Chemistry of Steroids 4

Dr. Beck/Dr. Carvalho

beclomethsone dipropionate structure

budesonide structure

flunisolide structure

triamcinolone acetonide structure

ciclesonide structure

fluticasone propionate structure

mometasone furoate structure

fluticasone furoate structure

beclomethasone-17-monopropionate (17-BMP) structure

beclomethasone-21-monopropionate (21-BMP) structure

dexamethasone structure

triamcinolone hexacetonide structure

methylprednisolone sodium succinate structure

methylprednisolone acetate structure

Beclomethasone dipropionate brand names

Qnasl, Beconase AQ, QVAR

Beclomethasone dipropionate routes of admin

nasal (aerosol solution, nasal supp spray, respiratory aerosol solution)

Budesonide brand names

Pulmicort flexhaler, Rhinocort aqua, pulmicort, Ortikos, Tarpeyo, Uceris

Budesonide routes of admin

inhalation (powder, nebulizer suspension), nasal (susp spray), oral (capsule), rectal (foam)

Budesonide: Uceris

ER tablet and rectal foam formulations

both used for topical application to the intestines

Tx Ulcerative Colitis

Budesonide: Ortikos

DR capsule formulation

local action in the intestines on GRs

Tx Chron’s disease

Budesonide: Tarpeyo

local effects on the GR in mucosal B-cells in hte ileum that produce IGA

Tx IGA nephropathy

flunisolide brand names

aerospan

flunisolide routes of admin

inhaled (aerosol)

traimcinolone acetonide brand names

nasocort

triamcinolone acetonide routes of admin

nasal spray (solution)

ciclesonide brand names

Zetonna, omnaris, alvesco

ciclesonide routes of admin

nasal (aerosol solution, suspension spray, inhalation aerosol)

fluticasone propionate brand names

flovent, flovent HFA, flonase

fluticasone propionate routes of admin

inhalation (powder, pressurized suspension), nasal (spray)

mometasone furoate brand names

asmanex, propel, sinuva

mometasone furoate routes of admin

inhaled (powder), nasal (suspension for spray), sinus implant

fluticasone furoate brand names

flonase, sensimist, arnuity ellipta

fluticasone furoate routes of admin

nasal spray, inhalation (powder)

lipophilicity and potency

relative receptor affinity (RRA/potency) of intranasal glucocorticoids is directly proportional to lipophilicity

beclomethasone dipropionate metabolism

metabolized in vivo by hydrolysis into 21-BMP (inactive) and 17-BMP (active)

furoate-receptor interactions

furoate group fits into the lipophilic pocket on the GR which is lined with Met, Leu, Met, Met, Cys, Ile and forms Van der Waals interactions with the receptor

which 2 inhaled and intranasal steroids have the highest binding affinity?

fluticasone propionate and mometasone furoate

RRA of dexamethasone

100

RRA of fluticasone propionate

1775

RRA of fluticasone furoate

2989

what is a steroid shot?

aqueous microcrystalline suspension of ketals and esters containing a glucocorticoid

triamcinolone hexacetonide: injection

suspension for injection, branched esters slowly hydrolyze

triamcinolone acetonide: injection

suspension for injection, also comes in formulations for ocular injections and ER injectables

6alpha-methylprednisolone: injection

Depo-Medrol, suspension for injection (21-acetate)

Betamethasone acetate: injection

Celestone Soluspan (suspension for injection): betamethasone acetate and betamethasone sodium phosphate (for immediate antiinflammatory action)

water-soluble ester prodrugs of glucocorticoids

have a succinate or a phosphate off of the 21-OH group

lipid-soluble ester prodrugs of glucocorticoids

have an acetate or other group off of the 21-OH group

typically topicals (skin, nasal, inhaled, ophthalmic) or injectables

methylprednisolone sodium succinate: injection

water-soluble ester prodrug

Solu-medrol solution for injection

methylprednisolone acetate: injection

lipid-soluble ester prodrug

Depo-medrol solution for injection