Mifamurtide sodium | CAS#90825-43-7 | osteosarcoma drug

MedKoo Cat#: 597644 | Name: Mifamurtide sodium

Description:

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

Mifamurtide sodium 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.

Chemical Structure

Mifamurtide sodium

CAS#90825-43-7

Theoretical Analysis

MedKoo Cat#: 597644

Name: Mifamurtide sodium

CAS#: 90825-43-7

Chemical Formula: C59H108N6NaO19P

Exact Mass: 1258.7305

Molecular Weight: 1259.49

Elemental Analysis: C, 56.26; H, 8.64; N, 6.67; Na, 1.83; O, 24.14; P, 2.46

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Mifamurtide sodium; CGP 19835A; L-MTP-PE; Junovan; Mepact; Muramyl tripeptide;

IUPAC/Chemical Name

sodium (R)-2,3-bis(palmitoyloxy)propyl ((4R,5R,7R,10S,13R,18S)-13-carbamoyl-4-formyl-7,10,18-trimethyl-2,8,11,16,19-pentaoxo-5-((1R,2R)-1,2,3-trihydroxypropyl)-6-oxa-3,9,12,17,20-pentaazadocosan-22-yl) phosphate

InChi Key

LRSAONQAUPMYDK-XNLRRNFISA-M

InChi Code

InChI=1S/C59H109N6O19P.Na/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);/q;+1/p-1/t43-,44-,45+,47+,48+,49-,50+,54+,55+;/m0./s1

SMILES Code

CCCCCCCCCCCCCCCC(OC[C@@H](OC(CCCCCCCCCCCCCCC)=O)COP([O-])(OCCNC([C@@H](NC(CC[C@H](C(N)=O)NC([C@@H](NC([C@H](O[C@H]([C@H](C=O)NC(C)=O)[C@@H]([C@@H](CO)O)O)C)=O)C)=O)=O)C)=O)=O)=O.[Na+]

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

Shelf Life

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,259.49 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.

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

1: Mifamurtide: osteosarcoma: ineffective and harmful. Prescrire Int. 2011 Apr;20(115):89. PubMed PMID: 21648206. 2: 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; PubMed Central PMCID: PMC4533988. 3: 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 Sep;36(9):6773-9. doi: 10.1007/s13277-015-3405-3. Epub 2015 Apr 3. PubMed PMID: 25835978. 4: 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. 5: 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. 6: 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. 7: Biteau K, Guiho R, Chatelais M, Taurelle J, Chesneau J, Corradini N, Heymann D, Redini F. L-MTP-PE and zoledronic acid combination in osteosarcoma: preclinical evidence of positive therapeutic combination for clinical transfer. Am J Cancer Res. 2016 Feb 15;6(3):677-89. eCollection 2016. PubMed PMID: 27152244; PubMed Central PMCID: PMC4851846. 8: 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. 9: 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. 10: 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. 11: 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. 12: 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. 13: Meyers PA, Chou AJ. Muramyl tripeptide-phosphatidyl ethanolamine encapsulated in liposomes (L-MTP-PE) in the treatment of osteosarcoma. Adv Exp Med Biol. 2014;804:307-21. doi: 10.1007/978-3-319-04843-7_17. Review. PubMed PMID: 24924182. 14: 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. 15: Brosa M, García del MX, Mora J, Villacampa A, Pozo T, Adán C, Grande M, García E, Cubells L. Economic Considerations On the Use of Mifamurtide In the Treatment of Osteosarcoma In Spain. Value Health. 2014 Nov;17(7):A526-7. doi: 10.1016/j.jval.2014.08.1662. Epub 2014 Oct 26. PubMed PMID: 27201662. 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: 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. 18: 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. 19: Ferrari S, Serra M. An update on chemotherapy for osteosarcoma. Expert Opin Pharmacother. 2015;16(18):2727-36. doi: 10.1517/14656566.2015.1102226. Epub 2015 Oct 29. Review. PubMed PMID: 26512909. 20: Luetke A, Meyers PA, Lewis I, Juergens H. Osteosarcoma treatment - where do we stand? A state of the art review. Cancer Treat Rev. 2014 May;40(4):523-32. doi: 10.1016/j.ctrv.2013.11.006. Epub 2013 Nov 27. Review. PubMed PMID: 24345772.