- Tacrolimus monohydrate
-
- $0.00 / 1g
-
2026-03-16
- CAS:109581-93-3
- Min. Order: 1g
- Purity: 98%-102%
- Supply Ability: 500G
- Tacrolimus Monohydrate
-
- $0.00 / 1gram
-
2026-03-16
- CAS:109581-93-3
- Min. Order: 1gram
- Purity: 98
- Supply Ability: 1000
|
| Product Name: | Tacrolimus Monohydrate | | Synonyms: | FK-506;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)-;Tacrolimus monohydrate;FK-506 monohydrate, >=98% | | CAS: | 109581-93-3 | | MF: | C44H71NO13 | | MW: | 822.05 | | EINECS: | 617-559-7 | | 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 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral | | 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 (Tacrolimus 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. | | 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).
| | Background | The calcium dependent protein phosphatase calcineurin is responsible for the de-phosphorylation of the transcriptional regulator nuclear factor of activated T cells and is essential for NFAT’s nuclear translocation and activation. Calcineurin is a target of two common immunosuppressants, cyclosporin A and FK-506, both of which can inhibit antigen and mitogen triggered T cell activation. These drugs interact with the immunophilins cyclophilin and FKBP-12, respectively, and the immunophilin-drug complex binds to calcineurin to inhibit substrate binding. FK-506 can be up to 100-fold more potent than CsA in various models. | | References | [1] Schulz, R.A. and Yutzey, K.E. (2004) Dev Biol 266, 1-16.
[2] Rusnak, F. and Mertz, P. (2000) Physiol Rev 80, 1483-521.
[3] Borel, J.F. et al. (1976) Agents Actions 6, 468-75.
[4] Kino, T. et al. (1987) J Antibiot (Tokyo) 40, 1249-55.
[5] Liu, J. et al. (1991) Cell 66, 807-15.
[6] Henderson, D.J. et al. (1991) Immunology 73, 316-21.
[7] Tocci, M.J. et al. (1989) J Immunol 143, 718-726.
[8] Yoshimura, N. et al. (1989) Transplantation 47, 351-6. |
| | Tacrolimus Monohydrate Preparation Products And Raw materials |
|