mifamurtide   Click here for help

GtoPdb Ligand ID: 8274

Synonyms: CGP 19835 | CGP-19835 | L-MTP-PE | liposomal muramyl tripeptide phosphatidyl ethanolamine | Mepact® | MLV 19835A
Approved drug
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].
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: mifamurtide

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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]