tacrolimus
Sign in to saveTacrolimus, 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
Article
25 sectionsContents
- 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 =
| pronounce = | tradename = Prograf, Advagraf, Protopic, Envarsus, others | Drugs.com = | MedlinePlus = a601117 | DailyMedID = Tacrolimus | pregnancy_AU = C | pregnancy_AU_comment = | pregnancy_category= | routes_of_administration = Topical, by mouth, intravenous | class = | ATC_prefix = D11 | ATC_suffix = AH01 | ATC_supplemental=
Gallery (10)
Connections
Categories
Alkene derivativesAllyl compoundsAstellas PharmaCYP3A4 inhibitorsDisulfiram-like drugsDrugboxes which contain changes to verified fieldsDrugboxes which contain changes to watched fieldsDrugs with non-standard legal statusECHA InfoCard ID from WikidataIARC Group 1 carcinogensImmunosuppressantsMacrolides