Prednisolone

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Prednisolone

Systematic (IUPAC) name

(11)-11,17,21-trihydroxypregna-1,4-diene-3,20-dione

Clinical data
AHFS/Drug monograph
s.com
MedlinePlu a682794
s
Licence

US FDA:link

data
Pregnancy
category

AU:

US: C

(Risk not ruled out)

Legal status
UK: Prescription-only (POM)

US: -only

Pharmacokinetic data
Biological

2-3 hours

half-life
Excretion

urine
Identifiers

CAS

50-24-8

Registry
Number
ATC code

A07EA01 C05AA04,D07AA03, H02AB06,R01AD02, S0

1BA04,S02BA03, S03BA02

PubChem

CID: 5755

IUPHAR/B 2866
PS
DrugBank

DB00860

ChemSpide 5552
r
UNII

9PHQ9Y1OLM

KEGG

D00472

ChEBI

CHEBI:8378

ChEMBL

CHEMBL131

Synonyms

11,17-dihydroxy-17- (2-hydroxyacetyl)- 10,13-dimethyl6,7,8,9,10,11,12,13,14,15,16,17- dodecahydrocyclopenta

[a]phenanthren-3-one

Chemical data
Formula

C21H28O5

Molecular

360.444 g/mol

mass
SMILES[show]

InChI[show]
(what is this?) (verify)

Prednisolone is a synthetic glucocorticoid, a derivative of cortisol, which is used to treat a

variety of inflammatory and auto-immuneconditions. It is the active metabolite of the
drug prednisone[1] and is used especially in patients with liver failure, as these individuals are
unable to metabolise prednisone into prednisolone.
Contents
[hide]

1 Uses

2 Mechanism of action

3 Adverse effects

4 Banned status in athletics

5 See also

6 References

Uses[edit]
Prednisolone is a corticosteroid drug with predominant glucocorticoid and
low mineralocorticoid activity, making it useful for the treatment of a wide range of
inflammatory and auto-immune conditions[2] such as asthma,[3] uveitis, pyoderma
gangrenosum,rheumatoid arthritis, ulcerative colitis, pericarditis, temporal
arteritis and Crohn's disease, Bell's palsy, multiple sclerosis,[4] cluster
headaches, vasculitis, acute lymphoblastic leukemia and autoimmune hepatitis,[5] systemic
lupus erythematosus, Kawasaki disease[6] and dermatomyositis. It is also used for treatment
of sarcoidosis, though the mechanism is unknown.
Prednisolone acetate ophthalmic suspension (eye drops) is an adrenocortical steroid
product, prepared as a sterile ophthalmic suspension and used to reduce swelling, redness,
itching, and allergic reactions affecting the eye.
Prednisolone can also be used as an immunosuppressive drug for organ transplants and in
cases of primary adrenal insufficiency (Addison's disease).
Corticosteroids inhibit the inflammatory response to a variety of inciting agents and, it is
presumed, delay or slow healing. They inhibit the edema, fibrin deposition, capillary dilation,
leukocyte migration, capillary proliferation, fibroblast proliferation, deposition ofcollagen, and
scar formation with inflammation.

Mechanism of action[edit]
Prednisolone irreversibly binds with glucocorticoid receptors (GR) alpha and beta for which
they have a high affinity. AlphaGR and BetaGR are found in virtually all tissues with variable
numbers between 3000 and 10000 per cell, depending on the tissue involved. Prednisolone

can activate and influence biochemical behaviour of most cells. The steroid/receptor
complexes dimerise and interact with cellular DNA in the nucleus, binding to steroidresponse elements and modifying gene transcription. They induce synthesis of some
proteins, and inhibit synthesis of others.[7][8]
Not all metabolic actions on genes are known. Most mediator proteins are enzymes, e.g.,
cAMP-dependent kinase
Anti-inflammatory and immunosuppressive actions:

Inhibition of gene transcription for COX-2, cytokines, cell

adhesion molecules, and inducible NO synthase

Blockage of Vitamin D3-mediated induction of osteocalcin

gene in osteoblasts

Modification of collegenase gene transcription

Increase synthesis annexin-1, important in negative

feedback on hypothalamus and anterior pituitary gland

Regulation of gene suppression leads to systemic suppression of inflammation and immune

response. This is of clinical usefulness but ultimately leads to gluconeogenesis, proteolysis
and lipolysis. Gene transcription returns to normal after cessation, but sudden stoppage can
cause Addison's disease. Osteoporosis is permanent.

Adverse effects[edit]
Possible side-effects include fluid retention of the face (moon face, Cushing's
syndrome), acne, constipation, and mood swings.
A lengthy course of prednisolone can cause bloody or black tarry stools from bleeding into
the stomach (this requires urgent medical attention); filling or rounding out of the face;
muscle cramps or pain; muscle weakness; nausea; pain in back, hips, ribs, arms, shoulders,
or legs; reddish-purple stretch marks on arms, face, legs, trunk, or groin; thin and shiny skin;
unusual bruising; urinating at night; rapid weight gain; and wounds that will not heal.
Prolonged use of prednisolone can lead to the development of osteoporosis which makes
bones more fragile and susceptible to fractures. One way to help alleviate this side effect is
through the use of calcium and vitamin D supplements.[9]
Swelling of the pancreas has also been reported.[10]
Prednisolone can cause increased blood sugar levels for diabetics.
Other effects include decreased or blurred vision, increased eye pressure, increased thirst,
cataract formation, confusion, rare cases of dementia in otherwise-healthy elderly patients,
and nervousness.
Loteprednol is an analog drug that has reduced adverse ocular effects.
Prednisolone may cause serious mental health problems, these affect around 5% who take
such steroids.[10] Symptoms include:

depression, including suicidal thoughts

feeling high (mania) or mood swings

anxiety

insomnia

difficulty in thinking / confusion

memory loss

visual, auditory or tactile hallucinations

having strange and frightening thoughts, changing

behaviour or having feelings of being alone

Nasal septum perforation and bowel perforation are also notable adverse effects that restrict
steroids' use in some pathologic conditions.[11][12]
Withdrawal from prednisolone can be problematic after taking large doses or over more than
two weeks.[13] This is caused by prednisolone inhibiting the natural production of
corticosteroids in the "Hypothalamic-Pituitary-Adrenal Axis" (HPAA) [13]

Banned status in athletics[edit]

As a glucocorticosteroid, unauthorized or ad-hoc use of prednisolone during competition via
oral, intravenous, intramuscular or rectal routes is banned under WADA anti-doping rules.
[14]
The drug may be used in competition with a TUE (Therapeutic Use Exemption), in
compliance with WADA regulations. Local or topical use of prednisolone during competition
as well as any use out of competition is not regulated.

See also[edit]

Methylprednisolone

Loteprednol

References[edit]
1.

Jump up^ Davis M, Williams R, Chakraborty J, et al. (June

1978). "Prednisone or prednisolone for the treatment of
chronic active hepatitis? A comparison of plasma
availability". British Journal of Clinical Pharmacology 5 (6):
5015. doi:10.1111/j.1365-2125.1978.tb01664.x.PMC 142935
8. PMID 656293.

2.

Jump up^ Czock D, Keller F, Rasche FM, Hussler U (2005).

"Pharmacokinetics and pharmacodynamics of systemically
administered glucocorticoids". Clin Pharmacokinet 44(1): 61
98. PMID 15634032.

3.

Jump up^ Fiel SB, Vincken W (Jun 2006). "Systemic

corticosteroid therapy for acute asthma exacerbations". J
Asthma 43 (5): 321
31. doi:10.1080/02770900600567163.PMID 16801135.

4.

Jump up^ Thrower BW (Jan 2009). "Relapse management in

multiple sclerosis". Neurologist 15 (1): 1
5. doi:10.1097/NRL.0b013e31817acf1a. PMID 19131851.

5.

Jump up^ Lambrou GI, Vlahopoulos S, Papathanasiou C,

Papanikolaou M, Karpusas M, Zoumakis E, TzortzatouStathopoulou F (2009). "Prednisolone exerts late mitogenic
and biphasic effects on resistant acute lymphoblastic
leukemia cells: Relation to early gene expression".Leuk
Res. 33 (12): 1684
95. doi:10.1016/j.leukres.2009.04.018. PMID 19450877.

6.

Jump up^ Miura M, Tamame T, Naganuma T, Chinen S,

Matsuoka M, Ohki H (2011). "Steroid pulse therapy for
Kawasaki disease unresponsive to additional immunoglobulin
therapy".Paediatrics & Child Health 16 (8): 479
84. PMC 3202387. PMID 23024586.

7.

Jump up^ Prednisolone. Australian Medicines Handbook

2010. Adelaide: Australian Medicines handbook Pty Ltd.;
2010. 497, 598.

8.

Jump up^ Rang HP, Dale MM, Ritter JM, Moore PK. The
pituitary and the adrenal Cortex. Hunter l, editor.
Pharmacology. 5th ed. London: Churchill Livingstone; 2003.
413, 415.

9.

Jump up^ "prednisolone, Pediapred Oral Liquid, Medrol

(cont.)".

10. ^ Jump up to:a b Drugs Information. "Prednisolone Tablets

1mg, 5mg (Actavis UK Ltd)". Retrieved13 December 2012.
11. Jump up^ "Bowel Perforation in Steroid-Treated Patients"
12. Jump up^ "Intranasal steroids and septum perforation--an
overlooked complication?"
13. ^ Jump up to:a b Kaminstein, David. "Steroid Withdrawal".
medicinenet. Retrieved 23 December2012.
14. Jump up^ "The 2011 Prohibited List".

[show]

Glucocorticoids and antiglucocorticoids (H02)

[show]

Antidiarrheals, intestinal anti-inflammatory and anti-infectiv

[show]

Vasoprotectives (C05)
[show]

Decongestants and other nasal preparations (R0

[show]

Drugs used for diseases of the ear (S02)

[show]

Glucocorticoid signaling
[show]

Mineralocorticoid signaling
Categories:

Glucocorticoids

Mineralocorticoids

Otologicals

World Health Organization essential medicines

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