81403-80-7COc1cc2nc(N(C)CCCNC(=O)C3CCCO3)nc(N)c2cc1OCWNMJYKCGWZFFKR-UHFFFAOYSA-NAlfuzosin is a monocarboxylic acid amide, a member of quinazolines and a tetrahydrofuranol. It has a role as an antineoplastic agent, an antihypertensive agent and an alpha-adrenergic antagonist.
81403-80-7log Kow = 1.86 /Estimated/
1.4
1.93
In water, 92 mg/L at 25 °C /Estimated/
2.82e-01 g/L
8.13
pKa = 8.13
Mol wt: 425.92. Crystals from ethanol + ether, mp 225 °C, also reported earlier as 235 °C (dec). pKa 8.13 /Hydrochloride/
193.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
194.6 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
193.08 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
Warning
H373 (100%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
P260, P319, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 6 reports by companies from 1 notifications to the ECHA C&L Inventory.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl alfuzosin hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Alfuzosin Hydrochloride/
Wilde MI et al; Alfuzosin. A Review of its Pharmacodynamic and Pharmacokinetic Properties, and Therapeutic Potential in Benign Prostatic Hyperplasia; Drugs 45 (3): 410-29 (1993)
Roehrborn CG; Alfuzosin: Overview of Pharmacokinetics, Safety, and Efficacy of a Clinically Uroselective alpha-Blocker; Urology 58 (6 Suppl 1): 55-63 (2001)
G04CA01
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
By selectively inhibiting alpha adrenergic receptors in the lower urinary tract, alfuzosin causes smooth muscle relaxation in the bladder neck and prostate, improving urine flow, thereby reducing BPH symptoms. Additionally, alfuzosin reduces the vasoconstrictor effect of catecholamines (epinephrine and norepinephrine), leading to peripheral vasodilation. This leads to a risk of postural hypotension/syncope, and prescribing information warns that caution should be exercised in patients who take nitrates, antihypertensives, or have experienced decreased blood pressure after using other medications.
Alpha(1)-adrenoreceptors are found in the prostate, bladder base, bladder neck, prostatic capsule, and prostatic urethra; their activation may lead to contraction of smooth muscle and urinary symptoms in patients with BPH. Alfuzosin selectively binds to and inhibits alpha(1)-adrenergic receptors in the lower urinary tract. This leads to the relaxation of smooth muscle in both the prostate and bladder neck, resulting in the improvement in urine flow and a reduction of urinary symptoms.
Alfuzosin hydrochloride, a quinazoline-derivative alpha1-adrenergic blocking agent, is structurally and pharmacologically related to prazosin. Alfuzosin is a non-subtype-specific alpha1-adrenergic blocking agent that exhibits selectivity for alpha1-adrenergic receptors in the lower urinary tract (e.g., bladder base, bladder neck, prostate, prostatic capsule, prostatic urethra). Blockade of these adrenoreceptors can cause relaxation of smooth muscle in the bladder neck and prostate, resulting in improvement in urine flow and a reduction in symptoms of benign prostatic hyperplasia (BPH).
The apparent elimination half-life of alfuzosin after oral administration is about 10 hours. The terminal half-life is 3-5 hours.
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DTXSID6048549CHEMBL709CHEBI:51141White to off-white crystalline powder that melts at approximately 240 °C. It is freely soluble in water, sparingly soluble in alcohol, and practically insoluble in dichloromethane. /Hydrochloride/
Hydroxyl radical reaction rate constant = 2.42X10-14 cu cm/molc-sec at 25 °C /Estimated/
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Single administration of 100 mg atenolol with a single dose of 2.5 mg of an immediate release alfuzosin tablet in eight healthy young male volunteers increased alfuzosin Cmax and AUC values by 28% and 21%, respectively. Alfuzosin increased atenolol Cmax and AUC values by 26% and 14%, respectively. In this study, the combination of alfuzosin with atenolol caused significant reductions in mean blood pressure and in mean heart rate.
Repeated administration of 1 g/day cimetidine increased both alfuzosin Cmax and AUC values by 20%.
Repeated co-administration of 240 mg/day of diltiazem, a moderately-potent inhibitor of CYP3A4, with 7.5 mg/day (2.5 mg three times daily) alfuzosin increased the Cmax and AUC0-24 of alfuzosin 1.5- and 1.3-fold, respectively. Alfuzosin increased the Cmax and AUC0-12 of diltiazem 1.4- fold. Although no changes in blood pressure were observed in this study, diltiazem is an antihypertensive medication and the combination of Uroxatral and antihypertensive medications has the potential to cause hypotension in some patients. /Alfuzosin Hydrochloride/
Repeated administration of 400 mg of ketoconazole, a potent inhibitor of CYP3A4, increased alfuzosin Cmax 2.3-fold and AUClast 3.2-fold following a single 10 mg dose of alfuzosin. Uroxatral should not be co-administered with potent inhibitors of CYP3A4,(e.g., ketoconazole, itraconazole, or ritonavir). /Alfuzosin Hydrochloride/
For more Interactions (Complete) data for ALFUZOSIN (9 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,300(SRC), determined from a structure estimation method(2), indicates that alfuzosin is expected to have low mobility in soil(SRC). The pKa of alfuzosin is 8.13(3), indicating that this compound will primarily exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(4). Volatilization of alfuzosin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.5X10-20 atm-cu m/mole(5), using a fragment constant estimation method(5). Alfuzosin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.6X10-13 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2004).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,300(SRC), determined from a structure estimation method(2), indicates that alfuzosin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a an estimated Henry's Law constant of 9.5X10-20 atm-cu m/mole(4), developed using a fragment constant estimation and the natural catioinic state of the compound. The pKa of alfuzosin is 8.13(5), indicating that this compound will primarily exist in the protonated form in the environment and cations generally adsorb more strongly to suspended solids and sediment than their neutral counterparts(6). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that may readily hydrolyze under environmental conditions. According to a classification scheme(7), an estimated BCF of 5(SRC), from an estimated log Kow of 1.86(8), and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2004).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), alfuzosin, which has an estimated vapor pressure of 4.6X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase. Particulate-phase alfuzosin may be removed from the air by wet and dry deposition(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc for alfuzosin can be estimated to be 1,300(SRC). According to a classification scheme(2), this estimated Koc value suggests that alfuzosin is expected to have low mobility in soil. The pKa of alfuzosin is 8.13(3), indicating that this compound will primarily exist in the protonated form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(4).
/CASE REPORTS/ Drug-induced hepatic injury is a potential complication of virtually all drugs because the liver is central to the metabolic disposition of almost all drugs, although precise mechanisms often are unknown. We report a case of severe acute mixed hepatitis (cholestatic and hepatocellular), probably induced by alfuzosin. ... Viral causes, autoimmune hepatitis and biliary tree obstruction were excluded. After discontinuation of the drug, liver function test results returned to normal.
/CASE REPORTS/ An 80-year-old man was evaluated because of jaundice and pruritus. He was diagnosed as having Child-Pugh A chronic liver disease due to hepatitis B virus. Other etiologies of hepatitis were appropriately ruled out, and the hepatitis B was non-replicative. Therefore, elevated liver enzyme levels were ascribed to alfuzosin treatment. DISCUSSION: Although alfuzosin-related mixed-type hepatotoxicity has been previously reported, this is the first published case describing probable hepatocellular-type hepatotoxicity resulting from use of alfuzosin in a patient with underlying chronic liver disease. According to the Naranjo probability scale, alfuzosin was a probable cause of the hepatotoxicity. The mechanism of alfuzosin-induced liver damage is unknown. Several features, such as absence of predictable dose-dependent toxicity of alfuzosin in previous studies and absence of hypersensitivity manifestations in our case, are suggestive of a metabolic type of idiosyncratic toxicity.
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
alfuzosin
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
An estimated BCF of 5 was calculated for alfuzosin(SRC), using an estimated log Kow of 1.86(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
The Henry's Law constant for alfuzosin is estimated as 9.47X10-20 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that alfuzosin is expected to be essentially nonvolatile. Alfuzosin is not expected to volatilize from dry soil surfaces(SRC) based upon a an estimated vapor pressure of 4.66X10-13 mm Hg(SRC), determined from a fragment constant method(3).
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ There was no evidence of a drug-related increase in the incidence of tumors in mice following dietary administration of 100 mg/kg/day alfuzosin for 98 weeks in females and males, respectively. The highest dose tested in female mice may not have constituted a maximally tolerated dose. Likewise, there was no evidence of a drug-related increase in the incidence of tumors in rats following dietary administration of 100 mg/kg/day alfuzosin for 104 weeks in females and males, respectively. /Alfuzosin Hydrochloride/
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ There was no evidence of reproductive organ toxicity when male rats were given alfuzosin at daily oral (gavage) doses of up to 250 mg/kg/day for 26 weeks ... No impairment of fertility was observed following oral (gavage) administration to male rats at doses of up to 125 mg/kg/day for 70 days. Estrous cycling was inhibited in rats and dogs at doses of 25 mg/kg and 20 mg/kg, respectively ... although this did not result in impaired fertility in rats. /Alfuzosin Hydrochloride/
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ There was no evidence of teratogenicity or embryotoxicity in rats at maternal (oral gavage) doses up to 250 mg/kg/day ... In rabbits, up to the dose of 100 mg/kg/day ... given orally (via gavage), no evidence of fetal toxicity or teratogenicity was seen. /Alfuzosin Hydrochloride/
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Gestation was slightly prolonged in rats with a maternal dose >5 mg/kg/day (oral gavage) ... but there were no difficulties with parturition. /Alfuzosin Hydrochloride/
/GENOTOXICITY/ Alfuzosin showed no evidence of mutagenic effect in the Ames and mouse lymphoma assays, and was free of any clastogenic effects in the Chinese hamster ovary cell and in vivo mouse micronucleus assays. Alfuzosin treatment did not induce DNA repair in a human cell line.
Particulate-phase alfuzosin may be removed from the air by wet and dry deposition(SRC). Alfuzosin is not expected to undergo hydrolysis this compound lacks functional groups that may readily hydrolyze under environmental conditions(1). By analogy to pyrimidine(2), alfuzosin is expected to absorb light in the environmental UV spectrum and may undergo direct photolysis in water or on soil(SRC).
Occupational exposure to alfuzosin may occur through inhalation and dermal contact with this compound at workplaces where alfuzosin is produced or used. The general population may be exposed to alfuzosin via ingestion of pharmaceutical products containing alufozosin. (SRC)
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl alfuzosin hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Alfuzosin Hydrochloride/
Following oral administration of Uroxatral 10 mg tablets, the apparent elimination half-life is 10 hours. /Extended Release Alfuzosin Hydrochloride/
Alfuzosin undergoes extensive hepatic metabolism; only 11% of the administered dose is detected unchanged in the urine. Alfuzosin is metabolism occurs via three metabolic pathways: oxidation, O-demethylations, and N-dealkylation. Metabolites of alfuzosin are not pharmacologically active and CYP3A4 is main hepatic cytochrome enzyme responsible for its metabolism.
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-demethylation, and N-dealkylation. The metabolites are not pharmacologically active. CYP3A4 is the principal hepatic enzyme isoform involved in its metabolism. /Alfuzosin Hydrochloride/
90347YTW5F
ALFUZOSIN
Mechanisms of Action [MoA] - Adrenergic alpha-Antagonists
Established Pharmacologic Class [EPC] - alpha-Adrenergic Blocker
Alfuzosin is an alpha-Adrenergic Blocker. The mechanism of action of alfuzosin is as an Adrenergic alpha-Antagonist.
Drugs that bind to and block the activation of ADRENERGIC ALPHA-1 RECEPTORS.
Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS.
Alfuzosin is readily absorbed in the gastrointestinal tract and the absolute bioavailability under fed conditions is 49%. In patients over 75 years of age, alfuzosin is absorbed more rapidly and peak plasma levels are higher. One source mentions a bioavailability of 64%. After multiple doses under fed conditions, Cmax is achieved in 8 hours. Cmax and AUC0-24 values are about 13.6 ng/mL and 194 ng·h/mL, respectively. Steady-state plasma concentrations are achieved after the second dose and are 1.2 to 1.6 times higher than after a single dose. With the extended-release formulation, alfuzosin release is sustained over 20 hours with a rate of dissolution ranging between 2 and 12 hours.
It is partially metabolised and excreted mainly in the bile and faeces. Following oral administration of a radiolabeled alfuzosin solution, the detection of radioactivity after one week was 69% in the feces and 24% in the urine.
The volume of distribution of alfuzosin after intravenous administration in healthy volunteers is about 3.2 L/kg. Alfuzosin distributes heavily to the tissues of the prostate.
Exercise caution if renal clearance is < 30 mL/min. The clearance of alfuzosin is increased in renal insufficiency (with or without dialysis), due to an increase in the free fraction.
Following oral administration of (14)C-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. /Alfuzosin Hydrochloride/
The volume of distribution following intravenous administration in healthy male middle-aged volunteers was 3.2 L/kg. Results of in vitro studies indicate that alfuzosin is moderately bound to human plasma proteins (82% to 90%), with linear binding over a wide concentration range (5 to 5,000 ng/mL). /Alfuzosin Hydrochloride/
Medication: antihypertensive
Use (kg; approx.) in Germany (2009): >250
Oral: Tablets, extended-release 10 mg Uroxatral (with povidone), (Sanofi-Synthelabo).
Uroxatral
Preparation: P.M.J. Manoury, DE 2904445; idem, US 4315007 (1979, 1982 both to Synthelabo)
Information available in 2004 indicated that Alfuzosin was used in the manufacture of pharmaceutical preparations in the following countries: Argentina, Romania
Information available in 2004 indicated that Alfuzosin hydrochloride was used in the manufacture of pharmaceutical preparations in the following countries: Algeria, Argentina, Austria, Belgium, Brazil, Canada, Chile, Colombia, Costa Rica, Czech Republic, Denmark, Dominican Republic, Ecuador, El Salvador, Finland, France, Germany, Greece, Guatemala, Honduras, Hong Kong, Hungary, Ireland, Israel, Italy, Luxembourg, Malaysia, Netherlands, Nicaragua, Norway, Panama, Poland, Portugal, Romania, Russian Federation, Singapore, South Africa, Spain, Sweden, Switzerland, Thailand, Turkey, United Kingdom, USA, Yugoslavia (1,2) /Alfuzosin hydrochloride/
개요Alfuzosin hydrochloride is a post-synaptic a-antagonist useful in the symptomatic treatment of benign prostatic hypertrophy and acute adenoma by lowering urethral contractions induced by alpha, stimulation. Alfuzosin is also being developed as an antihypertensive; its efficacy in this indication is comparable to prazosin with no significant change in heart rate.
용도dietary supplement
일반 설명Alfuzosin is also a quinazoline 1-blockerbut differs from terazosin in replacing the piperazine ring interazosin with an open piperazine ring (a rotatable propylenediaminegroup). Alfuzosin is more selective for thesubtype of α1A-receptor in the prostate gland than those invascular tissue. Thus, it has been used extensively in treatingBPH as a first-line drug with fewer cardiovascular sideeffects than terazosin and doxazosin.