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Cyclosporin A is a white or slightly yellow crystalline powder. It is usually in an amorphous granular or crystalline form. The relative molecular weight is about 1202.6 g/mol, CAS 59865-13-3, and the Molecular formula is C62H111N11O12. Soluble in organic solvents, with low solubility in water. It has high solubility in ethanol, Dimethyl sulfoxide, ethyl acetate, methanol and methane chloride. The solubility is influenced by pH value. Under acidic conditions, its solubility is lower, while under alkaline conditions, its solubility increases. It is a chiral compound with optical activity. Its specific rotation is from+44 ° to+60 ° (based on 20 ° C, 589 nm wavelength, and ethanol). It is a relatively stable compound, but may decompose under light, high temperature, and oxidation conditions. To maintain its chemical stability, it is necessary to avoid light and high temperature environments during storage. It is an important Immunosuppressive drug with wide clinical application. It inhibits the immune system and is used for preventing organ Transplant rejection, treating autoimmune diseases and other medical purposes.
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Chemical Formula |
C62H111N11O12 |
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Exact Mass |
1202 |
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Molecular Weight |
1203 |
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m/z |
1202 (100.0%), 1203 (67.1%), 1204 (22.1%), 1203 (4.1%), 1205 (4.0%), 1204 (2.7%), 1204 (2.5%), 1205 (1.7%), 1203 (1.3%) |
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Elemental Analysis |
C, 61.92; H, 9.30; N, 12.81; O, 15.96 |
Cyclosporin A is an important Immunosuppressive drug and has wide clinical application. It inhibits the immune system and is used for preventing organ Transplant rejection, treating autoimmune diseases and other medical purposes.
1. Organ Transplant rejection: it is one of the most commonly used Immunosuppressive drug and is widely used to prevent and treat rejection after organ transplantation. It reduces immune system attacks by inhibiting T lymphocyte activity and interfering with immune cell signaling, thereby improving organ survival rate.
2. Treatment of autoimmune diseases: it is also used to treat a variety of autoimmune diseases, such as Rheumatoid arthritis, systemic lupus erythematosus, psoriasis, etc. It reduces inflammation and immune responses by inhibiting the overactivation of the immune system, thereby reducing autoimmune diseases.
3. Treatment of skin diseases: it has shown significant efficacy in treating certain severe skin diseases. For example, it is used to treat psoriasis, stubborn eczema, pustulosis, and so on. It improves skin symptoms by inhibiting the activity of the immune system, reducing inflammation and abnormal proliferation of immune cells.
4. Treatment of ophthalmic diseases: It also has important applications in the field of ophthalmology. It is used to treat ocular inflammatory diseases such as Dry eye syndrome. It can alleviate the inflammatory response of eye tissue, promote tear secretion, and improve the wetness of the eye surface.
5. Treatment of kidney diseases: It also has certain applications in the treatment of kidney diseases. It is used to treat immune related kidney diseases such as primary glomerulonephritis and IgA nephropathy. It can alleviate renal inflammatory response and inhibit immune system attacks on the kidneys, thereby slowing down disease progression.
6. Other uses: In addition to the above main applications, it has also been studied to treat other diseases, such as Behcet's disease, systemic sclerosis, Pulmonary fibrosis, etc.
It should be noted that it is a powerful Immunosuppressive drug, which requires strict control of dosage and monitoring of patients' immune status. It may cause a series of side effects, such as renal dysfunction, hypertension, liver dysfunction, increased risk of infection, etc. Therefore, when using Cyclosporin A, it should be carried out under the guidance of a clinical doctor and regularly tested and monitored.
The Total synthesis of it can be traced back to 1982, when K.C. Nicolaou et al. first reported its Total synthesis route. This synthesis involves over 60 chemical steps and requires dozens of intermediates to complete. I will briefly introduce some key synthesis strategies. The Total synthesis mainly includes the following steps:
Bonding activation:
This method uses reagents such as Sulfuryl chloride or Copper(I) bromide to bond coenzyme A with mercaptopropionate to form mercapto Propionyl-CoA.
Preparation of specific proline derivatives:
Mercapto Propionyl-CoA is converted into specific proline derivatives through a series of conversion reactions, such as substitution, alkylation, etc.
Cyclization reaction:
Using Michael addition, Jones reagent oxidation, and other reactions to cyclize, forming the cyclic structure of Cyclosporin.
Side chain modification:
The side chain of Cyclosporin is modified through reactions such as substitution and hydrolysis to obtain the target compound product.
Although this is only a brief overview, you can obtain more detailed information by consulting relevant literature. Please note that the synthesis of Cyclosporin A is a complex and challenging task that needs to be carried out under professional laboratory conditions and operated by synthetic chemists or professional researchers.
Cyclosporin A (Ciclosporin A) is a natural cyclic peptide compound. Its Molecular formula is C62H111N11O12, and its relative molecular weight is about 1202.61 g/mol.
The molecular structure of it has a complex cyclic peptide skeleton, and contains multiple amino acid residues (D-Ala, D-Leu, Gly, D-MeLeu, D-Val, L-Val, L-Thr, L-Ala, L-Hyp, L-Leu) and non protein amino acid N-methylacrylamide (N-MeAla).
The structure of product determines its biological activity in the immune system. It inhibits the activation of T lymphocytes by binding to proteins within immune cells, thereby exerting an immunosuppressive effect. Due to its immunosuppressive and anti-inflammatory properties, it is widely used in immunosuppressive therapy after organ transplantation, the treatment of autoimmune diseases, and the treatment of some inflammatory skin diseases.
The name of Ciclosporin A refers to its molecular structure and source:
The term 'cyclosporin' refers to a type of cyclic peptide that belongs to this class of compounds. Cyclic peptides are circular structures formed by amino acid residues, usually connected by peptide bonds between amino and carboxyl groups. And 'A' represents the first discovered member of this type of compound.
The specific name "Cyclosporin " is to distinguish it from other Ciclosporin derivatives, such as Cyclosporin B, Cyclosporin C, etc. These derivatives have structural differences, but they all have similar pharmacological properties to product.
It was first isolated from a fungus (Tolypocladium inflatum). It is a Natural product. Therefore, 'Cyclosporin' also implies its natural source.
Overall, the name 'It' reflects the cyclic peptide structure, identity, and natural origin of the compound. This naming method is common in the field of chemistry and aims to provide information about the structure and characteristics of compounds.
Core Mechanism and Clinical Value Lay the Foundation for Development
Cyclosporin A (CsA), as a natural cyclic polypeptide immunosuppressant, forms a complex with intracellular cyclosporin binding protein (Cyp) to specifically inhibit the activity of calcineurin, blocking the key signaling pathways (such as NFAT dephosphorylation) for T cell activation. This results in the inhibition of cytokine transcription (such as IL-2) and achieves precise immunosuppression. This mechanism makes it a "milestone drug" in the field of organ transplantation, significantly increasing the one-year survival rate of organs such as kidneys, livers, and hearts to over 80%, while reducing the incidence of acute rejection to below 20%. Its selective inhibition of helper T cells (Th) without affecting the inhibition of T cells (Ts) reduces the risk of bone marrow suppression associated with traditional immunosuppressants, and its clinical safety advantage is prominent.
Continuous Expansion of Current Clinical Application Areas
Organ Transplantation: As a first-line anti-rejection drug, CsA is indispensable in solid organ transplantation. The global demand for organ transplantation is increasing by approximately 5% annually, and CsA further reduces side effects such as nephrotoxicity through optimization of dosage forms (such as microemulsion preparations) and combined medication regimens (such as combination with mycophenolate mofetil), thereby consolidating its market position.
Autoimmune Diseases: In diseases such as rheumatoid arthritis and systemic lupus erythematosus (SLE), CsA demonstrates unique efficacy by regulating the Th1/Th2 balance and inhibiting B cell activation. For example, in the treatment of SLE, CsA can reduce proteinuria by more than 50% and remains effective for patients intolerant to traditional drugs.
Dermatology Field: CsA is the first-line treatment drug for severe psoriasis (such as erythrodermic and generalized pustular types), and at a dose of 2.5-5 mg/kg/d, it can control the condition within 2-4 weeks, and when combined with biologics (such as TNF-α inhibitors), it can reduce the recurrence rate.
Breakthrough Potential in Emerging Application Areas
Reproductive Medicine
CsA restores the Th2-type immune bias at the maternal-fetal interface and induces the proliferation of regulatory T cells (Treg), providing new treatment strategies for recurrent miscarriage. Clinical trials show that CsA can increase the live birth rate of patients with unexplained recurrent miscarriage from 30% to 60%.
Cardiovascular Protection
In models of myocardial ischemia-reperfusion injury, CsA inhibits the opening of the mitochondrial permeability transition pore (mPTP), reducing the myocardial infarction area by 40%. It may be developed as an auxiliary medication for heart surgery in the future.
Tumor Immune Regulation
CsA enhances chemotherapy sensitivity by inhibiting the function of Treg and shows a synergistic anti-tumor effect in solid tumors such as prostate cancer and melanoma, providing new options for patients with immune therapy resistance.
Future Directions Driven by Technological Innovation
New Drug Formulation Development
Nanocrystal technology increases the bioavailability of CsA to 2-3 times that of traditional formulations and reduces the frequency of administration (from twice daily to once weekly), improving patient compliance.
Structural Optimized Drugs
Non-immunosuppressive derivatives (such as NIM811) developed based on the CsA framework retain the mPTP inhibitory effect while eliminating immunotoxicity and have entered phase II clinical trials for myocardial protection.
Innovative Combination Therapy
The combination therapy of CsA with new immunomodulatory agents such as JAK inhibitors and PD-1 antibodies is being explored, which is expected to break through the bottleneck of single-drug efficacy.
Challenges and Countermeasures
Long-term Toxicity Management
Through blood drug concentration monitoring (TDM) and individualized dosing regimens, the incidence of nephrotoxicity can be reduced from 30% to below 10%.
Drug Resistance Issues
Developing calcium-dependent non-immunosuppressive signaling pathway inhibitors (such as mTOR inhibitors) as alternatives.
Cost Control
The launch of biosimilar drugs has reduced the price of CsA by 60%, significantly expanding its accessibility in developing countries.
Cyclosporin A's discovery marked a watershed moment in immunology, enabling unprecedented success in organ transplantation and autoimmune therapy. Despite its nephrotoxic and oncogenic risks, CsA remains a vital tool, with ongoing research focused on enhancing safety, expanding indications, and leveraging biosimilars to improve global access. As personalized medicine and novel delivery systems evolve, CsA's legacy as a pioneering immunosuppressant will endure, shaping the future of immune-mediated disease management for decades to come.
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