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Merck
CN

A0936

N-Acetylmuramyl-Ala-D-isoglutaminyl-Nε-stearoyl-Lys

Synonym(s):

MDP-LYS(L18), Muroctasin, Romurtide

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About This Item

Empirical Formula (Hill Notation):
C43H78N6O13
CAS Number:
78113-36-7
Molecular Weight:
887.11
UNSPSC Code:
12352200
PubChem Substance ID:
24890471
MDL number:
MFCD00871261

Key Documents

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InChI

1S/C43H78N6O13/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23-34(52)45-26-21-20-22-32(42(58)59)48-35(53)25-24-31(39(44)55)49-40(56)28(2)46-41(57)29(3)61-38-36(47-30(4)51)43(60)62-33(27-50)37(38)54/h28-29,31-33,36-38,43,50,54,60H,5-27H2,1-4H3,(H2,44,55)(H,45,52)(H,46,57)(H,47,51)(H,48,53)(H,49,56)(H,58,59)/t28-,29+,31+,32-,33+,36+,37+,38+,43?/m0/s1

SMILES string

CCCCCCCCCCCCCCCCCC(=O)NCCCC[C@H](NC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1NC(C)=O)C(N)=O)C(O)=O

InChI key

FKHUGQZRBPETJR-FZKCHLSLSA-N

storage temp.

−20°C

Biochem/physiol Actions

Antibiotic peptide.
MDP-LYS(L18), a synthetic analogue of MDP (muramyl dipeptide) derived from bacterial cell walls, is used as a potent immunoadjuvant that enhances protective immunity through activation of monocyte-macrophage lineage cells, such as dendritic cells.
N-Acetylmuramyl-Ala-D-isoglutaminyl-Nε-stearoyl-Lys, Romurtide, a muramyl dipeptide analogue, is a granulocyte-macrophage colony-stimulating factor and a TNF-α inducer.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
1405775
1408642
018K1040
105K1073
095K1071

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H Ueda et al.
International immunopharmacology, 1(1), 97-104 (2001-05-23)
The novel applications of a muramyl dipeptide analogue, romurtide, were investigated. When mice were intravenously injected with 10-1000 micrograms/mouse of romurtide as a primer and 3 KE/mouse of OK-432 as a trigger, systemic tumor necrosis factor-alpha (TNF-alpha) activity was increased.
A Fukushima et al.
Vaccine, 14(6), 485-491 (1996-04-01)
To examine the effect of MDP-Lys(L18), a derivative of muramyl dipeptide (MDP), as a mucosal immunoadjuvant, we investigated its activity to augment host resistance against mucosal infections by Sendai virus and rotavirus in mice. In an experimental infection model using
T Sugawara et al.
Inflammation, 20(1), 43-56 (1996-02-01)
To examine the involvement of cytokines in the mechanisms of N2-[(N-acetylmuramoyl)-L-alanyl-D-isoglutaminyl]-N6-stearoyl-L-lysine, MDP-Lys(L18)-induced arthritis, we analyzed interleukin-1 (IL-1), tumor necrosis factor (TNF), colony-stimulating factor (CSF), and neutrophil chemotactic factor (NCF) by bioassays in the rat macrophage-conditioned medium (Mluminal diameter-CM) stimulated by
T Sugawara et al.
International journal of tissue reactions, 17(1), 5-13 (1995-01-01)
To examine the involvement of lymphocytes in the development of MDP-Lys(L18)-induced arthritis (MIA) in rats and the exacerbation of MIA by cyclosporin A (CsA), we analysed the spleen lymphocyte subset using monoclonal antibodies and flow cytometry during the development of
Y Nitta et al.
Oncology research, 12(1), 25-31 (2000-11-04)
MDP-Lys (N2-[(N-acetylmuramyl)-L-alanyl-D-isoglutaminyl]-N6-stearoyl-L-lysine), a macrophage activator, is a lipophilic derivative of muramyl dipeptide (MDP). Multilamellar liposome incorporated MDP-Lys was prepared using phosphatidylcholine and phosphatidylserine by conventional film method, and its inhibitory effect on lung metastasis was compared with MDP-Lys as a
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