CAS Number59865-13-3
Synonymsciclosporin A; sandimmun; Optimmune; cyclosporine A; sandimmun neoral; s7481f1; Cyclosporin A; Neoplanta; MFCD00274558; Restasis; Sandimmun optoral; Neoral; Cipol N; ol27-400; EINECS 200-835-2; CyclosporineA
Molecular FormulaC62H111N11O12
Molecular Weight1202.61
Purity98%
Density1.0±0.1 g/cm3
Boiling Point1293.8±65.0 °C at 760 mmHg
Melting Point148-151°C
AppearanceDMSO solution
EINECS200-664-3
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 59865-13-3 |
| Catalog No. | 2A-9009961 |
| Chinese Name | 环孢霉素A |
| Synonyms | ciclosporin A; sandimmun; Optimmune; cyclosporine A; sandimmun neoral; s7481f1; Cyclosporin A; Neoplanta; MFCD00274558; Restasis; Sandimmun optoral; Neoral; Cipol N; ol27-400; EINECS 200-835-2; CyclosporineA |
| Molecular Formula | C62H111N11O12 |
| Molecular Weight | 1202.61 |
| Purity | 98 |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 1293.8±65.0 °C at 760 mmHg |
| Melting Point | 148-151°C |
| Appearance | DMSO solution |
| Water Solubility | ethanol: 30 mg/mL |
| Storage Condition | 2-8℃ |
| Application | Cyclosporin A is an immunosuppressant that can bind to cyclophilin and inhibit calcineurin activity with an IC50 value of 7 nM. |
| EINECS | 200-664-3 |
| HTC | 2941909000 |
| SMILES | N1(C(C(=O)NC(C(=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(C1=O)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)CC)C(O)C(C\C=C\C)C)C |
| 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+ |
| InChI Key | PMATZTZNYRCHOR-IMVLJIQESA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| MSDS | msds/9961_1_59865_13_3.pdf |
| Bioactivity | Cyclosporin A is an immunosuppressant which binds to the cyclophilin and inhibits phosphatase activity of calcineurin with an IC50 of 5 nM. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Inflammation/Immunology Target IC50: 7 nM (calcineurin) In Vitro Cyclosporin A is able to bind with the cyclophilin in T cells[1]. Cyclosporin A works by forming a Cyclophilin-Cyclosporin A complex to inhibit calcineurin[2]. Cyclosporin A exhibits inhibitory effect on calcineurin with an IC50 of 7 nM[3]. Cyclosporin A suppresses the nuclear translocation of NF-AT[4]. Cyclosporin A shows an effect on mitochondria via preventing the MTP from opening with an IC50 of 39 nM[5]. In Vivo Cyclosporin A has immunosuppressive activity, and is active via parenteral and p.o. administration in mice, rat and guinea pigs[6]. Cyclosporin A can be used in organ transplantation to prevent rejection[7]. Kinase Assay Reaction mixtures with purified enzyme contains 100 nM calcineurin, 100 nM calmodulin, and 5 μM 32P-labeled phosphopeptide, in 60 μL (total volume) of assay buffer containing 20 mM Tris (pH 8), 100 mM NaCl, 6 mM MgCl2, 0.5 mM dithiothreitol, 0.1 mg of bovine serum albumin per mL, and either 0.1 mM CaCl2 or 5 mM EGTA. Reaction mixtures with cell lysates contains 20 μL of undiluted lysate, 5 μM 32P-labeled phosphopeptide, and 40 μL of assay buffer. Reaction mixtures contains 50 μM peptide 412 or 413 and/or 500 nM okadaic acid, a specific inhibitor of phosphatases 1 and 2A; 500 nM okadaic acid is sufficient for inhibition of Ca2+-independent phosphatases, whereas higher concentrations partially inhibit Ca2+-dependent activity as well. After 15 min at 30°C, reactions are terminated by the addition of 0.5 mL of 100 mM potassium phosphate buffer (pH 7.0) containing 5% trichloroacetic acid. Free inorganic phosphate is isolated by Dowex cation-exchange chromatography and quantitated by scintillation counting as described. Cell Assay Immunosuppressive agents are dissolved in ethanol at concentrations 1000-fold more than the concentration desired for cell treatments. Cells (106) are suspended in 1 mL of complete medium in microcentrifuge tubes; 1 μL of ethanol or of the ethanolic solution of Cyclosporin A is added, and the cells are incubated at 37°C for 1 hr. Cells are washed twice with 1 mL of PBS on ice and lysed in 50 μL of hypotonic buffer containing 50 mM Tris (pH 7.5); 0.1 mM EGTA; 1 mM EDTA; 0.5 mM dithiothreitol; and 50 μg of phenylmethylsulfonyl fluoride, 50 μg of soybean trypsin inhibitor, 5 μg of leupeptin, and 5 μg of aprotinin per mL. Lysates are subjected to three cycles of freezing in liquid nitrogen followed by thawing at 30°C and then are centrifuged at 4°C for 10 min at 12,000×g. Animal Admin Rats are immunized on day 0 i.p. with 0 5 mL and mice i.v. with 0 2 mL of a 10% suspension of washed sheep erythrocytes (SE). To elicit a secondary response, mice are boosted 8-11 weeks after the primary immunization with an i.v. injection of 0-2 mL of 0 25% washed SE (107 cells). For prolonged treatment the animals receive on the average 45 mg/kg cyclosporin A daily in the food during 13 weeks. These rats are immunized 5 days before killing. References [1]. Handschumacher RE, et al. Cyclophilin: a specific cytosolic binding protein for cyclosporin A. Science. 1984 Nov 2;226(4674):544-7. [2]. Liu J, et al. Calcineurin is a common target of cyclophilin-cyclosporin A and FKBP-FK506 complexes. Cell. 1991 Aug 23;66(4):807-15. [3]. Fruman DA, et al. Calcineurin phosphatase activity in T lymphocytes is inhibited by FK 506 and cyclosporin A. Proc Natl Acad Sci U S A. 1992 May 1;89(9):3686-90. [4]. Flanagan WM, et al. Nuclear association of a T-cell transcription factor blocked by FK-506 and cyclosporin A. Nature. 1991 Aug 29;352(6338):803-7. [5]. Nicolli A, et al. Interactions of cyclophilin with the mitochondrial inner membrane and regulation of the permeability transition pore, and cyclosporin A-sensitive channel. J Biol Chem. 1996 Jan 26;271(4):2185-92. [6]. Borel JF, et al. Effects of the new anti-lymphocytic peptide cyclosporin A in animals. Immunology. 1977 Jun;32(6):1017-25. [7]. Williams, R, et al. Randomised trial comparing tacrolimus (FK506) and cyclosporin in prevention of liver allograft rejection. European FK506 Multicentre Liver Study Group. Lancet, 1994, 344(8920), 423-428. Chemical & Physical Properties Density 1.0±0.1 g/cm3 Boiling Point 1293.8±65.0 °C at 760 mmHg Melting Point 148-151°C Molecular Formula C62H111N11O12 Molecular Weight 1202.611 Flash Point 736.3±34.3 °C Exact Mass 1201.841309 PSA 278.80000 LogP 3.35 Vapour Pressure 0.0±0.6 mmHg at 25°C Index of Refraction 1.468 InChIKey PMATZTZNYRCHOR-LQJDIJJQSA-N SMILES CC=CCC(C)C(O)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)C(=O)NC(C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C Storage condition 2-8°C Water Solubility ethanol: 30 mg/mL |
| Use of | Cyclosporin A is an immunosuppressant which binds to the cyclophilin and inhibits phosphatase activity of calcineurin with an IC50 of 5 nM. Properties Articles494 Name cyclosporin A Synonym More Synonyms Cyclosporin A Biological Activity Description Cyclosporin A is an immunosuppressant which binds to the cyclophilin and inhibits phosphatase activity of calcineurin with an IC50 of 5 nM. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Inflammation/Immunology IC50: 7 nM (calcineurin) In Vitro Cyclosporin A is able to bind with the cyclophilin in T cells[1]. Cyclosporin A works by forming a Cyclophilin-Cyclosporin A complex to inhibit calcineurin[2]. Cyclosporin A exhibits inhibitory effect on calcineurin with an IC50 of 7 nM[3]. Cyclosporin A suppresses the nuclear translocation of NF-AT[4]. Cyclosporin A shows an effect on mitochondria via preventing the MTP from opening with an IC50 of 39 nM[5]. In Vivo Cyclosporin A has immunosuppressive activity, and is active via parenteral and p.o. administration in mice, rat and guinea pigs[6]. Cyclosporin A can be used in organ transplantation to prevent rejection[7]. References [1]. Handschumacher RE, et al. Cyclophilin: a specific cytosolic binding protein for cyclosporin A. Science. 1984 Nov 2;226(4674):544-7. [3]. Fruman DA, et al. Calcineurin phosphatase activity in T lymphocytes is inhibited by FK 506 and cyclosporin A. Proc Natl Acad Sci U S A. 1992 May 1;89(9):3686-90. [4]. Flanagan WM, et al. Nuclear association of a T-cell transcription factor blocked by FK-506 and cyclosporin A. Nature. 1991 Aug 29;352(6338):803-7. [5]. Nicolli A, et al. Interactions of cyclophilin with the mitochondrial inner membrane and regulation of the permeability transition pore, and cyclosporin A-sensitive channel. J Biol Chem. 1996 Jan 26;271(4):2185-92. [6]. Borel JF, et al. Effects of the new anti-lymphocytic peptide cyclosporin A in animals. Immunology. 1977 Jun;32(6):1017-25. [7]. Williams, R, et al. Randomised trial comparing tacrolimus (FK506) and cyclosporin in prevention of liver allograft rejection. European FK506 Multicentre Liver Study Group. Lancet, 1994, 344(8920), 423-428. Chemical & Physical Properties Molecular Formula C62H111N11O12 Exact Mass 1201.841309 PSA 278.80000 Index of Refraction 1.468 InChIKey PMATZTZNYRCHOR-LQJDIJJQSA-N |
| Transport Info | Product Name: Cyclosporin A |
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