Oxprenolol: Difference between revisions
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{{ | {{Drugbox | ||
|IUPAC_name = 1- | | Verifiedfields = changed | ||
|image= | | Watchedfields = changed | ||
| | | verifiedrevid = 418877799 | ||
| | | IUPAC_name = (''RS'')-1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol | ||
| | | image = Oxprenolol.png | ||
| | | width = 200px | ||
| | | imagename = 1 : 1 mixture (racemate) | ||
| C | | drug_name = Oxprenolol | ||
| | |||
|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_US = | ||
| | | pregnancy_category = | ||
| | | legal_status = Rx-only | ||
| | | 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}}{{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]]. | |||
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 | 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> | ||
== 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 | 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]] | ||
[[Category: | [[Category:Phenol ethers]] | ||
[[Category:Alkenes]] | |||
[[Category:Alcohols]] | |||
[[Category:Cardiovascular Drugs]][[Category:Drugs]] | |||
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Revision as of 21:07, 24 July 2014
Clinical data | |
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AHFS/Drugs.com | Micromedex Detailed Consumer Information |
Pregnancy category |
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Routes of administration | oral |
ATC code | |
Legal status | |
Legal status |
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Pharmacokinetic data | |
Bioavailability | 20-70% |
Metabolism | Hepatic |
Elimination half-life | 1-2hours |
Excretion | Renal 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 | |
Formula | C15H23NO3 |
Molar mass | 265.348 |
3D model (JSmol) | |
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(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]
References
- ↑ 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.
- ↑ 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.
- ↑ 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.
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- Beta blockers
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