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| | Tacrolimus Monohydrate Basic information |
| Product Name: | Tacrolimus Monohydrate | | Synonyms: | 15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-, monohydrate, [3S-[3R*[E(1S*,3S*,4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*]]-;TACROLIMUS HYDRATE/TSUKUBAENOLIDE HYDRATE;(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-Hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)tetrone;Tacrolimus (150 mg);(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-Hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-Methoxycyclohexyl]-1-Methylethenyl]-14,16-diMethoxy-4,10,12,18-tetraMethyl-8-(2-propen-1-yl)-;FK-506 monohydrate, >=98%;Tacrolimus /FK506 monohydrate;,8s*,9e,12r*,14r*,15s*,16r*,18s*,19s*,26ar*))- | | CAS: | 109581-93-3 | | MF: | C44H71NO13 | | MW: | 822.05 | | EINECS: | | | Product Categories: | Signalling | | Mol File: | 109581-93-3.mol |  |
| | Tacrolimus Monohydrate Chemical Properties |
| Melting point | 127-129° | | alpha | D23 -84.4° (c = 1.02 in chloroform) | | storage temp. | -20°C | | solubility | DMSO: soluble20mg/mL | | form | powder | | color | White to Almost white | | Merck | 14,9025 | | InChIKey | NWJQLQGQZSIBAF-MLAUYUEBSA-N |
| Hazard Codes | T | | Risk Statements | 25 | | Safety Statements | 45 | | RIDADR | UN 2811 6.1/PG 3 | | WGK Germany | 3 | | RTECS | KD4201200 | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 2934990002 | | Toxicity | LD50 i.p. in mice: >200 mg/kg (Kino); LD50 in male, female rats (mg/kg): 57.0, 23.6 i.v.; 134, 194 orally (Ohara) |
| | Tacrolimus Monohydrate Usage And Synthesis |
| Uses | immune suppressant, antifungal | | Uses | FK-506 monohydrate has been used:
- as an immunosuppressive agent in coculture medium to study the effect of immunologic reaction
- as a calcineurin inhibitor, in anhydrous Me2SO solution
- to treat retinal pigment epithelial cells to measure possible cytotoxicity
| | Definition | ChEBI: A hydrate that is the monohydrate form of tacrolimus. | | Biological Activity | Potent calcineurin (protein phosphatase 2B) inhibitor that requires FK 506-binding protein 12 (FKBP12) for activity (IC 50 = 3 nM). Inhibits secretion of IL-1, IL-2 (IC 50 = 1 nM), IL-3, IL-4, IL-6 (IC 50 = 35 nM), GM-CSF, TNF α (IC 50 = 10 nM), IFN γ and Myc from activated T-cells in vitro . Exhibits potent immunosuppressive, neuroprotective and anticonvulsant activity in vivo . | | Biochem/physiol Actions | FK-506 also appears to inhibit Na+/Ca2+ exchange. FK-506 and its derivatives demonstrate significant neurodegenerative activity. This property seems to arise via different mechanisms. FK-506 is also useful in treating ophthalmologic complications such as corneal graft rejection, uveoretinitis and allergen induced conjunctivitis. | | Safety Profile | A poison by ingestion and intravenous routes. When heated to decomposition it emits toxic vapors of NOx. |
| | Tacrolimus Monohydrate Preparation Products And Raw materials |
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