Chemistry:Oxprenolol

Oxprenolol
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	AU: C; ;
Routes of; administration	By mouth
ATC code	C07AA02 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	20-70%
Metabolism	Liver
Elimination half-life	1-2hours
Excretion	Kidney ; 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;
IUPHAR/BPS	7255;
DrugBank	DB01580 ;
ChemSpider	4470 ;
UNII	519MXN9YZR;
KEGG	D08318 ;
ChEMBL	ChEMBL546 ;
Chemical and physical data
Formula	C15H23NO3
Molar mass	265.353 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	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 ;
	(what is this?) (verify)

Short description: Non-selective beta blocker

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 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 beta blockers with more hydrophilic molecules 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]

Pharmacology

Pharmacodynamics

Oxprenolol is a beta blocker. In addition, it has been found to act as an antagonist of the serotonin 5-HT_1A and 5-HT_1B receptors with respective K_i values of 94.2 nM and 642 nM in rat brain tissue.^[3]

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.^[4]

(R)-(+)-Oxprenolol (top) and (S)-(–)-oxprenolol

References

↑ "Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs". European Heart Journal. 8 8 Suppl M: 9–14. December 1987. doi:10.1093/eurheartj/8.suppl_M.9. PMID 2897304.
↑ "Severe asthma after inadvertent ingestion of oxprenolol". Thorax 35 (2): 160. February 1980. doi:10.1136/thx.35.2.160. PMID 7376124.
↑ "Structural analysis by the comparative molecular field analysis method of the affinity of beta-adrenoreceptor blocking agents for 5-HT1A and 5-HT1B receptors". European Journal of Pharmacology 244 (1): 77–87. January 1993. doi:10.1016/0922-4106(93)90061-d. PMID 8093601.
↑ "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): 365–371. 2011. doi:10.1007/s00706-011-0605-4.

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Oxprenolol. Read more

[1] "Comparison of pharmacokinetic properties of beta-adrenoceptor blocking drugs". European Heart Journal. 8 8 Suppl M: 9–14. December 1987. doi:10.1093/eurheartj/8.suppl_M.9. PMID 2897304.

[2] "Severe asthma after inadvertent ingestion of oxprenolol". Thorax 35 (2): 160. February 1980. doi:10.1136/thx.35.2.160. PMID 7376124.

[pmid8093601-3] "Structural analysis by the comparative molecular field analysis method of the affinity of beta-adrenoreceptor blocking agents for 5-HT1A and 5-HT1B receptors". European Journal of Pharmacology 244 (1): 77–87. January 1993. doi:10.1016/0922-4106(93)90061-d. PMID 8093601.

[Abounassif-4] "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): 365–371. 2011. doi:10.1007/s00706-011-0605-4.

[1]

[2]

[3]

[4]

v t e Beta blockers (C07)
β, non-selective	Alprenolol Bopindolol Bupranolol Carteolol Cloranolol Mepindolol Nadolol Oxprenolol Penbutolol Pindolol/Iodopindolol Propranolol Sotalol Tertatolol Timolol
β₁-selective	Acebutolol Atenolol Betaxolol Bevantolol Bisoprolol Celiprolol Epanolol Esmolol Landiolol Metoprolol Nebivolol Practolol S-Atenolol Talinolol
β₂-selective	Butaxamine
α₁- + β-selective	Arotinolol Carvedilol Labetalol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

v t e Adrenergic receptor modulators
α₁	Agonists: 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Desglymidodrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline Antagonists: Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., brexpiprazole, clozapine,Chemistry:Olanzapine
α₂	Agonists: (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rezatomidine Rilmenidine Romifidine Talipexole Tasipimidine Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil Vatinoxan XP21279 Xylazine Xylometazoline Antagonists: 1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, Chemistry:Brexpiprazole
β	Agonists: Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Colterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol Antagonists: Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

Anonymous

Search

Chemistry:Oxprenolol

Namespaces

More

Page actions

Contents

Pharmacology

Pharmacodynamics

Chemistry

Stereochemistry

References

Navigation

Navigation

Help

Translate

Wiki tools

Wiki tools

Clinical data

AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	AU: C
Routes of administration	By mouth
ATC code	C07AA02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	20-70%
Metabolism	Liver
Elimination half-life	1-2hours
Excretion	Kidney 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
IUPHAR/BPS	7255
DrugBank	DB01580^N
ChemSpider	4470^Y
UNII	519MXN9YZR
KEGG	D08318^Y
ChEMBL	ChEMBL546^Y
Chemical and physical data
Formula	C₁₅H₂₃NO₃
Molar mass	265.353 g·mol⁻¹
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
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)

Anonymous

Search

Chemistry:Oxprenolol

Pharmacology

Pharmacodynamics

Chemistry

Stereochemistry

References

Navigation

Wiki tools

Page tools

Other projects

Categories