Cyclosporin A

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Cyclosporin A
Category Cyclosporin Analogue Set
Catalog number BBF-05745
CAS 59865-13-3
Molecular Weight 1202.61
Molecular Formula C62H111N11O12
Purity 98%

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BBF-05745 5 g $292 In stock

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Cyclosporin A (Cyclosporine A) is an immunosuppressant that binds to cyclophilins, inhibiting calcineurin activity with an IC50 of 7 nM. It also inhibits CD11a/CD18 adhesion molecules.


Synonyms Ciclosporin; cyclosporine; Cyclosporine A; Sandimmun; Cyclosporin; Neoral; Ciclosporine; Sandimmune; Ramihyphin A
Sequence cyclo[Abu-Sar-N(Me)Leu-Val-N(Me)Leu-Ala-D-Ala-N(Me)Leu-N(Me)Leu-N(Me)Val-N(Me)Bmt(E)]
Storage 4°C, protect from light
IUPAC Name (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-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
Canonical 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
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


Appearance Solid
Antibiotic Activity Spectrum Fungi
Boiling Point 1293.8 °C at 760 mmHg
Melting Point 148-151 °C
Density 1.016 g/cm3
Solubility Soluble in Ethanol, Methanol, Chloroform, DMF, DMSO; Poorly soluble in Water


Carcinogenicity 1, carcinogenic to humans.
Mechanism Of Toxicity Cyclosporine binds to cyclophilin. The complex then inhibits calcineurin which is normally responsible for activating transcription of interleukin 2. Cyclosporine also inhibits lymphokine production and interleukin release. In ophthalmic applications, the precise mechanism of action is not known. Cyclosporine emulsion is thought to act as a partial immunomodulator in patients whose tear production is presumed to be suppressed due to ocular inflammation associated with keratoconjunctivitis sicca.
Toxicity LD50: 2329 mg/kg (oral, mice); LD50: 1480 mg/kg (oral, rats); LD50 > 1000 mg/kg (rabbits).

Reference Reading

1.Amorphous cyclosporin A nanoparticles for enhanced dermal bioavailability.
Romero GB;Arntjen A;Keck CM;Müller RH Int J Pharm. 2016 Feb 10;498(1-2):217-24. doi: 10.1016/j.ijpharm.2015.12.019. Epub 2015 Dec 11.
Cylosporin A (CyA) was formulated as amorphous nanoparticle suspension to increase dermal penetration, e.g. applicable in psoriasis. The suspension consisted of 5% CyA in water, stabilized with vitamin E polyethylene glycol succinate (TPGS, Kolliphor TPGS) and was produced by bead milling. The diameter of the bulk population was about 350 nm, laser diffraction diameter 99% was 690 nm. The suspension was physically stable over one year of storage at room temperature, and most important the amorphous state also remained stable. Despite the high dispersitivity and related large surface area in contact with water, the drug content reduced only by 5% over 1 year of storage. i.e. the formulation is feasible as commercial product with expiry date. The CyA nanoparticles and μm-sized CyA particles were incorporated into hydroxypropylcellulose (HPC) gels and the penetration studied into fresh pig ear skin applying the tape stripping method. At tape number 30, the penetrated cumulative amount of CyA from nanoparticles was 6.3 fold higher compared to the μm-sized raw drug powder (450.1 μg/cm(2) vs. 71.3 μg/cm(2)). A theoretical mechanism is presented to explain the observed superiority in penetration.
2.[The efficacy and safety of modified busulfan/fludarabine conditioning regimen in elderly or drug-intolerable patients with hematologic malignancies].
Wang FR;Huang XJ;Liu DH;Chen H;Wang Y;Tang FF;Sun YQ;Fu HX;Liu KY;Xu LP Zhonghua Nei Ke Za Zhi. 2013 Dec;52(12):1028-32.
OBJECTIVE: ;To evaluate the efficacy and safety of modified busulfan (Bu, 9.6 mg/kg)/fludarabine (Flu) conditioning regimen on malignant hematologic diseases in elderly and/or drug-intolerable patients.;METHODS: ;We utilized a new reduced intensity conditioning (RIC) containing of new dosage of intravenous Bu (9.6 mg/kg), Flu (150 mg/m(2)), cytarabine and semustine but without antithymocyte globulin (ATG) in 23 aged and/or intolerable patients with malignancies. All 23 patients, with a median age of 49 (8-66) years, received an allogeneic hematopoietic stem cell transplantation with human leukocyte antigen (HLA) identical sibling donors during January 2008 and January 2012. Stem cells were collected from granulocyte colony-stimulation factor (G-CSF) mobilized bone marrow plus G-CSF mobilized peripheral blood(G-PB) in 20 patients, G-PB alone in two, and non-mobilized BM in one. The graft had a median mononuclear cells (MNC) of 7.03 (4.04-9.9)×10(8)/kg and 1.76 (0.31-6.43)×10(6)/kg of CD(+)34 cells. Graft-versus-host disease (GVHD) prophylaxis included cyclosporin A, mycophenolate mofetil and methotrexate.;RESULTS: ;All patients were well tolerated to the regimen without serious drug related toxicity.
3.[Penetrating keratoplasty in high-risk children: prevention of graft rejection].
Pleskova AV;Khvatova AV Vestn Oftalmol. 2014 May-Jun;130(3):17-20.
PURPOSE: ;To evaluate the efficacy of prolonged courses of systemically administered subtherapeutic Metipred and cyclosporine in prevention of graft rejection in high-risk children.;MATERIAL AND METHODS: ;The study included 27 children at high risk of graft rejection due to re-keratoplasty (n = 8), limbo-keratoplasty for corneal staphyloma (n = 4), or transplantation into vascularized corneal bed (n = 15). All patients were divided into two groups--the study group (n =11) and the control group (n = 16). In order to evaluate the efficacy of two different prevention schemes, the occurrence of graft rejection, rejection crises, and crisis-associated clouding of the transplant was analyzed.;RESULTS: ;The occurrence of transplant opacity was two times lower in the Metipred-cyclosporine group than in the conventional prevention group. Kaplan-Meier one-year survival of the transplant was 53% in the study group and 27% in the control group. Two-year survival rate difference appeared even more significant--53% and 18% correspondingly.;CONCLUSION: ;It is clinically shown that subtherapeutic use of Metipred and cyclosporine decreases the occurrence of rejection crises and transplant failure almost by half in high-risk patients as compared with topical corticosteroids; at the same time the side effects of systemic immunosuppression are not substantial.

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