ChemicalBook > CAS DataBase List > Tacrolimus Monohydrate

Tacrolimus Monohydrate

Product Name
Tacrolimus Monohydrate
CAS No.
109581-93-3
Chemical Name
Tacrolimus Monohydrate
Synonyms
Tacrolimus monohydrate;FK-506;135175;CS-1308;Tacarolimus;[3R[E(1S,3S,4S);tacrolimushydrate;FK-506 MONOHYDRATE;Tacrolimus (150 mg);FR900506 monohydrate
CBNumber
CB4772400
Molecular Formula
C44H71NO13
Formula Weight
822.05
MOL File
109581-93-3.mol
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Tacrolimus Monohydrate Property

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
InChI
InChI=1/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+;/s3
InChIKey
NWJQLQGQZSIBAF-MLAUYUEBSA-N
SMILES
O([C@H]1C[C@@H](C)[C@@]2(C(C(N3CCCC[C@@]3([H])C(O[C@@H]([C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)C=C(C)C[C@H](C)C[C@H](OC)[C@@]1([H])O2)/C(/C)=C/[C@@H]1CC[C@@H](O)[C@H](OC)C1)=O)=O)=O)O)C.O |t:30,&1:1,3,5,13,17,18,20,25,33,36,39,45,48,50,r|
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Safety

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
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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0001926
Product name
Tacrolimus monohydrate
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
Y0001926
Price
$601
Updated
2024/03/01
Sigma-Aldrich
Product number
F4679
Product name
FK-506 monohydrate
Purity
≥98% (HPLC)
Packaging
5mg
Price
$271
Updated
2024/03/01
Sigma-Aldrich
Product number
1642802
Product name
Tacrolimus
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
100MG
Price
$1480
Updated
2024/03/01
Sigma-Aldrich
Product number
1642802
Product name
Tacrolimus
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
150mg
Price
$1590
Updated
2024/03/01
Sigma-Aldrich
Product number
Y0001933
Product name
Tacrolimus for system suitability
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
Y0001933
Price
$212
Updated
2023/06/20
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Tacrolimus Monohydrate Chemical Properties,Usage,Production

Uses

immune suppressant, antifungal

Uses

FK-506 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.

Tacrolimus Monohydrate Preparation Products And Raw materials

Raw materials

Preparation Products

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Tacrolimus Monohydrate Suppliers

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View Lastest Price from Tacrolimus Monohydrate manufacturers

Wuhan Boyuan Import & Export Co., LTD
Product
Tacrolimus Monohydrate 109581-93-3
Price
US $30.00-25.00/KG
Min. Order
1KG
Purity
99.50%
Supply Ability
20tons
Release date
2023-07-13
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Tacrolimus monohydrate 109581-93-3
Price
US $0.00-0.00/g
Min. Order
1g
Purity
98%-102%
Supply Ability
500G
Release date
2021-06-09
Weijer International Trade (Hebei) Co., Ltd
Product
Tacrolimus 109581-93-3
Price
US $50.00/KG
Min. Order
1KG
Purity
>99%
Supply Ability
20tons
Release date
2023-03-16

109581-93-3, Tacrolimus MonohydrateRelated Search:


  • 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%
  • Tacrolimus /FK506 monohydrate
  • Tacrolimus Monohydrate CAS 109581-93-3
  • ,8s*,9e,12r*,14r*,15s*,16r*,18s*,19s*,26ar*))-
  • 18-tetramethyl-8-(2-propenyl)-,monohydrate,(3s-(3r*(e(1s*,3s*,4s*)),4s*,5r*
  • 3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-9,10,12,
  • tacrolimushydrate
  • tsukubaenolidehydrate
  • FK-506 MONOHYDRATE
  • Tacarolimus
  • 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-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-te
  • FK506 Monohydrate[Tacrolimus Hydrate]
  • 135175
  • CS-1308
  • FK 506 monohydrate, Tacrolimus
  • Tacrolimus monohydroate
  • TacrolimusMonohydrate&gt
  • Tacrolimus monohydrate CRS
  • FR900506 monohydrate
  • Tacrolimus monohydrate (Fujimycin monohydrate
  • [3R[E(1S,3S,4S)
  • (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 monohydrate
  • Tacrolimus monohydrate (Y0001926)
  • Tacrolimus (1642802)
  • Lecithin Impurity 9 (L-α-Phosphatidylinositol)
  • Tacrolimus USP/IP/PH.Eur
  • Tacrolimus Reference Standard
  • 109581-93-3
  • C44H69NO12H2O
  • Cell Signaling and Neuroscience
  • Kinase/Phosphatase Biology
  • Protein Phosphatase 2B (Calcineurin/PP2B)
  • Serine/Threonine Phosphatase Inhibitors
  • BioChemical
  • Cell Biology
  • Signalling