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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 (Tacrolimus 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.

in vitro

Tacrolimus monohydrate (FK506 monohydrate; Fujimycin monohydrate; FR900506 monohydrate) inhibits calcium-dependent events, such as IL-2 gene transcription, NO synthase activation, cell degranulation, and apoptosis. Tacrolimus also potentiates the actions of glucocorticoids and progesterone by binding to FKBPs contained within the hormone receptor complex, preventing degradation. The agent may enhance the expression of the TGFβ-1 gene in a fashion analogous to that demonstrated for CsA. T cell proliferation in response to ligation of the T cell receptor is inhibited by Tacrolimus. Treatment with a low concentration of Tacrolimus (FK506,10 μg/L) does not significantly affect the proliferation of MH3924A cells (P=0.135). Upon treatment with higher concentrations of Tacrolimus (100-1,000 μg/L), the proliferation of MH3924A cells is significantly enhanced (P<0.01). Treatment with AMD3100 at any concentration (10, 50 or 100 μg/L) has no obvious effect on MH3924A cell proliferation (P>0.05). However, when different concentrations of AMD3100 are combined with 100 μg/L Tacrolimus, the in vitro proliferation of MH3924A cells is increased (P<0.01).

Tacrolimus Monohydrate Preparation Products And Raw materials

Raw materials

Preparation Products

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Tacrolimus Monohydrate Suppliers

Americas 1 China 218 Europe 1 Germany 1 India 14 Japan 1 Switzerland 1 United Kingdom 6 United States 22 Global 265
LGM Pharma
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View Lastest Price from Tacrolimus Monohydrate manufacturers

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
Hangzhou Hyper Chemicals Limited
Product
Tacrolimus Monohydrate 109581-93-3
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%, USP
Supply Ability
1,000KG
Release date
2024-05-22
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

109581-93-3, Tacrolimus MonohydrateRelated Search:

TacroliMus Methyl Acryl Aldehyde Δ23-FK-506 8-EpitacroliMus Tacrolimus N-LAUROYL-L-ALANINE Tacrolimus Monohydrate Ethyl1-butyl-2-piperidinecarbxylate Ascomycin N-LAUROYLSARCOSINE H-HOMOPRO-OME HCL 1-(2-methylpiperidin-1-yl)acetone

  • 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)
  • Tacrolimus USP/IP/PH.Eur
  • Tacrolimus Reference Standard
  • FK-506|||FR 900506|||Prograf|||FR900506|||Tacrolimus hydrate|||LCP-Tacro|||FK 506
  • Lecithin Impurity 9 (L-α-Phosphatidylinositol)
  • 109581-93-3
  • C44H69NO12H2O
  • Cell Signaling and Neuroscience
  • Kinase/Phosphatase Biology
  • Protein Phosphatase 2B (Calcineurin/PP2B)
  • Serine/Threonine Phosphatase Inhibitors
  • BioChemical
  • Cell Biology
  • Signalling