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1642802

USP

Tacrolimus

United States Pharmacopeia (USP) Reference Standard

Synonyma:

FK-506 monohydrate, Tacrolimus

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About This Item

Empirický vzorec (Hillův zápis):
C44H69NO12 · H2O
Číslo CAS:
109581-93-3
Molekulová hmotnost:
822.03
MDL number:
MFCD11045918
UNSPSC Code:
41116107
PubChem Substance ID:
329751216
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

tacrolimus

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

SMILES string

O.CO[C@@H]1C[C@@H](CC[C@H]1O)\C=C(/C)[C@H]2OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@]4(O)O[C@H]([C@H](C[C@@H](C)C\C(C)=C\[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)OC)[C@H](C[C@H]4C)OC

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

InChI key

NWJQLQGQZSIBAF-MLAUYUEBSA-N

Gene Information

human ... FKBP1A(2280)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Tacrolimus USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Tacrolimus Capsules
  • Tacrolimus Compounded Oral Suspension

Biochem/physiol Actions

FK-506 is a potent immunosuppressant, neuroprotective and neuroregenerative, and in vitro T cell proliferation blocker. FK-506 disrupts calcineurin-mediated signal transduction in T lymphocytes and interacts with its FK-506-binding protein-12 (FKBP12).

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (COA)

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Navštívit knihovnu dokumentů

Tacrolimus Compounded Oral Suspension
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 41(1), 4202-4202 (2016)
Tacrolimus
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 41(2), 4193-4193 (2021)
Tacrolimus capsules
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 41(2), 4196-4196 (2022)
Frank Stifft et al.
Transplantation, 97(7), 775-780 (2014-04-02)
Tacrolimus has originally been registered as a twice-daily formulation (Prograf, Tac BID), although a once-daily formulation (Advagraf, Tac QD) is also available. A reduced intrapatient variability of Tac Cmin, a surrogate marker for 24-hour drug exposure (AUC0-24), has been suggested.
Rania Rabie et al.
Liver transplantation : official publication of the American Association for the Study of Liver Diseases and the International Liver Transplantation Society, 19(1), 36-48 (2012-07-24)
Cyclosporine A (CSA), but not tacrolimus (TAC), inhibits hepatitis C virus (HCV) replication in vitro. Clinical reports on the efficacy of interferon-α (IFNα)-based antiviral therapy (AVT) for recurrent HCV after liver transplantation (LT) with CSA and TAC are conflicting. Our
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