Compound Detail

CHEMBL160

CYCLOSPORINE

💊 Approved Drug

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

💊 Approved Drug

C/C=C/C[C@@H](C)[C@@H](O)[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)C(=O)N[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N1C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL160
Name	CYCLOSPORINE
Phase	Approved
Structure Type	BOTH
InChI Key	PMATZTZNYRCHOR-CGLBZJNRSA-N
Therapeutic	✓ Yes

Known Names

27-400 ANTIBIOTIC S-7481F1 Atopica Capimune Capsorin Cequa Ciclosporin Ciclosporin a Ciclosporina Ciclosporine Ciclosporinum Cyclosporin +18 more

Targets

396

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

1202.6

MW (Da)

Drug Information

Molecule Type	Protein
First Approval	1983
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product

USAN Year

1981

Extended Properties

Molecular Formula	C62H111N11O12
MW	1202.63

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Cyclophilin A modulator	MODULATOR	Peptidyl-prolyl cis-trans isomerase A	✓	✓

Indications

Arthritis, Rheumatoid Conjunctivitis Corneal Diseases Eye Diseases Immune System Diseases Inflammation Keratitis Keratoconjunctivitis Psoriasis Anemia, Aplastic Anemia, Aplastic Anemia, Hemolytic, Autoimmune Behcet Syndrome Breast Neoplasms Bronchiolitis Obliterans Carcinoma, Hepatocellular Colorectal Neoplasms Conjunctivitis, Allergic Dermatitis, Atopic Dermatomyositis

ATC Classification

L04AD01

ciclosporin

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: IMMUNOSUPPRESSANTS

S01XA18

ciclosporin

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

Drug Warnings

Black Box Warning

carcinogenicity

Country: United States

Black Box Warning

immune system toxicity

Country: United States

Black Box Warning

nephrotoxicity

Country: United States

Black Box Warning

vascular toxicity

Country: United States

Black Box Warning

infectious disease

Country: United States

Activity Summary

IC50 281 meas. best 10.33

EC50 50 meas. best 8.51

Ki 48 meas. best 8.82

Kd 17 meas. best 8.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	10.33	6.9252	0.0	29
Neutrophil CHEMBL613710	IC50	10.33	10.33	0.0	1
Plasmodium falciparum CHEMBL364	IC50	9.33	7.5838	0.5	16
Trypanosoma brucei brucei CHEMBL612851	IC50	8.94	8.94	1.1	1
T-cell CHEMBL614309	IC50	8.87	7.2945	1.3	11
Peptidyl-prolyl cis-trans isomerase A CHEMBL1949	Ki	8.82	7.8467	1.5	9
Plasmodium berghei CHEMBL612653	IC50	8.78	8.78	1.6	1
Peptidyl-prolyl cis-trans isomerase A CHEMBL1949	IC50	8.7	7.752	2.0	15
Mus musculus CHEMBL375	IC50	8.6	7.7791	2.5	11
Peptidyl-prolyl cis-trans isomerase D CHEMBL1697657	Ki	8.59	8.075	2.6	4
PBMC CHEMBL613107	IC50	8.52	8.22	3.0	2
PBMC CHEMBL613107	EC50	8.51	8.51	3.1	1
Peptidyl-prolyl cis-trans isomerase D CHEMBL1697657	IC50	8.44	8.44	3.6	1
Hepatitis C virus CHEMBL379	EC50	8.4	6.458	4.0	20
Protein phosphatase 3 catalytic subunit alpha CHEMBL4445	Kd	8.4	8.4	4.0	1
Interleukin-2 CHEMBL2466	IC50	8.3	8.3	5.0	1
Jurkat CHEMBL397	EC50	8.3	8.235	5.0	2
Tolypocladium inflatum CHEMBL612346	IC50	8.3	8.3	5.0	1
Peptidyl-prolyl cis-trans isomerase A CHEMBL1949	Kd	8.22	7.5892	6.0	12
Peptidyl-prolyl cis-trans isomerase FKBP1B CHEMBL2430	Ki	8.22	8.22	6.0	1
Unchecked CHEMBL612545	Kd	8.22	8.22	6.0	1
T-cell CHEMBL614309	EC50	8.19	8.19	6.4	1
Jurkat CHEMBL397	IC50	8.15	7.6583	7.0	6
Peptidyl-prolyl cis-trans isomerase B CHEMBL2075	IC50	8.06	8.06	8.8	1
Peptidyl-prolyl cis-trans isomerase B CHEMBL2075	Kd	8.01	8.01	9.8	1
Splenocyte CHEMBL612422	IC50	8.0	7.0194	10.0	16
ADMET CHEMBL612558	IC50	8.0	6.4133	10.0	6
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.96	6.565	11.0	22
Peptidyl-prolyl cis-trans isomerase D CHEMBL1697657	Kd	7.89	7.705	13.0	2
Peptidyl-prolyl cis-trans isomerase FKBP4 CHEMBL4050	IC50	7.8	7.8	16.0	1
Mus musculus CHEMBL375	EC50	7.75	7.75	17.8	1
Peptidyl-prolyl cis-trans isomerase FKBP1A CHEMBL1902	Ki	7.7	7.7	20.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	Ki	7.7	6.1317	20.0	6
Homo sapiens CHEMBL372	EC50	7.64	7.64	23.0	1
Splenocyte CHEMBL612422	EC50	7.52	7.52	30.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	EC50	7.5	6.0788	32.0	8
Unchecked CHEMBL612545	EC50	7.5	5.4433	32.0	6
Unchecked CHEMBL612545	Ki	7.46	6.0033	35.0	3
Lymphocyte CHEMBL612599	IC50	7.27	7.1967	54.0	3
Homo sapiens CHEMBL372	IC50	7.22	7.22	60.0	1
Lymphocyte CHEMBL612599	EC50	7.22	7.22	60.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	6.99	5.8983	102.3	47
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	IC50	6.89	6.39	130.0	2
B-cell CHEMBL614701	IC50	6.8	6.8	159.0	1
Protein phosphatase 3 catalytic subunit alpha CHEMBL4445	IC50	6.74	6.74	183.0	1
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	Ki	6.7	6.4775	200.0	4
NCI/ADR-RES CHEMBL613829	IC50	6.54	6.3	290.0	3
Bile salt export pump CHEMBL2073674	Ki	6.52	6.52	300.0	1
Cytochrome P450 3A4 CHEMBL340	Ki	6.52	5.885	300.0	4
Bile salt export pump CHEMBL6020	IC50	6.4	6.0025	400.0	8

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	13800.0	ng.hr.mL-1	Rattus norvegicus
AUC	476000.0	ng.hr.mL-1	Rattus norvegicus
AUC	11556.0	ng.hr.mL-1	Homo sapiens
AUC	5971.0	ng.hr.mL-1	Homo sapiens
AUC	9939.0	ng.hr.mL-1	Homo sapiens
AUC	9399.0	ng.hr.mL-1	Homo sapiens
AUC	4471.0	ng.hr.mL-1	Homo sapiens
AUC	8799.0	ng.hr.mL-1	Homo sapiens
AUC	6467.0	ng.hr.mL-1	Homo sapiens
AUC	11479.0	ng.hr.mL-1	Homo sapiens
AUC	6637.0	ng.hr.mL-1	Homo sapiens
AUC	3689.0	ng.hr.mL-1	Homo sapiens
AUC	9485.0	ng.hr.mL-1	Homo sapiens
AUC	5509.0	ng.hr.mL-1	Homo sapiens
AUC	2553.0	ng.hr.mL-1	Homo sapiens
AUC	2232.0	ng.hr.mL-1	Homo sapiens
AUC	334.0	ng.hr.mL-1	Homo sapiens
AUC	853.0	ng.hr.mL-1	Homo sapiens
AUC	812.0	ng.hr.mL-1	Homo sapiens
AUC	569.0	ng.hr.mL-1	Homo sapiens
AUC	170.0	ng.hr.mL-1	Homo sapiens
AUC	266.0	ng.hr.mL-1	Homo sapiens
AUC	4471.0	ng.hr.mL-1	Homo sapiens
AUC	5856.81	ng.hr.mL-1	Homo sapiens
AUC	2900.0	ng.hr.mL-1	Mus musculus
CL	7.5	mL.min-1.kg-1	Homo sapiens
CL	7.4	mL.min-1.kg-1	Homo sapiens
CL	7.5	mL.min-1.kg-1	Homo sapiens
CL	77000.0	mL.min-1.g-1	Mus musculus
CL	29000.0	mL.min-1.g-1	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	0.047	nM	10.33	Inhibition of fMLP-OMe-induced chemotaxis in human neutrophils	17475488
Neutrophil	IC50	=	0.047	nM	10.33	Reduction of chemotaxis in human neutrophils assessed as inhibition of fMLP-OMe-...	19362486
Plasmodium falciparum	IC50	=	0.47	nM	9.33	Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr...	19734910
Plasmodium falciparum	IC50	=	0.56	nM	9.25	Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	0.56	nM	9.25	Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	0.63	nM	9.2	Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	0.71	nM	9.15	Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	0.83	nM	9.08	Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g...	19734910
Trypanosoma brucei brucei	IC50	=	1.14	nM	8.94	Antitrypanosomal activity against bloodstream form of Trypanosoma brucei brucei ...	23927763
Plasmodium falciparum	IC50	=	1.26	nM	8.9	Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g...	19734910
T-cell	IC50	=	1.34	nM	8.87	In vitro concentration of compound required to inhibit ConA-induced T cell proli...	15999998
T-cell	IC50	=	1.37	nM	8.86	Inhibition of ConA-induced BALB/c mouse T cell proliferation	17081761
Unchecked	IC50	=	1.4	nM	8.85	Inhibition of NFAT activation in PMA/ionomycin-stimulated human Jurkat T cells i...	23964991
Peptidyl-prolyl cis-trans isomerase A	Ki	=	1.5	nM	8.82	Protease-Free PPIase Assay: The protease-free PPIase assay measures the rate of ...	-
Plasmodium berghei	IC50	=	1.65	nM	8.78	HARVARD: Inhibition of liver stage Plasmodium berghei infection in HepG2 cells	22586124
Unchecked	IC50	=	1.8	nM	8.74	Inhibition of P-gp in human MDA435/LCC6MDR cells assessed as potentiation of pac...	27750197
Peptidyl-prolyl cis-trans isomerase A	IC50	=	2.0	nM	8.7	Immunosuppressive activity was measured by inhibition of the IL-2 production in ...	14643337
Mus musculus	IC50	=	2.5	nM	8.6	Inhibitory activity against the production of interleukin 4 (IL-4)	10617078
Peptidyl-prolyl cis-trans isomerase D	Ki	=	2.58	nM	8.59	Binding affinity to human recombinant cyclophilin D by surface plasmon resonance...	26985318
Peptidyl-prolyl cis-trans isomerase A	Ki	=	2.64	nM	8.58	Inhibition of calcineurin phosphatase activity of CyPA	19933795

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1396
-	10.6019/CHEMBL3885881	Rattus norvegicus	1062
-	10.1101/2024.03.28.586928	ADMET	100
8132853	10.1002/j.1552-4604.1994.tb03967.x	Blood	42
2391396	10.1002/j.1552-4604.1990.tb01868.x	Plasma	31
2391396	10.1002/j.1552-4604.1990.tb01868.x	Blood	26
8132853	10.1002/j.1552-4604.1994.tb03967.x	Plasma	19
34096287	10.1021/acs.jmedchem.1c00211	ADMET	17
19734910	10.1038/nchembio.215	Plasmodium falciparum	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
12699389	10.1021/jm021012t	ATP-dependent translocase ABCB1	13
30613324	10.1021/acsmedchemlett.8b00324	ATP-dependent translocase ABCB1	13
33508480	10.1016/j.ejmech.2021.113168	SH-SY5Y	12
18024584	10.1073/pnas.0709695104	H4	11
19451286	10.1128/aac.00189-09	West Nile virus	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
8893839	10.1021/jm960391l	Rattus norvegicus	10
27815116	10.1016/j.bmcl.2016.10.050	Peptidyl-prolyl cis-trans isomerase A	10
10956203	10.1021/jm000173z	Rattus norvegicus	9
21051535	10.1124/dmd.110.034629	ADMET	9

Data from ChEMBL 36 via Core Engine