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Details

Stereochemistry RACEMIC
Molecular Formula C23H16O6.C21H27ClN2O2
Molecular Weight 763.2754
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYZINE PAMOATE

SMILES

c1ccc2c(c1)cc(c(c2Cc3c4ccccc4cc(c3O)C(=O)O)O)C(=O)O.c1ccc(cc1)C(c2ccc(cc2)Cl)N3CCN(CC3)CCOCCO

InChI

InChIKey=ASDOKGIIKXGMNB-UHFFFAOYSA-N
InChI=1S/C23H16O6.C21H27ClN2O2/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29;22-20-8-6-19(7-9-20)21(18-4-2-1-3-5-18)24-12-10-23(11-13-24)14-16-26-17-15-25/h1-10,24-25H,11H2,(H,26,27)(H,28,29);1-9,21,25H,10-17H2

HIDE SMILES / InChI

Molecular Formula C21H27ClN2O2
Molecular Weight 374.905
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C23H16O6
Molecular Weight 388.3704
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Leishmania (L.) infantum promastigotes viability
59.57 µM [IC50]
38.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
VISTARIL

Approved Use

For 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 Date

7.8589441E11
Palliative
VISTARIL

Approved Use

For 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 Date

7.8589441E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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

Doses

DosePopulationAdverse 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)
Dry mouth (12 patients)
Irritability (7 patients)
Dizziness (3 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
yes [Ki 4 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets
PubMed

PubMed

TitleDatePubMed
Prolonged penile erections induced by hydroxyzine: possible mechanism of action.
1994
Inhibition of mediator release in RBL-2H3 cells by some H1-antagonist derived anti-allergic drugs: relation to lipophilicity and membrane effects.
1995 Feb
[Modification of cognitive functions by 2 anxiolytic treatments in patients suffering from generalized anxiety].
1995 Mar-Apr
Hydroxyzine inhibits neurogenic bladder mast cell activation.
1998 Oct
[Pruritus without skin manifestation--what kind of state of the art nursing intervention?].
2003 Oct
[Preoperative psychopharmacological correction in women with focal breast diseases].
2005 May-Jun
[The use of atarax in the treatment of tic hyperkinesia in children: a pilot study].
2006
Skin reaction to hydroxyzine (Atarax): patch test utility.
2006 Apr
Masitinib in the treatment of active rheumatoid arthritis: results of a multicentre, open-label, dose-ranging, phase 2a study.
2009
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
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
by admin
on Fri Jun 25 22:10:57 UTC 2021
Edited
by admin
on Fri Jun 25 22:10:57 UTC 2021
Record UNII
M20215MUFR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYDROXYZINE PAMOATE
MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
HYDROXYZINE EMBONATE [WHO-DD]
Common Name English
HYDROXYZINE EMBONATE [MART.]
Common Name English
HYDROXYZINE EMBONATE
MART.   WHO-DD  
Common Name English
HYDROXYZINE PAMOATE [USP]
Common Name English
HYDROXYZINE PAMOATE [VANDF]
Common Name English
HYDROXYZINE PAMOATE [MI]
Common Name English
NSC-757063
Code English
(+/-)-2-(2-(4-(P-CHLORO-.ALPHA.-PHENYLBENZYL)-1-PIPERAZINYL)ETHOXY)ETHANOL 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHOATE) (1:1)
Common Name English
HYDROXYZINE PAMOATE [USP-RS]
Common Name English
HYDROXYZINE PAMOATE [ORANGE BOOK]
Common Name English
HY-PAM
Brand Name English
ETHANOL, 2-(2-(4-((4-CHLOROPHENYL)PHENYLMETHYL)-1-PIPERAZINYL)ETHOXY)-, (+/-)-, COMPD. WITH 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHALENECARBOXYLIC ACID) (1:1)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
Code System Code Type Description
MERCK INDEX
M6159
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
PRIMARY Merck Index
EVMPD
SUB02597MIG
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
PRIMARY
RXCUI
203182
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
PRIMARY RxNorm
USP_CATALOG
1334006
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
PRIMARY USP-RS
FDA UNII
M20215MUFR
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL896
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
PRIMARY
NCI_THESAURUS
C47560
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
PRIMARY
CAS
10246-75-0
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
PRIMARY
PUBCHEM
25096
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
PRIMARY
DRUG BANK
DBSALT000984
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
233-582-1
Created by admin on Fri Jun 25 22:10:57 UTC 2021 , Edited by admin on Fri Jun 25 22:10:57 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SALT/SOLVATE -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY