A C5a receptor antagonist and antibiotic
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L-156,602

Item No. 23896

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S)-3-hydroxy-N-[(2S)-2-hydroxy-1-oxo-2-[(2R,5R,6R)-tetrahydro-2-hydroxy-6-methyl-5-[(2S)-2-methylbutyl]-2H-pyran-2-yl]propyl]-L-leucyl-(3R)-hexahydro-3-pyridazinecarbonyl-N-hydroxy-L-alanylglycyl-(3S)-hexahydro-3-pyridazinecarbonyl-N-hydroxy-D-alanine, (6→13)-lactone
CAS Number
125228-51-5
Synonyms
  • PD 124966
Molecular Formula
C38H64N8O13
Formula Weight
841.0
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: soluble
SMILES
O=C(CNC([C@H](C)N(O)C([C@](CCCN1)([H])N1C([C@](NC([C@](O)(C)[C@@]2(O)CC[C@H](C[C@@H](C)CC)[C@@H](C)O2)=O)([H])[C@H](C(C)C)OC([C@@H](C)N3O)=O)=O)=O)=O)N4[C@](CCCN4)([H])C3=O
InChi Code
InChI=1S/C38H64N8O13/c1-9-21(4)18-25-14-15-38(55,59-24(25)7)37(8,54)36(53)42-29-30(20(2)3)58-35(52)23(6)46(57)32(49)26-12-10-16-40-43(26)28(47)19-39-31(48)22(5)45(56)33(50)27-13-11-17-41-44(27)34(29)51/h20-27,29-30,40-41,54-57H,9-19H2,1-8H3,(H,39,48)(H,42,53)/t21-,22-,23+,24+,25+,26-,27+,29-,30-,37+,38+/m0/s1
InChi Key
ZJZOPNINWIGNQW-SYYWPETLSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Cayman Chemical
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    Product Description

    L-156,602 is an antagonist of the complement component 5A (C5a) receptor (IC50 = 1.7 µg/L in a radioligand binding assay using neutrophil membranes).1 It is also a cyclic depsipeptide antibiotic that is active against Gram-positive bacteria.2 L-156,602 has anti-inflammatory activity in mice, decreasing inflammation induced by muramyl dipeptide (MDP) when administered at a dose of 0.5 mg/kg and by concanavalin A (Item No. 14951) at doses of 0.25 and 0.5 mg/kg.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Durette, P.L., Kopka, I.E., Lanza, T.J., et al. The inhibition of C5a receptor binding by analogs of L-156,602, a cyclic hexadepsipeptide antibiotic. Bioor. Med. Chem. Lett. 2(9), 1033-1038 (1992).

    2. Hensens, O.D., Borris, R.P., Koupal, L.R., et al. L-156,602, a C5a antagonist with a novel cyclic hexadepsipeptide structure from Streptomyces sp. MA6348. Fermentation, isolation and structure determination. J. Antibiot. (Tokyo) 44(2), 249-254 (1991).

    3. Tsuji, R.F., Magae, J., Nagai, K., et al. Effects of L-156,602, a C5a receptor antagonist, on mouse experimental models of inflammation. Biosci. Biotech. Biochem. 56(12), 2034-2036 (1992).