Steroids - GIT Inflammation

What are steroids derived from in all animals?

• lanosterol

What do steroid molecules regulate in the body?

• sex hormones, inflammation, immunomodulation and stress and more

Where are steroids produced in the body?

• in adrenal glands

What kind of steroids are important in controlling inflammation?

• glucicorticosteroids (also called corticosteroids)

What is the steroid backbone structure?

• 4 organic rings (containing compounds with various functional groups)

• 3 rings are 6 membered while the end ring is 5 membered

• if the rings contain hydroxyls then known as sterols

What is a sterol?

• a steroid containing hydroxyl functional groups

What are characteristics of hydrocortisone (cortisol)?

• overall lipophilic

• not planar (due to sp3 hybridisation which is single bonds)

• not aromatic

• as many chiral centres

What is the main structural difference between hydrocortisone and beclometasone?

• beclomethasone contains 2 double bonds in the ring, while hydrocortisone only contains 1 double bond

• the extra double bond = more selectivity

• 

What functional group does budesonide contain?

What is budesonide primarily used for?

• isoprenaline group

• asthma and COPD

What is the Lipinski Rule of 5 (remember cant use in exam as reasoning, just a general rule of thumb)?

• for orally absorbed drugs and general characteristics

  • a MW <500

  • no more than 5 H bond donors

  • no more than 10 H bond acceptors

  • a logP <5

Why do you need to come off steroids gradually?

• so that adrenal glands can recover and go back to producing cortisol at normal levels 

• if dont come off gradually will experience withdrawal symptoms

Where are steroids absorbed?

How are steroids administered in IBS cases?

• either in the stomach or colon

• orally or rectally

What receptor do corticosteroids work at?

• glucocorticoid receptors

What is MW of hydrocortisone?

How many H bond donors and acceptors in hydrocortisone?

• MW = 362

• H bond donors = 3

• H bond acceptors = 5

What is MW of beclomethasone?

How many H bond donors and acceptors?

• MW = 408

• H bond donors = 3

• H bond acceptors = 5

What is the MW of budesonide?

How many H bond donors and acceptors?

• MW = 430

• H bond donors = 2

• H bond acceptors = 6

What is the range of logP of Glucocorticosteroids?

• 0.5 to 1.5

What drugs dont follow the Lipinski Rule of 5?

• metformin, ciclosporin