Details of the Drug

General Information of Drug (ID: DM8KSQH)

Drug Name
Phenoxybenzamine
Synonyms
Bensylyt; Bensylyte; Benzylyt; Dibenylene; Dibenylin; Dibenyline; Dibenziran; Dibenzylene; Dibenzylin; Dibenzyran; Fenossibenzamina; Fenoxibenzamina; Phenoxybenzaminum; Bensylyt NEN; Fenossibenzamina [DCIT]; POB HCl; Phenoxybenzamine Hcl; A 688; Dibenzyline (TN); Fenoxibenzamina [INN-Spanish]; Phenoxybenzamine (INN);Phenoxybenzamine [INN:BAN]; Phenoxybenzaminum [INN-Latin]; N-Phenoxyisopropyl-N-benzyl-beta-chloroethylamine; Benzyl(2-chloroethyl)-(1-methyl-2-phenoxyethyl)amine; N-(2-Chloroethyl)-N-(1-methyl-2-phenoxyethyl)benzenemethanamine; N-(2-Chloroethyl)-N-(1-methyl-2-phenoxyethyl)benzylamine; N-benzyl-N-(2-chloroethyl)-1-phenoxypropan-2-amine; N-(2-chloroethyl)-N-(phenylmethyl)-1-(phenyloxy)propan-2-amine; 2-(N-Benzyl-2-chloroethylamino)-1-phenoxypropane; 688A
Indication
Disease Entry ICD 11 Status REF
Malignant essential hypertension BA00 Approved [1]
Pheochromocytoma 5A75 Approved [2]
Therapeutic Class
Antihypertensive Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 303.8
Logarithm of the Partition Coefficient (xlogp) 4.4
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Bioavailability
The bioavailability of drug is 20-30% []
Half-life
The concentration or amount of drug in body reduced by one-half in 24 hours [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 2.821 micromolar/kg/day [5]
Chemical Identifiers
Formula
C18H22ClNO
IUPAC Name
N-benzyl-N-(2-chloroethyl)-1-phenoxypropan-2-amine
Canonical SMILES
CC(COC1=CC=CC=C1)N(CCCl)CC2=CC=CC=C2
InChI
InChI=1S/C18H22ClNO/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17/h2-11,16H,12-15H2,1H3
InChIKey
QZVCTJOXCFMACW-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4768
ChEBI ID
CHEBI:8077
CAS Number
59-96-1
DrugBank ID
DB00925
TTD ID
D0X2DK
VARIDT ID
DR00696
ACDINA ID
D00526
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dopamine D2 receptor (D2R) TTEX248 DRD2_HUMAN Antagonist [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cyclic AMP-dependent transcription factor ATF-3 (ATF3) OTC1UOHP ATF3_HUMAN Gene/Protein Processing [8]
Heat shock factor protein 1 (HSF1) OTYNJ4KP HSF1_HUMAN Gene/Protein Processing [9]
Hepatocyte growth factor receptor (MET) OT7K55MU MET_HUMAN Gene/Protein Processing [10]
Interleukin-24 (IL24) OT4VUWH1 IL24_HUMAN Gene/Protein Processing [10]
Metallothionein-1M (MT1M) OTVT8PLU MT1M_HUMAN Gene/Protein Processing [8]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [11]
Phosphatidylcholine translocator ABCB4 (ABCB4) OTE6PY83 MDR3_HUMAN Gene/Protein Processing [12]
Proepiregulin (EREG) OTRM4NQY EREG_HUMAN Gene/Protein Processing [10]
Solute carrier family 22 member 1 (SLC22A1) OT7817I4 S22A1_HUMAN Gene/Protein Processing [13]
Solute carrier family 22 member 2 (SLC22A2) OTGFK1AL S22A2_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Malignant essential hypertension
ICD Disease Classification BA00
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Dopamine D2 receptor (D2R) DTT DRD2 2.50E-02 -0.08 -0.49
Organic cation transporter 1 (SLC22A1) DTP SLC22A1 8.54E-01 1.24E-02 7.20E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Phenoxybenzamine
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Nadolol DMW6GVL Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Nadolol. Essential hypertension [BA00] [14]
Coadministration of a Drug Treating the Disease Different from Phenoxybenzamine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Cariprazine DMJYDVK Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Cariprazine. Bipolar disorder [6A60] [15]
Selegiline DM6034S Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Selegiline. Depression [6A70-6A7Z] [16]
Isocarboxazid DMAF1NB Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Isocarboxazid. Depression [6A70-6A7Z] [16]
OPC-34712 DMHG57U Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and OPC-34712. Depression [6A70-6A7Z] [15]
Metipranolol DMJMVKI Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Metipranolol. Glaucoma [9C61] [14]
Levobetaxolol DMSREPX Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Levobetaxolol. Glaucoma [9C61] [14]
Carvedilol DMHTEAO Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Carvedilol. Heart failure [BD10-BD1Z] [14]
Procarbazine DMIK367 Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Procarbazine. Hodgkin lymphoma [2B30] [16]
Acebutolol DM0TI4U Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Acebutolol. Hypertension [BA00-BA04] [14]
Captopril DM458UM Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Captopril. Hypertension [BA00-BA04] [17]
Penbutolol DM4ES8F Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Penbutolol. Hypertension [BA00-BA04] [14]
Nebivolol DM7F1PA Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Nebivolol. Hypertension [BA00-BA04] [14]
Pindolol DMD2NV7 Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Pindolol. Hypertension [BA00-BA04] [14]
ITI-007 DMUQ1DO Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and ITI-007. Insomnia [7A00-7A0Z] [15]
Ozanimod DMT6AM2 Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Ozanimod. Multiple sclerosis [8A40] [16]
Promethazine DM6I5GR Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Promethazine. Nausea/vomiting [MD90] [15]
Rasagiline DM3WKQ4 Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Rasagiline. Parkinsonism [8A00] [16]
Silodosin DMJSBT6 Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Silodosin. Prostate hyperplasia [GA90] [18]
Levomepromazine DMIKFEL Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Levomepromazine. Psychotic disorder [6A20-6A25] [15]
Quetiapine DM1N62C Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Quetiapine. Schizophrenia [6A20] [15]
Mesoridazine DM2ZGAN Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Mesoridazine. Schizophrenia [6A20] [15]
Aripiprazole DM3NUMH Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Aripiprazole. Schizophrenia [6A20] [15]
Iloperidone DM6AUFY Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Iloperidone. Schizophrenia [6A20] [15]
Paliperidone DM7NPJS Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Paliperidone. Schizophrenia [6A20] [15]
Molindone DMAH70G Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Molindone. Schizophrenia [6A20] [15]
Thiothixene DMDINC4 Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Thiothixene. Schizophrenia [6A20] [15]
Amisulpride DMSJVAM Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Amisulpride. Schizophrenia [6A20] [15]
Asenapine DMSQZE2 Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Asenapine. Schizophrenia [6A20] [15]
Trimeprazine DMEMV9D Moderate Additive hypotensive effects by the combination of Phenoxybenzamine and Trimeprazine. Vasomotor/allergic rhinitis [CA08] [19]
⏷ Show the Full List of 29 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Allura red AC dye E00338 33258 Colorant
D&C red no. 33 E00261 19116 Colorant
Isopropyl alcohol E00070 3776 Antimicrobial preservative; Solvent
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF E00255 17730 Colorant
Ammonia E00007 222 Alkalizing agent
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Butyl alcohol E00011 263 Flavoring agent; Solvent
Ethanol E00023 702 Antimicrobial preservative; Penetration agent; Solvent
FD&C red no. 3 E00629 Not Available Colorant
Ferric hydroxide oxide yellow E00539 23320441 Colorant
Ferrosoferric oxide E00231 14789 Colorant
Gelatin E00630 Not Available Other agent
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Potassium hydroxide E00233 14797 Alkalizing agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Water E00035 962 Solvent
Shellac E00695 Not Available Coating agent; Film/membrane-forming agent; Microencapsulating agent; Modified-release agent
⏷ Show the Full List of 21 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Phenoxybenzamine 10 mg capsule 10 mg Oral Capsule Oral
Phenoxybenzamine Hydrochloride 10mg/capsule capsule 10mg/capsule Capsule Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Phenoxybenzamine FDA Label
3 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 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
6 Catecholamine-secreting neuroblastoma in a 4-month-old infant: perioperative management. J Clin Anesth. 2009 Feb;21(1):54-6.
7 Implications of genetic polymorphisms in drug transporters for pharmacotherapy. Cancer Lett. 2006 Mar 8;234(1):4-33.
8 Identification of novel activators of the metal responsive transcription factor (MTF-1) using a gene expression biomarker in a microarray compendium. Metallomics. 2020 Sep 23;12(9):1400-1415. doi: 10.1039/d0mt00071j.
9 A Gene Expression Biomarker Predicts Heat Shock Factor 1 Activation in a Gene Expression Compendium. Chem Res Toxicol. 2021 Jul 19;34(7):1721-1737. doi: 10.1021/acs.chemrestox.0c00510. Epub 2021 Jun 25.
10 An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20.
11 Identification of novel agonists by high-throughput screening and molecular modelling of human constitutive androstane receptor isoform 3. Arch Toxicol. 2019 Aug;93(8):2247-2264. doi: 10.1007/s00204-019-02495-6. Epub 2019 Jul 16.
12 Evaluating the Role of Multidrug Resistance Protein 3 (MDR3) Inhibition in Predicting Drug-Induced Liver Injury Using 125 Pharmaceuticals. Chem Res Toxicol. 2017 May 15;30(5):1219-1229. doi: 10.1021/acs.chemrestox.7b00048. Epub 2017 May 4.
13 Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36.
14 Chrysant SG "Experience with terazosin administered in combination with other antihypertensive agents." Am J Med 80 (1986): 55-61. [PMID: 2872808]
15 Aronowitz JS, Chakos MH, Safferman AZ, Lieberman JA "Syncope associated with the combination of clozapine and enalapril." J Clin Psychopharmacol 14 (1994): 429-30. [PMID: 7884028]
16 Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
17 Baba T, Tomiyama T, Takebe K "Enhancement by an ACE inhibitor of first-dose hypotension caused by an alpha-blocker." N Engl J Med 322 (1990): 1237. [PMID: 1970122]
18 Product Information. Flomax (tamsulosin). Boehringer-Ingelheim, Ridgefield, CT.
19 Product Information. Clozaril (clozapine). Novartis Pharmaceuticals, East Hanover, NJ.