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Cyclosporine

Immunosuppressant drug CAS# 79217-60-0

Cyclosporine

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Chemical structure

Cyclosporine

3D structure

Chemical Properties of Cyclosporine

Cas No. 79217-60-0 SDF Download SDF
PubChem ID 6435893 Appearance Powder
Formula C62H111N11O12 M.Wt 1202.61
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in DMSO > 10 mM
Chemical Name 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
SMILES CCC1C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1)C(C(C)CC=CC)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C
Standard InChIKey PMATZTZNYRCHOR-KMSBSJHKSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Cyclosporine Dilution Calculator

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Cyclosporine Molarity Calculator

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Preparing Stock Solutions of Cyclosporine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.8315 mL 4.1576 mL 8.3152 mL 16.6305 mL 20.7881 mL
5 mM 0.1663 mL 0.8315 mL 1.663 mL 3.3261 mL 4.1576 mL
10 mM 0.0832 mL 0.4158 mL 0.8315 mL 1.663 mL 2.0788 mL
50 mM 0.0166 mL 0.0832 mL 0.1663 mL 0.3326 mL 0.4158 mL
100 mM 0.0083 mL 0.0416 mL 0.0832 mL 0.1663 mL 0.2079 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Cyclosporine

Cydosporin A, a immunosuppressive agent, inhibits phosphatase activity of calcineurin with IC50 value of 5 nM [1].
The immunosuppressive agent cydosporin A (CsA) binds to soluble cytosolic proteins named cyclophilins, and the complex of cyclophilin–CsA blocks calcineurin, which inhibits stimulation of the NFAT-induced genes which are required for the activation of T cells.
As a widely used immunosuppressive agent, cyclosporin A has been reported to be effective against HCV infection. The anti-viral effects of CsA has been investigated by an HCV replicon system. Huh7/Rep-Feo cells treated with CsA with an IC50 value of about 0.5 μg/ml resulted in suppression of the replication of the HCV replicon in a dose-dependent manner. There were no changes in the rate of cell growth or viability, revealing that the specific effect of CsA against HCV is not due to cytotoxicity. CsA inhibits HCV replication in vitro specifically at clinical concentrations [2].
Transplantation of CSA-expanded FCV cells to chronic myocardial infarction was performed in the model of rat. Transplanted FCV cells were successfully differentiated into cardiomyocytes and integrated in the infarct heart to form GFP+/cTnT+ donor cell-derived cardiomyocyte bundle in the scar tissue in 2 weeks after the injection. The result show that CSA-expanded FCV cells can show highly cardiogenic potentials also in vivo after cell transplantation [3].
References:
[1]. Fruman DA , Klee CB, Bierer BE, et al. Calcineurin Phosphatase-Activity In Lymphocytes-T Is Inhibited By Fk-506 And Cyclosporine-A. Proceedings Of The National Academy Of Sciences Of The United States Of America. 1992, 89(9): 3686-3690.
[2]. Nakagawa M, Sakamoto N, Enomoto N, et al. Specific inhibition of hepatitis C virus replication by cyclosporin A. Biochemical And Biophysical Research Communications. 2004, 313(1): 42-47.
[3]. Yan P, Nagasawa A, Uosaki H, et al. Cyclosporin-A potently induces highly cardiogenic progenitors from embryonic stem cells. Biochemical And Biophysical Research Communications. 2009, 379(1): 115-120.

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References on Cyclosporine

Effectiveness, safety and tolerability of cyclosporine versus supportive treatment in Stevens-Johnson Syndrome/Toxic Epidermal Necrolysis: A record-based study.[Pubmed:28366923]

Indian J Dermatol Venereol Leprol. 2017 May-Jun;83(3):312-316.

BACKGROUND: Toxic epidermal necrolysis and Stevens-Johnson syndrome comprise life-threatening, drug-induced mucocutaneous disease spectrum. Interest in Cyclosporine, a calcineurin inhibitor that can block the function of T-cells, has increased with the discovery of the importance of granulysin in apoptosis in toxic epidermal necrolysis. In our hospital, Cyclosporine is given to Stevens-Johnson syndrome/toxic epidermal necrolysis patients as an adjunctive therapy. AIMS: This study is an observational, record-based study comparing the effectiveness and safety of patients receiving Cyclosporine versus only supportive therapy. METHODOLOGY: Medical records as bed-head tickets and laboratory investigation reports of Stevens-Johnson syndrome/toxic epidermal necrolysis patients admitted in the hospital over a period of 1 year were collected. Data regarding clinico-demographic profile, suspected drug causing Stevens-Johnson's syndrome/toxic epidermal necrolysis, SCORTEN, body surface area involved, treatment received and outcome were obtained. RESULTS: Twenty-eight patients were analyzed. Nineteen belonged to the Cyclosporine group (supportive treatment + Cyclosporine), nine to supportive treatment only group. Among the suspected drugs, antiepileptics formed the major group (28.6%). Five patients in the supportive only group and one in the Cyclosporine group died. Time for stabilization and reepithelialization and duration of recovery were significantly lower in the Cyclosporine group (P < 0.001, P= 0.007, P= 0.01, respectively). The standardized mortality ratio was 0.32 in Cyclosporine group which is nearly 3.3 times lower than the only supportive treatment. LIMITATIONS: As it was a record-based study, certain confounding factors (serum blood urea nitrogen) could not be adjusted. CONCLUSION: Cyclosporine (5 mg/kg/day) for 10 days from onset of Stevens-Johnson syndrome/toxic epidermal necrolysis may decrease the risk of dying, may provide faster healing of lesions and might lead to early discharge from hospital.

Protective Effect of Edaravone Against Cyclosporine-Induced Chronic Nephropathy Through Antioxidant and Nitric Oxide Modulating Pathways in Rats.[Pubmed:28360443]

Iran J Med Sci. 2017 Mar;42(2):170-178.

BACKGROUND: Cyclosporine A (CsA) is an immunosuppressant with therapeutic indications in various immunological diseases; however, its use is associated with chronic nephropathy. Oxidative stress has a crucial role in CsA-induced nephrotoxicity. The present study evaluates the protective effect of edaravone on CsA-induced chronic nephropathy and investigates its antioxidant and nitric oxide modulating property. METHODS: Male Sprague-Dawley rats (n=66) were distributed into nine groups, including a control (group 1) (n=7). Eight groups received CsA (15 mg/kg) for 28 days while being treated. The groups were categorized as: Group 2: Vehicle (n=10)Groups 3, 4, and 5: Edaravone (1, 5, and 10 mg/kg) (n=7 each)Group 6: Diphenyliodonium chloride, a specific endothelial nitric oxide synthase (eNOS) inhibitor (n=7)Group 7: Aminoguanidine, a specific inducible nitric oxide synthase (iNOS) inhibitor (n=7)Group 8: Edaravone (10 mg/kg) plus diphenyliodonium chloride (n=7)Group 9: Edaravone (10 mg/kg) plus aminoguanidine (n=7) Blood urea nitrogen and serum creatinine levels, malondialdehyde, superoxide dismutase, and glutathione reductase enzyme activities were measured using standard kits. Renal histopathological evaluations and measurements of eNOS and iNOS gene expressions by RT-PCR were also performed. Data were analyzed using one-way analysis of variance (ANOVA) followed by Tukey's test (SPSS software version 18.0). RESULTS: Edaravone (10 mg/kg) significantly attenuated CsA-induced oxidative stress, renal dysfunction, and kidney tissue injury. Aminoguanidine improved the renoprotective effect of edaravone. Edaravone reduced the elevated mRNA level of iNOS, but could not alter the level of eNOS mRNA significantly. CONCLUSION: Edaravone protects against CsA-induced chronic nephropathy using antioxidant property and probably through inhibiting iNOS gene expression.

Infection rates in tacrolimus versus cyclosporine-treated pediatric kidney transplant recipients on a rapid discontinuation of prednisone protocol: 1-year analysis.[Pubmed:28371243]

Pediatr Transplant. 2017 Jun;21(4).

AR is lower in pKTx recipients on Tac vs CsA. Data comparing infection outcomes for children treated with these agents are limited. We retrospectively studied infection outcomes in 96 pKTx recipients on a RDP. PS, DCGS, AR, and infection-free survival were assessed using Kaplan-Meier/log-rank tests and proportional hazards models. There were no differences in 1-year PS, DCGS, or AR between Tac and CsA recipients. After adjusting for AR, the hazard of CMV viremia was 4.0 times higher (95%CI: 1.04, 15.5; P = .044) and that of BK viremia was 3.8 times higher (95%CI: 1.5, 10.2; P = .007) in Tac recipients. The incidence of EBV viremia was similar between the groups (P = .56). PostTx lymphoproliferative disease was only observed in Tac recipients (3%). There was no difference in the incidence of pneumonia, urinary tract, or Clostridium difficile infections between Tac and CsA recipients. Among KTx recipients on RDP, the hazards of CMV and BK viremia within 1 year post-KTx were significantly higher in Tac recipients compared to CsA. Regular assessment for infections and lower Tac trough levels may be warranted in Tac recipients.

A randomized study of the efficacy and safety of 0.1% cyclosporine A cationic emulsion in treatment of moderate to severe dry eye.[Pubmed:28362054]

Eur J Ophthalmol. 2017 Aug 30;27(5):520-530.

PURPOSE: The SICCANOVE study aimed to compare the efficacy and safety of 0.1% Cyclosporine A cationic emulsion (CsA CE) versus vehicle in patients with moderate to severe dry eye disease (DED). METHODS: In this multicenter, double-masked, parallel-group, controlled study, patients were randomized (1:1) to receive CsA CE (Ikervis(R)) or vehicle for 6 months. The co-primary efficacy endpoints at month 6 were mean change from baseline in corneal fluorescein staining (CFS; modified Oxford scale) and in global ocular discomfort (visual analogue scale [VAS]). RESULTS: The mean change in CFS from baseline to month 6 (CsA CE: n = 241; vehicle: n = 248) was significantly greater with CsA CE than with vehicle (-1.05 +/- 0.98 and -0.82 +/- 0.94, respectively; p = 0.009). Ocular discomfort improved similarly in both groups; however, the percentage of patients with >/=25% improvement in VAS was significantly higher with CsA CE (50.2%) than with vehicle (41.9%; p = 0.048). In a post hoc analysis of patients with severe ocular surface damage (CFS score 4) at baseline (CsA CE: n = 43; vehicle: n = 42), the percentage of patients with improvements of >/=2 grades in CFS score and >/=30% in Ocular Surface Disease Index score was significantly greater with CsA CE (p = 0.003). Treatment compliance and ocular tolerability were satisfactory and as expected for CsA use. CONCLUSION: Cyclosporine A CE was well-tolerated and effectively improved signs and symptoms in patients with moderate to severe DED over 6 months, especially in patients with severe disease, who are at risk of irreversible corneal damage.

Description

Cyclosporine is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

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