Skip to Content
MilliporeSigma
All Photos(1)

Documents

1642802

USP

Tacrolimus

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

FK-506 monohydrate, Tacrolimus

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C44H69NO12 · H2O
CAS Number:
109581-93-3
Molecular Weight:
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)

Looking for similar products? Visit Product Comparison Guide

Related Categories

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 is intended for use in specified quality tests and assays as per USP compendia.

Also used to prepare standard and system suitability solutions for assay, and impurity analysis according to the given below monographs of United States Pharmacopeia (USP):
  • Tacrolimus
  • 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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 8

1 of 8

Pimecrolimus ≥97% (HPLC)

Sigma-Aldrich

SML1437

Pimecrolimus

ID-8 ≥98% (HPLC)

Sigma-Aldrich

I1786

ID-8

Ascomycin solution 1.0 mg/mL in acetonitrile, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

A-094

Ascomycin solution

Calcineurin Inhibitor VIII, CN585 The Calcineurin Inhibitor VIII, CN585, also referenced under CAS 1213234-31-1, controls the biological activity of Calcineurin. This small molecule/inhibitor is primarily used for Phosphorylation & Dephosphorylation applications.

Sigma-Aldrich

207003

Calcineurin Inhibitor VIII, CN585

Cyclosporine United States Pharmacopeia (USP) Reference Standard

USP

1158504

Cyclosporine

Cyclosporin A 97.0-101.5% (on dried basis)

Sigma-Aldrich

30024

Cyclosporin A

Ascomycin from Streptomyces hygroscopicus var. ascomyceticus

Sigma-Aldrich

A3835

Ascomycin from Streptomyces hygroscopicus var. ascomyceticus

Cyclosporine Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1092

Cyclosporine

Tacrolimus Compounded Oral Suspension
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 41(1), 4202-4202 (2016)
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.
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
Frank Stifft et al.
British journal of clinical pharmacology, 78(5), 996-1004 (2014-05-09)
The immunosuppressant tacrolimus is usually administered orally. When this is not feasible, other routes of administration may be useful. Previous research suggested that tacrolimus may be applied sublingually or rectally. Pharmacokinetic data are sparse. The aim of this study was
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service