Fludrocortisone Explained

Fludrocortisone, sold under the brand name Florinef, among others, is a corticosteroid used to treat adrenogenital syndrome, postural hypotension, and adrenal insufficiency.[1] [2] In adrenal insufficiency, it is generally taken together with hydrocortisone. Fludrocortisone is taken by mouth[3] and is most commonly used in its acetate form.[4]

Common side effects of fludrocortisone include high blood pressure, swelling, heart failure, and low blood potassium.[3] Other serious side effects can include low immune-system function, cataracts, muscle weakness, and mood changes.[3] Whether use of fludrocortisone during pregnancy is safe for the fetus is unknown.[5] Fludrocortisone is mostly a mineralocorticoid, but it also has glucocorticoid effects.[3]

Fludrocortisone was patented in 1953.[6] It is on the World Health Organization's List of Essential Medicines.[7]

Medical uses

Fludrocortisone has been used in the treatment of cerebral salt-wasting syndrome.[8] It is used primarily to replace the missing hormone aldosterone in various forms of adrenal insufficiency such as Addison's disease and the classic salt-wasting (21-hydroxylase deficiency) form of congenital adrenal hyperplasia. Due to its effects on increasing Na+ levels, and therefore blood volume, fludrocortisone is the first-line of treatment for orthostatic intolerance, and postural orthostatic tachycardia syndrome (POTS).[9] It can be used to treat low blood pressure.[10]

Fludrocortisone is also a confirmation test for diagnosing Conn's syndrome (aldosterone-producing adrenal adenoma), the fludrocortisone suppression test. Loading the patient with fludrocortisone would suppress serum aldosterone level in a normal patient, whereas the level would remain elevated in a Conn's patient. The fludrocortisone suppression test is an alternative to the NaCl challenge (which would use normal saline or salt tablets).

Side effects

Use of fludrocortisone can lead to one or more of the following side effects:[11]

Pharmacology

Fludrocortisone is a corticosteroid and acts as a powerful mineralocorticoid, along with some additional but comparatively very weak glucocorticoid activity.[12] Relative to cortisol, it is said to have 10 times the glucocorticoid potency but 250 to 800 times the mineralocorticoid potency. Fludrocortisone acetate is a prodrug of fludrocortisone, which is the active form of the drug.[13]

Plasma renin, sodium, and potassium are checked through blood tests to verify that the correct dosage is reached.

Chemistry

Fludrocortisone, also known as 9α-fluorocortisol (9α-fluorohydrocortisone) or as 9α-fluoro-11β,17α,21-trihydroxypregn-4-ene-3,20-dione, is a synthetic pregnane steroid and a halogenated derivative of cortisol (11β,17α,21-trihydroxypregn-4-ene-3,20-dione). Specifically, it is a modification of cortisol with a fluorine atom substituted in place of one hydrogen atom at the C9α position. Fluorine is a good bioisostere for hydrogen because it is similar in size, with the major difference being in its electronegativity. The acetate form of fludrocortisone, fludrocortisone acetate, is the C21 acetate ester of fludrocortisone, and is hydrolyzed into fludrocortisone in the body.

History

Fludrocortisone was described in the literature in 1953[14] and was introduced for medical use (as the acetate ester) in 1954.[15] [16] It was the first synthetic corticosteroid to be marketed, and followed the introduction of cortisone in 1948 and hydrocortisone (cortisol) in 1951.[17] Fludrocortisone was also the first fluorine-containing pharmaceutical drug to be marketed.[18]

Society and culture

Generic name

Fludrocortisone is the generic name of fludrocortisone and its,,,, and, whereas fludrocortisone acetate is the generic name of fludrocortisone acetate and its, and .[19]

Brand names

Fludrocortisone is marketed mainly under the brand names Astonin and Astonin-H, whereas the more widely used fludrocortisone acetate is sold mainly as Florinef, but also under several other brand names including Cortineff, Florinefe, and Fludrocortison.

Availability

Fludrocortisone is marketed in Austria, Croatia, Denmark, Germany, Luxembourg, Romania, and Spain, whereas fludrocortisone acetate is more widely available throughout the world and is marketed in the United States, Canada, the United Kingdom, various other European countries, Australia, Japan, China, Brazil, and many other countries.

External links

Notes and References

  1. Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 558–. live. https://web.archive.org/web/20171105200659/https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA558. 5 November 2017.
  2. Book: Index Nominum 2000: International Drug Directory. 2000. Taylor & Francis. 978-3-88763-075-1. 450–. live. https://web.archive.org/web/20171105200659/https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA450. 2017-11-05.
  3. Web site: Fludrocortisone Acetate. The American Society of Health-System Pharmacists. 8 December 2016. live. https://web.archive.org/web/20170705084019/https://www.drugs.com/monograph/fludrocortisone-acetate.html. 5 July 2017.
  4. Book: Medicinal Chemistry of the Disease Modifying Antirheumatic Drugs . Day RO, Furst DE, van Riel PL, Bresnihan B . Antirheumatic Therapy: Actions and Outcomes. https://books.google.com/books?id=OqKTuL9ePhsC&pg=PA21. 30 May 2010. Springer Science & Business Media. 978-3-7643-7726-7. 21–. live. https://web.archive.org/web/20171105200659/https://books.google.com/books?id=OqKTuL9ePhsC&pg=PA21. 5 November 2017.
  5. Web site: Fludrocortisone Use During Pregnancy . Drugs.com . 24 December 2016. live. https://web.archive.org/web/20161224235323/https://www.drugs.com/pregnancy/fludrocortisone.html. 24 December 2016.
  6. Book: Fischer J, Ganellin CR . Analogue-based Drug Discovery. 2006. John Wiley & Sons. 9783527607495. 484. en. live. https://web.archive.org/web/20171105200659/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA484. 2017-11-05.
  7. Book: ((World Health Organization)) . World Health Organization model list of essential medicines: 21st list 2019 . 2019 . 10665/325771 . World Health Organization . World Health Organization . Geneva . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO . free .
  8. Taplin CE, Cowell CT, Silink M, Ambler GR . Fludrocortisone therapy in cerebral salt wasting . Pediatrics . 118 . 6 . e1904–e1908 . December 2006 . 17101713 . 10.1542/peds.2006-0702 . 28871495 .
  9. Freitas J, Santos R, Azevedo E, Costa O, Carvalho M, de Freitas AF . Clinical improvement in patients with orthostatic intolerance after treatment with bisoprolol and fludrocortisone . Clinical Autonomic Research . 10 . 5 . 293–299 . October 2000 . 11198485 . 10.1007/BF02281112 . 20843222 .
  10. Veazie S, Peterson K, Ansari Y, Chung KA, Gibbons CH, Raj SR, Helfand M . Fludrocortisone for orthostatic hypotension . The Cochrane Database of Systematic Reviews . 2021 . 5 . CD012868 . May 2021 . 10.1002/14651858.CD012868.pub2 . 34000076 . 8128337 .
  11. Web site: Fludrocortisone Oral: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD . 2023-09-05 . www.webmd.com . en.
  12. Book: De Groot LJ, Chrousos G, Dungan K, Feingold KR, Grossman A, Hershman JM, Koch C, Korbonits M, McLachlan R, New M, Purnell J, Rebar R, Singer F, Vinik A, Chrousos, Pavlaki AN, Magiakou MA . 6 . Glucocorticoid Therapy and Adrenal Suppression . https://www.ncbi.nlm.nih.gov/books/NBK279156/ . 2000 . 25905379 . Feingold KR, Anawalt B, Blackman MR, Boyce A, Chrousos G, Corpas E, de Herder WW, Dhatariya K, Dungan K, Hofland J, Kalra S, Kaltsas G, Kapoor N, Koch C, Kopp P, Korbonits M, Kovacs CS, Kuohung W, Laferrère B, Levy M, McGee EA, McLachlan R, New M, Purnell J, Sahay R, Shah AS, Singer F, Sperling MA, Stratakis CA, Trence DL, Wilson DP . 6 . Endotext [Internet]. . South Dartmouth (MA) . MDText.com, Inc. .
  13. Polito A, Hamitouche N, Ribot M, Polito A, Laviolle B, Bellissant E, Annane D, Alvarez JC . 6 . Pharmacokinetics of oral fludrocortisone in septic shock . British Journal of Clinical Pharmacology . 82 . 6 . 1509–1516 . December 2016 . 27416887 . 5099539 . 10.1111/bcp.13065 .
  14. Calvert DN . Anti-inflammatory steroids . Wisconsin Medical Journal . 61 . 403–404 . August 1962 . 13875857 .
  15. Book: Lemke TL, Williams DA . Foye's Principles of Medicinal Chemistry. 2008. Lippincott Williams & Wilkins. 978-0-7817-6879-5. 890–. live. https://web.archive.org/web/20171105200659/https://books.google.com/books?id=R0W1ErpsQpkC&pg=PA890. 2017-11-05.
  16. Book: William Andrew Publishing. Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. 22 October 2013. Elsevier. 978-0-8155-1856-3. 1642–. live. https://web.archive.org/web/20171105200659/https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1642. 5 November 2017.
  17. Khan MO, Park KK, Lee HJ . Antedrugs: an approach to safer drugs . Current Medicinal Chemistry . 12 . 19 . 2227–2239 . 2005 . 16178782 . 10.2174/0929867054864840 .
  18. Walker MC, Chang MC . Natural and engineered biosynthesis of fluorinated natural products . Chemical Society Reviews . 43 . 18 . 6527–6536 . September 2014 . 24776946 . 10.1039/c4cs00027g . 205904152 .
  19. Web site: Fludrocortisone Uses, Side Effects & Warnings . 2017-07-16 . live . https://web.archive.org/web/20150513235052/http://www.drugs.com/international/fludrocortisone.html . 2015-05-13 .

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