Tacrolimus
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| Category | Tacrolimus Analogue Set |
| Catalog number | BBF-05768 |
| CAS | 104987-11-3 |
| Molecular Weight | 804.02 |
| Molecular Formula | C44H69NO12 |
| Purity | >98% |
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Description
FK-506 is a 23-membered macrolide lactone, it reduces peptidyl-prolyl isomerase activity by binding to the immunophilin FKBP12 (FK506 binding protein) creating a new complex.
Specification
| Related CAS | 109581-93-3 (monohydrate) |
| Synonyms | Prograf; Fujimycin; FK506; Protopy |
| Storage | Store at -20°C |
| IUPAC Name | (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-prop-2-enyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone |
| Canonical SMILES | CC1CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC(=O)C(C=C(C1)C)CC=C)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC |
| InChI | InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1 |
| InChI Key | QJJXYPPXXYFBGM-LFZNUXCKSA-N |
| Source | Streptomyces hygroscopicus |
Properties
| Appearance | White to Off-white Solid |
| Application | drug |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 871.7°C at 760 mmHg |
| Melting Point | 127-129°C |
| Flash Point | 481°C |
| Density | 1.19 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO |
| LogP | 3.3 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | The mechanism of action of tacrolimus in atopic dermatitis is not known. While the following have been observed, the clinical significance of these observations in atopic dermatitis is not known. It has been demonstrated that tacrolimus inhibits T-lymphocyte activation by first binding to an intracellular protein, FKBP-12. A complex of tacrolimus-FKBP-12, calcium, calmodulin, and calcineurin is then formed and the phosphatase activity of calcineurin is inhibited. This prevents the dephosphorylation and translocation of nuclear factor of activated T-cells (NF-AT), a nuclear component thought to initiate gene transcription for the formation of lymphokines. Tacrolimus also inhibits the transcription for genes which encode IL-3, IL-4, IL-5, GM-CSF, and TNF-, all of which are involved in the early stages of T-cell activation. Additionally, tacrolimus has been shown to inhibit the release of pre-formed mediators from skin mast cells and basophils, and to downregulate the expression of FceRI on Langerhans cells. |
| Toxicity | LD50 = 134-194 mg/kg (rat). |
Reference Reading
1. Tacrolimus successfully used to control refractory eosinophilic granulomatosis with polyangiitis complicated by invasive aspergillosis and chronic hepatitis B.
Hirano F1,2, Mizoguchi F1, Harigai M1,2, Miyasaka N1, Kohsaka H1. Int J Rheum Dis. 2016 Apr 29. doi: 10.1111/1756-185X.12869. [Epub ahead of print]
While several alternatives to cyclophosphamide have been proposed for refractory eosinophilic granulomatosis with polyangiitis (EGPA), therapeutic options are limited in patients with chronic infections. We report a case of refractory EGPA complicated by invasive aspergillosis and chronic hepatitis B. Although multiple immunosuppressants, including cyclophosphamide, were not effective, tacrolimus was used successfully to control disease without exacerbating concomitant infections in the long term. Tacrolimus could be an alternative choice in the treatment of EGPA, especially when aggressive immunosuppression is unfeasible.
2. After Intestinal Transplantation Kidney Function Is Impaired by Downregulation of Epithelial Ion Transporters in the Ileum.
Reiner J1, Hsieh CJ2, Straarup C3, Bodammer P3, Schäffler H3, Graepler F2, Stüker D4, Kratt T4, Linnebacher M5, Nadalin S4, Witte M6, Königsrainer A4, Lamprecht G7. Transplant Proc. 2016 Mar;48(2):499-506. doi: 10.1016/j.transproceed.2015.12.068.
BACKGROUND: Intestinal transplantation is a treatment option for intestinal failure. Although nephrotoxic medication after transplantation is a major cause for posttransplant renal insufficiency, it remains unclear why kidney dysfunction is particularly frequent after intestinal transplantation.
3. Reduced-dose methotrexate in combination with tacrolimus was associated with rapid engraftment and recovery from oral mucositis without affecting the incidence of GVHD.
Matsukawa T1, Hashimoto D2, Sugita J2, Nakazawa S3, Matsushita T3, Kashiwazaki H3, Goto H2, Onozawa M2, Kahata K2, Fujimoto K2, Endo T2, Kondo T2, Hashino S4, Yamazaki Y3, Teshima T2. Int J Hematol. 2016 Apr 27. [Epub ahead of print]
Allogeneic hematopoietic stem cell transplantation is a curable treatment for hematological diseases. Graft-versus-host disease (GVHD) causes morbidity and mortality after HSCT. Methotrexate (MTX) is used for GVHD prophylaxis, but its appropriate dose remains unclear. In the present study, we compared the efficacy and toxicity of 15-10-10 MTX (day +1: 15 mg/m2; days +3 and +6: 10 mg/m2) with 10-7-7 MTX (day +1: 10 mg/m2; day +3 and +6: 7 mg/m2) in combination with tacrolimus. The cumulative incidence rates of grades II-IV acute GVHD, grades III-IV acute GVHD and chronic GVHD in the 15-10-10 MTX and 10-7-7 MTX groups did not differ to a statistically significant extent. The median time for neutrophil engraftment in the 15-10-10 MTX group was 16 days (range, 11-31 days), while that in the 10-7-7 group was 15 days (range, 12-19 days) (P = 0.024). Moreover, the median time for platelet recovery was significantly shorter in the 10-7-7 MTX group (22 days; range, 13-49 days) than that in the 15-10-10 MTX group (27 days; range, 9-405 days) (P = 0.
Spectrum
Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C44H69NO12
Molecular Weight (Monoisotopic Mass): 803.482 Da
Molecular Weight (Avergae Mass): 804.0182 Da
Derivative Type: TMS_1_1
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C44H69NO12
Molecular Weight (Monoisotopic Mass): 803.482 Da
Molecular Weight (Avergae Mass): 804.0182 Da
Derivative Type: TMS_1_1
LC-MS/MS Spectrum - Linear Ion Trap , negative
Experimental Conditions
Instrument Type: Linear Ion Trap
Ionization Mode: negative
Ionization Mode: negative
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C44H69NO12
Molecular Weight (Monoisotopic Mass): 803.482 Da
Molecular Weight (Avergae Mass): 804.0182 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C44H69NO12
Molecular Weight (Monoisotopic Mass): 803.482 Da
Molecular Weight (Avergae Mass): 804.0182 Da
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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 ╳
