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Prednisone

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Subject: Chemotherapy regimen, Prednisolone, Corticosteroid, Dexamethasone, Deflazacort
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Prednisone

Prednisone
Systematic (IUPAC) name
17,21-dihydroxypregna-1,4-diene-3,11,20-trione
Clinical data
AHFS/Drugs.com
MedlinePlus
Pregnancy
category
  • C
Legal status
  • Rx Only (US)(AUS)
Routes of
administration
Oral, Nasal, Rectal, Injection, IV
Pharmacokinetic data
Bioavailability 70%
Metabolism prednisolone (liver)
Biological half-life 1 hour
Excretion Renal
Identifiers
CAS Registry Number  Y
ATC code A07 H02
PubChem CID:
IUPHAR/BPS
DrugBank  Y
ChemSpider  Y
UNII  N
KEGG  Y
ChEBI  Y
ChEMBL  Y
Synonyms Deltasone, Liquid Pred, Orasone, Adasone, Deltacortisone, Prednisonum
Chemical data
Formula C21H26O5
Molecular mass 358.428 g/mol
 N   
Micrograph of fatty liver, as may be seen due to long-term prednisone use. Trichrome stain.

Prednisone is a synthetic corticosteroid drug that is particularly effective as an immunosuppressant drug. It is used to treat certain inflammatory diseases (such as moderate allergic reactions) and (at higher doses) some types of cancer, but has significant adverse effects.

Contents

  • Medical uses 1
  • Side effects 2
    • Major 2.1
    • Minor 2.2
    • Dependency 2.3
    • Withdrawal 2.4
  • Pharmacology 3
  • Industry 4
  • History 5
  • Synthesis 6
  • See also 7
  • References 8
    • Further reading 8.1
  • External links 9

Medical uses

Prednisone is used for many different indications including:


  • Kelly, Janis (July 2000). "Prednisone-related growth impairment persists in children with CF". Respiratory Reviews 5 (7). 
  • National Inventors Hall of Fame induction of Arthur Nobile
  • U.S. National Library of Medicine: Drug Information Portal - Prednisone
  • The National Center for Biotechnology Information: Prednisone

External links

  • International Journal of Immunopharmacology, Vol. 7, Issue 5, 1985, pp 731–737

Further reading

  1. ^ "Prednisone". The American Society of Health-System Pharmacists. Retrieved 3 April 2011. 
  2. ^ [U.S.] National Library of Medicine, Medical Subject Headings. Antineoplastic Agents, Hormonal (2009). Retrieved 9-11-2010
  3. ^ RIEMER, AD (April 1958). "Application of the newer corticosteroids to augment diuresis in congestive heart failure.". The American journal of cardiology 1 (4): 488–96.  
  4. ^ NEWMAN, DA (15 February 1959). "Reversal of intractable cardiac edema with prednisone.". New York state journal of medicine 59 (4): 625–33.  
  5. ^ Zhang, H; Liu, C; Ji, Z; Liu, G; Zhao, Q; Ao, YG; Wang, L; Deng, B; Zhen, Y; Tian, L; Ji, L; Liu, K (September 2008). "Prednisone adding to usual care treatment for refractory decompensated congestive heart failure.". International heart journal 49 (5): 587–95.  
  6. ^ Liu, C; Liu, G; Zhou, C; Ji, Z; Zhen, Y; Liu, K (September 2007). "Potent diuretic effects of prednisone in heart failure patients with refractory diuretic resistance.". The Canadian journal of cardiology 23 (11): 865–8.  
  7. ^ Liu, C; Chen, H; Zhou, C; Ji, Z; Liu, G; Gao, Y; Tian, L; Yao, L; Zheng, Y; Zhao, Q; Liu, K (October 2006). "Potent potentiating diuretic effects of prednisone in congestive heart failure.". Journal of cardiovascular pharmacology 48 (4): 173–6.  
  8. ^ Massari, F; Mastropasqua, F; Iacoviello, M; Nuzzolese, V; Torres, D; Parrinello, G (March 2012). "The glucocorticoid in acute decompensated heart failure: Dr Jekyll or Mr Hyde?". The American journal of emergency medicine 30 (3): 517.e5–10.  
  9. ^ Liu, C; Chen, Y; Kang, Y; Ni, Z; Xiu, H; Guan, J; Liu, K (October 2011). "Glucocorticoids improve renal responsiveness to  
  10. ^ http://www.gihealth.com/html/education/drugs/prednisone.html gihealth.com
  11. ^ Prednisone Information from Drugs.com
  12. ^ Prednisone: MedlinePlus Drug Information
  13. ^ a b http://www.mayoclinic.com/health/steroids/HQ01431 Mayo Clinic
  14. ^ "Therapeutic and Adverse Effects of Glucocorticoids". Bello CS, Garrett SD. U.S. Pharmacist Continuing Education Program no. 430-000-99-028-H01, August 1999. 
  15. ^ http://www.medicinescomplete.com/mc/bnf/current/PHP4341-withdrawal-of-corticosteroids.htm
  16. ^ Medline drug information for prednisone
  17. ^ Wainwright, M. "The secret of success: Arthur Nobile's discovery of the steroids prednisone and prednisolone in the 1950s revolutionised the treatment of arthritis". Chemistry in Britain. Retrieved 15 June 2011. 
  18. ^ "National Inventors Hall of Fame". 
  19. ^ "New Jersey Inventors Hall of Fame". 
  20. ^ Merck Index, 14th Edition, p.1327. Published by Merck & Co. Inc.
  21. ^ H.L. Herzog et al. Science, Vol. 121, p 176 (1955).
  22. ^ H.L. Herzog et al Science, Vol. 121, p 176 (1955).
  23. ^ Drugs@FDA: FDA Approved Drug Products
  24. ^ U.S. Patent 3,134,718
  25. ^ Meystre, Ch. (1956). "Gewinnung von 1;4-Bisdehydro-3-oxo-steroiden. Uber Steroide, 139. Mitteilung". Helvetica Chimica Acta 39 (3): 734–742.  
  26. ^ DE 1135899 
  27. ^ Nobile, A.; Charney, W.; Perlman, P. L.; Herzog, H. L.; Payne, C. C.; Tully, M. E.; Jevnik, M. A.; Hershberg, E. B. (1955). "Microbiological Transformation of Steroids. I. Δ1,4-Diene-3-Ketosteroids". Journal of the American Chemical Society 77 (15): 4184.  

References

See also

[27][26][25][24] bond in 2-C1 Prednisone can be synthesized by dehydrogenation of the C

Prednisolone differs from prednisone in that the keto-group at C11 of prednisone is replaced by a hydroxyl group.

Synthesis

Prednisone and prednisolone were introduced in 1955 by Schering and Upjohn, under the brand names Meticorten and Delta-Cortef, respectively.[23] These prescription medicines are now available from a number of manufacturers as generic drugs.

The enhanced adrenocorticoid activity of these compounds over cortisone and hydrocortisone was demonstrated in mice.[22]

The first isolation and structure identifications of prednisone and prednisolone were done in 1950 by Arthur Nobile.[17][18][19] The first commercially feasible synthesis of prednisone was carried out in 1955 in the laboratories of Schering Corporation, which later became Schering-Plough Corporation, by Arthur Nobile and coworkers.[20] They discovered that cortisone could be microbiologically oxidized to prednisone by the bacterium Corynebacterium simplex. The same process was used to prepare prednisolone from hydrocortisone.[21]

History

The pharmaceutical industry uses prednisone tablets for the calibration of dissolution testing equipment according to the United States Pharmacopeia (USP).

Prednisone 20 mg oral tablet

Industry

Prednisone has no substantial biological effects until converted via hepatic metabolism to prednisolone.[16]

Pharmacology

The magnitude and speed of dose reduction in corticosteroid withdrawal should be determined on a case-by-case basis, taking into consideration the underlying condition being treated, and individual patient factors such as the likelihood of relapse and the duration of corticosteroid treatment. Gradual withdrawal of systemic corticosteroids should be considered in those whose disease is unlikely to relapse and have:
· received more than 40 mg prednisolone (or equivalent) daily for more than 1 week
· been given repeat doses in the evening;
· received more than 3 weeks' treatment
· recently received repeated courses (particularly if taken for longer than 3 weeks)
· taken a short course within 1 year of stopping long-term therapy
· other possible causes of adrenal suppression
Systemic corticosteroids may be stopped abruptly in those whose disease is unlikely to relapse and who have received treatment for 3 weeks or less and who are not included in the patient groups described above.
During corticosteroid withdrawal, the dose may be reduced rapidly down to physiological doses (equivalent to prednisolone 7.5 mg daily) and then reduced more slowly. Assessment of the disease may be needed during withdrawal to ensure that relapse does not occur.[15]

Withdrawal

Glucocorticoids act to inhibit feedback of both the hypothalamus, decreasing corticotropin-releasing hormone [CRH], and corticotrophs in the anterior pituitary gland, decreasing the amount of adrenocorticotropic hormone [ACTH]. For this reason, glucocorticoid analogue drugs such as prednisone down-regulate the natural synthesis of glucocorticoids. This mechanism leads to dependence in a short time and can be dangerous if medications are withdrawn too quickly. The body must have time to begin synthesis of CRH and ACTH and for the adrenal glands to begin functioning normally again.

Adrenal suppression will begin to occur if prednisone is taken for longer than seven days. Eventually, this may cause the body to temporarily lose the ability to manufacture natural corticosteroids (especially cortisol), which results in dependence on prednisone. For this reason, prednisone should not be abruptly stopped if taken for more than seven days; instead, the dosage should be gradually reduced. This weaning process may be over a few days, if the course of prednisone was short, but may take weeks or months if the patient had been on long-term treatment. Abrupt withdrawal may lead to an Addison crisis. For those on chronic therapy, alternate-day dosing may preserve adrenal function and thereby reduce side effects.[14]

Dependency

[13]

Minor

[13]

Major

Long-term side effects include Cushing's syndrome, steroid dementia syndrome, truncal weight gain, osteoporosis, glaucoma and cataracts, type II diabetes mellitus, and depression upon dose reduction or cessation.

It can also cause depression or depressive symptoms and anxiety in some individuals.[11][12]

Short-term side effects, as with all glucocorticoids, include high blood glucose levels (especially in patients with diabetes mellitus or on other medications that increase blood glucose, such as tacrolimus) and mineralocorticoid effects such as fluid retention.[10] The mineralocorticoid effects of prednisone are minor, which is why it is not used in the management of adrenal insufficiency, unless a more potent mineralocorticoid is administered concomitantly.

Side effects

Prednisone can also be used in the treatment of decompensated heart failure to potentiate renal responsiveness to diuretics, especially in heart failure patients with refractory diuretic resistance with large dose of loop diuretics.[3][4][5][6][7][8] The mechanism is prednisone, as a glucocorticoid, can improve renal responsiveness to atrial natriuretic peptide by increasing the density of natriuretic peptide receptor type A in the renal inner medullary collecting duct, inducing a potent diuresis.[9]

Prednisone is also used for the treatment of the Herxheimer reaction, which is common during the treatment of syphilis, and to delay the onset of symptoms of Duchenne muscular dystrophy and also for uveitis. The mechanism for the delay of symptoms is unknown. Because it suppresses the adrenal glands, it is also sometimes used in the treatment of congenital adrenal hyperplasia. Prednisone is also used to treat sarcoidosis.

Prednisone has also been used in the treatment of migraine headaches and cluster headaches and for severe aphthous ulcer. Prednisone is used as an antitumor drug.[2] It is important in the treatment of acute lymphoblastic leukemia, non-Hodgkin lymphomas, Hodgkin's lymphoma, multiple myeloma, and other hormone-sensitive tumors, in combination with other anticancer drugs.

[1]

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