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07-SEPTEMBER-2008 03:17:44 - Dexamethasone Dexamethasone Systematic IUPAC name 8S,9R,10S,11S,13S,14S,16R,17R- 9-Fluoro-11,17-dihydroxy-17- 2-hydroxyacetyl-10,13,16-trimethyl- 6,7,8,11,12,14,15,16- octahydrocyclopentaaphenanthren- 3-one Identifiers CAS number 50-02-2 ATC code A01AC02 C05AA09, D07AB19, H02AB02, R01AD03, S01BA01, S02BA06, S03BA01 PubChem 5743 DrugBank APRD00674 Chemical data Formula C22H29FO5 Mol. mass 392.464 g/mol Pharmacokinetic data Bioavailability 80-90% Protein binding 70% Metabolism hepatic Half life 36-54 hours Excretion renal Therapeutic considerations Pregnancy cat. CUS Legal status â„ž Prescription only Routes Oral, IV, IM, SC and IO Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid hormones. It acts as an anti-inflammatory and immunosuppressant. Its potency is about 20-30 times that of hydrocortisone and 4-5 times of prednisone. Contents 1 Therapeutic use 1.1 Anti-inflammatory 1.2 Oncologic uses 1.3 Endocrine 1.4 Obstetrics 1.5 High altitude illnesses 2 Diagnostic use 3 Veterinary use 4 Contraindications 5 Side effects 6 Interactions 7 Dosage 8 Sports doping 9 References 10 External links Therapeutic use Anti-inflammatory Dexamethasone is used to treat many inflammatory and autoimmune conditions, e.g., rheumatoid arthritis. It is also given in small amounts usually 5-6 tablets before and/or after some forms of dental surgery, such as the extraction of the wisdom teeth, an operation which often leaves the patient with puffy, swollen cheeks. It is injected into the heel when treating plantar fasciitis, sometimes in conjunction with triamcinolone acetonide. It is useful to counteract allergic anaphylactic shock, if given in high doses. It is present in certain eye drops and as a nasal spray trade name Dexacort. Dexamethasone is used in transvenous screw-in cardiac pacing leads to minimize the inflammatory response of the myocardium. The steroid is released into the myocardium as soon as the screw is extended and can play a significant role in minimizing the acute pacing threshold due to the reduction of inflammatory response. The typical quantity present in a lead tip is less than 1.0 mg. Dexamethasone is often administered before antibiotics in cases of bacterial meningitis. It then acts to reduce the inflammatory response of the body to the bacteria killed by the antibiotics bacterial death releases pro-inflammatory mediators that can cause a response which is harmful to the patient, thus improving prognosis and outcome.1 Oncologic uses In oncology, it is given to cancer patients undergoing chemotherapy, to counteract certain side-effects of their antitumor treatment. Dexamethasone can augment the antiemetic effect of 5-HT3 receptor antagonists like ondansetron. Dexamethasone is also used in certain hematological malignancies, especially in the treatment of multiple myeloma, in which dexamethasone is given alone or together with thalidomide thal-dex or a combination of Adriamycin doxorubicin and vincristine VAD. In brain tumours primary or metastatic, dexamethasone is used to counteract the development of edema, which could eventually compress other brain structures. Dexamethasone is also given in cord compression where a tumor is compressing the spinal cord. Endocrine Dexamethasone can be used in the context of congenital adrenal hyperplasia, to prevent virilisation of a female fetus. If one or both parents are carriers of mutations to the CYP21A gene, the mother may start dexamethasone treatment within 7 weeks of conception. At the 12th week, a chorionic villus sample will determine whether the fetus is male in which case the dexamethasone is stopped or female. Subsequent DNA analysis can then reveal whether the female fetus is a carrier of the mutation, in which case dexamethasone treatment must continue until birth. The side-effects for the mother can be severe and the long-term impact on the child is not clear. Obstetrics Dexamethasone may be given to women at risk of delivering prematurely in order to promote maturation of the fetus' lungs. This has been associated with low birth weight, although not with increased rates of neonatal death.2 High altitude illnesses Dexamethasone is used in the treatment of high altitude cerebral edema as well as pulmonary edema. It is commonly carried on mountain climbing expions to help climbers deal with altitude sickness. 3 Diagnostic use Dexamethasone is also used in a diagnostic context, namely in its property to suppress the natural pituitary-adrenal axis. Patients presenting with clinical signs of glucocorticoid excess Cushing's syndrome are generally diagnosed by a 24-hour urine collection for cortisol or by a dexamethasone suppression test. During the latter, the response of the body to a high dose of glucocorticoids is monitored. Various forms are performed. In the most common form, a patient takes a nighttime dose of either 1 or 4 mg of dexamethasone, and the serum cortisol levels are measured in the morning. If the levels are relatively high over 5 µg/dl or 150 nmol/l, then the test is positive and the patient has an autonomous source of either cortisol or ACTH, indicating Cushing's syndrome where the tumor does not have a feedback mechanism. If ACTH levels are lowered by at least 50%, this would indicate Cushing's Disease, since the pituitary adenoma has a feedback mechanism that has been reset to a higher level of cortisol. Longer versions rely on urine collections on oral dexamethasone over various days. Veterinary use Combined with marbofloxacin and clotrimazole, dexamethasone is available under the name Aurizon , CAS number 115550-35-1, and used to treat difficult ear infections, especially in dogs. It can also be combined with Trichlormethiazide to treat horses with swelling of distal limbs and general bruising.4 Contraindications Some of these contraindications are relative: Existing gastrointestinal ulceration Cushing's syndrome Severe forms of heart insufficiency Severe hypertension Uncontrolled diabetes mellitus Systemic tuberculosis Severe systemic viral, bacterial, and fungal infections Preexisting wide angle glaucoma Osteoporosis Side effects If dexamethasone is given orally or by injection parenteral over a period of more than a few days, side-effects common to systemic glucocorticoids may occur. These may include: Stomach upset, increased sensitivity to stomach acid to the point of ulceration of esophagus, stomach, and duodenum Increased appetite leading to significant weight gain A latent diabetes mellitus often becomes manifest. Glucose intolerance is worsened in patients with preexisting diabetes. Immunsuppressant action, particularly if given together with other immunosuppressants such as ciclosporine. Bacterial, viral, and fungal disease may progress more easily and can become life-threatening. Fever as a warning symptom is often suppressed. Psychiatric disturbances, including personality changes, irritability, euphoria, mania Osteoporosis under long term treatment, pathologic fractures e.g., hip Muscle atrophy, negative protein balance catabolism Elevated liver enzymes, fatty liver degeneration usually reversible Cushingoid syndrome resembling hyperactive adrenal cortex with increase in adiposity, hypertension, bone demineralization, etc. Depression of the adrenal gland is usually seen, if more than 1.5 mg daily are given for more than three weeks to a month. Hypertension, fluid and sodium retention, edema, worsening of heart insufficiency due to mineral corticoid activity Dependence with withdrawal syndrome is frequently seen. Increased intraocular pressure, certain types of glaucoma, cataract serious clouding of eye lenses Dermatologic: Acne, allergic dermatitis, dry scaly skin, ecchymoses and petechiae, erythema, impaired wound-healing, increased sweating, rash, striae, suppression of reactions to skin tests, thin fragile skin, thinning scalp hair, urticaria. Allergic reactions though infrequently: Anaphylactoid reaction, anaphylaxis, angioedema. Highly unlikely, since dexamethasone is given to prevent anaphylactoid reactions. Other side-effects have been noted, and should cause concern if they are more than mild. The short time treatment for allergic reaction, shock, and diagnostic purposes usually does not cause serious side effects. Interactions NSAIDs and alcohol: increased risk of gastrointestinal ulceration Mineralocorticoids: increased risk of hypertension, edema and heart problems Oral antidiabetic drugs and insulin: antidiabetic therapy may have to be adjusted Other interactions with certain antibiotics, estrogens, ephedrine, digoxin are known. Dosage Shock: 4 to 8 mg intravenously initially, repeat if necessary to a total dose of 24 mg. Autoimmune diseases and inflammations: longterm therapy with 0.5 to 1.5 mg oral per day. Avoid more than 1.5 mg daily, because serious side effects are more frequently encountered with higher doses. Adjuvant to or part of chemotherapy: individual schedule Diagnostic purposes: special schedule Sports doping In 2005, Polish cross country skier Justyna Kowalczyk was disqualified from the Under 23 U23 OPA Alpine nations Intercontinential Competition in Germany and issued a 2-year suspension for her doping offenses on dexamethasone.5 This was eventually reduced to one year during 2005 and later rescinded by the Court of Arbitration for Sport in December 2005.6 She would later earn a bronze in the women's 30 km freestyle mass start at the 2006 Winter Olympics in Turin. References December 2007 ^ van de Beek D, de Gans J, McIntyre P, Prasad K 2007. Corticosteroids for acute bacterial meningitis. Cochrane Database Syst Rev 1: CD004405. doi:10.1002/14651858.CD004405.pub2. PMID 17253505. ^ Bloom SL, Sheffield JS, McIntire DD, Leveno KJ 2001. Antenatal dexamethasone and decreased birth weight. Obstet Gynecol 97 4: 485-90. doi:10.1016/S0029-78440001206-0. PMID 11275014. ^ COMMENTS AND RESPONSES Reducing the Incidence of High-Altitude Pulmonary Edema Annals of Internal Medicine PDF ^ Trichlormethiazide and Dexamethasone for veterinary use. Wedgewood Pharmacy. Retrieved on 2008-01-23. ^ June 13, 2005 FIS Doping Control statement on Kowalcyzk Digitized version. - Accessed July 30, 2006 ^ December 14, 2005 FIS Newsflash on her overturned suspension Digitized version. - Accessed July 30, 2006 External links Understanding Dexamethasone and Other Steroids v d e Corticosteroids - glucocorticoid/receptor and mineralocorticoid/receptor A07EA, C05AA, D07, D10AA, H02, R01AD, R03BA, S01BA, S02B, and S03B Endogenous in CAPS Mineralocorticoids ALDOSTERONE, Deoxycorticosterone, Fludrocortisone Glucocorticoids CORTISONE, HYDROCORTISONE/CORTISOL, DESOXYCORTONE, Beclometasone, Betamethasone, Budesonide, Ciclesonide, Cloprednol, Cortivazol, Deflazacort, Dexamethasone, Fluticasone, Flunisolide, Hydrocortisone aceponate, Hydrocortisone buteprate, Hydrocortisone butyrate, Meprednisone, Methylprednisolone, Methylprednisolone aceponate, Mometasone furoate, Paramethasone, Prednicarbate, Prednisolone, Prednisone, Prednylidene, Rimexolone, Triamcinolone Other/ungrouped corticosteroids Alclometasone, Amcinonide, Clobetasol, Clobetasone, Clocortolone, Desonide, Desoximetasone, Diflorasone, Diflucortolone, Difluprednate, Fluclorolone, Fludroxycortide, Flumetasone, Fluocinolone acetonide, Fluocinonide, Fluocortin, Fluocortolone, Fluorometholone, Fluperolone, Fluprednidene, Formocortal, Halcinonide, Halometasone, Loteprednol, Medrysone, Tixocortol, Ulobetasol Aldosterone antagonists Spironolactone, Eplerenone, Potassium canrenoate, Canrenone v d e Stomatological preparations A01 Caries prophylactic agents Sodium fluoride - Sodium monofluorophosphate - Olaflur - Stannous fluoride Anti-infectives and antiseptics Hydrogen peroxide - Chlorhexidine - Amphotericin B - Polynoxylin - Domiphen - Oxyquinoline - Neomycin - Miconazole - Natamycin - Hexetidine - Tetracycline - Benzoxonium chloride - Tibezonium iodide - Mepartricin - Metronidazole - Clotrimazole - Sodium perborate - Chlortetracycline - Doxycycline - Minocycline - Eugenol Corticosteroids Glucocorticoids Triamcinolone - Dexamethasone - Hydrocortisone Other Epinephrine/Adrenalone - Benzydamine - Acetylsalicylic acid - Amlexanox v d e Vasoprotectives C05 Antihemorrhoidals for topical use corticosteroids Hydrocortisone, Prednisolone, Betamethasone, Fluorometholone, Fluocortolone, Dexamethasone, Fluocinolone acetonide, Fluocinonide local anesthetics Lidocaine, Tetracaine, Benzocaine, Cinchocaine, Procaine, Oxetacaine, Pramocaine other Tribenoside Antivaricose therapy heparins or heparinoids for topical use Organo-heparinoid, Sodium apolate, Heparin, Pentosan polysulfate sclerosing agents for local injection Monoethanolamine oleate, Polidocanol, Invert sugar, Sodium tetradecyl sulfate, Phenol other Calcium dobesilate Capillary stabilising agents bioflavonoids Rutoside, Monoxerutin, Diosmin, Troxerutin, Hidrosmin - other Tribenoside v d e Corticosteroids for systemic use H02 Mineralocorticoids Aldosterone - Fludrocortisone - Desoxycortone Glucocorticoids Betamethasone - Dexamethasone - Fluocortolone - Methylprednisolone - Paramethasone - Prednisolone - Prednisone - Triamcinolone - Hydrocortisone - Cortisone - Prednylidene - Rimexolone - Deflazacort - Cloprednol - Meprednisone - Cortivazol Anticorticosteroids Trilostane v d e Decongestants and other nasal preparations R01 Topical Sympathomimetics, plain Cyclopentamine - Ephedrine - Phenylephrine - Oxymetazoline - Tetryzoline - Xylometazoline - Naphazoline - Tramazoline - Metizoline - Tuaminoheptane - Fenoxazoline - Tymazoline - Epinephrine Antiallergic agents, excluding corticosteroids Spaglumic acid histamine antagonists Levocabastine, Antazoline, Thonzylamine mast cell stabilizer some are also antihistamines Cromoglicic acid, Nedocromil, Azelastine, Olopatadine Corticosteroids Beclometasone - Prednisolone - Dexamethasone - Flunisolide - Budesonide - Betamethasone - Tixocortol - Fluticasone - Mometasone furoate - Triamcinolone - Ciclesonide Other nasal preparations Calcium hexamine thiocyanate - Retinol - Ipratropium bromide - Ritiometan - Mupirocin - Hexamidine - Framycetin Systemic use: Sympathomimetics Phenylpropanolamine - Pseudoephedrine - Phenylephrine v d e Otologicals S02 Anti-infectives Chloramphenicol - Nitrofural - Boric acid - Aluminium acetotartrate - Clioquinol - Hydrogen peroxide - Neomycin - Tetracycline - Chlorhexidine - Acetic acid - Polymyxin B - Rifamycin - Miconazole - Gentamicin Corticosteroids Hydrocortisone - Prednisolone - Dexamethasone - Betamethasone Other otologicals Lidocaine - Cocaine Retrieved from http://en..org/wiki/Dexamethasone Categories: Glucocorticoids | OrganofluoridesHidden category: Articles needing additional references from December 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français Italiano 日本語 ‪Norsk bokmÃ¥l‬ Polski Português РуÑ?Ñ?кий SlovenÅ¡Ä?ina Svenska This page was last modified on 13 August 2008, at 07:59
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