Tacrolimus hydrateProduct ingredient for Tacrolimus
- Name
- Tacrolimus hydrate
- Drug Entry
- Tacrolimus
Tacrolimus (also FK-506 or Fujimycin) is an immunosuppressive drug whose main use is after organ transplant to reduce the activity of the patient's immune system and so the risk of organ rejection. It is also used in a topical preparation in the treatment of severe atopic dermatitis, severe refractory uveitis after bone marrow transplants, and the skin condition vitiligo. It was discovered in 1984 from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis. Tacrolimus is chemically known as a macrolide. It reduces peptidyl-prolyl isomerase activity by binding to the immunophilin FKBP-12 (FK506 binding protein) creating a new complex. This FKBP12-FK506 complex inhibits calcineurin which inhibits T-lymphocyte signal transduction and IL-2 transcription.
- Accession Number
- DBSALT000167
- Structure
Structure for Tacrolimus hydrate (DBSALT000167)
- Synonyms
- Tacrolimus / Tacrolimus monohydrate
- UNII
- WM0HAQ4WNM
- CAS Number
- 109581-93-3
- Weight
- Average: 822.0334
Monoisotopic: 821.492541363 - Chemical Formula
- C44H71NO13
- InChI Key
- NWJQLQGQZSIBAF-MSLXHMNKSA-N
- InChI
- InChI=1S/C44H69NO12.H2O/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;1H2/b25-19-,27-21+;/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+;/m0./s1
- IUPAC Name
- (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone hydrate
- SMILES
- O.[H]\C(=C(\C)[C@@]1([H])OC(=O)[C@]2([H])CCCCN2C(=O)C(=O)[C@]2(O)O[C@@]([H])([C@]([H])(C[C@@]2([H])C)OC)[C@]([H])(C[C@@]([H])(C)C\C(C)=C([H])\[C@@]([H])(CC=C)C(=O)C[C@]([H])(O)[C@@]1([H])C)OC)[C@]1([H])CC[C@@]([H])(O)[C@@]([H])(C1)OC
- External Links
- PubChem Compound
- 5282315
- ChemSpider
- 20118181
- ChEBI
- 61057
- ChEMBL
- CHEMBL4303277
- Predicted Properties
Property Value Source Water Solubility 0.00402 mg/mL ALOGPS logP 3.19 ALOGPS logP 5.59 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 9.96 Chemaxon pKa (Strongest Basic) -2.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 178.36 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 215.62 m3·mol-1 Chemaxon Polarizability 87.48 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon