109581-93-3

Basic information

• Product Name: TACROLIMUS
• Synonyms: FK-506;,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
• CAS NO: 109581-93-3
• Molecular Formula: C44H69NO12
• Molecular Weight: 822.04
• Product Categories: Signalling
• Mol File: 109581-93-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 127-129°
• Boiling Point: 871.7 °C at 760 mmHg
• Flash Point: 481 °C
• Appearance: /
• Vapor Pressure: 1.73E-35mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: DMSO: soluble20mg/mL
• Merck: 14,9025
• CAS DataBase Reference: TACROLIMUS(CAS DataBase Reference)
• NIST Chemistry Reference: TACROLIMUS(109581-93-3)
• EPA Substance Registry System: TACROLIMUS(109581-93-3)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: KD4201200
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 109581-93-3(Hazardous Substances Data)

Usage

Description

TACROLIMUS, also known as FK-506, is an immunosuppressive agent that belongs to the macrolide family of antibiotics. It is a hydrate in the form of FK-506 monohydrate and has potent immunosuppressive and antifungal properties. TACROLIMUS works by inhibiting the enzyme calcineurin, which plays a crucial role in the immune response. This inhibition helps prevent the activation of T-cells, thereby suppressing the immune system.

Uses

Used in Pharmaceutical Industry:
TACROLIMUS is used as an immunosuppressive agent for preventing organ rejection in transplant patients. It is particularly effective in reducing the risk of rejection after liver, kidney, and heart transplants.
Used in Research Applications:
TACROLIMUS is used as a calcineurin inhibitor in coculture medium to study the effects of immunologic reactions. This helps researchers understand the role of the immune system in various diseases and develop targeted therapies.
Used in Ophthalmology:
TACROLIMUS is used to treat retinal pigment epithelial cells to measure possible cytotoxicity. This application is crucial in the development of treatments for eye diseases and conditions related to the retinal pigment epithelium.
Used in Antifungal Treatments:
TACROLIMUS is used as an antifungal agent to treat various fungal infections. Its potent antifungal properties make it an effective treatment option for patients with severe or resistant fungal infections.

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.

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+;/m0./s1

Related news

Comparison of anti-atopic dermatitis activities between DHMEQ and TACROLIMUS (cas 109581-93-3) ointments in mouse model without stratum corneum07/31/2019

This study is aimed to further investigate the anti-atopic dermatitis (AD) activities of dehydroxymethylepoxyquinomicin (DHMEQ) ointment and compare its effect with that of tacrolimus ointment based on the previous study that DHMEQ improves AD-like lesions. AD were induced by 2,4-dinitroclilorob...detailed

An open-label, randomized trial indicates that everolimus with TACROLIMUS (cas 109581-93-3) or cyclosporine is comparable to standard immunosuppression in de novo kidney transplant patients07/30/2019

This is a randomized trial (ATHENA study) in de novo kidney transplant patients to compare everolimus versus mycophenolic acid (MPA) with similar tacrolimus exposure in both groups, or everolimus with concomitant tacrolimus or cyclosporine (CsA), in an unselected population. In this 12-month, mu...detailed

Relationships between concomitant biologic DMARDs and prednisolone administration and blood TACROLIMUS (cas 109581-93-3) exposure or serum CYP3A4/5-related markers in rheumatoid arthritis patients07/29/2019

BackgroundThis study aimed to evaluate the relationships between concomitant biologic disease-modifying anti-rheumatic drugs (DMARDs) and prednisolone administration and blood tacrolimus exposure or serum CYP3A4/5-related markers in rheumatoid arthritis (RA) patients without severe disease activity.detailed

Recipient ABCB1, donor and recipient CYP3A5 genotypes influence TACROLIMUS (cas 109581-93-3) pharmacokinetics in liver transplant cases07/28/2019

BackgroundEffective immunosuppression through optimization of trough levels tacrolimus reduces post-transplant mortality rate in liver transplant cases.detailed

Inhibitory effect of immunosuppressive drug TACROLIMUS (cas 109581-93-3) on voltage-gated K+ current in rabbit coronary arterial smooth muscle cells07/27/2019

In the present study, we investigated the inhibitory effect of tacrolimus, a macrolide immunosuppressive drug that acts through calcineurin inhibition, on voltage-gated K+ (Kv) channels expressed in native smooth muscle cells isolated from the coronary arteries of rabbits. Tacrolimus reduced the...detailed

Effectiveness and safety of TACROLIMUS (cas 109581-93-3) therapy for myasthenia gravis: A single arm meta-analysis07/26/2019

To evaluate the effectiveness and safety of tacrolimus in myasthenia gravis (MG) patients, a systematic review and meta-analysis was performed. Researches published between January 1, 2000 and December 31, 2017 in English language were searched in Medline, Embase, Cochrane Central Register of Co...detailed

Conversion From Immediate-Release TACROLIMUS (cas 109581-93-3) to Prolonged-Release TACROLIMUS (cas 109581-93-3) in Stable Heart Transplant Patients: A Retrospective Study07/25/2019

BackgroundLifelong adherence with post-transplant immunosuppression is challenging, with nonadherence associated with greater acute rejection (AR) risk.detailed

Therapeutic drug monitoring of cyclosporine and TACROLIMUS (cas 109581-93-3) in Myanmar kidney transplant patients07/23/2019

IntroductionRenal transplantation is one of the best options for patients suffering from end stage renal disease (ESRD). Cyclosporine and Tacrolimus are mainly applied in immunosuppressive therapy after transplantation of liver, kidney, heart, and other organs. The used of immunosuppressant drug...detailed

TACROLIMUS (cas 109581-93-3) ointment in the management of atopic keratoconjunctivitis07/22/2019

SummaryIntroductionAtopic keratoconjunctivitis is frequently associated with atopic eyelid dermatitis. It may require topical steroids, the prolonged use of which may cause ocular complications. Tacrolimus is an immunosuppressant used topically on the skin in atopic dermatitis. The purpose of th...detailed