Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C62H111N11O12 |
| Molecular Weight | 1202.6112 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@@]([H])(C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](CC)NC1=O)C(C)C
InChI
InChIKey=PMATZTZNYRCHOR-JLPRAAIDSA-N
InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50-,51+,52-/m1/s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8387097 | http://onlinelibrary.wiley.com/doi/10.1002/hlca.19820650538/abstract | https://www.ncbi.nlm.nih.gov/pubmed/17687636
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8387097 | http://onlinelibrary.wiley.com/doi/10.1002/hlca.19820650538/abstract | https://www.ncbi.nlm.nih.gov/pubmed/17687636
The ciclosporin analogue ciclosporin H is a potent and selective inhibitor of mediator release from basophils induced by activation of the formyl peptide receptor, and therefore has potential as an anti-inflammatory agent. It acts by interfering with agonist binding to formylmethionylleucylphenylalanine (FMLP) receptors. Unlike ciclosporin [ciclosporin A], ciclosporin H has Dmethyl valine (rather than the Lisomer) at position 11, has an extremely low affinity for cyclophilin, and is devoid of immunosuppressive activity. Ciclosporin H was undergoing preclinical investigation with researchers at the University of Naples Federico II in Italy as an antiinflammatory agent. However, no recent development has been reported.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cyclosporin H is a potent and selective formyl peptide receptor antagonist. Comparison with N-t-butoxycarbonyl-L-phenylalanyl-L-leucyl-L-phenylalanyl-L- leucyl-L-phenylalanine and cyclosporins A, B, C, D, and E. | 1993 May 15 |
|
| Cyclosporin H, Boc-MLF and Boc-FLFLF are antagonists that preferentially inhibit activity triggered through the formyl peptide receptor. | 2007 Dec |
Patents
Sample Use Guides
Ciclosporin H activity was determined in calcium imaging assay. HL-60 cells and HEL cells were incubated for 3 min with or without ciclosporin H before the addition of agonist N-Formyl-Met-Leu-Phe (FMLP). Ciclosporin H inhibited the stimulatory effects of FMLP on cytosolic Ca2+ concentration with Ki values of 0.08 mkM
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83602-39-5
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6476564
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DTXSID801017527
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FUO6O3NDNH
Created by
admin on Sat Dec 16 18:31:07 GMT 2023 , Edited by admin on Sat Dec 16 18:31:07 GMT 2023
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SUBSTANCE RECORD
