mifamurtide   

GtoPdb Ligand ID: 8274

Synonyms: CGP 19835 | CGP-19835 | L-MTP-PE | liposomal muramyl tripeptide phosphatidyl ethanolamine | Mepact® | MLV 19835A
mifamurtide is an approved drug (EMA (2009))
Compound class: Synthetic organic
Comment: Mifamurtide is a synthetic analogue of the bacterial cell wall component, muramyl dipeptide (MDP). MDP stimulates the immune system via activation of microbial pattern recognition receptors such as TLR4 and NOD2 [3,9].
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 25
Hydrogen bond donors 10
Rotatable bonds 59
Topological polar surface area 385.91
Molecular weight 1236.75
XLogP 9.69
No. Lipinski's rules broken 4
SMILES / InChI / InChIKey
Canonical SMILES CCCCCCCCCCCCCCCC(=O)OC(COP(=O)(OCCNC(=O)C(NC(=O)CCC(C(=O)N)NC(=O)C(NC(=O)C(OC1C(NC(=O)C)C(O)OC(C1O)CO)C)C)C)O)COC(=O)CCCCCCCCCCCCCCC
Isomeric SMILES CCCCCCCCCCCCCCCC(=O)OC(COP(=O)(OCCNC(=O)[C@@H](NC(=O)CC[C@H](C(=O)N)NC(=O)[C@@H](NC(=O)[C@H](O[C@@H]1[C@@H](NC(=O)C)[C@H](O)O[C@@H](C1O)CO)C)C)C)O)COC(=O)CCCCCCCCCCCCCCC
InChI 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
InChI Key JMUHBNWAORSSBD-ZXSMYVEWSA-N
References
1. Anderson PM, Tomaras M, McConnell K. (2010)
Mifamurtide in osteosarcoma--a practical review.
Drugs Today, 46 (5): 327-37. [PMID:20517534]
2. Ando K, Mori K, Corradini N, Redini F, Heymann D. (2011)
Mifamurtide for the treatment of nonmetastatic osteosarcoma.
Expert Opin Pharmacother, 12 (2): 285-92. [PMID:21226638]
3. Kim TH, Park JH, Park YM, Ryu SW, Shin SJ, Park JH, Kim DJ. (2015)
Synergistic effect of muramyl dipeptide with heat shock protein 70 from Mycobacterium tuberculosis on immune activation.
Immunobiology, 220 (1): 26-31. [PMID:25446399]
4. Meyer T, Fabbro D, Eppenberger U, Matter A. (1986)
The lipophilic muramyltripeptide MTP-PE, a biological response modifier, is an activator of protein kinase C.
Biochem. Biophys. Res. Commun., 140 (3): 1043-50. [PMID:3465326]
5. Meyers PA, Chou AJ. (2014)
Muramyl tripeptide-phosphatidyl ethanolamine encapsulated in liposomes (L-MTP-PE) in the treatment of osteosarcoma.
Adv. Exp. Med. Biol., 804: 307-21. [PMID:24924182]
6. Murray JL, Kleinerman ES, Cunningham JE, Tatom JR, Andrejcio K, Lepe-Zuniga J, Lamki LM, Rosenblum MG, Frost H, Gutterman JU et al.. (1989)
Phase I trial of liposomal muramyl tripeptide phosphatidylethanolamine in cancer patients.
J. Clin. Oncol., 7 (12): 1915-25. [PMID:2479721]
7. Pahl JH, Kwappenberg KM, Varypataki EM, Santos SJ, Kuijjer ML, Mohamed S, Wijnen JT, van Tol MJ, Cleton-Jansen AM, Egeler RM et al.. (2014)
Macrophages inhibit human osteosarcoma cell growth after activation with the bacterial cell wall derivative liposomal muramyl tripeptide in combination with interferon-γ.
J. Exp. Clin. Cancer Res., 33: 27. [PMID:24612598]
8. Vavricka SR, Musch MW, Chang JE, Nakagawa Y, Phanvijhitsiri K, Waypa TS, Merlin D, Schneewind O, Chang EB. (2004)
hPepT1 transports muramyl dipeptide, activating NF-kappaB and stimulating IL-8 secretion in human colonic Caco2/bbe cells.
Gastroenterology, 127 (5): 1401-9. [PMID:15521010]
9. Viswanathan VK. (2014)
Muramyl dipeptide: Not just another brick in the wall.
Gut Microbes, 5 (3): 275-6. [PMID:25068259]