, Oliva C. A pharmacokinetic, pharmacodynamic, and electrocardiographic study of liposomal mifamurtide (L-MTP-PE) in healthy adult volunteers. Eur J Clin Pharmacol. 2012 Oct;68(10):1347-55. doi: 10.1007/s00228-012-1262-1. Epub 2012 Mar 30. PubMed PMID: 22460239.

10: Mifamurtide: osteosarcoma: ineffective and harmful. Prescrire Int. 2011 Apr;20(115):89. PubMed PMID: 21648206.

11: Ando K, Mori K, Corradini N, Redini F, Heymann D. Mifamurtide for the treatment of nonmetastatic osteosarcoma. Expert Opin Pharmacother. 2011 Feb;12(2):285-92. doi: 10.1517/14656566.2011.543129. Review. PubMed PMID: 21226638; PubMed Central PMCID: PMC3413631.

12: Kager L, Pötschger U, Bielack S. Review of mifamurtide in the treatment of patients with osteosarcoma. Ther Clin Risk Manag. 2010 Jun 24;6:279-86. PubMed PMID: 20596505; PubMed Central PMCID: PMC2893760.

13: Anderson PM, Tomaras M, McConnell K. Mifamurtide in osteosarcoma--a practical review. Drugs Today (Barc). 2010 May;46(5):327-37. doi: 10.1358/dot.2010.46.5.1500076. Review. PubMed PMID: 20517534.

14: Frampton JE. Mifamurtide: a review of its use in the treatment of osteosarcoma. Paediatr Drugs. 2010 Jun;12(3):141-53. doi: 10.2165/11204910-000000000-00000. Review. PubMed PMID: 20481644.

15: Molecule of the month. Mifamurtide. Drug News Perspect. 2010 Apr;23(3):199. doi: 10.1358/dnp.2010.23.3.1492241. PubMed PMID: 20440421.

16: Meyers PA. Muramyl tripeptide (mifamurtide) for the treatment of osteosarcoma. Expert Rev Anticancer Ther. 2009 Aug;9(8):1035-49. doi: 10.1586/era.09.69. Review. PubMed PMID: 19671023.

17: Mifamurtide: CGP 19835, CGP 19835A, L-MTP-PE, liposomal MTP-PE, MLV 19835A, MTP-PE, muramyltripeptide phosphatidylethanolamine. Drugs R D. 2008;9(2):131-5. Review. PubMed PMID: 18298131.



Additional Information

Mifamurtide (trade name Mepact, marketed by Takeda) is a drug against osteosarcoma, a kind of bone cancer mainly affecting children and young adults, which is lethal in about a third of cases. The drug was approved in Europe in March 2009.
 
The drug was invented by Ciba-Geigy (now Novartis) in the early 1980s and sold to Jenner Biotherapies in the 1990s. In 2003, IDM Pharma bought the rights and developed it further.  IDM Pharma was acquired by Takeda along with mifamurtide in June 2009.  Mifamurtide had already been granted orphan drug status by the U.S. Food and Drug Administration (FDA) in 2001, and the European Medicines Agency (EMEA) followed in 2004. It was approved in the 27 European Union member states plus Iceland, Liechtenstein and Norway via a centralized marketing authorization in March 2009. The drug was denied approval by the FDA in 2007. See wikipedia.com for detail.