Oxprenolol

Structural formula
	( R ) -oxprenolol (top) and ( S ) -oxprenolol (bottom), 1: 1 stereoisomeric mixture
General
Non-proprietary name	Oxprenolol
other names	(±) -1- (2-Allyloxyphenoxy) -3- (isopropylamino) propan-2-ol; ( RS ) -1- (2-Allyloxyphenoxy) -3-isopropylamino-2-propanol;
Molecular formula	C 15 H 23 NO 3
Brief description	whitish, crystalline powder
External identifiers / databases
EC number	229-257-9
ECHA InfoCard	100,026,598
PubChem	4631
ChemSpider	4470
DrugBank	DB01580
Wikidata	Q425963
Drug information
ATC code	C07 AA02
Drug class	Beta blockers
properties
Molar mass	265,35 g · mol -1
Physical state	firmly
Melting point	78-80 ° C
pK s value	9.6
solubility	Water: 3180 mg l −1 (25 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 301
	P: 264-270-301 + 310-321-405-501
Toxicological data	375 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oxprenolol is a drug from the group of beta blockers and is used, among other things, to treat arterial hypertension (high blood pressure). Oxprenolol was patented by Ciba in 1966.

Clinical information

Oxprenolol is one of the nonselective beta blockers, as it does not specifically bind to the β ₁ adrenoceptors . It exhibits intrinsic sympathomimetic activity ( ISA ), as do the beta blockers acebutolol and pindolol . The potency of oxprenolol is the same as that of propranolol.

Pharmacological properties

The fat-soluble oxprenolol is subject to a pronounced first-pass effect , the bioavailability is very variable and fluctuates between 20% and 70%. Oxprenolol is broken down in the liver.

Other Information

particularities

All beta blockers with ISA are said to lead to sleep disorders more often than beta blockers without ISA.

Stereochemistry

Oxprenolol is chiral , the racemate is used medicinally . The importance of the enantiomeric purity of synthetically produced active ingredients is being given increasing attention, because the two enantiomers of a chiral medicinal substance almost always show different pharmacology and pharmacokinetics. In the past, this was often ignored due to a lack of knowledge of stereochemical relationships. Analytical methods for the HPLC separation of ( R ) - (+) - oxprenolol and ( S ) - (-) - oxprenolol in pharmaceutical formulations and in the urine of patients are described in the literature.

Trade names

Monopreparations

Trasicor (D and CH except trade)

Combination preparations

Slow-Trasitensin (CH)

literature

T. Karow / R. Lang-Roth: General and special pharmacology and toxicology . 2003, pp. 62-66.
G. Herold: Internal Medicine 2004

Individual evidence

↑ ^a ^b entry on oxprenolol. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
^ V. Martinez, MI Maguregui, RM Jimenez, RM Alonso: Determination of the pKa values of β-blockers by automated potentiometric titrations. In: Journal of Pharmaceutical and Biomedical Analysis . 23, 2000, pp. 459-468, doi : 10.1016 / S0731-7085 (00) 00324-1 .
↑ ^a ^b Entry on oxprenolol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b Oxprenolol Hydrochloride ( Memento from October 31, 2016 in the Internet Archive )
↑ EJ Ariëns, Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology , European Journal of Clinical Pharmacology 26 (1984) 663-668. doi : 10.1007 / BF00541922 .
↑ Mohammed A. Abounassif, Mohammed M. Hefnawy, Gamal A. E- Mostafa: Separation and quantitation of oxprenolol in urin ans pharmaceutical formulations by HPLC using a Chiralpak IC and UV detection , monthly. Chem. 143 ( 2012 ) 365-371, doi : 10.1007 / s00706-011-0605-4 .

[Römpp-1] try on oxprenolol. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.

[2] V. Martinez, MI Maguregui, RM Jimenez, RM Alonso: Determination of the pKa values of β-blockers by automated potentiometric titrations. In: Journal of Pharmaceutical and Biomedical Analysis . 23, 2000, pp. 459-468, doi : 10.1016 / S0731-7085 (00) 00324-1 .

[ChemIDplus-3] Entry on oxprenolol in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[lgcstandards-4] Oxprenolol Hydrochloride ( Memento from October 31, 2016 in the Internet Archive )

[Ariëns-5] EJ Ariëns, Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology , European Journal of Clinical Pharmacology 26 (1984) 663-668. doi : 10.1007 / BF00541922 .

[Abounassif-6] Mohammed A. Abounassif, Mohammed M. Hefnawy, Gamal A. E- Mostafa: Separation and quantitation of oxprenolol in urin ans pharmaceutical formulations by HPLC using a Chiralpak IC and UV detection , monthly. Chem. 143 ( 2012 ) 365-371, doi : 10.1007 / s00706-011-0605-4 .