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Dexamethasone

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Dexamethasone
Skeletal formula of dexamethasone
Ball-and-stick model of the dexamethasone molecule
Clinical data
Trade namesDextenza, Ozurdex, others
AHFS/Drugs.comMonograph
MedlinePlusa682792
License data
Pregnancy
category
  • AU: A(oral); C (parenteral)[1]
Routes of
administration		By mouth, intravenous therapy (IV), intramuscular injection (IM), subcutaneous injection (IM), intraosseous (IO), eye drop
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability80–90%
Protein binding77%
MetabolismLiver
Elimination half-life190 minutes (3.2 hours)
ExcretionUrine (65%)
Identifiers
  • (8S,9R,10S,11S,13S,14S,16R,17R)-9-Fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.004 Edit this at Wikidata
Chemical and physical data
FormulaC22H29FO5
Molar mass392.461 g·mol−1
3D model (JSmol)
Melting point262 °C (504 °F)
  • O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]1(C(=CC(=O)C=C1)CC[C@H]4[C@@H]2C[C@H]3C)C)C
  • InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1 checkY
  • Key:UREBDLICKHMUKA-CXSFZGCWSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Dexamethasone is a type of corticosteroid medication.[2] It is used in the treatment of many conditions, including rheumatic problems, a number of skin diseases, severe allergies, asthma, chronic obstructive lung disease, croup, brain swelling, eye pain following eye surgery, and along with antibiotics in tuberculosis.[2] In adrenocortical insufficiency, it should be used together with a medication that has greater mineralocorticoid effects such as fludrocortisone.[2] In preterm labor, it may be used to improve outcomes in the baby.[2] It may be taken by mouth, as an injection into a muscle, or intravenously.[2] The effects of dexamethasone are frequently seen within a day and last for about three days.[2]

The long-term use of dexamethasone may result in thrush, bone loss, cataracts, easy bruising, or muscle weakness.[2] It is pregnancy category C in the United States meaning use should be based on benefits being predicted to be greater than risks.[1] In Australia, the oral use is category A, meaning it has been frequently used in pregnancy and not been found to cause problems to the baby.[3] It should not be taken when breastfeeding.[2] Dexamethasone has anti-inflammatory and immunosuppressant effects.[2]

Dexamethasone was first made in 1957 by Philip Showalter Hench and was approved for medical use in 1961.[4][5][6] It is on the World Health Organization's List of Essential Medicines.[7] In 2017, it was the 321st most commonly prescribed medication in the United States, with more than one million prescriptions.[8]

Medical uses

Dexamethasone phosphate injection vials

Anti-inflammatory

Dexamethasone is used to treat many inflammatory and autoimmune conditions, such as rheumatoid arthritis and bronchospasm.[9] Idiopathic thrombocytopenic purpura, a decrease in numbers of platelets due to an immune problem, responds to 40 mg daily for four days; it may be administered in 14-day cycles. It is unclear whether dexamethasone in this condition is significantly better than other glucocorticoids.[10]

It is also given in small amounts[11] 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.

Dexamethasone is commonly given as a treatment for croup in children, as a single dose can reduce the swelling of the airway to improve breathing and reduce discomfort.[12]

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 – particularly after eye surgery – and as a nasal spray, and certain ear drops (can be combined with an antibiotic and an antifungal). Dexamethasone intravitreal steroid implants have been approved by the FDA to treat ocular conditions such as diabetic macular edema, central retinal vein occlusion, and uveitis.[13] Dexamethasone has also been used with antibiotics to treat acute endophthalmitis.[14]

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 may be administered before antibiotics in cases of bacterial meningitis. It acts to reduce the inflammatory response of the body to the bacteria killed by the antibiotics (bacterial death releases proinflammatory mediators that can cause a response which is harmful), thus reducing hearing loss and neurological damage.[15]

A single vial of dexamethasone phosphate for injection

Cancer

People with cancer undergoing chemotherapy are often given dexamethasone to counteract certain side effects of their antitumor treatments. Dexamethasone can increase the antiemetic effect of 5-HT3 receptor antagonists, such as ondansetron.[16] The exact mechanism of this interaction is not well-defined, but it has been theorized that this effect may be due to, among many other causes, inhibition of prostaglandin synthesis, anti-inflammatory effects, immunosuppressive effects, decreased release of endogenous opioids, or a combination of the aforementioned.[17]

In brain tumors (primary or metastatic), dexamethasone is used to counteract the development of edema, which could eventually compress other brain structures. It is also given in cord compression, where a tumor is compressing the spinal cord.

Dexamethasone is also used as a direct chemotherapeutic agent in certain haematological malignancies, especially in the treatment of multiple myeloma, in which dexamethasone is given alone or in combination with other chemotherapeutic drugs, including most commonly with thalidomide (Thal-dex), lenalidomide, bortezomib (Velcade, Vel-dex),[18] or a combination of doxorubicin (Adriamycin) and vincristine or bortezomib/lenalidomide/dexamethasone.

Endocrine

Dexamethasone is the treatment for the very rare disorder of glucocorticoid resistance.[19][20]

In adrenal insufficiency and Addison's disease, dexamethasone is prescribed when the patient does not respond well to prednisone or methylprednisolone.

It can be used in congenital adrenal hyperplasia in older adolescents and adults to suppress ACTH production. It is typically given at night.[21]

Pregnancy

Dexamethasone may be given to women at risk of delivering prematurely to promote maturation of the fetus' lungs. This administration, given from day to one week before delivery, has been associated with low birth weight, although not with increased rates of neonatal death.[22]

Dexamethasone has also been used during pregnancy as an off-label prenatal treatment for the symptoms of congenital adrenal hyperplasia (CAH) in female babies. CAH causes a variety of physical abnormalities, notably ambiguous genitalia. Early prenatal CAH treatment has been shown to reduce some CAH symptoms, but it does not treat the underlying congenital disorder. This use is controversial: it is inadequately studied, only around one in ten of the foetuses of women treated are at risk of the condition, and serious adverse events have been documented.[23] Experimental use of dexamethasone in pregnancy for foetal CAH treatment was discontinued in Sweden when one in five cases suffered adverse events.[24]

A small clinical trial found long-term effects on verbal working memory among the small group of children treated prenatally, but the small number of test subjects means the study cannot be considered definitive.[25][26]

High-altitude illnesses

Dexamethasone is used in the treatment of high-altitude cerebral edema (HACE), as well as high-altitude pulmonary edema (HAPE). It is commonly carried on mountain-climbing expeditions to help climbers deal with complications of altitude sickness.[27][28]

Nausea and vomiting

Intravenous dexamethasone is effective for prevention of nausea and vomiting in people who had surgery and whose post-operative pain was treated with long-acting spinal or epidural spinal opioids.[29]

The combination of dexamethasone and a 5-HT3 receptor antagonist such as ondansetron is more effective than a 5-HT3 receptor antagonist alone in preventing postoperative nausea and vomiting.[30]

Dexamethasone, when used as an anti emetic during surgery, does not appear to increase rates of wound infection and it is unclear if it has an effect on wound healing.[31]

Sore throat

A single dose of dexamethasone or another steroid speeds improvement of a sore throat.[32]

Contraindications

Contraindications of dexamethasone include,[33][34] but are not limited to:

Adverse effects

The exact incidence of the adverse effects of dexamethasone are not available, hence estimates have been made as to the incidence of the adverse effects below based on the adverse effects of related corticosteroids and on available documentation on dexamethasone.[34][35][36][37][38]

Common

  • Acne
  • Insomnia
  • Vertigo
  • Increased appetite
  • Weight gain
  • Impaired skin healing
  • Depression
  • Euphoria
  • Hypertension
  • Increased risk of infection
  • Raised intraocular pressure
  • Vomiting
  • Dyspepsia
  • Confusion
  • Amnesia
  • Irritability
  • Nausea
  • Malaise
  • Headaches
  • Cataract (in cases of long-term treatment it occurs in about 10% of patients)

Unknown frequency

Withdrawal

Sudden withdrawal after long-term treatment with corticosteroids can lead to:[34]

Interactions

Known drug interactions include:[34]

Pharmacology

As a glucocorticoid, dexamethasone is an agonist of the glucocorticoid receptor (GR). It has no mineralocorticoid activity.[39][40]

Chemistry

Dexamethasone is a synthetic pregnane corticosteroid and derivative of cortisol (hydrocortisone) and is also known as 1-dehydro-9α-fluoro-16α-methylhydrocortisone or as 9α-fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione.[41][42]

Synthesis

To synthesize dexamethasone, 16β-methylprednisolone acetate is dehydrated to the 9,11-dehydro derivative.[43][44] This is then reacted with a source of hypobromite, such as basic N-bromosuccinimide, to form the 9α-bromo-11β-hydrin derivative, which is then ring-closed to an epoxide. A ring-opening reaction with hydrogen fluoride in tetrahydrofuran gives dexamethasone.

Dexamethasone synthesis

History

Dexamethasone was first synthesized by Philip Showalter Hench in 1957.[45][5] It was introduced for medical use in 1958.[40]


Society and culture

Price

Dexamethasone is inexpensive.[46] In the United States a month of medication is typically priced less than US$25.[2] In India, a course of treatment for preterm labor is about US$0.50.[46] The drug is available in most areas of the world.[46]

Route

It may be taken by mouth, as a tablet or elixir, as an injection into a muscle, intravenously, or via an eye drop.[2]

Nonmedical use

Dexamethasone is given in legal Bangladesh brothels to prostitutes not yet of legal age, causing weight gain aimed at making them appear older and healthier to customers and police.[47]

Dexamethasone and most glucocorticoids are banned by sporting bodies including the World Anti-Doping Agency.[48]

Research

COVID-19

See also: COVID-19_drug_repurposing_research § Dexamethasone

In June 2020, the RECOVERY Trial announced preliminary results stating that dexamethasone improves survival rates of hospitalized patients with COVID-19 receiving oxygen or on a ventilator, although benefits were only observed in patients requiring respiratory support.[49] Several experts have called for the full dataset to be published quickly to allow wider analysis of the results.[50][51] The World Health Organization (WHO) states that dexamethasone should be reserved for seriously ill and critical patients receiving COVID-19 treatment in a hospital setting.[52]

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.[53]

See also

References

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