cyclosporin A   Click here for help

GtoPdb Ligand ID: 1024

Synonyms: ciclosporin | cyclosporine | cyclosporine A | Ikervis® (opthalmic solution) | Neoral® | Sandimmun® | Verkazia® (opthalmic solution)
Approved drug Immunopharmacology Ligand
cyclosporin A is an approved drug (FDA and UK (1983), EMA (2015))
Compound class: Peptide
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: cyclosporin a

cyclosporin A is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
FPR1 Hs Antagonist Antagonist 6.2 – 6.3 pEC50 - 11
⤷ pEC50 6.2 – 6.3 [11]
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
peptidylprolyl isomerase A Hs Inhibitor Inhibition 7.8 pKi - 6
⤷ pKi 7.8 (Ki 1.72x10-8 M) [6]
peptidylprolyl isomerase A Primary target of this compound Hs Inhibitor Inhibition 8.3 pIC50 - 3
⤷ pIC50 8.3 (IC50 5x10-9 M) Inhibition of the phosphatase activity of calcineurin in Jurkat cells. [3]
peptidylprolyl isomerase D Hs Inhibitor Inhibition 8.0 pIC50 - 6,9
⤷ pIC50 8.0 (IC50 1.01x10-8 M) [6,9]
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
OATP1B1 Hs Inhibitor Inhibition 7.3 pKi - 2,4
⤷ pKi 7.3 (Ki 5.1x10-8 M) [2,4]
ABCG2 Hs Inhibitor Inhibition 6.3 pKi - 8
⤷ pKi 6.3 (Ki 5x10-7 M) [8]
Description: Inhibition of ABCG2-ATPase activity induced by substrate binding.
Sodium/bile acid and sulphated solute cotransporter 1 Hs Inhibitor Inhibition 5.1 pKi - 1
⤷ pKi 5.1 (Ki 7.6x10-6 M) [1]
OATP1B3 Hs Inhibitor Inhibition 6.1 pIC50 - 4,10
⤷ pIC50 6.1 (IC50 8x10-7 M) [4,10]
Sodium/bile acid and sulphated solute cotransporter 1 Hs Inhibitor Inhibition 6.0 pIC50 - 5
⤷ pIC50 6.0 (IC50 1x10-6 M) [5]