Prednisone


Prednisone
Prednisone
Systematic (IUPAC) name
17,21-dihydroxypregna-1,4-diene-3,11,20-trione
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a601102
Pregnancy cat. C
Legal status Rx Only (US)
Routes Oral, Nasal, Rectal, Injection, IV
Pharmacokinetic data
Bioavailability 70%
Metabolism prednisolone (liver)
Half-life 1 hour
Excretion Renal
Identifiers
CAS number 53-03-2 YesY
ATC code A07EA03 H02AB07
PubChem CID 5865
DrugBank APRD00340
ChemSpider 5656 YesY
UNII 3EN3HG4WSW YesY
KEGG C07370 N
ChEBI CHEBI:8382 N
ChEMBL CHEMBL635 YesY
Synonyms Deltasone, Liquid Pred, Orasone, Adasone, Deltacortisone, Prednisonum
Chemical data
Formula C21H26O5 
Mol. mass 358.428 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Prednisone is a synthetic corticosteroid drug that is particularly effective as an immunosuppressant drug. It is used to treat certain inflammatory diseases and (at higher doses) some types of cancer, but has significant adverse effects. Because it suppresses the immune system, it leaves patients more susceptible to infections.

It is usually taken orally but can be delivered by intramuscular injection or intravenous injection. It has a mainly glucocorticoid effect. Prednisone is a prodrug that is converted by the liver into prednisolone, which is the active drug and also a steroid.

Contents

Medical uses

Prednisone is used for many different indications including: asthma, COPD, rheumatic disorders, allergic disorders, ulcerative colitis and Crohn’s disease, adrenocortical insufficiency, hypercalcemia due to cancer, thyroiditis, severe tuberculosis, lipid pneumonitis, multiple sclerosis, nephrotic syndrome, myasthenia gravis, and as part of a drug regimen to prevent rejection post organ transplant.[1]

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] Prednisone 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.

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. The mechanism for the delay of symptoms is unknown. Because it suppresses the adrenals, it is also sometimes used in the treatment of congenital adrenal hyperplasia. Prednisone is also used to treat sarcoidosis and lupus.

Side-effects

Micrograph of fatty liver, as may be seen due to long-term prednisone use. Trichrome stain.

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 (it is worth noting, however, that the mineralocorticoid effects of prednisone are very minor; this is why it is not used in the management of adrenal insufficiency, unless a more potent mineralocorticoid is administered concomitantly).

Additional short-term side-effects can include insomnia, euphoria and, rarely, mania (in particular, in those suffering from Bipolar disorders I and II).

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

Major

Minor

Dependency

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 Addisonian crisis. For those on chronic therapy, alternate-day dosing may preserve adrenal function and thereby reduce side-effects.[3]

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 very 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.

In industry

Prednisone 20 mg oral tablet

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

History

The first isolation and structure identifications of prednisone and prednisolone were done in 1950 by Arthur Nobile.[4][5][6] 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.[7] 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.[8]

The enhanced adrenocorticoid activity of these compounds over cortisone and hydrocortisone was demonstrated in mice.[9]

Prednisone and prednisolone were introduced in 1955 by Schering and Upjohn, under the brand names Meticorten and Delta-Cortef, respectively.[10] These prescription medicines are now available from a number of manufacturers as generic drugs.

References

  1. ^ "Prednisone". The American Society of Health-System Pharmacists. http://www.drugs.com/monograph/prednisone.html. Retrieved 3 April 2011. 
  2. ^ [U.S.] National Library of Medicine, Medical Subject Headings. Antineoplastic Agents, Hormonal (2009). Retrieved 9-11-2010
  3. ^ "Therapeutic and Adverse Effects of Glucocorticoids". Bello CS, Garrett SD. U.S. Pharmacist Continuing Education Program no. 430-000-99-028-H01, August 1999. http://www.uspharmacist.com/NewLook/CE/glucocort/lesson.htm. 
  4. ^ 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. http://www.worldcat.org/title/the-secret-of-success-arthur-nobiles-discovery-of-the-steroids-prednisone-and-prednisolone-in-the-1950s-revolutionised-the-treatment-of-arthritis/oclc/106716069&referer=brief_results. Retrieved 15 June 2011. 
  5. ^ "National Inventors Hall of Fame". http://www.invent.org/hall_of_fame/355.html. 
  6. ^ "New Jersey Inventors Hall of Fame". http://www.stevens.edu/njinvent/2000/inductees_2000/nobile.html. 
  7. ^ Merck Index, 14th Edition, p.1327. Published by Merck & Co. Inc.
  8. ^ H.L. Herzog et al. Science, Vol. 121, p 176 (1955).
  9. ^ H.L. Herzog et al. Science, Vol. 121, p 176 (1955).
  10. ^ http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm

External links


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Look at other dictionaries:

  • Prednisone — Général No CAS …   Wikipédia en Français

  • prednisone — ● prednisone nom féminin Médicament stéroïdien de synthèse dérivé de la cortisone et possédant un pouvoir anti inflammatoire plus élevé que celle ci, avec une toxicité moindre. ● prednisone (synonymes) nom féminin Médicament stéroïdien de… …   Encyclopédie Universelle

  • prednisone — (n.) 1955, probably from pregnadiene, from the stem of PREGNANCY (Cf. pregnancy), + ending from CORTISONE (Cf. cortisone) …   Etymology dictionary

  • prednisone — ☆ prednisone [pred′nə sōn΄ ] n. [< pre(gnane), a steroid hydrocarbon (< PREGNANT + ANE: found in urine during pregnancy) + D(I) + (E)N(E) + (CORT)ISONE] a chemical derivative, C21H26O5, of cortisone, but with fewer side effects, used in the …   English World dictionary

  • prednisone — A drug that is used to treat several types of cancer and other disorders. Prednisone also inhibits the body s immune response. It is a type of steroid …   English dictionary of cancer terms

  • prednisone — noun Etymology: probably from pregnane (C21H36) + diene (compound containing two double bonds) + cortisone Date: 1955 a glucocorticoid C21H26O5 that is a dehydrogenated analog of cortisone and is used as an anti inflammatory agent, as an… …   New Collegiate Dictionary

  • prednisone — (= 1,4 pregnadiene 17a, 21 diol 3,11,20 trione) Synthetic steroid that acts as a glucocorticoid, with powerful anti inflammatory and anti allergic activity …   Dictionary of molecular biology

  • prednisone — /pred neuh sohn , zohn /, n. Pharm. an analogue of cortisone, C21H26O5, used as an anti inflammatory, immunosuppressive, and antineoplastic in the treatment of various diseases. [1950 55; pre(gna)d(ie)n(e), a component of its chemical name +… …   Universalium

  • prednisone — noun A synthetic corticosteroid used to treat a large number of conditions …   Wiktionary

  • prednisone — A dehydrogenated analogue of cortisone with the same actions and uses; must be converted to prednisolone before active; inhibits proliferation of lymphocytes. * * * pred·ni·sone pred nə .sōnalso .zōn n a glucocorticoid C21H26O5 that is a… …   Medical dictionary


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