U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C62H111N11O12
Molecular Weight 1202.6112
Optical Activity ( - )
Defined Stereocenters 12 / 12
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CYCLOSPORINE

SMILES

CC[C@@H]1NC(=O)[C@H]([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)C1=O)C(C)C

InChI

InChIKey=PMATZTZNYRCHOR-CGLBZJNRSA-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

HIDE SMILES / InChI

Molecular Formula C62H111N11O12
Molecular Weight 1202.6112
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 12 / 12
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Cyclosporins are cyclic polypeptide macrolides that were originally derived from the soil fungus Tolypocladium inflatum. Cyclosporine (also known as cyclosporine A) was discovered by Sandoz and developed for the tretment of immune disorders. The drug was approved by FDA for such diseases as Rheumatoid Arthritis, Psoriasis (Neoral), Keratoconjunctivitis sicca (Restasis) and prevention of transplant rejections (Neoral and Sandimmune). Cyclosporine’s primary immunosuppressive mechanism of action is inhibition of T-lymphocyte function. Upon administration cyclosporine binds to cyclophilin A and thus inhibits calcineurin, leading to immune system suppression.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Nephrotoxicity after orthotopic liver transplantation in cyclosporin A and FK 506-treated patients.
1994
Renal complications and development of hypertension in the European study of FK 506 and cyclosporin in primary liver transplant recipients.
1994
Acute myopathy induced by colchicine in a cyclosporine treated heart transplant recipient: possible role of the multidrug resistance transporter.
1999 Aug
Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity.
1999 Dec
Relation between long-term steroid treatment after heart transplantation, hypofibrinolysis and myocardial microthrombi generation.
1999 Jul
Aplastic anemia responsive to cyclosporine complicating the evolution of polycythemia vera.
1999 May
Enhancement of low density lipoprotein catabolism by non-steroidal anti-inflammatory drugs in cultured HepG2 cells.
1999 May 21
Which calcineurin inhibitor is preferred in renal transplantation: tacrolimus or cyclosporine?
1999 Nov
Hemolytic-uremic syndrome in association with both cyclosporine and tacrolimus.
2000
Rhabdomyolysis and acute renal failure in a cardiac transplant recipient due to multiple drug interactions.
2000 Dec
Cyclosporine withdrawal in stable renal transplant recipients after azathioprine-mycophenolate mofetil conversion.
2000 Dec
Suppressive effects of cyclosporin A and FK-506 on superoxide generation in human polymorphonuclear leukocytes primed by tumor necrosis factor alpha.
2000 Dec
Up-regulation of multidrug resistance P-glycoprotein via nuclear factor-kappaB activation protects kidney proximal tubule cells from cadmium- and reactive oxygen species-induced apoptosis.
2000 Jan 21
Comparison of enalapril and valsartan in cyclosporine A-induced hypertension and nephrotoxicity in spontaneously hypertensive rats on high-sodium diet.
2000 Jul
Phenytoin and cyclosporin A suppress the expression of MMP-1, TIMP-1, and cathepsin L, but not cathepsin B in cultured gingival fibroblasts.
2000 Jun
Ticlopidine-induced aplastic anemia: development of chromosomal abnormalities and response to immunosuppressive therapy.
2000 Mar
Design of a Gag pentapeptide analogue that binds human cyclophilin A more efficiently than the entire capsid protein: new insights for the development of novel anti-HIV-1 drugs.
2000 May 4
Tacrolimus has less fibrogenic potential than cyclosporin A in a model of renal ischaemia-reperfusion injury.
2000 Nov
Fatal cerebral hemorrhage associated with cyclosporin-A/FK506-related encephalopathy after allogeneic bone marrow transplantation.
2000 Oct
Cyclosporine and tacrolimus-associated thrombotic microangiopathy.
2000 Oct
Toxic epidermal necrolysis in a patient with severe aplastic anemia treated with cyclosporin A and G-CSF.
2001
Renal cholesterol accumulation: a durable response after acute and subacute renal insults.
2001 Aug
Calcineurin-inhibitor related nephrotoxicity- reversibility in paediatric liver transplant recipients.
2001 Aug 27
Bone marrow aplasia after pipobroman: an immune-mediated mechanism?
2001 Dec
End-stage renal disease (ESRD) after orthotopic liver transplantation (OLTX) using calcineurin-based immunotherapy: risk of development and treatment.
2001 Dec 27
Mycophenolate mofetil monotherapy in liver transplantation.
2001 Feb 24
Cyclosporin A for the treatment of patients with chronic idiopathic thrombocytopenic purpura refractory to corticosteroids or splenectomy.
2001 Jul
Targeting keratinocyte apoptosis in the treatment of atopic dermatitis and allergic contact dermatitis.
2001 Nov
Buerger's disease in a patient with minimal-change nephrotic syndrome.
2001 Nov
Severe neurotoxicity of tacrolimus (FK506) after renal transplantation: two case reports.
2001 Nov-Dec
Cyclosporin A-induced encephalopathy after allogeneic bone marrow transplantation with prevention of graft-versus-host disease by tacrolimus.
2001 Oct
Use of rapamycin in a transplant patient who developed cyclosporin neurotoxicity.
2001 Oct
Sirolimus and mycophenolate mofetil for calcineurin-free immunosuppression in renal transplant recipients.
2001 Oct
Changes in lipid metabolism and effect of simvastatin in renal transplant recipients induced by cyclosporine or tacrolimus.
2001 Oct
Sirolimus: new preparation. No tangible advance in renal transplantation.
2002 Dec
Expression of TGF-beta and fibrogenic genes in transplant recipients with tacrolimus and cyclosporine nephrotoxicity.
2002 Dec
Colchicine myoneuropathy in a renal transplant patient.
2002 Jul
Calcineurin inhibitors, cyclosporin A and tacrolimus inhibit expression of inducible nitric oxide synthase in colon epithelial and macrophage cell lines.
2002 Jul 19
Enhancement by cyclosporin A of taxol-induced apoptosis of human urinary bladder cancer cells.
2002 May
Oxidative stress in kidney transplant patients with calcineurin inhibitor-induced hypertension: effect of ramipril.
2002 Oct
Long-term comparison of tacrolimus- and cyclosporine-induced nephrotoxicity in pediatric heart-transplant recipients.
2002 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Organs transplantation: the initial oral dose of cyclosporine (Sandimmune) should be given 4 to 12 hours prior to transplantation as a single dose of 15 mg/kg. Rheumatoid Arthritis, Psoriasis: the initial dose of cyclosporine (Neoral) is 2.5 mg/kg/day, taken twice daily as a divided (BID) oral dose. Keratoconjunctivitis sicca: instill one drom twice a day in each eye, approximately 12 hours apart.
Route of Administration: Oral; Ophthalmic
In Vitro Use Guide
Human CD4+CD25+ cells isolated from healthy donors were cultured in the presence of 40 or 400 ng/mL of cyclosporine. The suppressive activity of Treg was assessed in mixed leukocyte reactions (MLR) using CD25+ and autologous activated peripheral blood mononuclear cells (PBMC). The drug inhibited the proliferative capacity of PBMC and CD4+CD25+ Treg in a dose-dependent manner.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:41:45 UTC 2019
Edited
by admin
on Mon Oct 21 20:41:45 UTC 2019
Record UNII
83HN0GTJ6D
Record Status Validated (UNII)
Record Version
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Name Type Language
CYCLOSPORINE
GREEN BOOK   HSDB   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
CYCLOSPORIN A [MI]
Common Name English
CICLOSPORINUM [WHO-IP LATIN]
Common Name English
EQUORAL
Common Name English
CYCLOSPORIN
Common Name English
CYCLOSPORINE [GREEN BOOK]
Common Name English
CICLOSPORIN A
Common Name English
GENGRAF
Brand Name English
RAMIHYPHIN A
Common Name English
(R-(R*,R*-(E)))-CYCLIC(L-ALANYL-D-ALANYL-N-METHYL-L-LEUCYL-N-METHYL-L-LEUCYL-N-METHYL-L-VALYL-3-HYDROXY-N,4-DIMETHYL-L-2-AMINO-6-OCTENOYL-L-.ALPHA.-AMINOBUTYRYL-N-METHYLGLYCYL-N-METHYL-L-LEUCYL-L-VALYL-N-METHYL-L-LEUCYL)
Common Name English
NSC-290193
Code English
NEOPLANTA
Common Name English
SANDIMMUNE
Brand Name English
NEORAL
Brand Name English
SDZ-OXL-400
Code English
MITOGARD
Brand Name English
OL-27-400
Code English
NEUROSTAT
Brand Name English
CYCLOSPORINE [USP-RS]
Common Name English
CICLOSPORIN [EP]
Common Name English
ATOPICA
Brand Name English
CYCLOSPORINE [HSDB]
Common Name English
OPTIMMUNE
Brand Name English
CYCLOSPORINE [USP]
Common Name English
CYCLO(((E)-(2S,3R,4R)-3-HYDROXY-4-METHYL-2-(METHYLAMINO)-6-OCTENOYL)-L-2-AMINOBUTYRYL-N-METHYLGLYCYL-N-METHYL-L-LEUCYL-L-VALYL-N-METHYL-L-LEUCYL-L-ALANYL-D-ALANYL-N-METHYL-L-LEUCYL-N-METHYL-L-LEUCYL-N-METHYL-L-VALYL)
Common Name English
CYCLOSPORINE MICROEMULSION
Common Name English
CICLOSPORIN [WHO-DD]
Common Name English
IKERVIS
Brand Name English
CYCLOSPORINE [IARC]
Common Name English
CYCLOSPORINE, MODIFIED
Common Name English
CYCLOSPORINE [VANDF]
Common Name English
ANTIBIOTIC S-7481F1
Code English
CICLOSPORIN [JAN]
Common Name English
CYCLOSPORINE [USAN]
Common Name English
CICLOSPORIN
EP   INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
CICLOSPORIN [INN]
Common Name English
CYCLOSPORIN A
MI  
Common Name English
SANG-35
Code English
27-400
Code English
CEQUA
Brand Name English
CYCLOSPORINE [ORANGE BOOK]
Common Name English
CYCLOSPORINE A
Common Name English
CICLOSPORIN [WHO-IP]
Common Name English
RESTASIS
Brand Name English
ZINOGRAF ME
Common Name English
SANDIMMUN
Brand Name English
CICLOSPORIN [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QS01XA18
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 252207
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 252107
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 224106
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
NCI_THESAURUS C574
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 319710
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 138500
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 273308
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 58991
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 176303
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 29988
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 239907
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
NDF-RT N0000175458
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 254807
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
EMA ASSESSMENT REPORTS IKERVIS (AUTHORIZED: CORNEAL DISEASES)
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
LIVERTOX 250
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 275108
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 8.1
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
WHO-ATC S01XA18
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
CFR 21 CFR 862.1235
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 194704
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
NCI_THESAURUS C1744
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 112798
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
NDF-RT N0000175457
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
CFR 21 CFR 520.522
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
WHO-VATC QL04AD01
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 254907
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 180103
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
FDA ORPHAN DRUG 51790
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
NCI_THESAURUS C146638
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
WHO-ATC L04AD01
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
CFR 21 CFR 524.575
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
EU-Orphan Drug EU/3/06/415
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
Code System Code Type Description
WIKIPEDIA
CICLOSPORIN
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
INN
5086
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
CAS
59865-13-3
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
MESH
D016572
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
IUPHAR
1024
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
LactMed
59865-13-3
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
EVMPD
SUB06250MIG
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
PUBCHEM
5284373
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
RXCUI
3008
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
EVMPD
SUB129839
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CYCLOSPORINE
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY Description: A white or almost white powder.Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS and dichloromethane R.Category: Immunosuppressant drug.Storage: Ciclosporin should be kept in a well-closed container, protected from light.
HSDB
59865-13-3
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
RXCUI
236077
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
ALTERNATIVE
NDF-RT
N0000185503
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY P-Glycoprotein Inhibitors [MoA]
DRUG BANK
DB00091
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
NDF-RT
N0000182141
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
RXCUI
484788
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
ALTERNATIVE
NCI_THESAURUS
C406
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
MERCK INDEX
M4020
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL160
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
EPA CompTox
59865-13-3
Created by admin on Mon Oct 21 20:41:46 UTC 2019 , Edited by admin on Mon Oct 21 20:41:46 UTC 2019
PRIMARY
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