User:Mr. Ibrahem/Tacrolimus

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Mr. Ibrahem/Tacrolimus
Clinical data
Trade namesPrograf, Advagraf, Protopic, others
Other namesFK-506, fujimycin
AHFS/Drugs.comSystemic: Monograph
Topical: Monograph
MedlinePlusa601117
License data
Pregnancy
category
Routes of
administration		Topical, by mouth, intravenous
Legal status
Legal status
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability24% (5–67%), less after eating food rich in fat
Protein binding≥98.8%
MetabolismLiver CYP3A4, CYP3A5
Elimination half-life11.3 h post transplant (range 3.5–40.6 h)
ExcretionMostly faecal
Identifiers
  • (−)-(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
Chemical and physical data
FormulaC44H69NO12
Molar mass804.018 g·mol−1
3D model (JSmol)
  • O=C3C(=O)N1CCCC[C@H]1C(=O)O[C@H](C(=C/[C@@H]2CC[C@@H](O)[C@H](OC)C2)/C)[C@H](C)[C@@H](O)CC(=O)[C@@H](/C=C(/C[C@@H](C[C@H](OC)[C@H]4O[C@]3(O)[C@H](C)C[C@@H]4OC)C)C)C\C=C
  • InChI=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 checkY
  • Key:QJJXYPPXXYFBGM-LFZNUXCKSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tacrolimus is a medication used by mouth or by injection to prevent rejection after organ transplant.[2][3] Levels of the medication should be regularly monitored.[3] As a cream it is used for moderate to severe eczema or psoriasis when other treatments are not sufficient.[2][4]

Common side effects when take by mouth or injection include kidney problems, diarrhea, nausea, high blood potassium, and infection.[5] Other side effects may include high blood sugar, neurological problems, lymphoma, and anaphylaxis.[3] Common side effects when used as a cream include itchiness, headache, and red skin.[4] It is unclear if the cream is safe in pregnancy.[6] Tacrolimus is a calcineurin inhibitor.[2] It is believed to works by decreasing the activity of T cells.[3]

Tacrolimus was discovered in 1987, and approved for medical use in the United States in 1994.[5] It is available as a generic medication.[7] In the United Kingdom 50 tablets of 5 mg costs the NHS about 206 pounds in 2020.[2] In the United States this amount costs about 82 USD as of 2020 while 30 grams of 0.1% cream costs about 36 USD.[7][8] It was initially made from a soil sample in Japan that contained the bacterium Streptomyces tsukubaensis.[9]

References[edit]

  1. ^ a b "Tacrolimus Use During Pregnancy". Drugs.com. 3 October 2019. Retrieved 29 April 2020.
  2. ^ a b c d BNF 79 : March 2020. London: Royal Pharmaceutical Society. 2020. p. 868. ISBN 9780857113658.
  3. ^ a b c d "Tacrolimus Monograph for Professionals". Drugs.com. Retrieved 12 October 2020.
  4. ^ a b "Tacrolimus topical Monograph for Professionals". Drugs.com. Retrieved 12 October 2020.
  5. ^ a b "Tacrolimus Monograph for Professionals". Drugs.com. Retrieved 12 October 2020.
  6. ^ "Tacrolimus topical (Protopic) Use During Pregnancy". Drugs.com. Retrieved 12 October 2020.
  7. ^ a b "Tacrolimus Prices, Coupons & Savings Tips". GoodRx. Retrieved 12 October 2020.
  8. ^ "Tacrolimus Prices and Tacrolimus Coupons". GoodRx. Retrieved 12 October 2020.
  9. ^ Chakravarty, Dilip; Chakravarty, Dilip K.; Lee, W. C. (2010). Liver Transplantation. Boydell & Brewer Ltd. p. 169. ISBN 978-81-8448-770-1.
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