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104987-11-3

Basic Information
CAS No.: 104987-11-3
Name: Tacrolimus
Article Data: 18
Molecular Structure:
Molecular Structure of 104987-11-3 (Tacrolimus)
Formula: C44H69NO12
Molecular Weight: 804.031
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;
EINECS: 1308068-626-2
Density: 1.19 g/cm3
Melting Point: 113-115 °C
Boiling Point: 871.7 °C at 760 mmHg
Flash Point: 481 °C
Solubility: DMSO: >3 mg/mL
Appearance: White or off-white crystalline powder
Hazard Symbols: ToxicT,IrritantXi
Risk Codes: 25-36/37/38
Safety: 45-36-26
Transport Information: UN 2811 6.1/PG 3
PSA: 178.36000
LogP: 4.57690
Synthetic route
118977-96-1

C56H97NO12Si2

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%
133941-75-0

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

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;
128685-18-7

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

104987-11-3

Tacrolimus

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

C66H101NO11Si2

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;
197250-11-6

C66H101NO12Si2

104987-11-3

Tacrolimus

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

C55H95NO13Si2

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

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
197250-10-5

C69H107NO12Si2

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

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

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
Downstream Products
3105-95-1
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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.

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.

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.