cyclosporin A   

GtoPdb Ligand ID: 1024

Synonyms: ciclosporin | cyclosporine | cyclosporine A | Ikervis® (opthalmic solution) | Neoral® | Sandimmun® | Verkazia® (opthalmic solution)
cyclosporin A is an approved drug (FDA and UK (1983), EMA (2015))
Comment: Originally isolated from Tolypocladium inflatum, cyclosporin A acts as a calcineurin inhibitor.
There is some ambiguity in the literature as to the exact stereochemistry of cyclosporin A. Other common representations on PubChem are CID 5280754, and CID 24883466.
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2D Structure
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SMILES / InChI / InChIKey
Canonical SMILES CC=CCC(C(C1C(=O)NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)O)C
Isomeric SMILES C/C=C/C[C@H]([C@H]([C@H]1C(=O)N[C@@H](CC)C(=O)N(C)CC(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)O)C
InChI 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
InChI Key PMATZTZNYRCHOR-CGLBZJNRSA-N
Classification
Compound class Peptide or derivative
Approved drug? Yes (FDA and UK (1983), EMA (2015))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
International Nonproprietary Names
INN number INN
5086 ciclosporin
Synonyms
ciclosporin | cyclosporine | cyclosporine A | Ikervis® (opthalmic solution) | Neoral® | Sandimmun® | Verkazia® (opthalmic solution)
Database Links
CAS Registry No. 59865-13-3 (source: Scifinder)
ChEBI CHEBI:4031
ChEMBL Ligand CHEMBL160
DrugBank Ligand DB00091
DrugCentral Ligand 760
GtoPdb PubChem SID 135652074
Immunopaedia Search cyclosporin A
PubChem CID 5284373
Search Google for chemical match using the InChIKey PMATZTZNYRCHOR-CGLBZJNRSA-N
Search Google for chemicals with the same backbone PMATZTZNYRCHOR
Search PubMed clinical trials ciclosporin
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Search PubMed titles/abstracts ciclosporin
Search UniChem for chemical match using the InChIKey PMATZTZNYRCHOR-CGLBZJNRSA-N
Search UniChem for chemicals with the same backbone PMATZTZNYRCHOR
SynPHARM 79182 (in complex with peptidylprolyl isomerase A)
Wikipedia Cyclosporin

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Tocris
Cyclosporin A
Cat. No. 1101