Details of the Drug

General Information of Drug (ID: DM51OQW)

• Drug Name: Oxprenolol
• Synonyms: Coretal; Koretal; Laracor; Osprenololo; Oxprenololum; Tevacor; Trasacor; Trasicor; Osprenololo [DCIT]; Slow Trasicor; Trasicor 80; Captol (TN); Corbeton (TN); Coretal (TN); Dl-Alprenolol; Dl-Oxprenolol; Laracor (TN); Oxprenolol (INN); Oxprenolol (TN); Oxprenolol [INN:BAN]; Oxprenololum [INN-Latin]; Slow-pren; Tevacor (TN);Trasacor (TN); Trasicor (TN); Trasidex (TN); Trasitensin (TN); Slow-Pren (TN); Slow-Trasicor (TN); Coretal (*hydrochloride*); Laracor (*hydrochloride*); Oxprenolol Ba 39089 (*hydrochloride*); Trasacor (*hydrochloride*); Trasicor (*hydrochloride*); Slow-Pren (*hydrochloride*); (+)-1-(o-(Allyloxy)phenoxy)-3-(isopropylamino)propan-2-ol; (+-)-Oxprenolol; (1)-1-(o-(Allyloxy)phenoxy)-3-(isopropylamino)propan-2-ol; 1-((1-Methylethyl)amino)-3-(2-(2-propenyloxy)phenoxy)-2-propanol; 1-(Isopropylamino)-2-hydroxy-3-(o-(allyloxy)phenoxy)propane; 1-(o-(Allyloxy)phenoxy)-3-(isopropylamino)-2-propanol; 1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)propan-2-ol; 1-[(1-Methylethyl)amino]-3-[2-(2-propenyloxy)phenoxy]-2-propanol; 1-[2-(Allyloxy)phenoxy]-3-(isopropylamino)-2-propanol

Indication

Disease Entry	ICD 11	Status	REF
Hypertension	BA00-BA04	Approved	[1], [2], [3], [4]

• Therapeutic Class: Antihypertensive Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 265.35
  Topological Polar Surface Area (xlogp); 2.1
  Rotatable Bond Count (rotbonds); 9
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 4
• ADMET Property:
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [5]
  Bioavailability: The bioavailability of drug is 20-70% [6]
  Clearance: The drug present in the plasma can be removed from the body at the rate of 7.7 mL/min/kg [7]
  Elimination: 3% of drug is excreted from urine in the unchanged form [5]
  Half-life: The concentration or amount of drug in body reduced by one-half in 1 - 2 hours [7]
  Metabolism: The drug is metabolized via the hepatic [6]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 15.1442 micromolar/kg/day [8]
  Unbound Fraction: The unbound fraction of drug in plasma is 0.19% [7]
  Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.72 L/kg [7]
  Water Solubility: The ability of drug to dissolve in water is measured as 30.86 mg/mL [5]
• Chemical Identifiers:
  Formula: C15H23NO3
  IUPAC Name: 1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)propan-2-ol
  Canonical SMILES: CC(C)NCC(COC1=CC=CC=C1OCC=C)O
  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
  InChIKey: CEMAWMOMDPGJMB-UHFFFAOYSA-N
• Cross-matching ID:
  PubChem CID: 4631
  ChEBI ID: CHEBI:91704
  CAS Number: 6452-71-7
  DrugBank ID: DB01580
  TTD ID: D0X2MB
  VARIDT ID: DR00697
  INTEDE ID: DR1216

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adrenergic receptor beta-1 (ADRB1)	TTR6W5O	ADRB1_HUMAN	Antagonist	[9]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6) Main DME	DECB0K3	CP2D6_HUMAN	Substrate	[10]

References

• [1] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7255).
• [2] Controlled evaluation of the beta adrenoceptor blocking drug oxprenolol in anxiety. Med J Aust. 1976 Jun 12;1(24):909-12.
• [3] The beta 1- and beta 2-adrenoceptor stimulatory effects of alprenolol, oxprenolol and pindolol: a study in the isolated right atrium and uterus of the rat. Br J Pharmacol. 1986 Apr;87(4):657-64.
• [4] FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 018166.
• [5] BDDCS applied to over 900 drugs
• [6] FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
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• [15] Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
• [16] Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol. 2003 Apr;16(4):450-9.
• [17] Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
• [18] Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
• [19] Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
• [20] Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.
• [21] Beta-blockers in the treatment of hypertension: are there clinically relevant differences Postgrad Med. 2009 May;121(3):90-8.
• [22] Adrenergic activation of electrogenic K+ secretion in guinea pig distal colonic epithelium: involvement of beta1- and beta2-adrenergic receptors. Am J Physiol Gastrointest Liver Physiol. 2009 Aug;297(2):G269-77.
• [23] Impact of exogenous beta-adrenergic receptor stimulation on hepatosplanchnic oxygen kinetics and metabolic activity in septic shock. Crit Care Med. 1999 Feb;27(2):325-31.
• [24] Topical dorzolamide 2%/timolol 0.5% ophthalmic solution: a review of its use in the treatment of glaucoma and ocular hypertension. Drugs Aging. 2006;23(12):977-95.
• [25] Current therapeutic uses and potential of beta-adrenoceptor agonists and antagonists. Eur J Clin Pharmacol. 1998 Feb;53(6):389-404.
• [26] beta-adrenergic enhancement of brain kynurenic acid production mediated via cAMP-related protein kinase A signaling. Prog Neuropsychopharmacol Biol Psychiatry. 2009 Apr 30;33(3):519-29.
• [27] beta(2)-adrenoceptors are critical for antidepressant treatment of neuropathic pain. Ann Neurol. 2009 Feb;65(2):218-25.