Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H27ClN2O2 |
Molecular Weight | 374.904 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OCCOCCN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(Cl)C=C3
InChI
InChIKey=ZQDWXGKKHFNSQK-UHFFFAOYSA-N
InChI=1S/C21H27ClN2O2/c22-20-8-6-19(7-9-20)21(18-4-2-1-3-5-18)24-12-10-23(11-13-24)14-16-26-17-15-25/h1-9,21,25H,10-17H2
Molecular Formula | C21H27ClN2O2 |
Molecular Weight | 374.904 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB00557Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/011459s048,011795s025lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00557
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/011459s048,011795s025lbl.pdf
Hydroxyzine, a piperazine antihistamine structurally related to buclizine, cyclizine, and meclizine, is used to treat histamine-mediated pruritus or pruritus due to allergy, nausea and vomiting, and, in combination with an opiate agonist, anxiolytic pain. Hydroxyzine is also used as a perioperative sedative and anxiolytic and to manage acute alcohol withdrawal. Hydroxyzine competes with histamine for binding at H1-receptor sites on the effector cell surface, resulting in suppression of histaminic edema, flare, and pruritus. The sedative properties of hydroxyzine occur at the subcortical level of the CNS. Secondary to its central anticholinergic actions, hydroxyzine may be effective as an antiemetic. It is used for symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Leishmania (L.) infantum promastigotes viability Sources: https://www.ncbi.nlm.nih.gov/pubmed/24905294 |
59.57 µM [IC50] | ||
Target ID: CHEMBL231 Sources: http://www.drugbank.ca/drugs/DB00557 |
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Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17447421 |
38.0 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | VISTARIL Approved UseFor symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested.
Useful in the management of pruritus due to allergic conditions such as chronic urticaria and atopic and contact dermatoses, and in histamine-mediated pruritus. Launch Date7.8589441E11 |
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Palliative | VISTARIL Approved UseFor symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested.
Useful in the management of pruritus due to allergic conditions such as chronic urticaria and atopic and contact dermatoses, and in histamine-mediated pruritus. Launch Date7.8589441E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
31.371 ng/mL |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROXYZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
72.5 ng/mL |
0.7 mg/kg bw single, oral dose: 0.7 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
HYDROXYZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
72.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6141198/ |
0.7 mg/kg bw single, oral dose: 0.7 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
HYDROXYZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
479.174 ng × h/mL |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROXYZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.4 h |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROXYZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
20 h |
0.7 mg/kg bw single, oral dose: 0.7 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
HYDROXYZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
20 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6141198/ |
0.7 mg/kg bw single, oral dose: 0.7 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
HYDROXYZINE serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
50 mg 3 times / day multiple, oral Highest studied dose Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, 19 - 34 yars n = 19 Health Status: unhealthy Condition: seasonal allergic rhinitis Age Group: 19 - 34 yars Sex: M+F Population Size: 19 Sources: |
Disc. AE: Drowsiness... Other AEs: Drowsiness, Dry mouth... AEs leading to discontinuation/dose reduction: Drowsiness (1 patient) Other AEs:Drowsiness (17 patients) Sources: Dry mouth (12 patients) Irritability (7 patients) Dizziness (3 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Drowsiness | 1 patient Disc. AE |
50 mg 3 times / day multiple, oral Highest studied dose Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, 19 - 34 yars n = 19 Health Status: unhealthy Condition: seasonal allergic rhinitis Age Group: 19 - 34 yars Sex: M+F Population Size: 19 Sources: |
Dry mouth | 12 patients | 50 mg 3 times / day multiple, oral Highest studied dose Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, 19 - 34 yars n = 19 Health Status: unhealthy Condition: seasonal allergic rhinitis Age Group: 19 - 34 yars Sex: M+F Population Size: 19 Sources: |
Drowsiness | 17 patients | 50 mg 3 times / day multiple, oral Highest studied dose Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, 19 - 34 yars n = 19 Health Status: unhealthy Condition: seasonal allergic rhinitis Age Group: 19 - 34 yars Sex: M+F Population Size: 19 Sources: |
Dizziness | 3 patients | 50 mg 3 times / day multiple, oral Highest studied dose Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, 19 - 34 yars n = 19 Health Status: unhealthy Condition: seasonal allergic rhinitis Age Group: 19 - 34 yars Sex: M+F Population Size: 19 Sources: |
Irritability | 7 patients | 50 mg 3 times / day multiple, oral Highest studied dose Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, 19 - 34 yars n = 19 Health Status: unhealthy Condition: seasonal allergic rhinitis Age Group: 19 - 34 yars Sex: M+F Population Size: 19 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/11290874/ Page: 5.0 |
likely | |||
yes [Ki 4 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/12584158/ Page: 6.0 |
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Peripheral antihistamine and central sedative effects of three H1-receptor antagonists. | 1985 |
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A comparison of acrivastine versus hydroxyzine and placebo in the treatment of chronic idiopathic urticaria. | 1989 |
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Prolongation of simple and choice reaction times in a double-blind comparison of twice-daily hydroxyzine versus terfenadine. | 1989 Sep |
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Controlled trial of H1 antagonists in the treatment of chronic idiopathic urticaria. | 1991 Oct |
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Prolonged penile erections induced by hydroxyzine: possible mechanism of action. | 1994 |
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Hydroxyzine inhibits neurogenic bladder mast cell activation. | 1998 Oct |
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Cetirizine-induce cholestasis. | 2000 Oct |
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Binding characteristics of cetirizine and levocetirizine to human H(1) histamine receptors: contribution of Lys(191) and Thr(194). | 2002 Feb |
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[Pruritus without skin manifestation--what kind of state of the art nursing intervention?]. | 2003 Oct |
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P-glycoprotein influences the brain concentrations of cetirizine (Zyrtec), a second-generation non-sedating antihistamine. | 2003 Oct |
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Case studies: Use of salicylic acid (Avosil) and hydrogel (Avogel) in limiting scar formation. | 2005 Mar 28 |
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Free radical oxidation in rat brain during chronic stress and pharmacological regulation of this process. | 2005 Oct |
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[The use of atarax in the treatment of tic hyperkinesia in children: a pilot study]. | 2006 |
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[Use of anxiolytic atarax as a substitutive drug for benzodiazepine tranquilizers]. | 2007 |
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Depressive symptoms in urticaria patients treated with first- or second-generation histamine 1 receptor antagonists. | 2007 Aug |
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Masitinib in the treatment of active rheumatoid arthritis: results of a multicentre, open-label, dose-ranging, phase 2a study. | 2009 |
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Characterization of anti-inflammatory properties and evidence for no sedation liability for the novel antihistamine SUN-1334H. | 2010 |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Patents
Sample Use Guides
For symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested: in adults, 50-100 mg q.i.d.; children under 6 years, 50 mg daily in divided doses; and over 6 years, 50-100 mg daily in divided doses.
For use in the management of pruritus due to allergic conditions such as chronic urticaria and atopic and contact dermatoses, and in histamine-mediated pruritus: in adults, 25 mg t.i.d. or q.i.d.; children under 6 years, 50 mg daily in divided doses; and over 6 years, 50-100 mg daily in divided doses.
As a sedative when used as a premedication and following general anesthesia: 50-100 mg in adults, and 0.6 mg/kg in children.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9839659
Hydroxyzine reduced carbachol-induced serotonin release by 25% at 10(-6) M and 34% at 10(-5) M in rat bladder mast cells
Substance Class |
Chemical
Created
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on
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Record UNII |
30S50YM8OG
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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LIVERTOX |
NBK548128
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NDF-RT |
N0000175750
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NDF-RT |
N0000000207
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WHO-VATC |
QN05BB01
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NCI_THESAURUS |
C29578
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WHO-ATC |
N05BB01
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WHO-VATC |
QN05BB51
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WHO-ATC |
N05BB51
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Code System | Code | Type | Description | ||
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169188
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Hydroxyzine
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3658
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C29103
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5553
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30S50YM8OG
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3098
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DTXSID8023137
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100000083664
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147152-21-4
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M6159
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599
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HYDROXYZINE
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200-693-1
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7199
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5818
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D006919
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1400
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30S50YM8OG
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DB00557
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CHEMBL896
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SUB08088MIG
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68-88-2
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET -> INHIBITOR |
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METABOLIC ENZYME -> INHIBITOR |
Inhibition of bufuralol 1′-hydroxylation. Could be clinically relevant concentration in liver is within these values.
COMPETITIVE INHIBITOR
Ki
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OFF-TARGET->INHIBITOR |
IC50
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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PLASMA CONCENTRATION | PHARMACOKINETIC |
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LIVER/PLASMA RATIO | PHARMACOKINETIC |
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LIVER CONCENTRATION | PHARMACOKINETIC |
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