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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:56 UTC
HMDB IDHMDB0015293
Secondary Accession Numbers
  • HMDB15293
Metabolite Identification
Common NameTerazosin
DescriptionTerazosin, also known as hytrin or terazosabb, belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group. Terazosin is a very strong basic compound (based on its pKa). Terazosin is a potentially toxic compound. Terazosin, sold under the brand name Hytrin among others, is a medication used to treat symptoms of an enlarged prostate and high blood pressure. It is available as a generic medication. It is taken by mouth. It is available in 1 mg, 2 mg, 5 mg or 10 mg doses. For high blood pressure, it is a less preferred option. A month supply in the United Kingdom costs the NHS less than 2 £ as of 2019. Prostate cancer should be ruled out before starting treatment.
Structure
Data?1582753280
Synonyms
ValueSource
1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)piperazineChEBI
TerazosinaChEBI
TerazosineChEBI
TerazosinumChEBI
TerazosabbKegg
Abbott 45975HMDB
MagnurolHMDB
Nu-terazosinHMDB
Ratio-terazosinHMDB
Apo-terazosinHMDB
HeitrinHMDB
HytrinHMDB
Terazosin azuHMDB
Terazosin hexalHMDB
Terazosin hydrochlorideHMDB
Terazosina alterHMDB
Terazosina kernHMDB
ZayaselHMDB
AdecurHMDB
DefloxHMDB
DysalfaHMDB
FlotrinHMDB
HytrineHMDB
Novo-terazosinHMDB
SutifHMDB
TazusinHMDB
TerazofloHMDB
Terazosin, monohydrochloride, dihydrateHMDB
Hexal brand OF terazosin hydrochlorideHMDB
Hytrin BPHHMDB
PMS-TerazosinHMDB
Terazosina qualixHMDB
Terazosin hydrochloride anhydrousHMDB
Chemical FormulaC19H25N5O4
Average Molecular Weight387.4329
Monoisotopic Molecular Weight387.190654313
IUPAC Name6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]quinazolin-4-amine
Traditional Nameterazosin
CAS Registry Number63590-64-7
SMILES
COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1CCCO1
InChI Identifier
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)
InChI KeyVCKUSRYTPJJLNI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentN-arylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Quinazolinamine
  • Diazanaphthalene
  • Quinazoline
  • Anisole
  • Dialkylarylamine
  • Alkyl aryl ether
  • Aminopyrimidine
  • Pyrimidine
  • Imidolactam
  • Benzenoid
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point273 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.5 g/LNot Available
LogP1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.5 g/LALOGPS
logP1.12ALOGPS
logP1.18ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)19.93ChemAxon
pKa (Strongest Basic)7.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.04 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.18 m³·mol⁻¹ChemAxon
Polarizability41.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.4931661259
DarkChem[M-H]-190.42531661259
DeepCCS[M+H]+187.27830932474
DeepCCS[M-H]-184.86230932474
DeepCCS[M-2H]-219.28330932474
DeepCCS[M+Na]+194.43930932474
AllCCS[M+H]+191.732859911
AllCCS[M+H-H2O]+189.232859911
AllCCS[M+NH4]+194.132859911
AllCCS[M+Na]+194.732859911
AllCCS[M-H]-189.932859911
AllCCS[M+Na-2H]-190.232859911
AllCCS[M+HCOO]-190.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TerazosinCOC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1CCCO13896.8Standard polar33892256
TerazosinCOC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1CCCO13305.3Standard non polar33892256
TerazosinCOC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1CCCO13807.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Terazosin,1TMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N[Si](C)(C)C)=C2C=C1OC3784.8Semi standard non polar33892256
Terazosin,1TMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N[Si](C)(C)C)=C2C=C1OC3350.5Standard non polar33892256
Terazosin,1TMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N[Si](C)(C)C)=C2C=C1OC5321.7Standard polar33892256
Terazosin,2TMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C=C1OC3758.5Semi standard non polar33892256
Terazosin,2TMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C=C1OC3421.3Standard non polar33892256
Terazosin,2TMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C=C1OC4962.8Standard polar33892256
Terazosin,1TBDMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N[Si](C)(C)C(C)(C)C)=C2C=C1OC4009.6Semi standard non polar33892256
Terazosin,1TBDMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N[Si](C)(C)C(C)(C)C)=C2C=C1OC3570.7Standard non polar33892256
Terazosin,1TBDMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N[Si](C)(C)C(C)(C)C)=C2C=C1OC5258.5Standard polar33892256
Terazosin,2TBDMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C=C1OC4131.6Semi standard non polar33892256
Terazosin,2TBDMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C=C1OC3866.5Standard non polar33892256
Terazosin,2TBDMS,isomer #1COC1=CC2=NC(N3CCN(C(=O)C4CCCO4)CC3)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C=C1OC4897.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Terazosin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9375000000-51e0b50a02ca9182132a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Terazosin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Terazosin LC-ESI-qTof , Positive-QTOFsplash10-000i-0049000000-86650e3e374df663aa352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terazosin , positive-QTOFsplash10-000i-0049000000-86650e3e374df663aa352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terazosin , positive-QTOFsplash10-000i-0059000000-ca9adf5daab9e5e9b6e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terazosin , positive-QTOFsplash10-000e-1292000000-9081c5bb64e8d096db782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terazosin 35V, Negative-QTOFsplash10-0079-0019000000-d7e59834a3bdfe524c512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Terazosin 35V, Positive-QTOFsplash10-000l-0097000000-c8329e54acf1c8a72d7c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 10V, Positive-QTOFsplash10-000i-0029000000-b9509509936fd20822e42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 20V, Positive-QTOFsplash10-007c-3069000000-196d536a1f876cf3fe0f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 40V, Positive-QTOFsplash10-006t-2090000000-f24db01089337864b16f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 10V, Negative-QTOFsplash10-000i-1019000000-f4c3728d09b25d55b2f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 20V, Negative-QTOFsplash10-00dr-6098000000-81e55b539bff879104532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 40V, Negative-QTOFsplash10-00em-3091000000-b40b6a5be295255d01ea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 10V, Positive-QTOFsplash10-000i-0009000000-6fee4cbd3c043ea0f36a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 20V, Positive-QTOFsplash10-000i-0009000000-0967bc8cd13ea87322832021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 40V, Positive-QTOFsplash10-006y-3149000000-56db17d16ac03814def32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 10V, Negative-QTOFsplash10-000i-0009000000-8d31d2aa0ab8d99cf8d72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 20V, Negative-QTOFsplash10-001r-0019000000-55003a7c1cdca21b9dfd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Terazosin 40V, Negative-QTOFsplash10-001v-0197000000-499a38ef1791a534e75c2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01162 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01162 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01162
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5208
KEGG Compound IDC07127
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTerazosin
METLIN IDNot Available
PubChem Compound5401
PDB IDNot Available
ChEBI ID9445
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cushman WC, Ford CE, Cutler JA, Margolis KL, Davis BR, Grimm RH, Black HR, Hamilton BP, Holland J, Nwachuku C, Papademetriou V, Probstfield J, Wright JT Jr, Alderman MH, Weiss RJ, Piller L, Bettencourt J, Walsh SM: Success and predictors of blood pressure control in diverse North American settings: the antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT). J Clin Hypertens (Greenwich). 2002 Nov-Dec;4(6):393-404. [PubMed:12461301 ]

Enzymes

General function:
Involved in ion channel activity
Specific function:
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:
KCNH2
Uniprot ID:
Q12809
Molecular weight:
126653.5
References
  1. Thomas D, Wimmer AB, Wu K, Hammerling BC, Ficker EK, Kuryshev YA, Kiehn J, Katus HA, Schoels W, Karle CA: Inhibition of human ether-a-go-go-related gene potassium channels by alpha 1-adrenoceptor antagonists prazosin, doxazosin, and terazosin. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):462-72. Epub 2004 Apr 20. [PubMed:15098086 ]
General function:
Involved in ion channel activity
Specific function:
Pore-forming (alpha) subunit of voltage-gated potassium channel. Elicits a slowly activating, rectifying current. Channel properties may be modulated by cAMP and subunit assembly
Gene Name:
KCNH6
Uniprot ID:
Q9H252
Molecular weight:
109923.7
References
  1. Thomas D, Wimmer AB, Wu K, Hammerling BC, Ficker EK, Kuryshev YA, Kiehn J, Katus HA, Schoels W, Karle CA: Inhibition of human ether-a-go-go-related gene potassium channels by alpha 1-adrenoceptor antagonists prazosin, doxazosin, and terazosin. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):462-72. Epub 2004 Apr 20. [PubMed:15098086 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Chapple CR: Medical therapy and quality of life. Eur Urol. 1998;34 Suppl 2:10-7; discussion 46. [PubMed:9732824 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Lee E, Lee C: Clinical comparison of selective and non-selective alpha 1A-adrenoreceptor antagonists in benign prostatic hyperplasia: studies on tamsulosin in a fixed dose and terazosin in increasing doses. Br J Urol. 1997 Oct;80(4):606-11. [PubMed:9352700 ]
  4. Michel MC, Grubbel B, Taguchi K, Verfurth F, Otto T, Kropfl D: Drugs for treatment of benign prostatic hyperplasia: affinity comparison at cloned alpha 1-adrenoceptor subtypes and in human prostate. J Auton Pharmacol. 1996 Feb;16(1):21-8. [PubMed:8736427 ]
  5. Na YJ, Guo YL, Gu FL: Clinical comparison of selective and non-selective alpha 1A-adrenoceptor antagonists for bladder outlet obstruction associated with benign prostatic hyperplasia: studies on tamsulosin and terazosin in Chinese patients. The Chinese Tamsulosin Study Group. J Med. 1998;29(5-6):289-304. [PubMed:10503165 ]
  6. Roehrborn CG, Schwinn DA: Alpha1-adrenergic receptors and their inhibitors in lower urinary tract symptoms and benign prostatic hyperplasia. J Urol. 2004 Mar;171(3):1029-35. [PubMed:14767264 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular weight:
56835.4
References
  1. Boyle P, Robertson C, Manski R, Padley RJ, Roehrborn CG: Meta-analysis of randomized trials of terazosin in the treatment of benign prostatic hyperplasia. Urology. 2001 Nov;58(5):717-22. [PubMed:11711348 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Simpson P: Stimulation of hypertrophy of cultured neonatal rat heart cells through an alpha 1-adrenergic receptor and induction of beating through an alpha 1- and beta 1-adrenergic receptor interaction. Evidence for independent regulation of growth and beating. Circ Res. 1985 Jun;56(6):884-94. [PubMed:2988814 ]
  4. Vincent J, Dachman W, Blaschke TF, Hoffman BB: Pharmacological tolerance to alpha 1-adrenergic receptor antagonism mediated by terazosin in humans. J Clin Invest. 1992 Nov;90(5):1763-8. [PubMed:1358918 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular weight:
60462.2
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in ion channel activity
Specific function:
Pore-forming (alpha) subunit of voltage-gated potassium channel. Channel properties may be modulated by cAMP and subunit assembly
Gene Name:
KCNH7
Uniprot ID:
Q9NS40
Molecular weight:
134998.5
References
  1. Thomas D, Wimmer AB, Wu K, Hammerling BC, Ficker EK, Kuryshev YA, Kiehn J, Katus HA, Schoels W, Karle CA: Inhibition of human ether-a-go-go-related gene potassium channels by alpha 1-adrenoceptor antagonists prazosin, doxazosin, and terazosin. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):462-72. Epub 2004 Apr 20. [PubMed:15098086 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Takara K, Sakaeda T, Kakumoto M, Tanigawara Y, Kobayashi H, Okumura K, Ohnishi N, Yokoyama T: Effects of alpha-adrenoceptor antagonist doxazosin on MDR1-mediated multidrug resistance and transcellular transport. Oncol Res. 2009;17(11-12):527-33. [PubMed:19806783 ]