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Merck

1642802

USP

Tacrolimus

United States Pharmacopeia (USP) Reference Standard

Sinónimos:

FK-506 monohydrate, Tacrolimus

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Fórmula empírica (notación de Hill):
C44H69NO12 · H2O
Número CAS:
109581-93-3
Peso molecular:
822.03
NACRES:
NA.24
PubChem Substance ID:
329751216
UNSPSC Code:
41116107
MDL number:
MFCD11045918

Documentos clave

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Nombre del producto

Tacrolimus, United States Pharmacopeia (USP) Reference Standard

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

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 key

NWJQLQGQZSIBAF-MLAUYUEBSA-N

grade

pharmaceutical primary standard

API family

tacrolimus

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

human ... FKBP1A(2280)

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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.  ​

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).
FK-506 is a potent immunosuppressant; neuroprotective and neuroregenerative; in vitro T cell proliferation blocker.

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.

Other Notes

Sales restrictions may apply.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Clase de almacenamiento

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number

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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)
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
Miwa Uesugi et al.
Pharmacogenetics and genomics, 24(7), 356-366 (2014-06-10)
We investigated whether the cytochrome P450 3A5*3 (CYP3A5*3) genotype affects tacrolimus pharmacokinetics and the risk of acute cellular rejection in living-donor liver transplant patients in Japan. Between July 2004 and June 2011, we enrolled 410 living-donor liver transplant patients receiving
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