Details of the Drug

General Information of Drug (ID: DMUT9IQ)

• Drug Name: Bupranolol
• Synonyms: BUPRANOLOL; Betadrenol; Bupranol; Bupranolol [INN:DCF]; Bupranololum; Bupranololum [INN-Latin]; HQIRNZOQPUAHHV-UHFFFAOYSA-N; KL 255; KL-255 [AS HYDROCHLORIDE]; Ophtorenin; SK&F 16805-A; 1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol; 14556-46-8; 2-Propanol, 1-(2-chloro-5-methylphenoxy)-3-((1,1-dimethylethyl)amino)-; 2-Propanol, 1-(tert-butylamino)-3-(6-chloro-m-tolyloxy)-; 3-(tert-Butylamino)-1-(6-chloro-m-tolyloxy)-2-propanol; B 1312; BRN 2272923; C14H22ClNO2

Indication

Disease Entry	ICD 11	Status	REF
Tachyarrhythmias	BC71	Investigative	[1]

• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 271.78
  Topological Polar Surface Area (xlogp); 2.8
  Rotatable Bond Count (rotbonds); 6
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 3
• ADMET Property:
  Absorption: The drug is quickly and completely absorbed from the gut with less than 10% oral bioavailability [2]
  Half-life: The concentration or amount of drug in body reduced by one-half in 2 - 4 hours [3]
  Metabolism: The drug is metabolized via renal [2]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 7.414 micromolar/kg/day [4]
• Chemical Identifiers:
  Formula: C14H22ClNO2
  IUPAC Name: 1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
  Canonical SMILES: CC1=CC(=C(C=C1)Cl)OCC(CNC(C)(C)C)O
  InChI: HQIRNZOQPUAHHV-UHFFFAOYSA-N
  InChIKey: 1S/C14H22ClNO2/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4/h5-7,11,16-17H,8-9H2,1-4H3
• Cross-matching ID:
  PubChem CID: 2475
  ChEBI ID: CHEBI:135123
  CAS Number: 14556-46-8
  DrugBank ID: DB08808
  INTEDE ID: DR0244

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6) Main DME	DECB0K3	CP2D6_HUMAN	Substrate	[5]

References

• [1] National Center for Advancing Translational Science-Inxight: drug (7ZRO0SC54Y)
• [2] 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.
• [3] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [4] Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
• [5] Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
• [6] Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
• [7] Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):117-23.
• [8] CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
• [9] Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
• [10] 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.
• [11] 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.
• [12] Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
• [13] Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
• [14] Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
• [15] Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.