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].
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View more information in the IUPHAR Pharmacology Education Project: mifamurtide

2D Structure
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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.

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Physico-chemical Properties
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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.

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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
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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/)

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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/)
No information available.
Summary of Clinical Use Click here for help
The EMA granted mifamurtide orphan drug designation for the treatment of osteosarcoma in children and young adults in 2004. The drug was subsequently fully approved by the EMA in 2009. Mifamurtide is indicated for the treatment of high-grade, nonmetastasizing, resectable osteosarcoma following complete surgical removal and/or in combination with chemotherapy. Further reading: [1-2,4,6].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Mifamurtide activates the pattern recognition receptor NOD2 (gene symbol NLRC2) on monocytes and macrophages, stimulating the production of pro-inflammatory cytokines. This activates an antibacterial-like immune response which kills cancer cells [5,7].
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
European Medicines Agency (EMA)