Oxprenolol: Difference between revisions

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{{drugbox |
{{Drugbox
|IUPAC_name = 1-propan-2-ylamino-3-(2<br>-prop-2-enoxyphenoxy)-propan-2-ol
| Verifiedfields = changed
|image=oxprenolol.png
| Watchedfields = changed
|CAS_number = 6452-71-7
| verifiedrevid = 418877799
| ATC_prefix=C07
| IUPAC_name = (''RS'')-1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol
| ATC_suffix=AA02
| image = Oxprenolol.png
| PubChem=4631
| width = 200px
| DrugBank=
| imagename = 1 : 1 mixture (racemate)
| C=15 | H=23 | N=1 | O=3
| drug_name = Oxprenolol
|molecular_weight = 265.348
 
|bioavailability = 20-70%
<!--Clinical data-->
|metabolism = [[Liver|Hepatic]]
| tradename =
|elimination_half-life = 1-2hours
| Drugs.com = {{drugs.com|CONS|oxprenolol}}
|excretion = [[Kidney|Renal]] <br> [[Mammary gland|Lactic]] (In lactiferous females)
| pregnancy_AU = C
|pregnancy_AU = C  
| pregnancy_US =
|pregnancy_US =  
| pregnancy_category =
|pregnancy_category =  
| legal_status = Rx-only
|legal_status = Rx-only
| routes_of_administration = oral
|routes_of_administration = oral
 
<!--Pharmacokinetic data-->
| bioavailability = 20-70%
| metabolism = [[Liver|Hepatic]]
| elimination_half-life = 1-2hours
| excretion = [[Kidney|Renal]] <br>[[Mammary gland|Lactic]] (In lactiferous females)
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| 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
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4470
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 519MXN9YZR
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08318
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 546
 
<!--Chemical data-->
| C=15 | H=23 | N=1 | O=3
| molecular_weight = 265.348
| smiles = O(c1ccccc1OC\C=C)CC(O)CNC(C)C
| InChI = 1/C15H23NO3/c1-4-9-18-14-7-5-6-8-15(14)19-11-13(17)10-16-12(2)3/h4-8,12-13,16-17H,1,9-11H2,2-3H3
| InChIKey = CEMAWMOMDPGJMB-UHFFFAOYAX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C15H23NO3/c1-4-9-18-14-7-5-6-8-15(14)19-11-13(17)10-16-12(2)3/h4-8,12-13,16-17H,1,9-11H2,2-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CEMAWMOMDPGJMB-UHFFFAOYSA-N
}}
}}
{{CMG}}


{{CMG}}{{AE}}{{SS}}


'''Oxprenolol''' ('''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]].


==Overview==
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 hydrophilic ligands such as [[atenolol]], [[sotalol]] and [[nadolol]].<ref>{{cite journal |author=McDevitt DG |title=Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs |series=8 |journal=Eur. Heart J. |volume=Suppl M |issue= |pages=9–14 |year=1987 |pmid=2897304 |doi=10.1093/eurheartj/8.suppl_M.9}}</ref>
'''Oxprenolol''' is a non-selective [[beta blocker]] with some intrinsic [[sympathomimetic amine|sympathomimetic]] activity. It is used for the treatment of [[angina pectoris]] and abnormal [[heart]] rhythms. It is also used for treating [[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 [[CNS]]-related side effects than hydrophilic ligands such as [[atenolol]], [[sotalol]] and [[nadolol]].<ref>{{cite journal |author=McDevitt DG |title=Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs |journal=Eur. Heart J. |volume=8 Suppl M |issue= |pages=9-14 |year=1987 |pmid=2897304 |doi=}}</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 | doi = 10.1136/thx.35.2.160 | journal = Thorax | year = 1980 | volume = 35 | pmc = 471246 | issue = 2 | pages = 160 | title = Severe asthma after inadvertent ingestion of oxprenolol | author = I P Williams and F J Millard | pmid = 7376124}}</ref>


Oxprenolol is an potent beta-blocker and should not be administered to asthmatics because it can cause irreversible airway failure and inflammation.
== Stereochemistry ==
==References==
{{Reflist}}


{{beta blockers}}
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 | 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 | last1 = Abounassif | first1 = Mohammed A. | last2 = Hefnawy | first2 = Mohammed M. | last3 = Mostafa | first3 = Gamal A. E. | journal = Monatshefte für Chemie - Chemical Monthly | volume = 143 | issue = 3 | pages = 365}}</ref>
:[[File:(±)-Oxoprenolol Structural Formulae V.2.svg|thumb|left|(''R'')-(+)-Oxprenolol (top) and (''S'')-(–)-oxprenolol]]{{clear-left}}
 
== References ==
{{Reflist|2}}
 
{{Beta blockers}}
{{Adrenergics}}
{{Serotonergics}}


[[Category:Beta blockers]]
[[Category:Beta blockers]]
[[Category:Sympathomimetic amines]]
[[Category:Sympathomimetic amines]]
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[[Category:Phenol ethers]]
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Revision as of 21:07, 24 July 2014

Oxprenolol
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • AU: C
Routes of
administration
oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability20-70%
MetabolismHepatic
Elimination half-life1-2hours
ExcretionRenal
Lactic (In lactiferous females)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC15H23NO3
Molar mass265.348
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]Associate Editor(s)-in-Chief: Sheng Shi, M.D. [2]

Oxprenolol (Trasacor, Trasicor, Coretal, Laracor, Slow-Pren, Captol, Corbeton, Slow-Trasicor, Tevacor, Trasitensin, Trasidex) is a non-selective beta blocker with some intrinsic sympathomimetic activity. It is used for the treatment of angina pectoris, abnormal heart rhythms and 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 CNS-related side effects than hydrophilic ligands such as atenolol, sotalol and nadolol.[1]

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.[2]

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. [3]

File:(±)-Oxoprenolol Structural Formulae V.2.svg
(R)-(+)-Oxprenolol (top) and (S)-(–)-oxprenolol
Template:Clear-left

References

  1. McDevitt DG (1987). "Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs". Eur. Heart J. 8. Suppl M: 9–14. doi:10.1093/eurheartj/8.suppl_M.9. PMID 2897304.
  2. I P Williams and F J Millard (1980). "Severe asthma after inadvertent ingestion of oxprenolol". Thorax. 35 (2): 160. doi:10.1136/thx.35.2.160. PMC 471246. PMID 7376124.
  3. Abounassif, Mohammed A.; Hefnawy, Mohammed M.; Mostafa, Gamal A. E. (2011). "Separation and quantitation of oxprenolol in urine and pharmaceutical formulations by HPLC using a Chiralpak IC and UV detection". Monatshefte für Chemie - Chemical Monthly. 143 (3): 365. doi:10.1007/s00706-011-0605-4.