| Identification | Back Directory | [Name]
TACROLIMUS | [CAS]
109581-93-3 | [Synonyms]
FK-506
135175
CS-1308
Tacarolimus
[3R[E(1S,3S,4S)
tacrolimushydrate
FK-506 MONOHYDRATE
Tacrolimus (150 mg)
FR900506 monohydrate
tsukubaenolidehydrate
Tacrolimus monohydrate
Tacrolimus monohydroate
TacrolimusMonohydrate>
FK-506 monohydrate, >=98%
Tacrolimus monohydrate CRS
Tacrolimus /FK506 monohydrate
FK 506 monohydrate, Tacrolimus
FK506 Monohydrate[Tacrolimus Hydrate]
Tacrolimus Monohydrate CAS 109581-93-3
TACROLIMUS HYDRATE/TSUKUBAENOLIDE HYDRATE
Tacrolimus monohydrate (Fujimycin monohydrate
,8s*,9e,12r*,14r*,15s*,16r*,18s*,19s*,26ar*))-
18-tetramethyl-8-(2-propenyl)-,monohydrate,(3s-(3r*(e(1s*,3s*,4s*)),4s*,5r*
3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-9,10,12,
(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, 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-te
(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
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*]]- | [EINECS(EC#)]
617-559-7 | [Molecular Formula]
C44H69NO12 | [MDL Number]
MFCD00869853 | [MOL File]
109581-93-3.mol | [Molecular Weight]
822.04 |
| Chemical Properties | Back Directory | [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 Information | Back Directory | [Uses]
immune suppressant, antifungal | [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. | [in vitro]
Tacrolimus monohydrate (FK506 monohydrate; Fujimycin monohydrate; FR900506 monohydrate) inhibits calcium-dependent events, such as IL-2 gene transcription, NO synthase activation, cell degranulation, and apoptosis. Tacrolimus also potentiates the actions of glucocorticoids and progesterone by binding to FKBPs contained within the hormone receptor complex, preventing degradation. The agent may enhance the expression of the TGFβ-1 gene in a fashion analogous to that demonstrated for CsA. T cell proliferation in response to ligation of the T cell receptor is inhibited by Tacrolimus. Treatment with a low concentration of Tacrolimus (FK506,10 μg/L) does not significantly affect the proliferation of MH3924A cells (P=0.135). Upon treatment with higher concentrations of Tacrolimus (100-1,000 μg/L), the proliferation of MH3924A cells is significantly enhanced (P<0.01). Treatment with AMD3100 at any concentration (10, 50 or 100 μg/L) has no obvious effect on MH3924A cell proliferation (P>0.05). However, when different concentrations of AMD3100 are combined with 100 μg/L Tacrolimus, the in vitro proliferation of MH3924A cells is increased (P<0.01).
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| Safety Data | Back Directory | [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 | [Safety Profile]
A poison by ingestion and intravenous routes. When heated to decomposition it emits toxic vapors of NOx. | [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) |
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