LKT Labs

Biochemicals for Life Science Research

Tacrolimus

Tacrolimus

Product ID T0008
Cas No. 104987-11-3
Purity ≥98%
Product Unit SizeCostQuantityStock
1 mg $45.30 In stock
5 mg $75.10 In stock
25 mg $240.30 In stock
100 mg $631.20 In stock
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Description

Tacrolimus is a calcineurin inhibitor that exhibits immunosuppressive, anti-fibrotic, anti-inflammatory, and anti-allergic activities. Clinically, tacrolimus is used to treat atopic dermatitis and conjunctivitis. In vivo, tacrolimus inhibits synthesis of type I collagen polypeptides and the interaction between LARP6 and FKBP3, suppressing the development of alcohol-induced liver fibrosis. In animal models of OVA-induced allergy, tacrolimus decreases allergic symptoms and levels of IgE, eosinophils, IL-5, and GATA-3.

Product Info

Cas No.

104987-11-3
Purity

≥98%
Formula

C44H69NO12
Formula Wt.

804.02
Chemical Name

3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R, 26aS)5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-5,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone

IUPAC Name

(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-prop-2-enyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
Synonym

FK-506, Fujimycin, Prograf, Protopic, CCRIS 7124.
Melting Point

126-130°C

Solubility

Soluble in DMSO (20 mg/ml), ethanol (30 mg/ml), acetone, ethyl acetate, diethyl ether or chloroform.
Appearance

White Crystal Powder

Shipping and Storage

Store Temp

Ambient
Ship Temp

Ambient

Downloads

MSDS

T0008 MSDS PDF
Info Sheet

T0008 Info Sheet PDF

References

Carr WW. Topical calcineurin inhibitors for atopic dermatitis: review and treatment recommendations. Paediatr Drugs. 2013 Aug;15(4):303-10. PMID: 23549982.

Manojlovic Z, Blackmon J, Stefanovic B. Tacrolimus (FK506) prevents early stages of ethanol induced hepatic fibrosis by targeting LARP6 dependent mechanism of collagen synthesis. PLoS One. 2013 Jun 3;8(6):e65897. PMID: 23755290.

Grigoriu S, Bond R, Cossio P, et al. The molecular mechanism of substrate engagement and immunosuppressant inhibition of calcineurin. PLoS Biol. 2013;11(2):e1001492. PMID: 23468591.

Shin JH, Park HR, Kim SW, et al. The effect of topical FK506 (tacrolimus) in a mouse model of allergic rhinitis. Am J Rhinol Allergy. 2012 Mar-Apr;26(2):e71-5. PMID: 22487280.

Izumi S, Nozaki Y, Komori T, et al. Substrate-dependent inhibition of organic anion transporting polypeptide 1B1: comparative analysis with prototypical probe substrates estradiol-17beta-glucuronide, estrone-3-sulfate, and sulfobromophthalein. Drug Metab Dispos. 2013 Oct;41(10):1859-1866. PMID: 23920221.

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