Cyclosporin

Cyclosporin

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Cyclosporin
Category Enzyme inhibitors
Catalog number BBF-01751
CAS 79217-60-0
Molecular Weight 1202.61
Molecular Formula C62H111N11O12
Purity >98%

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Description

It is produced by the strain of Polypocladiurn inflatum. It has a strong immunosuppressive action, but also has anti-inflammatory and weak antifungal effects. The mechanism of immunosuppression is the combination of cyclosporin A and cyclosporin-binding protein in T cells, which inhibits the activity of Calcineurin, and then impedes the transposition of intracellular transcription factors into the nucleus, and inhibits the interleukin-2 transcription, resulting in immunosuppression. It is mainly used for kidney transplantation, bone marrow and heart transplantation, and is one of the most important immunosuppressive agents in clinical application.

Specification

Synonyms Restasis; Cyclosporine; Gengraf; Sandimmune; SangCyA; Atopica
Storage -20 °C
IUPAC 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
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
InChI Key PMATZTZNYRCHOR-KMSBSJHKSA-N

Properties

Appearance White Crystalline Powder
Application Enzyme Inhibitors
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 Methanol, Chloroform

Reference Reading

1. Endoscopic ultrasound-guided inoculation of transmissible venereal tumor in the colon: A large animal model for colon neoplasia.
Bhutani MS1, Uthamanthil R, Suzuki R, Shetty A, Klumpp SA, Nau W, Stafford RJ. Endosc Ultrasound. 2016 Mar-Apr;5(2):85-93. doi: 10.4103/2303-9027.180471.
BACKGROUND: To develop and evaluate the feasibility of emerging interventions, animal models with accurate anatomical environment are required.
2. Modern approaches to the ocular delivery of cyclosporine A.
Agarwal P1, Rupenthal ID2. Drug Discov Today. 2016 Apr 11. pii: S1359-6446(16)30106-4. doi: 10.1016/j.drudis.2016.04.002. [Epub ahead of print]
Cyclosporine A (CsA) has long been the mainstay treatment for dry eye syndrome (DES), one of the most common disorders of the eye. However, the poor water solubility of CsA renders it difficult to formulate it into topical ocular dosage forms. Restasis® is currently the only US Food and Drug Administration (FDA)-approved CsA formulation, while Ikervis® has recently been launched in Europe, with both commonly associated with severe ocular discomfort. Therefore, several CsA formulations have been investigated with the aim to improve bioavailability while reducing adverse effects associated with the marketed formulations. In this review, we summarize recent advances in ocular CsA delivery that provide safer and more effective alternatives for the management of DES and other ocular inflammatory conditions.
3. Keratoconjunctivitis sicca exacerbation in a dog treated with systemic atenolol.
Barsotti G1, Vezzosi T1. J Small Anim Pract. 2016 Apr 13. doi: 10.1111/jsap.12477. [Epub ahead of print]
A 6-year-old, intact, male English cocker spaniel was referred for treatment of chronic conjunctivitis and unilateral keratitis. The dog was diagnosed with bilateral immune-mediated keratoconjunctivitis sicca, treated with topical cyclosporine 0·2% ointment and sodium hyaluronate eye drops and improved considerably. After 2 months, pulmonic stenosis was diagnosed, and the dog commenced treatment with oral atenolol; the ophthalmological disease worsened dramatically within a few days. The ophthalmic signs rapidly improved after discontinuation of atenolol, and there was bilateral complete remission after 3 weeks. No oral β-blocker therapy was reintroduced, and thereafter, keratoconjunctivitis sicca was well-controlled with topical therapy.

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