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81403-80-7 molecular structure
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N-{3-[(4-amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino]propyl}oxolane-2-carboxamide

ChemBase ID: 230
Molecular Formular: C19H27N5O4
Molecular Mass: 389.44878
Monoisotopic Mass: 389.20630437
SMILES and InChIs

SMILES:
O1C(CCC1)C(=O)NCCCN(c1nc2c(c(n1)N)cc(OC)c(OC)c2)C
Canonical SMILES:
COc1cc2nc(nc(c2cc1OC)N)N(CCCNC(=O)C1CCCO1)C
InChI:
InChI=1S/C19H27N5O4/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23)
InChIKey:
WNMJYKCGWZFFKR-UHFFFAOYSA-N

Cite this record

CBID:230 http://www.chembase.cn/molecule-230.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-{3-[(4-amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino]propyl}oxolane-2-carboxamide
IUPAC Traditional name
alfuzosin
N-{3-[(4-amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino]propyl}oxolane-2-carboxamide
Brand Name
Uroxatral
Xatral
Synonyms
Alfusosine
alfuzosin
Alfuzosin
Zatral
Alfoten
Mittoral
Urion
Alfuzosin
CAS Number
81403-80-7
PubChem SID
160963693
46508512
PubChem CID
2092

DATA SOURCES

DATA SOURCES

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CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.639695  H Acceptors
H Donor LogD (pH = 5.5) -0.34812674 
LogD (pH = 7.4) 0.936928  Log P 1.1875362 
Molar Refractivity 107.1141 cm3 Polarizability 41.11549 Å3
Polar Surface Area 111.83 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.02  LOG S -3.14 
Solubility (Water) 2.82e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Product Information Bioassay(PubChem)
Hydrophobicity(logP)
1.4 expand Show data source
Mechanism of Action
alpha 1-Adrenoceptor antagonist expand Show data source
Application(s)
Antihypertensive agent expand Show data source
Used in the treatment of benign prostatic hypertrophy expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00346 external link
Item Information
Drug Groups approved; investigational
Description Alfuzosin (INN, provided as the hydrochloride salt) is an alpha-adrenergic blocker used to treat benign prostatic hyperplasia (BPH). It works by relaxing the muscles in the prostate and bladder neck, making it easier to urinate. [Wikipedia]
Indication For the reduction of urinary obstruction and relief of associated manifestations (eg. sensation of incomplete bladder emptying or straining, urgency, interrupted or weak stream) in patients with symptomatic beningn prostatic hyperplasia.
Pharmacology Alfuzosin is a quinazoline-derivative alpha-adrenergic blocking agent used to treat hypertension and benign prostatic hyperplasia. Accordingly, alfuzosin is a selective inhibitor of the alpha(1) subtype of alpha adrenergic receptors. In the human prostate, alfuzosin antagonizes phenylephrine (alpha(1) agonist)-induced contractions, in vitro, and binds with high affinity to the alpha1a adrenoceptor, which is thought to be the predominant functional type in the prostate. Studies in normal human subjects have shown that alfuzosin competitively antagonized the pressor effects of phenylephrine (an alpha(1) agonist) and the systolic pressor effect of norepinephrine. The antihypertensive effect of alfuzosin results from a decrease in systemic vascular resistance and the parent compound alfuzosin is primarily responsible for the antihypertensive activity.
Toxicity Side effects are dizziness (due to postural hypotension), upper respiratory tract infection, headache, and fatigue.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Alfuzosin undergoes extensive metabolism by the liver, with only 11% of the administered dose excreted unchanged in the urine. Alfuzosin is metabolized by three metabolic pathways: oxidation, O-demethylations, and N-dealkylation. The metabolites are not pharmacologically active. CYP3A4 is the principal hepatic enzyme isoform involved in its metabolism.
Absorption Absorption is 50% lower under fasting conditions
Half Life 10 hours
Protein Binding 82%-90%
Elimination Following oral administration of 14C-labeled alfuzosin solution, the recovery of radioactivity after 7 days (expressed as a percentage of the administered dose) was 69% in feces and 24% in urine.
Distribution * 3.2 L/kg [healthy male middle-aged volunteers]
References
McKeage K, Plosker GL: Alfuzosin: a review of the therapeutic use of the prolonged-release formulation given once daily in the management of benign prostatic hyperplasia. Drugs. 2002;62(4):633-53. [Pubmed]
Wilde MI, Fitton A, McTavish D: Alfuzosin. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in benign prostatic hyperplasia. Drugs. 1993 Mar;45(3):410-29. [Pubmed]
Andersson KE, Lepor H, Wyllie MG: Prostatic alpha 1-adrenoceptors and uroselectivity. Prostate. 1997 Feb 15;30(3):202-15. [Pubmed]
Elhilali MM: Alfuzosin: an alpha1-receptor blocker for the treatment of lower urinary tract symptoms associated with benign prostatic hyperplasia. Expert Opin Pharmacother. 2006 Apr;7(5):583-96. [Pubmed]
Roehrborn CG: Alfuzosin: overview of pharmacokinetics, safety, and efficacy of a clinically uroselective alpha-blocker. Urology. 2001 Dec;58(6 Suppl 1):55-63; discussion 63-4. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • McKeage K, Plosker GL: Alfuzosin: a review of the therapeutic use of the prolonged-release formulation given once daily in the management of benign prostatic hyperplasia. Drugs. 2002;62(4):633-53. Pubmed
  • • Wilde MI, Fitton A, McTavish D: Alfuzosin. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in benign prostatic hyperplasia. Drugs. 1993 Mar;45(3):410-29. Pubmed
  • • Andersson KE, Lepor H, Wyllie MG: Prostatic alpha 1-adrenoceptors and uroselectivity. Prostate. 1997 Feb 15;30(3):202-15. Pubmed
  • • Elhilali MM: Alfuzosin: an alpha1-receptor blocker for the treatment of lower urinary tract symptoms associated with benign prostatic hyperplasia. Expert Opin Pharmacother. 2006 Apr;7(5):583-96. Pubmed
  • • Roehrborn CG: Alfuzosin: overview of pharmacokinetics, safety, and efficacy of a clinically uroselective alpha-blocker. Urology. 2001 Dec;58(6 Suppl 1):55-63; discussion 63-4. Pubmed
  • • U.S. Pat., 1982, Synthelabo, 4 315 007; CA, 96, 162737e, (synth)
  • • Allen, J., J. Labelled Compd. Radiopharm., 1983, 20, 1283, (synth)
  • • Scott, M.G. et al., Eur. J. Clin. Pharmacol., 1989, 37, 53, (pharmacokinet)
  • • Rouchouse, A. et al., J. Chromatogr., 1990, 506, 601, (hplc, enantiomers)
  • • Lefevre-Borg, F. et al., Br. J. Pharmacol., 1993, 109, 1282, (pharmacol)
  • • Wilde, M.I. et al., Drugs, 1993, 45, 410, (rev)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 342
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PATENTS

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