Oxprenolol: Difference between revisions

{{Short description|Non-selective beta blocker}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 418877799

| IUPAC_name = (''RS'')-1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol

| image = Oxprenolol.svg

| chirality = [[Racemic mixture]]

<!--Clinical data-->

| tradename =

| Drugs.com = {{drugs.com|CONS|oxprenolol}}

| pregnancy_AU = C

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = [[Oral administration|By mouth]]

<!--Pharmacokinetic data-->

| bioavailability = 20-70%

| metabolism = [[Liver]]

| elimination_half-life = 1-2hours

| excretion = [[Kidney]] <br />[[Mammary gland|Lactic]] (in lactiferous females)

<!--Identifiers-->

| IUPHAR_ligand = 7255

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 6452-71-7

| ATC_prefix = C07

| ATC_suffix = AA02

| PubChem = 4631

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB01580

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08318

<!--Chemical data-->

| C=15 | H=23 | N=1 | O=3

| SMILES = O(c1ccccc1OC\C=C)CC(O)CNC(C)C

'''Oxprenolol''' (brand names '''Trasacor''', '''Trasicor''', '''Coretal''', '''Laracor''', '''Slow-Pren''', '''Captol''', '''Corbeton''', '''Slow-Trasicor''', '''Tevacor''', '''Trasitensin''', '''Trasidex''') is a non-selective [[beta blocker]] with some intrinsic [[sympathomimetic amine|sympathomimetic]] activity. It is used for the treatment of [[angina pectoris]], abnormal [[heart]] rhythms and [[arterial hypertension|high blood pressure]].

Oxprenolol is a [[lipophilic]] beta blocker which passes the [[blood–brain barrier]] more easily than water-soluble beta blockers. As such, it is associated with a higher incidence of [[Central nervous system|CNS]]-related side effects than beta blockers with more hydrophilic molecules such as [[atenolol]], [[sotalol]] and [[nadolol]].<ref>{{cite journal | vauthors = McDevitt DG | title = Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs | journal = European Heart Journal | volume = 8 Suppl M | pages = 9–14 | date = December 1987 | pmid = 2897304 | doi = 10.1093/eurheartj/8.suppl_M.9 | series = 8 }}</ref>

Oxprenolol is a potent beta blocker and should not be administered to asthmatics under any circumstances due to their low beta levels as a result of depletion due to other asthma medication, and because it can cause irreversible, often fatal, airway failure and inflammation.<ref>{{cite journal | vauthors = Williams IP, Millard FJ | title = Severe asthma after inadvertent ingestion of oxprenolol | journal = Thorax | volume = 35 | issue = 2 | pages = 160 | date = February 1980 | pmid = 7376124 | pmc = 471246 | doi = 10.1136/thx.35.2.160 }}</ref>

==Pharmacology==

===Pharmacodynamics===

Oxprenolol is a [[beta blocker]]. In addition, it has been found to act as an [[receptor antagonist|antagonist]] of the [[serotonin]] [[5-HT1A receptor|5-HT_1A]] and [[5-HT1B receptor|5-HT_1B receptor]]s with respective K_i values of 94.2&nbsp;nM and 642&nbsp;nM in rat brain tissue.<ref name="pmid8093601">{{cite journal | vauthors = Langlois M, Brémont B, Rousselle D, Gaudy F | title = Structural analysis by the comparative molecular field analysis method of the affinity of beta-adrenoreceptor blocking agents for 5-HT1A and 5-HT1B receptors | journal = European Journal of Pharmacology | volume = 244 | issue = 1 | pages = 77–87 | date = January 1993 | pmid = 8093601 | doi = 10.1016/0922-4106(93)90061-d }}</ref>

==Chemistry==

===Stereochemistry===

Oxprenolol is a chiral compound, the beta blocker is used as a [[racemate]], e. g. a 1:1 mixture of (''R'')-(+)-oxprenolol and (''S'')-(–)-oxprenolol. Analytical methods ([[HPLC]]) for the separation and quantification of (''R'')-(+)-oxprenolol and (''S'')-(–)-oxprenolol in urine and in pharmaceutical formulations have been described in the literature.<ref name=Abounassif>{{cite journal | vauthors = Abounassif MA, Hefnawy MM, Mostafa GA | doi = 10.1007/s00706-011-0605-4 | title = Separation and quantitation of oxprenolol in urine and pharmaceutical formulations by HPLC using a Chiralpak IC and UV detection | year = 2011 | journal = Monatshefte für Chemie - Chemical Monthly | volume = 143 | issue = 3 | pages = 365–371| s2cid = 95959906 }}</ref>

:[[File:(±)-Oxoprenolol Structural Formulae V.2.svg|thumb|left|(''R'')-(+)-Oxprenolol (top) and (''S'')-(–)-oxprenolol]]{{clear-left}}

== References ==

{{Reflist|2}}

{{Beta blockers}}

{{Adrenergic receptor modulators}}

{{Serotonin receptor modulators}}

[[Category:5-HT1A antagonists]]

[[Category:5-HT1B antagonists]]

[[Category:Abandoned drugs]]

[[Category:Allyl compounds]]

[[Category:Beta blockers]]

[[Category:N-isopropyl-phenoxypropanolamines]]

[[Category:Sympathomimetic amines]]

[[Category:Catechol ethers]]