Oxprenolol: Difference between revisions

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Oxprenolol
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	AU: C ; ;
Routes of; administration	oral
ATC code	C07AA02 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	20-70%
Metabolism	Hepatic
Elimination half-life	1-2hours
Excretion	Renal ; Lactic (In lactiferous females)
Identifiers
	IUPAC name (RS)-1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol;
CAS Number	6452-71-7 ;
PubChem CID	4631;
DrugBank	DB01580 ;
ChemSpider	4470 ;
UNII	519MXN9YZR;
KEGG	D08318 ;
ChEMBL	ChEMBL546 ;
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)	Interactive image;
	SMILES O(c1ccccc1OC\C=C)CC(O)CNC(C)C;
	InChI InChI=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 ; Key:CEMAWMOMDPGJMB-UHFFFAOYSA-N ;
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VisualWikitext

Latest revision as of 02:41, 25 July 2014

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.

[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.

[Abounassif-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.

[1]

[2]

[3]

@@ Line 53: / Line 53: @@
 | StdInChIKey = CEMAWMOMDPGJMB-UHFFFAOYSA-N
 }}
+__NOTOC__
+{{SI}}
+{{CMG}}
-{{CMG}}{{AE}}{{SS}}
+==Overview==
 '''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]].
@@ Line 64: / Line 67: @@
 == 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>
+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>
-== References ==
+==References==
-{{Reflist|2}}
+{{reflist|2}}
 {{Beta blockers}}
-{{Adrenergics}}
-{{Serotonergics}}
+[[Category:Cardiovascular Drugs]]
+[[Category:Drug]]
 [[Category:Beta blockers]]
-[[Category:Sympathomimetic amines]]
-[[Category:Phenol ethers]]
-[[Category:Alkenes]]
-[[Category:Alcohols]]
-[[Category:Cardiovascular Drugs]][[Category:Drugs]]

v t e Beta blockers (C07)
Non-selective β antagonists	Metipranolol • Nadolol • Oxprenolol • Penbutolol • Pindolol • Propranolol • Tertatolol • Timolol • Sotalol
β₁ antagonists (cardioselective)	Atenolol • Acebutolol • Celiprolol • Betaxolol • Bisoprolol • Esmolol • Metoprolol • Nebivolol
Mixed α₁/β antagonists	Carvedilol • Labetalol

Clinical data

AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	AU: C
Routes of administration	oral
ATC code	C07AA02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	20-70%
Metabolism	Hepatic
Elimination half-life	1-2hours
Excretion	Renal Lactic (In lactiferous females)
Identifiers
IUPAC name (RS)-1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)propan-2-ol
CAS Number	6452-71-7^Y
PubChem CID	4631
DrugBank	DB01580^N
ChemSpider	4470^Y
UNII	519MXN9YZR
KEGG	D08318^Y
ChEMBL	ChEMBL546^Y
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)	Interactive image
SMILES O(c1ccccc1OC\C=C)CC(O)CNC(C)C
InChI InChI=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^Y Key:CEMAWMOMDPGJMB-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Oxprenolol: Difference between revisions

Latest revision as of 02:41, 25 July 2014

Overview

Stereochemistry

References

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