Geclosporin

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Geclosporin
Category Cyclosporin Analogue Set
Catalog number BBF-05767
CAS 74436-00-3
Molecular Weight 1216.662
Molecular Formula C63H113N11O12
Purity ≥90% by HPLC

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BBF-05767 5 mg $519 In stock

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Description

Geclosporin is an impurity of cycloporine, which is an immunosuppressant used in the treatment of rheumatoid arthritis, psoriasis, Crohn's disease, nephrotic syndrome, etc.

Specification

Synonyms Cyclosporin G; Cyclosporine G
Storage Store at -20°C
IUPAC Name (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-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)-30-propyl-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 CCCC1C(=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/C63H113N11O12/c1-25-27-29-41(15)53(76)52-57(80)66-44(28-26-2)59(82)68(18)34-49(75)69(19)45(30-35(3)4)56(79)67-50(39(11)12)62(85)70(20)46(31-36(5)6)55(78)64-42(16)54(77)65-43(17)58(81)71(21)47(32-37(7)8)60(83)72(22)48(33-38(9)10)61(84)73(23)51(40(13)14)63(86)74(52)24/h25,27,35-48,50-53,76H,26,28-34H2,1-24H3,(H,64,78)(H,65,77)(H,66,80)(H,67,79)/b27-25+/t41-,42+,43-,44+,45+,46+,47+,48+,50+,51+,52+,53-/m1/s1
InChI Key ZMKGDQSIRSGUDJ-VSROPUKISA-N

Properties

Appearance White to Off-white Solid
Application immunosuppressant
Boiling Point 1297.8±65.0 °C(Predicted)
Melting Point 182-187°C
Density 1.013±0.06 g/cm3(Predicted)
Solubility Soluble in Chloroform, Methanol

Reference Reading

1.Tumorigenesis of nuclear transfer-derived embryonic stem cells is reduced through differentiation and enrichment following transplantation in the infarcted rat heart.
Fu Q1, Su D1, Wang K1, Zhao Y2. Mol Med Rep. 2016 Apr 7. doi: 10.3892/mmr.2016.5092. [Epub ahead of print]
The aim of the present study was to evaluate the tumorigenic potential of nuclear transfer-derived (nt) mouse embryonic stem cells (mESCs) transplanted into infarcted rat hearts. The nt‑mESCs were cultured using a bioreactor system to develop embryoid bodies, which were induced with 1% ascorbic acid to differentiate into cardiomyocytes. The nt‑mESC‑derived cardiomyocytes (nt‑mESCs‑CMs) were enriched using Percoll density gradient separation to generate nt‑mESCs‑percoll‑enriched (PE)‑CMs. Ischemia was induced by ligating the left anterior descending coronary artery in female Sprague‑Dawley rats. Immunosuppressed rats (daily intraperitoneal injections of cyclosporine A and methylprednisolone) were randomly assigned to receive an injection containing 5x106 mESCs, nt‑mESCs, nt‑mESC‑CMs or nt‑mESC‑PE‑CMs. Analysis performed 8 weeks following transplantation revealed teratoma formation in 80, 86.67 and 33.33% of the rats administered with the mESCs, nt‑mESCs and nt‑mESC‑CMs, respectively, indicating no significant difference between the mESCs and nt‑mESCs; but significance (P<0.
2.[Above-standard proceeding in nephrotic syndrome - case report].
Matyjek A1, Brodowska-Kania D1, Niemczyk S1. Pol Merkur Lekarski. 2016 Mar;40(237):190-2.
The nephrotic syndrome is characterized by the loss of many proteins, via the urinary system. It exceeds the bodies compensatory abilities and results in abnormalities in blood clotting system, particularly due to antithrombin deficiency. It significantly increases the risk of thromboembolic complications. A loss of erythropoietin and transferrin leads to anemia. Polycythemia is a rarely reported phenomenon. The case describes a 20-years old patient with massive nephrotic syndrome and polycythemia, complicated by a pulmonary embolism. The patient had a steroid-dependent submicroscopic glomerulonephritis with a severe episode of nephrotic syndrome associated with centralization of circulation, proteinuria 40.9 g/day, deep hypoproteinemia (albumin=1.2 g/dl), hyperlipidemia, hypercoagulable state (antithrombin activity 29%), polycythemia (Hb=21.1 g/dl, HTC=60%). Kidney function parameters were normal. We started the immunosupression (glycocorticosteroids i.
3.Safety of Eplerenone for Kidney-Transplant Recipients with Impaired Renal Function and Receiving Cyclosporine A.
Bertocchio JP1,2, Barbe C3, Lavaud S1, Toupance O1, Nazeyrollas P3, Jaisser F2, Rieu P1. PLoS One. 2016 Apr 18;11(4):e0153635. doi: 10.1371/journal.pone.0153635. eCollection 2016.
BACKGROUND: Animal studies have highlighted the role of vascular mineralocorticoid receptor during Cyclosporine A-induced nephrotoxicity. Mineralocorticoid receptor antagonists could improve kidney survival but are not commonly used during renal impairment and in association with several immunosuppressive drugs due to a supposed higher risk of adverse events. We tested the tolerance of eplerenone according to its expected adverse events: hyperkalemia, metabolic acidosis, hypotension, acute kidney failure, or any other adverse event.
4.Readily restoring freeze-dried probilosomes as potential nanocarriers for enhancing oral delivery of cyclosporine A.
Guan P1, Lu Y2, Qi J2, Wu W3. Colloids Surf B Biointerfaces. 2016 Apr 6;144:143-151. doi: 10.1016/j.colsurfb.2016.04.006. [Epub ahead of print]
Formulating vesicular nanocarriers into dried precursors so as to overcome the drawbacks associated with liquid formulations is challengeable due to low efficiency of restoration. In this study, bilosomes interiorly thickened with gelatin (G-BLs) was evaluated for the ability to withstand freeze-drying stress and enhanced oral bioavailability of a model drug, cyclosporine A (CyA). The restoration efficiency of freeze-dried pro-G-BLs is investigated by comparing the particle size distribution, entrapment efficiency and morphology of the bilosomes before and after freeze-drying. Particle size and polydispersity index (PI) of pro-G-BLs after restoration was similar to that before freeze-drying, whereas freeze-dried bilosomes without gelatin thickening (pro-BLs) show irreversible damage and aggregation along with significantly increased particle size and PI after restoration. Entrapment efficiency of pro-G-BLs remains as high as 83.7%, in sharp contrast with 66.

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