Details
Stereochemistry | RACEMIC |
Molecular Formula | C23H25N5O5 |
Molecular Weight | 451.4751 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=NC(=NC(N)=C2C=C1OC)N3CCN(CC3)C(=O)C4COC5=CC=CC=C5O4
InChI
InChIKey=RUZYUOTYCVRMRZ-UHFFFAOYSA-N
InChI=1S/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)
Molecular Formula | C23H25N5O5 |
Molecular Weight | 451.4751 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Doxazosin mesylate is a quinazoline compound sold by Pfizer under the brand name CARDURA. CARDURA is indicated for the treatment of both the
urinary outflow obstruction and obstructive and irritative symptoms associated with BPH: obstructive symptoms (hesitation, intermittency, dribbling, weak urinary stream, incomplete emptying of the bladder) and irritative symptoms (nocturia, daytime frequency, urgency, burning). CARDURA may be used in all BPH patients whether hypertensive or normotensive. In
patients with hypertension and BPH, both conditions were effectively treated with CARDURA monotherapy. CARDURA provides rapid improvement in symptoms and urinary flow rate in 66–71% of patients. CARDURA is also indicated for the treatment of hypertension. CARDURA
may be used alone or in combination with diuretics, beta-adrenergic blocking agents, calcium channel blockers, or angiotensin-converting enzyme inhibitors. Doxazosin acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation.
Originator
Sources: http://adisinsight.springer.com/drugs/800010345
Curator's Comment: # Pfizer
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
9.27 null [pKi] | |||
9.09 null [pKi] | |||
9.09 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CARDURA Approved UseINDICATIONS AND USAGE
A. Benign Prostatic Hyperplasia (BPH). CARDURA is indicated for the treatment of both the
urinary outflow obstruction and obstructive and irritative symptoms associated with BPH:
obstructive symptoms (hesitation, intermittency, dribbling, weak urinary stream, incomplete
emptying of the bladder) and irritative symptoms (nocturia, daytime frequency, urgency,
burning). CARDURA may be used in all BPH patients whether hypertensive or normotensive. In
patients with hypertension and BPH, both conditions were effectively treated with CARDURA
monotherapy. CARDURA provides rapid improvement in symptoms and urinary flow rate in
66–71% of patients. Sustained improvements with CARDURA were seen in patients treated for
up to 14 weeks in double-blind studies and up to 2 years in open-label studies.
B. Hypertension. CARDURA is also indicated for the treatment of hypertension. CARDURA
may be used alone or in combination with diuretics, beta-adrenergic blocking agents, calcium
channel blockers, or angiotensin-converting enzyme inhibitors. Launch Date1990 |
|||
Primary | CARDURA Approved UseINDICATIONS AND USAGE
A. Benign Prostatic Hyperplasia (BPH). CARDURA is indicated for the treatment of both the
urinary outflow obstruction and obstructive and irritative symptoms associated with BPH:
obstructive symptoms (hesitation, intermittency, dribbling, weak urinary stream, incomplete
emptying of the bladder) and irritative symptoms (nocturia, daytime frequency, urgency,
burning). CARDURA may be used in all BPH patients whether hypertensive or normotensive. In
patients with hypertension and BPH, both conditions were effectively treated with CARDURA
monotherapy. CARDURA provides rapid improvement in symptoms and urinary flow rate in
66–71% of patients. Sustained improvements with CARDURA were seen in patients treated for
up to 14 weeks in double-blind studies and up to 2 years in open-label studies.
B. Hypertension. CARDURA is also indicated for the treatment of hypertension. CARDURA
may be used alone or in combination with diuretics, beta-adrenergic blocking agents, calcium
channel blockers, or angiotensin-converting enzyme inhibitors. Launch Date1990 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2139337/ |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
13.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2139337/ |
1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
14.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2951261/ |
1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
151.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2951261/ |
16 mg 1 times / day steady-state, oral dose: 16 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
42.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2951261/ |
4 mg 1 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
65.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2951261/ |
8 mg 1 times / day steady-state, oral dose: 8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
162 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2139337/ |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
268 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2139337/ |
1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2139337/ |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2139337/ |
1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
11.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2951261/ |
1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
11.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2951261/ |
16 mg 1 times / day steady-state, oral dose: 16 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
12.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2951261/ |
4 mg 1 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
8.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2951261/ |
8 mg 1 times / day steady-state, oral dose: 8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DOXAZOSIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
60 mg single, oral Overdose |
healthy, 19 years n = 1 Health Status: healthy Age Group: 19 years Sex: F Population Size: 1 Sources: |
Disc. AE: Sinus tachycardia... AEs leading to discontinuation/dose reduction: Sinus tachycardia (1 patient) Sources: |
16 mg single, oral (max) Highest studied dose Dose: 16 mg Route: oral Route: single Dose: 16 mg Sources: |
unhealthy, adult n = 665 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: unknown Population Size: 665 Sources: |
DLT: Postural edema... Dose limiting toxicities: Postural edema (2.7%) Sources: |
4 mg 1 times / day steady, oral Recommended Dose: 4 mg, 1 times / day Route: oral Route: steady Dose: 4 mg, 1 times / day Sources: |
healthy, adult n = 35 Health Status: healthy Age Group: adult Sex: unknown Population Size: 35 Sources: |
Disc. AE: Orthostatic dizziness... AEs leading to discontinuation/dose reduction: Orthostatic dizziness (1 patient) Sources: |
16 mg 1 times / day steady, oral (max) Highest studied dose Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Sources: |
unhealthy, mean 59 years n = 97 Health Status: unhealthy Condition: Hypertension Age Group: mean 59 years Sex: M+F Population Size: 97 Sources: |
Disc. AE: Fatigue, Urinary incontinence... Other AEs: Rhinitis... AEs leading to discontinuation/dose reduction: Fatigue (3 patients) Other AEs:Urinary incontinence (2 patients) Rhinitis (1 patient) Sources: |
8 mg 1 times / day steady, oral Dose: 8 mg, 1 times / day Route: oral Route: steady Dose: 8 mg, 1 times / day Sources: |
unhealthy n = 22 Health Status: unhealthy Condition: cocaine dependence Population Size: 22 Sources: |
Other AEs: Nausea, Constipation... Other AEs: Nausea (below serious, 2 patients) Sources: Constipation (below serious, 1 patient) Allergy (below serious, 1 patient) Dizziness (below serious, 1 patient) Numbness (below serious, 1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Sinus tachycardia | 1 patient Disc. AE |
60 mg single, oral Overdose |
healthy, 19 years n = 1 Health Status: healthy Age Group: 19 years Sex: F Population Size: 1 Sources: |
Postural edema | 2.7% DLT |
16 mg single, oral (max) Highest studied dose Dose: 16 mg Route: oral Route: single Dose: 16 mg Sources: |
unhealthy, adult n = 665 Health Status: unhealthy Condition: Hypertension Age Group: adult Sex: unknown Population Size: 665 Sources: |
Orthostatic dizziness | 1 patient Disc. AE |
4 mg 1 times / day steady, oral Recommended Dose: 4 mg, 1 times / day Route: oral Route: steady Dose: 4 mg, 1 times / day Sources: |
healthy, adult n = 35 Health Status: healthy Age Group: adult Sex: unknown Population Size: 35 Sources: |
Rhinitis | 1 patient | 16 mg 1 times / day steady, oral (max) Highest studied dose Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Sources: |
unhealthy, mean 59 years n = 97 Health Status: unhealthy Condition: Hypertension Age Group: mean 59 years Sex: M+F Population Size: 97 Sources: |
Urinary incontinence | 2 patients Disc. AE |
16 mg 1 times / day steady, oral (max) Highest studied dose Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Sources: |
unhealthy, mean 59 years n = 97 Health Status: unhealthy Condition: Hypertension Age Group: mean 59 years Sex: M+F Population Size: 97 Sources: |
Fatigue | 3 patients Disc. AE |
16 mg 1 times / day steady, oral (max) Highest studied dose Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Sources: |
unhealthy, mean 59 years n = 97 Health Status: unhealthy Condition: Hypertension Age Group: mean 59 years Sex: M+F Population Size: 97 Sources: |
Allergy | below serious, 1 patient | 8 mg 1 times / day steady, oral Dose: 8 mg, 1 times / day Route: oral Route: steady Dose: 8 mg, 1 times / day Sources: |
unhealthy n = 22 Health Status: unhealthy Condition: cocaine dependence Population Size: 22 Sources: |
Constipation | below serious, 1 patient | 8 mg 1 times / day steady, oral Dose: 8 mg, 1 times / day Route: oral Route: steady Dose: 8 mg, 1 times / day Sources: |
unhealthy n = 22 Health Status: unhealthy Condition: cocaine dependence Population Size: 22 Sources: |
Dizziness | below serious, 1 patient | 8 mg 1 times / day steady, oral Dose: 8 mg, 1 times / day Route: oral Route: steady Dose: 8 mg, 1 times / day Sources: |
unhealthy n = 22 Health Status: unhealthy Condition: cocaine dependence Population Size: 22 Sources: |
Numbness | below serious, 1 patient | 8 mg 1 times / day steady, oral Dose: 8 mg, 1 times / day Route: oral Route: steady Dose: 8 mg, 1 times / day Sources: |
unhealthy n = 22 Health Status: unhealthy Condition: cocaine dependence Population Size: 22 Sources: |
Nausea | below serious, 2 patients | 8 mg 1 times / day steady, oral Dose: 8 mg, 1 times / day Route: oral Route: steady Dose: 8 mg, 1 times / day Sources: |
unhealthy n = 22 Health Status: unhealthy Condition: cocaine dependence Population Size: 22 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | likely (co-administration study) Comment: Boceprevir may increase doxazosin concentrations through CYP3A inhibition |
|||
minor | ||||
minor | ||||
minor |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Quality-of-life assessment in patients with benign prostatic hyperplasia: effects of various interventions. | 2001 |
|
Effects of two atypical neuroleptics, olanzapine and risperidone, on the function of the urinary bladder and the external urethral sphincter in anesthetized rats. | 2001 |
|
Discontinuation of alpha-blockade after initial treatment with finasteride and doxazosin for bladder outlet obstruction. | 2001 |
|
Reduced heat shock proteins: a mechanism to explain higher cardiovascular events associated with doxazosin. | 2001 Apr |
|
Apoptotic activity of doxazosin on prostate stroma in vitro is mediated through an autocrine expression of TGF-beta1. | 2001 Aug 1 |
|
Tamsulosin: current clinical experience. | 2001 Dec |
|
Low-dose ACE with alpha- or beta-adrenergic receptor inhibitors have beneficial SHR cardiovascular effects. | 2001 Jan |
|
pH-mediated field-amplified sample stacking of pharmaceutical cations in high-ionic strength samples. | 2001 Jan |
|
A quantitative analysis of antagonism and inverse agonism at wild-type and constitutively active hamster alpha1B-adrenoceptors. | 2001 Jan |
|
On call. I'm a 76-year-old man with an enlarged prostate. I've been taking Cardura and it's helped a lot, but my doctor stopped it because he said a study found the drug could cause heart failure. Now I'm getting up three or four times a night again. Is Cadura safe? | 2001 Jul |
|
Safety and availability of doxazosin in treating hypertensive patients with chronic renal failure. | 2001 Jul |
|
Antihypertensive effect of alpha- and beta-adrenergic blockade in obese and lean hypertensive subjects. | 2001 Jul |
|
Reduction of human prostate tumor vascularity by the alpha1-adrenoceptor antagonist terazosin. | 2001 Jul 1 |
|
Doxazosin added to single-drug therapy in hypertensive patients with benign prostatic hypertrophy. | 2001 Jul-Aug |
|
US FDA weighs options for warning on antihypertensive drug. | 2001 Jun 2 |
|
[Long-term therapy of benign prostatic hyperplasia. Our experience]. | 2001 Mar |
|
The release of the substrate for xanthine oxidase in hypertensive patients was suppressed by angiotensin converting enzyme inhibitors and alpha1-blockers. | 2001 Mar |
|
The cost-effectiveness of doxazosin for the treatment of hypertension in type II diabetic patients in the UK and Italy. | 2001 Mar |
|
Reversible renal impairment induced by treatment with the angiotensin II receptor antagonist candesartan in a patient with bilateral renal artery stenosis. | 2001 May 17 |
|
[Doksazozin "Cardura" in acute urinary retention caused by benign prostatic hyperplasia]. | 2001 May-Jun |
|
Effects of antihypertensive agents on blood pressure during exercise. | 2001 Nov |
|
Ventricular production of natriuretic peptides and ventricular structural remodeling in hypertensive heart failure. | 2001 Oct |
|
The choice of antihypertensive drugs in patients with erectile dysfunction. | 2002 |
|
Effect of doxazosin on rat urinary bladder function after partial outlet obstruction. | 2002 |
|
Acute effects of serotonin on rat bladder contractility. | 2002 |
|
Efficacy and safety of doxazosin for perioperative management of patients with pheochromocytoma. | 2002 Aug |
|
Medical therapy for benign prostatic hyperplasia progression. | 2002 Aug |
|
Effect of doxazosin on stretch-activated adenosine triphosphate release in bladder urothelial cells from patients with benign prostatic hyperplasia. | 2002 Aug |
|
Microalbuminuria reduction with valsartan in patients with type 2 diabetes mellitus: a blood pressure-independent effect. | 2002 Aug 6 |
|
Modeling of relationships between pharmacokinetics and blockade of agonist-induced elevation of intraurethral pressure and mean arterial pressure in conscious dogs treated with alpha(1)-adrenoceptor antagonists. | 2002 Feb |
|
Quinazoline-derived alpha1-adrenoceptor antagonists induce prostate cancer cell apoptosis via an alpha1-adrenoceptor-independent action. | 2002 Jan 15 |
|
Doxazosin, an inferior antihypertensive agent? | 2002 Jun |
|
Doxazosin and congestive heart failure. | 2002 May-Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/doxazosin.html
Usual Adult Dose for Hypertension
Initial dose: 1 mg orally once a day.
Maintenance dose: 1 to 16 mg orally once a day.
Usual Adult Dose for Benign Prostatic Hyperplasia
Initial dose:
Immediate-release: 1 mg orally once a day.
Extended-release: 4 mg orally once a day with breakfast
Maintenance dose:
Immediate-release: 1 to 8 mg orally once a day.
Extended-release: 4 to 8 mg orally once a day with breakfast. Depending on the patient's symptomatic response and tolerability, the dose may be increased to 8 mg (the maximum recommended dose). The recommended titration interval is 3 to 4 weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2977161
Ring segments of splanchnic, peripheral, coronary, pulmonary and uterine conduit arteries obtained during surgery were studied in tissue baths. Resistance arteries dissected from various sites were studied in a myograph. Both conduit and resistance vessels contracted in response to the alpha 1-agonist phenylephrine (10(-7) to 10(-4) mol/l), an effect that was antagonized by the alpha 1-antagonist doxazosin (10(-8) to 10(-6) mol/l).
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:39:35 GMT 2023
by
admin
on
Sat Dec 16 17:39:35 GMT 2023
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Record UNII |
NW1291F1W8
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175553
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N0000000099
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NCI_THESAURUS |
C29713
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LIVERTOX |
NBK548718
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QC02CA04
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C02CA04
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C29707
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Code System | Code | Type | Description | ||
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DOXAZOSIN
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49276
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74191-85-8
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3157
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Doxazosin
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100000080772
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m4752
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CHEMBL707
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DB00590
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
FECAL; URINE
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METABOLITE -> PARENT |
known active and inactive metabolites of doxazosin were detected
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METABOLITE -> PARENT |
known active and inactive metabolites of doxazosin were detected
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METABOLITE -> PARENT |
FECAL; URINE
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METABOLITE -> PARENT |
MINOR
FECAL; URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
FECAL; URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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