Drug Details

General Information of the Drug (ID: DR1567)
Name
Terazosin
Synonyms
terazosin; Terazosine; 63590-64-7; Hytrin; Terazosina; Terazosinum; Flumarc; Fosfomic; Vasomet; Blavin; Terazosine [INN-French]; Terazosinum [INN-Latin]; Terazosina [INN-Spanish]; 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)piperazine; CHEMBL611; MLS000069703; Abbott-45975; CHEBI:9445; Terazosin (hydrochloride); [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(oxolan-2-yl)methanone; SMR000058309; Terazosin [INN:BAN]; 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(tetrahydro-2-furoyl)piperazine; 6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]quinazolin-4-amine; (4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)(tetrahydrofuran-2-yl)methanone; [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl](tetrahydrofuran-2-yl)methanone; 6,7-dimethoxy-2-[4-(tetrahydrofuran-2-ylcarbonyl)piperazin-1-yl]quinazolin-4-amine; Abbott 45975; 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(tetrahydro-2-furanyl)carbonyl]piperazine; Terazosabb (TN); Terazosin (INN); 141269-45-6; MFCD00467965; 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)4-[(tetrahydro-2-furanyl)carbonyl]piperazine; terazosin a; terazosinhydrochloride; 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-[(tetrahydro-2-furanyl)carbonyl]piperazine hydrochloride; 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)4-[(tetrahydro-2-furanyl)carbonyl]piperazine hydrochloride; Opera_ID_1910; Prestwick0_000751; Prestwick1_000751; Prestwick2_000751; Prestwick3_000751; 141269-44-5; SCHEMBL6528; Lopac0_001138; REGID_for_CID_5401; BSPBio_000762; MLS001201836; MLS006011889; SPBio_002701; BPBio1_000840; GTPL7302; MET029; DTXSID3023639; HMS2090P21; HMS2232N21; HMS3259F04; HMS3369P14; HMS3371E20; HMS3742I09; 109351-34-0; HY-B0371; 4097AH; BBL010743; BDBM50033111; STK567029; AKOS005266642; CCG-205212; DB01162; MCULE-4030111564; NC00689; SDCCGSBI-0051105.P002; VA11839; 6,7-bis(methyloxy)-2-[4-(tetrahydrofuran-2-ylcarbonyl)piperazin-1-yl]quinazolin-4-amine; Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)-; NCGC00016026-04; NCGC00016026-05; NCGC00016026-08; NCGC00016026-11; NCGC00025191-03; AC-11120; H963; LS-14728; FT-0630739; C07127; D08569; 590T647; L000692; Q280786; BRD-A22256192-003-03-7; BRD-A22256192-003-14-4; Z1172269406; 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-tetrahydrofuroyl)piperazine; 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-tetrahydrofuroyl)-piperazine; 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-{(tetnaphydro-2-furanyl)carbonyl}piperazine; 6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]-3,4-dihydroquinazolin-4-imine; 6,7-Dimethoxy-2-[4-(tetrahydro-2-furanylcarbonyl)-1-piperazinyl]-4-quinazolinamine #; 6,7-dimethoxy-2-{4-[(oxolan-2-yl)carbonyl]piperazin-1-yl}quinazolin-4-amine; Methanone, [4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1-piperazinyl](tetrahydro-2-furanyl)-; 1-(4-amino-6,7-dimethoxyquinazolin-2-yl)-4-[[(2RS)-2,3,4,5-tetrahydrofuran-2-yl]carbonyl]piperazine
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Molecular Type
Small molecule
Disease Prostate hyperplasia [ICD-11: GA90] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption
The absorption of drug is 90%
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Bioavailability
90% of drug becomes completely available to its intended biological destination(s)
Clearance
The renal clearance of drug is 10 mL/min
Elimination
Approximately 10% of the oral dose is excreted unchanged in the urine and approximately 20% is excreted in the feces
Half-life
The concentration or amount of drug in body reduced by one-half in 12 hours
Metabolism
The drug is metabolized via the hepatic
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.85948 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.08%
Vd
The volume of distribution (Vd) of drug is 25-30 L
Water Solubility
The ability of drug to dissolve in water is measured as 24.2 mg/mL
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C19H25N5O4
PubChem CID
5401
Canonical SMILES
COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4CCCO4)N)OC
InChI
1S/C19H25N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h10-11,14H,3-9H2,1-2H3,(H2,20,21,22)
InChIKey
VCKUSRYTPJJLNI-UHFFFAOYSA-N
CAS Number
CAS 63590-64-7
ChEBI ID
CHEBI:9445
TTD Drug ID
D0P9RF
DrugBank ID
DB01162
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Genistein      Glycine max     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BCL-xL  Molecule Info 
Pathway MAP
Down-regulation Expression NRP1  Molecule Info 
Pathway MAP
                    In-vitro Model DU145 CVCL_0105 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)		 The terazosin/genistein combination was more effective in inhibiting cell growth and VEGF expression as well as inducing apoptosis of the metastatic, androgen-independent prostate cancer cell line, DU-145, than either alone.
Target and Pathway
Target(s) Adrenergic receptor alpha-1D (ADRA1D)  Molecule Info  [3]
KEGG Pathway Calcium signaling pathway Click to Show/Hide
2 cGMP-PKG signaling pathway
3 Neuroactive ligand-receptor interaction
4 Adrenergic signaling in cardiomyocytes
5 Vascular smooth muscle contraction
6 Salivary secretion
NetPath Pathway IL2 Signaling Pathway Click to Show/Hide
Reactome Adrenoceptors Click to Show/Hide
2 G alpha (q) signalling events
3 G alpha (12/13) signalling events
WikiPathways Monoamine GPCRs Click to Show/Hide
2 Calcium Regulation in the Cardiac Cell
3 GPCRs, Class A Rhodopsin-like
4 Gastrin-CREB signalling pathway via PKC and MAPK
5 GPCR ligand binding
6 GPCR downstream signaling
7 GPCRs, Other
References
Reference 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: 7302).
Reference 2 Combined effects of terazosin and genistein on a metastatic, hormone-independent human prostate cancer cell line. Cancer Lett. 2009 Apr 8;276(1):14-20.
Reference 3 Induction of prostate apoptosis by alpha1-adrenoceptor antagonists: mechanistic significance of the quinazoline component. Prostate Cancer Prostatic Dis. 2002;5(2):88-95.
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