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Merck

1642802

USP

Tacrolimus

United States Pharmacopeia (USP) Reference Standard

Sinónimos:

FK-506 monohydrate, Tacrolimus

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About This Item

Fórmula empírica (notación de Hill):
C44H69NO12 · H2O
Número de CAS:
Peso molecular:
822.03
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
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

signalword

Danger

hcodes

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


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

Tacrolimus
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 41(2), 4193-4193 (2021)
Tacrolimus Compounded Oral Suspension
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 41(1), 4202-4202 (2016)
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
Violette M G J Gijsen et al.
Pediatric transplantation, 17(3), 205-215 (2013-03-02)
Renal dysfunction after non-renal transplantation in adult tacrolimus-treated transplant patients is well documented. Little is known about its prevalence in children. Age-related changes in both disposition and effect of tacrolimus as well as renal function may preclude extrapolation of adult

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