CYCLOSPORINE

Search structure
Synonyms:
Status: Approved (1983)
Entry Type: Protein
Molecule Category: UNKNOWN
UNII: 83HN0GTJ6D

Structure
InChI Key PMATZTZNYRCHOR-CGLBZJNRSA-N
Smile 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
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C62H111N11O12
Molecular Weight 1202.63
AlogP None
Hydrogen Bond Acceptor None
Hydrogen Bond Donor None
Number of Rotational Bond None
Polar Surface Area None
Molecular species None
Aromatic Rings None
Heavy Atoms None

Pharmacology

Action Mechanism of Action Reference
MODULATOR Cyclophilin A modulator FDA PubMed PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 7000 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 38800 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 1450-6600 - 300-7600 -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A5
- 1240-1470 - 980 -
Enzyme Hydrolase
- 455 - -
Enzyme Isomerase
- 2-950 8-6420 3-231 50
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase PIKK family Atypical protein kinase FRAP subfamily
- - - - 10
Enzyme Oxidoreductase
- 1240-1470 - 980 -
Enzyme Phosphatase Protein Phosphatase Serine/threonine protein phosphatase
- 183 4 - -
Enzyme Transferase
- 570 - - -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 2000 - - -
Secreted protein
- 5 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 700-1400 - 200-1300 4-104
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 4
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
32-80000 102-9340 - - 43-100
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
1700 2700-6630 - - 100
Transporter Primary active transporter ATP-binding cassette ABCG subfamily
1750 63096 - - -
Transporter Primary active transporter P-type ATPase Calcium ATPase
- 62000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Arthritis, Rheumatoid 4 D001172 ClinicalTrials
Glomerulosclerosis, Focal Segmental 3 D005923 ClinicalTrials
Glomerulonephritis, Membranous 3 D015433 ClinicalTrials
Dermatitis, Atopic 3 D003876 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Anemia, Aplastic 3 D000741 ClinicalTrials
Myelodysplastic Syndromes 3 D009190 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Dry Eye Syndromes 3 D015352 ClinicalTrials
Renal Insufficiency, Chronic 3 D051436 ClinicalTrials
Conjunctivitis, Allergic 3 D003233 ClinicalTrials
Hepatitis C, Chronic 3 D019698 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 3 D016553 ClinicalTrials
Bronchiolitis Obliterans 3 D001989 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 3 D015464 ClinicalTrials
Infections 3 D007239 ClinicalTrials
Dermatomyositis 3 D003882 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Diabetes Mellitus, Type 1 3 D003922 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Heart Diseases 3 D006331 ClinicalTrials
Stevens-Johnson Syndrome 3 D013262 ClinicalTrials
Hepatitis, Autoimmune 3 D019693 ClinicalTrials
Lupus Nephritis 3 D008181 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Anemia, Aplastic 3 D000741 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Eczema 3 D004485 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Waldenstrom Macroglobulinemia 3 D008258 ClinicalTrials
Heart Arrest 3 D006323 ClinicalTrials
Lymphoma, Mantle-Cell 3 D020522 ClinicalTrials
Renal Insufficiency 3 D051437 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Red-Cell Aplasia, Pure 3 D012010 ClinicalTrials
Skin Neoplasms 3 D012878 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Lymphohistiocytosis, Hemophagocytic 3 D051359 ClinicalTrials
Purpura, Thrombotic Thrombocytopenic 3 D011697 ClinicalTrials
Behcet Syndrome 3 D001528 ClinicalTrials
Retinal Vasculitis 3 D031300 ClinicalTrials
Endocardial Cushion Defects 3 D004694 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Retinoblastoma 2 D012175 ClinicalTrials
Kidney Diseases 2 D007674 ClinicalTrials
Pterygium 2 D011625 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Neuroblastoma 2 D009447 ClinicalTrials
Leukemia, Prolymphocytic, T-Cell 2 D015461 ClinicalTrials
Epidermolysis Bullosa 2 D004820 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Lacrimal Apparatus Diseases 2 D007766 ClinicalTrials
Reperfusion Injury 2 D015427 ClinicalTrials
Liver Diseases 2 D008107 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Lymphoma, AIDS-Related 2 D016483 ClinicalTrials
Lung Diseases 2 D008171 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Leprosy 2 D007918 ClinicalTrials
Burkitt Lymphoma 2 D002051 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Kidney Neoplasms 2 D007680 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Leukemia, Mast-Cell 2 D007946 ClinicalTrials
Cystitis, Interstitial 2 D018856 ClinicalTrials
Myelodysplastic-Myeloproliferative Diseases 2 D054437 ClinicalTrials
Diabetes Mellitus 2 D003920 ClinicalTrials
Glaucoma 2 D005901 ClinicalTrials
Systemic Inflammatory Response Syndrome 2 D018746 ClinicalTrials
Optic Atrophy, Hereditary, Leber 2 D029242 ClinicalTrials
Myocarditis 2 D009205 ClinicalTrials
Neoplasm Metastasis 2 D009362 ClinicalTrials
Periodontitis 2 D010518 ClinicalTrials
Hyperlipoproteinemia Type I 2 D008072 ClinicalTrials
Aortic Aneurysm, Abdominal 2 D017544 ClinicalTrials
Granulomatous Disease, Chronic 2 D006105 ClinicalTrials
Paraparesis, Tropical Spastic 2 D015493 ClinicalTrials
Acute Kidney Injury 2 D058186 ClinicalTrials
Leukemia, Prolymphocytic, B-Cell 2 D054403 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Hepatitis C 2 D006526 ClinicalTrials
Lymphoma, Follicular 2 D008224 ClinicalTrials
Leukemia, Large Granular Lymphocytic 2 D054066 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Myositis 2 D009220 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Brain Injuries 1 D001930 ClinicalTrials
Anemia, Sickle Cell 1 D000755 ClinicalTrials
DiGeorge Syndrome 1 D004062 ClinicalTrials
Osteogenesis Imperfecta 1 D010013 ClinicalTrials
Mucopolysaccharidoses 1 D009083 ClinicalTrials
Fanconi Anemia 1 D005199 ClinicalTrials
beta-Thalassemia 1 D017086 ClinicalTrials
Angioedemas, Hereditary 1 D054179 ClinicalTrials
Diabetes Mellitus, Type 2 1 D003924 ClinicalTrials
Brain Neoplasms 1 D001932 ClinicalTrials
Sezary Syndrome 1 D012751 ClinicalTrials
Mycosis Fungoides 1 D009182 ClinicalTrials
Uveitis 1 D014605 ClinicalTrials
Respiratory Syncytial Virus Infections 1 D018357 ClinicalTrials
Myeloproliferative Disorders 1 D009196 ClinicalTrials
Carcinoma, Renal Cell 1 D002292 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 1 D029424 ClinicalTrials
Aspergillosis 1 D001228 ClinicalTrials
Neutropenia 1 D009503 ClinicalTrials
Venous Thromboembolism 1 D054556 ClinicalTrials
Urticaria 1 D014581 ClinicalTrials
Neoplasms, Neuroepithelial 0 D018302 ClinicalTrials

Cross References

Resources Reference
ChEBI 4031
ChEMBL CHEMBL160
DrugBank DB00091
DrugCentral 760
EPA CompTox DTXSID0020365
FDA SRS 83HN0GTJ6D
Guide to Pharmacology 1024
SureChEMBL SCHEMBL4442
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