Product Name

  • Name

    Tacrolimus

  • EINECS 1308068-626-2
  • CAS No. 104987-11-3
  • Article Data18
  • CAS DataBase
  • Density 1.19 g/cm3
  • Solubility DMSO: >3 mg/mL
  • Melting Point 113-115 °C
  • Formula C44H69NO12
  • Boiling Point 871.7 °C at 760 mmHg
  • Molecular Weight 804.031
  • Flash Point 481 °C
  • Transport Information UN 2811 6.1/PG 3
  • Appearance White or off-white crystalline powder
  • Safety 45-36-26
  • Risk Codes 25-36/37/38
  • Molecular Structure Molecular Structure of 104987-11-3 (Tacrolimus)
  • Hazard Symbols ToxicT,IrritantXi
  • Synonyms 4,5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-heptadecahydro-5,19-dihydroxy-3-;FK-506;FK506;15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine- 1,7,20,21(4H,23H)-tetrone,5,6,8,11,- 12,13,14,15,16,17,18,19,24,25,26,26ahexadecahydro- 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-propenyl)-,(3S,4R,5S,8R,- 9E,12S,14S,15R,16S,18R,19R,26aS)-;FR 900506;Prograf;dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-,(3S,4R,5S,8R,12S,14S,15R,16S,18R,19R,26aS)-;FK 506;Fujimycin;FR-900506;[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-;Tacrolimus (FK506);Tacrolimus(FK-506);Tacrolimus(FK506);Tacrolimus, FK-506;Taccrolimus;Tacrolimus [GMP];15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(23H)-tetrone,;Prograde metamorphismPrograf;
  • PSA 178.36000
  • LogP 4.57690

Synthetic route

C56H97NO12Si2
118977-96-1

C56H97NO12Si2

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile at 20℃; for 0.05h;100%
With hydrogen fluoride; acetonitrile In dichloromethane at 0℃; for 0.0833333h;81%
With hydrogen fluoride In acetonitrile at 20℃;81%
24,33-Bis-(t.butyl-dimethylsilyl)-FK 506
133941-75-0

24,33-Bis-(t.butyl-dimethylsilyl)-FK 506

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile at 50℃; for 0.2h;100%
With hydrogen fluoride In acetonitrile at 20℃; for 2.5h;
14-<(tert-butyldimethylsilyl)oxy>-24,32-bis<(triisopropylsilyl)oxy>-FK506
128685-18-7

14-<(tert-butyldimethylsilyl)oxy>-24,32-bis<(triisopropylsilyl)oxy>-FK506

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile for 18h; Ambient temperature;73%
C66H101NO11Si2
176656-40-9

C66H101NO11Si2

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
With hydrogen fluoride; 3,3-dimethyldioxirane 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h; Yield given. Multistep reaction;
C66H101NO12Si2
197250-11-6

C66H101NO12Si2

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile at 20℃; for 10h; Cyclization; desilylation;10.5 mg
C55H95NO13Si2

C55H95NO13Si2

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 46 percent / epichlorohydrin / 1,2-dichloro-benzene / 0.05 h / 140 °C
2: 100 percent / aq. HF / acetonitrile / 0.2 h / 50 °C
View Scheme
{1-hydroxy-23,25-dimethoxy-12-[2-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-1-methyl-vinyl]-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-14-triethylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-en-17-yl}-acetaldehyde

{1-hydroxy-23,25-dimethoxy-12-[2-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-1-methyl-vinyl]-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-14-triethylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-en-17-yl}-acetaldehyde

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 43 percent / epichlorohydrin / 1,2-dichloro-benzene / 0.05 h / 140 °C
2: 100 percent / aq. HF / acetonitrile / 0.05 h / 20 °C
View Scheme
C69H107NO12Si2
197250-10-5

C69H107NO12Si2

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / dimethyl dioxirane / acetone / 2.17 h / -50 - -26 °C
2: 10.5 mg / aq. HF / acetonitrile / 10 h / 20 °C
View Scheme
C72H112INO13Si2

C72H112INO13Si2

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 110 percent / C8K-ZnCl2-AgOAc / tetrahydrofuran / 1 h / 0 °C
2: 100 percent / dimethyl dioxirane / acetone / 2.17 h / -50 - -26 °C
3: 10.5 mg / aq. HF / acetonitrile / 10 h / 20 °C
View Scheme
C72H113NO14Si2

C72H113NO14Si2

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 88 percent / triphenylphosphine; imidazole; iodine / toluene / 0.5 h / 70 °C
2: 110 percent / C8K-ZnCl2-AgOAc / tetrahydrofuran / 1 h / 0 °C
3: 100 percent / dimethyl dioxirane / acetone / 2.17 h / -50 - -26 °C
4: 10.5 mg / aq. HF / acetonitrile / 10 h / 20 °C
View Scheme
C80H121NO15Si2

C80H121NO15Si2

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / DDQ / CH2Cl2; H2O / 0.83 h / 20 °C
2: 88 percent / triphenylphosphine; imidazole; iodine / toluene / 0.5 h / 70 °C
3: 110 percent / C8K-ZnCl2-AgOAc / tetrahydrofuran / 1 h / 0 °C
4: 100 percent / dimethyl dioxirane / acetone / 2.17 h / -50 - -26 °C
5: 10.5 mg / aq. HF / acetonitrile / 10 h / 20 °C
View Scheme
C80H123NO16Si2

C80H123NO16Si2

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 21.0 mg / Et3N; methyl-2-chloropyridinium iodide / CH2Cl2 / 14 h / 20 °C
2: 92 percent / DDQ / CH2Cl2; H2O / 0.83 h / 20 °C
3: 88 percent / triphenylphosphine; imidazole; iodine / toluene / 0.5 h / 70 °C
4: 110 percent / C8K-ZnCl2-AgOAc / tetrahydrofuran / 1 h / 0 °C
5: 100 percent / dimethyl dioxirane / acetone / 2.17 h / -50 - -26 °C
6: 10.5 mg / aq. HF / acetonitrile / 10 h / 20 °C
View Scheme
C63H93NO13Si

C63H93NO13Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
2: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
4: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
5: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
6: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C63H92INO12Si

C63H92INO12Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
2: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
3: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C63H93NO13Si

C63H93NO13Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
2: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
3: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
4: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C63H93NO14Si

C63H93NO14Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
2: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
4: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
5: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
6: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C63H95NO14Si

C63H95NO14Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
2: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
3: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
4: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
5: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
6: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
7: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C63H91NO13Si

C63H91NO13Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
2: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
3: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
4: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
5: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C68H105NO15Si

C68H105NO15Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: NaHCO3, KBr, 4-methoxy-2,2,6,6-tetramethylpiperidinyloxy free radical, NaOCl / CH2Cl2 / 1.33 h / 0 °C
2: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
3: 495 mg / diethyl ether
4: Dess-Martin periodinane / CH2Cl2 / 1 h
5: LiOH*H2O / tetrahydrofuran / 0.5 h
6: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
7: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
8: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
9: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
10: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
11: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
12: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
Multi-step reaction with 10 steps
1: NaHCO3, KBr, 4-methoxy-2,2,6,6-tetramethylpiperidinyloxy free radical, NaOCl / CH2Cl2 / 1.33 h / 0 °C
2: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
3: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1 h, 2) THF, 0 deg C, 1 h
4: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
5: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
6: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
7: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
8: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
9: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
10: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C69H106INO12Si2

C69H106INO12Si2

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
2: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C68H103NO15Si

C68H103NO15Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
2: 495 mg / diethyl ether
3: Dess-Martin periodinane / CH2Cl2 / 1 h
4: LiOH*H2O / tetrahydrofuran / 0.5 h
5: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
6: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
7: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
8: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
9: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
10: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
11: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
Multi-step reaction with 9 steps
1: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
2: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1 h, 2) THF, 0 deg C, 1 h
3: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
4: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
5: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
6: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
7: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
8: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
9: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C68H101NO16Si

C68H101NO16Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
2: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
3: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
4: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
5: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
6: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
7: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C68H103NO16Si

C68H103NO16Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 495 mg / diethyl ether
2: Dess-Martin periodinane / CH2Cl2 / 1 h
3: LiOH*H2O / tetrahydrofuran / 0.5 h
4: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
5: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
6: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
7: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
8: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
9: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
10: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
Multi-step reaction with 8 steps
1: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1 h, 2) THF, 0 deg C, 1 h
2: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
3: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
4: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
5: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
6: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
7: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
8: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C69H105NO16Si

C69H105NO16Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: LiOH*H2O / tetrahydrofuran; H2O / 5 h / Ambient temperature
2: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1 h, 2) THF, 0 deg C, 1 h
3: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
4: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
5: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
6: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
7: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
8: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
9: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
Multi-step reaction with 9 steps
1: Dess-Martin periodinane / CH2Cl2 / 1 h
2: LiOH*H2O / tetrahydrofuran / 0.5 h
3: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
4: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
5: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
6: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
7: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
8: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
9: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C69H103NO16Si

C69H103NO16Si

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: LiOH*H2O / tetrahydrofuran / 0.5 h
2: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
3: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
4: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
5: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
6: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
7: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
8: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
C80H133NO15Si3

C80H133NO15Si3

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 71 percent / TBAF / tetrahydrofuran / 2 h
2: NaHCO3, KBr, 4-methoxy-2,2,6,6-tetramethylpiperidinyloxy free radical, NaOCl / CH2Cl2 / 1.33 h / 0 °C
3: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
4: 495 mg / diethyl ether
5: Dess-Martin periodinane / CH2Cl2 / 1 h
6: LiOH*H2O / tetrahydrofuran / 0.5 h
7: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
8: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
9: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
10: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
11: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
12: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
13: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
Multi-step reaction with 11 steps
1: 71 percent / TBAF / tetrahydrofuran / 2 h
2: NaHCO3, KBr, 4-methoxy-2,2,6,6-tetramethylpiperidinyloxy free radical, NaOCl / CH2Cl2 / 1.33 h / 0 °C
3: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
4: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1 h, 2) THF, 0 deg C, 1 h
5: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
6: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
7: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
8: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
9: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
10: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
11: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
(9RS,22S)-14-<(tert-butyldimethylsilyl)oxy>-9,22-tetrahydro-24,32-bis<(triisopropylsilyl)oxy>-FK506
128685-16-5, 128777-66-2

(9RS,22S)-14-<(tert-butyldimethylsilyl)oxy>-9,22-tetrahydro-24,32-bis<(triisopropylsilyl)oxy>-FK506

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / Dess-Martin periodinane / CH2Cl2 / 15 h / Ambient temperature
2: 73 percent / aq. HF / acetonitrile / 18 h / Ambient temperature
View Scheme
tacrolimus

tacrolimus

Tacrolimus
104987-11-3

Tacrolimus

Conditions
ConditionsYield
With polymer resin accoring to the invention In methanol; acetone`; water Purification / work up;
triisopropylsilyl trifluoromethanesulfonate
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

Tacrolimus
104987-11-3

Tacrolimus

C62H109NO12Si2
123747-39-7

C62H109NO12Si2

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane 1) 0 deg C, 1,5 h, 2) 25 deg C, 16 h;99%
Tacrolimus
104987-11-3

Tacrolimus

2-propenamide
79-06-1

2-propenamide

C45H70N2O13
1190108-68-9

C45H70N2O13

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-benzene at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;99%
Tacrolimus
104987-11-3

Tacrolimus

acrylic acid
79-10-7

acrylic acid

C45H69NO14
1190108-69-0

C45H69NO14

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-benzene at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;99%
With Hoveyda-Grubbs catalyst second generation In 1,2-dichloro-ethane at 85℃; for 1h; Inert atmosphere; Sealed tube; Microwave irradiation;96%
With Hoveyda-Grubbs catalyst second generation In 1,2-dichloro-ethane at 85℃; for 1h; Inert atmosphere; Sealed tube;96%
Tacrolimus
104987-11-3

Tacrolimus

D,L-dithiothreitol
3483-12-3, 6892-68-8, 7634-42-6, 16096-97-2, 27565-41-9, 35454-97-8

D,L-dithiothreitol

C92H148N2O26S2

C92H148N2O26S2

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane for 0.25h; UV-irradiation;99%
2-[(tert-butoxycarbonyl)amino]-1-ethanethiol
67385-09-5

2-[(tert-butoxycarbonyl)amino]-1-ethanethiol

Tacrolimus
104987-11-3

Tacrolimus

C51H84N2O14S

C51H84N2O14S

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane at 20℃; for 0.25h; Solvent; Reagent/catalyst; UV-irradiation;98%
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane at 23℃; for 0.25h; Inert atmosphere; Irradiation;96%
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane at 23℃; for 0.25h; UV-irradiation; Inert atmosphere;96%
Tacrolimus
104987-11-3

Tacrolimus

3-mercaptopropionic acid
107-96-0

3-mercaptopropionic acid

C47H75NO14S

C47H75NO14S

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane for 0.25h; Reagent/catalyst; UV-irradiation;98%
methanol
67-56-1

methanol

Tacrolimus
104987-11-3

Tacrolimus

C45H73NO13
133523-40-7

C45H73NO13

Conditions
ConditionsYield
With zinc(II) chloride for 3h; Ambient temperature;97%
for 3h; Heating;82%
Tacrolimus
104987-11-3

Tacrolimus

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

C46H71NO14

C46H71NO14

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-benzene at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;97%
Tacrolimus
104987-11-3

Tacrolimus

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

24,33-Bis-(t.butyl-dimethylsilyl)-FK 506
133941-75-0

24,33-Bis-(t.butyl-dimethylsilyl)-FK 506

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide96.7%
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;
Tacrolimus
104987-11-3

Tacrolimus

Cysteamine
60-23-1

Cysteamine

C46H76N2O12S

C46H76N2O12S

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In methanol for 0.25h; UV-irradiation;96%
Tacrolimus
104987-11-3

Tacrolimus

acrylic acid
79-10-7

acrylic acid

C45H69NO14

C45H69NO14

Conditions
ConditionsYield
With Hoveyda-Grubbs catalyst second generation In 1,2-dichloro-ethane at 85℃; for 1h; Inert atmosphere; Microwave irradiation;96%
t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

Tacrolimus
104987-11-3

Tacrolimus

24,33-Bis-(t.butyl-dimethylsilyl)-FK 506
133941-75-0

24,33-Bis-(t.butyl-dimethylsilyl)-FK 506

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 1h; Inert atmosphere;95%
C6H12N4OS
1277177-82-8

C6H12N4OS

Tacrolimus
104987-11-3

Tacrolimus

C50H81N5O13S

C50H81N5O13S

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane for 0.25h; UV-irradiation;95%
L-Cysteine
52-90-4

L-Cysteine

Tacrolimus
104987-11-3

Tacrolimus

C47H76N2O14S

C47H76N2O14S

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In methanol; water for 0.25h; UV-irradiation;95%
With 2,2-dimethoxy-2-phenylacetophenone In methanol; water at 23℃; for 0.25h; Inert atmosphere; UV-irradiation;92%
succinic acid anhydride
108-30-5

succinic acid anhydride

Tacrolimus
104987-11-3

Tacrolimus

C48H73NO15

C48H73NO15

Conditions
ConditionsYield
With Novozym SP435 In toluene at 45℃; for 80h; Inert atmosphere; Schlenk technique;95%
Tacrolimus
104987-11-3

Tacrolimus

22(S)-dihydro-FK-506
118949-52-3, 124152-71-2, 137694-88-3

22(S)-dihydro-FK-506

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at -78℃; for 1.5h;90%
With tetramethylammonium triacetoxyborohydride In acetic acid; acetonitrile at -5 - 0℃; for 5h;25%
Multi-step reaction with 3 steps
1: imidazole / dimethylformamide
2: 66 percent / tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / 5 h / -5 - 0 °C
3: 87 percent / 40percent aq. HF / acetonitrile / 2 h / 10 °C
View Scheme
Tacrolimus
104987-11-3

Tacrolimus

acryloyl chloride
814-68-6

acryloyl chloride

C45H68ClNO13
1190108-71-4

C45H68ClNO13

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In isopropyl alcohol at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;88%
diazomethane
186581-53-3, 908094-01-9

diazomethane

Tacrolimus
104987-11-3

Tacrolimus

C45H71NO12
133941-69-2

C45H71NO12

Conditions
ConditionsYield
palladium diacetate In dichloromethane Ambient temperature;87%
4-bromo-N-methylaniline
6911-87-1

4-bromo-N-methylaniline

Tacrolimus
104987-11-3

Tacrolimus

C51H76N2O12

C51H76N2O12

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere; Schlenk technique;82%
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 20h; Heck Reaction; Inert atmosphere; Schlenk technique;62%
methanol
67-56-1

methanol

Tacrolimus
104987-11-3

Tacrolimus

C45H71NO13
124125-40-2

C45H71NO13

Conditions
ConditionsYield
With lead(IV) acetate81%
diazomethane
186581-53-3, 908094-01-9

diazomethane

Tacrolimus
104987-11-3

Tacrolimus

(E)-(1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-12-[(E)-2-((1R,3R,4R)-3,4-dimethoxy-cyclohexyl)-1-methyl-vinyl]-1-hydroxy-14,23,25-trimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone
124554-15-0

(E)-(1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-12-[(E)-2-((1R,3R,4R)-3,4-dimethoxy-cyclohexyl)-1-methyl-vinyl]-1-hydroxy-14,23,25-trimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃;80%
Tacrolimus
104987-11-3

Tacrolimus

(E)-(8S,11S,12R,13S,16R,20S,22S,23R,24S,26R)-16-Allyl-1,13-dihydroxy-11-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-22,24-dimethoxy-12,18,20,26-tetramethyl-10,28-dioxa-3-aza-tricyclo[21.4.1.03,8]octacos-17-ene-2,9,15,27-tetraone

(E)-(8S,11S,12R,13S,16R,20S,22S,23R,24S,26R)-16-Allyl-1,13-dihydroxy-11-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-22,24-dimethoxy-12,18,20,26-tetramethyl-10,28-dioxa-3-aza-tricyclo[21.4.1.03,8]octacos-17-ene-2,9,15,27-tetraone

Conditions
ConditionsYield
With zinc(II) chloride In dichloromethane for 15h; Ambient temperature;80%
4-ethenylbenzoic acid
1075-49-6

4-ethenylbenzoic acid

Tacrolimus
104987-11-3

Tacrolimus

C51H73NO14
1190108-85-0

C51H73NO14

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-benzene at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;79%
4-vinyl benzylamine
1520-21-4

4-vinyl benzylamine

Tacrolimus
104987-11-3

Tacrolimus

C50H74N2O12
1190108-83-8

C50H74N2O12

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-benzene at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;79%
Tacrolimus
104987-11-3

Tacrolimus

3-fluoro-4-iodopyridine
22282-75-3

3-fluoro-4-iodopyridine

C49H71FN2O12

C49H71FN2O12

Conditions
ConditionsYield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 24h; Heck Reaction; Inert atmosphere; Schlenk technique;78%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

Tacrolimus
104987-11-3

Tacrolimus

C45H70N2O12
133523-41-8

C45H70N2O12

Conditions
ConditionsYield
With potassium cyanide; 18-crown-6 ether In benzene at 23℃; for 20h;76%
Tacrolimus
104987-11-3

Tacrolimus

(3R,5S,6R)-6-[(5E,13E)-(1S,3S,7R,10S,11R,12S)-7-Allyl-10,12-dihydroxy-14-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methoxy-3,5,11,13-tetramethyl-8-oxo-tetradeca-5,13-dienyl]-5-methoxy-3-methyl-tetrahydro-pyran-2-one

(3R,5S,6R)-6-[(5E,13E)-(1S,3S,7R,10S,11R,12S)-7-Allyl-10,12-dihydroxy-14-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methoxy-3,5,11,13-tetramethyl-8-oxo-tetradeca-5,13-dienyl]-5-methoxy-3-methyl-tetrahydro-pyran-2-one

Conditions
ConditionsYield
With tetra-n-butylammonium cyanide In tetrahydrofuran; water at 5℃; for 2h;76%

Tacrolimus History

 Tacrolimus (CAS NO.104987-11-3) was among the first macrolide immunosuppressants discovered, which was discovered in 1984 by a Japanese team headed by T. Goto, T. Kino and H. Hatanaka. The name tacrolimus is derived from 'Tsukuba macrolide immunosuppressant'. Tacrolimus is owned by Astellas Pharma Inc., and is sold under the tradenames Prograf, Advagraf, and Protopic. It was first approved by the Food and Drug Administration (FDA) in 1994 use in liver transplantation, trachea, skin, cornea, and limb transplants.

Tacrolimus Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 200mg/kg (200mg/kg)   Journal of Antibiotics. Vol. 40, Pg. 1249, 1987.

Tacrolimus Specification

The Tacrolimus, with the CAS registry number 104987-11-3,is also known as Tsukubaenolide. It belongs to the product categories of Pharmaceuticals; API;Chiral Reagents.Its EINECS number is 242-042-4. This chemical's molecular formula is C44H69NO12 and molecular weight is 804.02. What's more,Its systematic name is 15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone.It is a White Crystalline Solid which is used after allogeneic organ transplant to reduce the activity of the patient's immune system and so lower the risk of organ rejection. In recent years, it has been used to suppress the inflammation associated with ulcerative colitis. It is a recent addition in the treatment of eczema, particularly atopic dermatitis, and suppresses inflammation in a similar way to steroids.

Physical properties about Tacrolimus are:
(1)ACD/LogP:  3.96; (2)# of Rule of 5 Violations:  2; (3)ACD/LogD (pH 5.5):  3.96; (4)ACD/LogD (pH 7.4):  3.96; (5)ACD/BCF (pH 5.5):  602.10; (6)ACD/BCF (pH 7.4):  600.47; (7)ACD/KOC (pH 5.5):  3398.48; (8)ACD/KOC (pH 7.4):  3389.29; (9)#H bond acceptors:  13; (10)#H bond donors:  3; (11)#Freely Rotating Bonds:  10; (12)Index of Refraction:  1.549; (13)Molar Refractivity:  214.131 cm3; (14)Molar Volume:  673.124 cm3; (15)Surface Tension:  51.2929992675781 dyne/cm; (16)Density:  1.194 g/cm3; (17)Flash Point:  481 °C; (18)Enthalpy of Vaporization:  143.946 kJ/mol; (19)Boiling Point:  871.721 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C3C(=O)N1CCCC[C@H]1C(=O)O[C@H](C(=C/[C@@H]2CC[C@@H](O)[C@H](OC)C2)/C)[C@H](C)[C@@H](O)CC(=O)[C@@H](/C=C(\C[C@@H](C[C@H](OC)[C@H]4O[C@]3(O)[C@H](C)C[C@@H]4OC)C)C)C\C=C;
(2)Std. 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;
(3)Std. InChIKey:QJJXYPPXXYFBGM-LFZNUXCKSA-N.

The toxicity data of Tacrolimus are as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 200mg/kg (200mg/kg)   Journal of Antibiotics. Vol. 40, Pg. 1249, 1987.

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