Cyclosporin T
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Cyclosporin Analogue Set |
| Catalog number | BBF-05758 |
| CAS | 108027-44-7 |
| Molecular Weight | 1188.58 |
| Molecular Formula | C61H109N11O12 |
| Purity | ≥90% by HPLC |
Online Inquiry
Description
Cyclosporin T is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.
Specification
| Synonyms | (3R,4R)-3-Hydroxy-N-methyl-5-[(E)-1-propenyl]-cyclo(L-Leu-L-Abu-Sar-N-methyl-L-Leu-L-Val-N-methyl-L-Leu-L-Ala-D-Ala-N-methyl-L-Leu-L-Leu-N-methyl-L-Val-); Cyclosporin A, 4-L-leucine-; 4-L-Leucinecyclosporin A; Cyclo[L-alanyl-D-alanyl-N-methyl-L-leucyl-L-leucyl-N-methyl-L-valyl-(3R,4R,6E)-6,7-didehydro-3-hydroxy-N,4-dimethyl-L-2-aminooctanoyl-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl] |
| Storage | Store at 2-8°C |
| IUPAC Name | (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,10,12,15,19,25,28-octamethyl-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)NC(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)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C |
| InChI | InChI=1S/C61H109N11O12/c1-24-26-27-39(15)51(74)50-56(79)64-42(25-2)58(81)67(18)32-47(73)68(19)44(29-34(5)6)55(78)66-48(37(11)12)60(83)70(21)45(30-35(7)8)53(76)62-40(16)52(75)63-41(17)57(80)69(20)46(31-36(9)10)54(77)65-43(28-33(3)4)59(82)71(22)49(38(13)14)61(84)72(50)23/h24,26,33-46,48-51,74H,25,27-32H2,1-23H3,(H,62,76)(H,63,75)(H,64,79)(H,65,77)(H,66,78)/b26-24+/t39-,40+,41-,42+,43+,44+,45+,46+,48+,49+,50+,51-/m1/s1 |
| InChI Key | NPEONIHYDZZZGH-WKHWYDSQSA-N |
Properties
| Boiling Point | 1306.2±65.0°C at 760 mmHg |
| Melting Point | 168-171°C |
| Density | 1.0±0.1 g/cm3 |
| Solubility | Soluble in Chloroform |
Reference Reading
1. Cyclosporin in dermatology: A practical compendium
Tazein Amber, Saadia Tabassum Dermatol Ther. 2020 Nov;33(6):e13934. doi: 10.1111/dth.13934. Epub 2020 Sep 6.
Cyclosporine A (CYA) belongs to calcineurin inhibitor family, which has the ability to selectively suppress T cells. Owing to its immune-modulatory effects, it had been in use for graft vs host diseases and organ transplant rejection for many years, but in dermatology, it was first approved for use in 1997 in the treatment of psoriasis. Other off-label indications for skin diseases include atopic dermatitis, chronic spontaneous urticaria, lichen planus, pyoderma gangrenosum, alopecia areata, granuloma annulare, and several others. A thorough search of Medline-PubMed database, Google Scholar, and Uptodate was performed for evidence-based and peer-reviewed information. We have summarized the use of cyclosporine in dermatological diseases with respect to its, dosage, safety considerations, and monitoring guidelines. Furthermore, brief overview of its pharmacology, drug interactions, use in pregnancy, and lactation has been discussed. Despite of its common adverse effects like nephrotoxicity and hypertension, cyclosporine offers good safety profile when used in skin diseases. Decision to start cyclosporine therapy is individualized and it should be based on analysis of risk vs benefit. Nevertheless, CYA is preferred over other immunosuppressants in dermatology because of early therapeutic response and less myelosupression. This article offers concise but detailed summary of this beneficial immune-suppressive agent in skin diseases.
2. Oral cyclosporin A inhibits CD4 T cell P-glycoprotein activity in HIV-infected adults initiating treatment with nucleoside reverse transcriptase inhibitors
Todd Hulgan, John P Donahue, Laura Smeaton, Minya Pu, Hongying Wang, Michael M Lederman, Kimberly Smith, Hernan Valdez, Christopher Pilcher, David W Haas; AIDS Clinical Trials Group Study A Team Eur J Clin Pharmacol. 2009 Nov;65(11):1081-8. doi: 10.1007/s00228-009-0725-5.
Purpose: P-glycoprotein limits the tissue penetration of many antiretroviral drugs. The aim of our study was to characterize the effects of the P-glycoprotein substrate cyclosporin A on T cell P-glycoprotein activity in human immunodeficiency virus-infected participants in the AIDS Clinical Trials Group study A5138. Methods: We studied P-glycoprotein activity on CD4 and CD8 T cells in 16 participants randomized to receive oral cyclosporin A (n=9) or not (n=7) during initiation antiretroviral therapy (ART) that did not include protease or non-nucleoside reverse transcriptase inhibitors. Results: CD4 T cell P-glycoprotein activity decreased by a median of 8 percentage points with cyclosporin A/ART (difference between cyclosporin A/ART vs. ART only, P= 0.001). Plasma trough cyclosporin A concentrations correlated with the change in P-glycoprotein activity in several T cell subsets. Conclusions: Oral cyclosporin A can inhibit peripheral blood CD4 T cell P-glycoprotein activity. Targeted P-glycoprotein inhibition may enhance the delivery of ART to T cells.
3. Cyclosporin A: Conformational Complexity and Chameleonicity
Satoshi Ono, Matthew R Naylor, Chad E Townsend, Chieko Okumura, Okimasa Okada, Hsiau-Wei Lee, R Scott Lokey J Chem Inf Model. 2021 Nov 22;61(11):5601-5613. doi: 10.1021/acs.jcim.1c00771. Epub 2021 Oct 21.
The chameleonic behavior of cyclosporin A (CsA) was investigated through conformational ensembles employing multicanonical molecular dynamics simulations that could sample the cis and trans isomers of N-methylated amino acids; these assessments were conducted in explicit water, dimethyl sulfoxide, acetonitrile, methanol, chloroform, cyclohexane (CHX), and n-hexane (HEX) using AMBER ff03, AMBER10:EHT, AMBER12:EHT, and AMBER14:EHT force fields. The conformational details were discussed employing the free-energy landscapes (FELs) at T = 300 K; it was observed that the experimentally determined structures of CsA were only a part of the conformational space. Comparing the ROESY measurements in CHX-d12 and HEX-d14, the major conformations in those apolar solvents were essentially the same as that in CDCl3 except for the observation of some sidechain rotamers. The effects of the metal ions on the conformations, including the cis/trans isomerization, were also investigated. Based on the analysis of FELs, it was concluded that the AMBER ff03 force field best described the experimentally derived conformations, indicating that CsA intrinsically formed membrane-permeable conformations and that the metal ions might be the key to the cis/trans isomerization of N-methylated amino acids before binding a partner protein.
Recommended Products
| BBF-03753 | Baicalin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
