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Key Documents

A0936

Sigma-Aldrich

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:
Molecular Weight:
887.11
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

storage temp.

−20°C

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

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

InChI key

FKHUGQZRBPETJR-FZKCHLSLSA-N

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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T Sugawara et al.
International journal of experimental pathology, 76(3), 191-199 (1995-06-01)
Muramyl dipeptide-Lys(L18) given by daily subcutaneous injection for 14 days induced arthritis in male Lewis, Fischer and nude rats, to a lesser degree in the last two than in the first strain. On the other hand, a single intradermal administration
S Simcic et al.
Pflugers Archiv : European journal of physiology, 440(5 Suppl), R64-R66 (2000-09-27)
Some synthetic analogues of the immunomodulatory agent muramyl dipeptide (MDP), i.e. phthalimido- (LK-511, LK-413, LK-512, LK-423, LK-508), adamantyl- (LK-415, LK-517), 7-oxoalkyl-(LK-409) desmuramylpeptides were assessed for the tumour necrosis factor (TNF) inducing activity and the ability to modulate TNF production in
K Namba et al.
Vaccine, 14(14), 1322-1326 (1996-10-01)
We investigated the therapeutic effects of romurtide, a synthetic muramyl dipeptide derivative, on experimental thrombocytopenia induced by carboplatin in cynomolgus monkeys. A prolonged thrombocytopenia due to a severe myelosuppression was induced by carboplatin. Romurtide given subcutaneously elevated significantly the peripheral
Neil Cartwright et al.
American journal of respiratory and critical care medicine, 175(6), 595-603 (2007-01-20)
NLRs (nucleotide oligomerisation domain [NOD] proteins containing a leucine-rich repeat) are cytosolic pattern recognition receptors. NOD1 senses diaminopimelic acid-containing peptidoglycan present in gram-negative bacteria, whereas NOD2 senses the muramyl dipeptide (MDP) present in most organisms. Bacteria are the most common
K Suzuki et al.
Immunopharmacology, 28(1), 31-38 (1994-07-01)
The immunostimulatory reagents muramyl dipeptide (MDP) and its stearoyl derivative romurtide [MDP-Lys(L18)] were assessed for cytokine inducing activity in human monocytes. Both MDP and romurtide stimulated the production of interleukin-1 (IL-1), IL-6, tumor necrosis factor (TNF) and IL-1 receptor antagonist

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