tacrolimus

Also known as fujimycin, (-)-FK 506, FK506, tacrolimus anhydrous, anhydrous tacrolimus

Tacrolimus, sold under the brand name Prograf among others, is an immunosuppressive drug. After an allogenic organ transplant, the risk of organ rejection is moderate; tacrolimus is used to lower the risk of organ rejection. Tacrolimus is also sold as a topical medication for treating T cell-mediated diseases, such as eczema and psoriasis. For example, it is prescribed for severe refractory uveitis after a bone marrow transplant, exacerbations of minimal change disease, Kimura's disease, and vitiligo. It can be used to treat dry eye syndrome in cats and dogs.

Key facts

Drug.IUPAC_name: (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,26aS)-8-allyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-{(E)-2-[(1R,3R,4R)-4-hydroxy-3-methylcyclohexyl]-1-methylvinyl}-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosane-1,7,20,21(4H,23H)-tetrone
Drug.C: 44
Drug.H: 69
Drug.N: 1
Drug.O: 12
Drug.SMILES: C=CC[C@@H]1/C=C(\C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)[C@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC
Drug.StdInChI: 1S/C44H69NO12/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/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1
Drug.StdInChIKey: QJJXYPPXXYFBGM-LFZNUXCKSA-N
Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 461746192
Drug.image: Tacrolimus2DCSD.svg
Drug.image_class: skin-invert-image
Drug.width: 250
Drug.image2: Tacrolimus-1YAT-ball-and-stick-model.png
Drug.image_class2: bg-transparent
Drug.width2: 250
Drug.tradename: Prograf, Advagraf, Protopic, Envarsus, others

via Wikipedia infobox

Chemical data

Formula: C44H69NO12
Molecular weight: 804 g/mol
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
SMILES: C[C@@H]1C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC(=O)[C@@H](/C=C(/C1)\C)CC=C)O)C)/C(=C/[C@@H]4CC[C@H]([C@@H](C4)OC)O)/C)O)C)OC)OC
InChIKey: QJJXYPPXXYFBGM-LFZNUXCKSA-N
XLogP: 2.7
Polar surface area: 178 Å²
H-bond donors: 3
H-bond acceptors: 12
Formal charge: 0

via PubChem

Research

31,555 papers

Tacrolimus - Pharmacokinetic Considerations for Clinicians.Current drug metabolism · 2018
Clinical pharmacokinetics of tacrolimus.Clinical pharmacokinetics · 1995
[Tacrolimus].Nihon rinsho. Japanese journal of clinical medicine · 2005
Tacrolimus (FK 506).Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology · 1999
[Biosynthesis of immunosuppressant tacrolimus: a review].Sheng wu gong cheng xue bao = Chinese journal of biotechnology · 2023

via PubMed

Wikidata facts

Mass: 803.482

Show 6 more facts

chemical formula: C₄₄H₆₉NO₁₂
canonical SMILES: CC1CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC(=O)C(C=C(C1)C)CC=C)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC
isomeric SMILES: C[C@@H]1C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC(=O)[C@@H](/C=C(/C1)\C)CC=C)O)C)/C(=C/[C@@H]4CC[C@H]([C@@H](C4)OC)O)/C)O)C)OC)OC
World Health Organisation international non-proprietary name: 他克莫司
Commons category: Tacrolimus
defined daily dose: 5

Sources (11)

via Wikidata · CC0

~19 min read

Article

25 sections

Contents

History
Medical uses
Organ transplantation
Skin
Eyes
Contraindications and precautions
Topical use
Side effects
By mouth or intravenous use
Carcinogenesis and mutagenesis
Topical use
Cancer risks
Interactions
Pharmacology
Mechanism of action
Pharmacokinetics
Pharmacogenetics
Available forms
Biosynthesis
Research
Lupus nephritis
Ulcerative colitis
References
Further reading
External links

{{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 461746192 | image = Tacrolimus2DCSD.svg | image_class = skin-invert-image | width = 250 | alt = | image2 = Tacrolimus-1YAT-ball-and-stick-model.png | image_class2 = bg-transparent | width2 = 250 | alt2 = | caption =