U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H9Cl2N3O
Molecular Weight 246.093
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GUANFACINE

SMILES

NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl

InChI

InChIKey=INJOMKTZOLKMBF-UHFFFAOYSA-N
InChI=1S/C9H9Cl2N3O/c10-6-2-1-3-7(11)5(6)4-8(15)14-9(12)13/h1-3H,4H2,(H4,12,13,14,15)

HIDE SMILES / InChI

Molecular Formula C9H9Cl2N3O
Molecular Weight 246.093
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TENEX

Approved Use

Tenex (guanfacine hydrochloride) is indicated in the management of hypertension. Tenex may be given alone or in combination with other antihypertensive agents, especially thiazide-type diuretics.

Launch Date

5.30755191E11
Primary
TENEX

Approved Use

INTUNIV® is a central alpha2A-adrenergic receptor agonist indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) as monotherapy and as adjunctive therapy to stimulant medications

Launch Date

5.30755191E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7 ng/mL
4 mg 1 times / day multiple, oral
dose: 4 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GUANFACINE plasma
Homo sapiens
population: UNKNOWN
age: ADOLESCENT
sex: UNKNOWN
food status: UNKNOWN
10 ng/mL
4 mg 1 times / day multiple, oral
dose: 4 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GUANFACINE plasma
Homo sapiens
population: UNKNOWN
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
2.5 ng/mL
1 mg 1 times / day multiple, oral
dose: 1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GUANFACINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
116 ng × h/mL
4 mg 1 times / day multiple, oral
dose: 4 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GUANFACINE plasma
Homo sapiens
population: UNKNOWN
age: ADOLESCENT
sex: UNKNOWN
food status: UNKNOWN
162 ng × h/mL
4 mg 1 times / day multiple, oral
dose: 4 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GUANFACINE plasma
Homo sapiens
population: UNKNOWN
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
56 ng × h/mL
1 mg 1 times / day multiple, oral
dose: 1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GUANFACINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
16 h
1 mg 1 times / day multiple, oral
dose: 1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GUANFACINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
30%
1 mg 1 times / day multiple, oral
dose: 1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GUANFACINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
12 mg single, oral
Overdose
Dose: 12 mg
Route: oral
Route: single
Dose: 12 mg
Sources:
unhealthy, 12 years
n = 1
Health Status: unhealthy
Condition: ADHD and Tourette syndrome
Age Group: 12 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Hypertensive...
AEs leading to
discontinuation/dose reduction:
Hypertensive (1%)
Sources:
80 mg single, oral
Overdose
Dose: 80 mg
Route: oral
Route: single
Dose: 80 mg
Sources:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Condition: ADHD
Age Group: 17 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Cardiogenic pulmonary edema...
AEs leading to
discontinuation/dose reduction:
Cardiogenic pulmonary edema (1%)
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:
unhealthy, children and adolescents
n = 513
Health Status: unhealthy
Condition: ADHD
Age Group: children and adolescents
Sex: M+F
Population Size: 513
Sources:
Disc. AE: Somnolence, Fatigue...
AEs leading to
discontinuation/dose reduction:
Somnolence (6%)
Fatigue (2%)
Hypotension (1%)
Headache (1%)
Dizziness (1%)
Sources:
4 mg 1 times / day steady, oral
Dose: 4 mg, 1 times / day
Route: oral
Route: steady
Dose: 4 mg, 1 times / day
Sources:
unhealthy, children
n = 16
Health Status: unhealthy
Condition: Attention Deficit Hyperactivity Disorder
Age Group: children
Population Size: 16
Sources:
Other AEs: Sedation, Fatigue...
Other AEs:
Sedation (below serious, 5 patients)
Fatigue (below serious, 3 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypertensive 1%
Disc. AE
12 mg single, oral
Overdose
Dose: 12 mg
Route: oral
Route: single
Dose: 12 mg
Sources:
unhealthy, 12 years
n = 1
Health Status: unhealthy
Condition: ADHD and Tourette syndrome
Age Group: 12 years
Sex: M
Population Size: 1
Sources:
Cardiogenic pulmonary edema 1%
Disc. AE
80 mg single, oral
Overdose
Dose: 80 mg
Route: oral
Route: single
Dose: 80 mg
Sources:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Condition: ADHD
Age Group: 17 years
Sex: M
Population Size: 1
Sources:
Dizziness 1%
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:
unhealthy, children and adolescents
n = 513
Health Status: unhealthy
Condition: ADHD
Age Group: children and adolescents
Sex: M+F
Population Size: 513
Sources:
Headache 1%
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:
unhealthy, children and adolescents
n = 513
Health Status: unhealthy
Condition: ADHD
Age Group: children and adolescents
Sex: M+F
Population Size: 513
Sources:
Hypotension 1%
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:
unhealthy, children and adolescents
n = 513
Health Status: unhealthy
Condition: ADHD
Age Group: children and adolescents
Sex: M+F
Population Size: 513
Sources:
Fatigue 2%
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:
unhealthy, children and adolescents
n = 513
Health Status: unhealthy
Condition: ADHD
Age Group: children and adolescents
Sex: M+F
Population Size: 513
Sources:
Somnolence 6%
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:
unhealthy, children and adolescents
n = 513
Health Status: unhealthy
Condition: ADHD
Age Group: children and adolescents
Sex: M+F
Population Size: 513
Sources:
Fatigue below serious, 3 patients
4 mg 1 times / day steady, oral
Dose: 4 mg, 1 times / day
Route: oral
Route: steady
Dose: 4 mg, 1 times / day
Sources:
unhealthy, children
n = 16
Health Status: unhealthy
Condition: Attention Deficit Hyperactivity Disorder
Age Group: children
Population Size: 16
Sources:
Sedation below serious, 5 patients
4 mg 1 times / day steady, oral
Dose: 4 mg, 1 times / day
Route: oral
Route: steady
Dose: 4 mg, 1 times / day
Sources:
unhealthy, children
n = 16
Health Status: unhealthy
Condition: Attention Deficit Hyperactivity Disorder
Age Group: children
Population Size: 16
Sources:
Overview

Overview

Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
yes (co-administration study)
Comment: There was a significant decrease in the rate and extent of guanfacine exposure when co-administered with rifampin, a CYP3A4 inducer. The exposure to guanfacine decreased by 70% (AUC)
Page: 10.0
weak
yes
yes (co-administration study)
Comment: There was a substantial increase in the rate and extent of guanfacine exposure when administered with ketoconazole; the guanfacine exposure increased 3-fold (AUC)
Page: 10.0
Tox targets

Tox targets

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Guanfacine and secondary mania in children.
1999 Aug
Centrally acting imidazoline I1-receptor agonists: do they have a place in the management of hypertension?
2001
Respiratory pattern and hypoxic ventilatory response in mice functionally lacking alpha2A-adrenergic receptors.
2001
Effects of alpha(2)-adrenergic agonists on lipopolysaccharide-induced aqueous flare elevation in pigmented rabbits.
2001 May-Jun
Presynaptic autoregulation of norepinephrine release from the sympathetic nerve fibers in the pineal gland of the domestic pig. Pharmacological characterization of alpha(2)adrenoceptors mediating this process.
2002 Apr
Testosterone dependence of salt-induced hypertension in Sabra rats and role of renal alpha(2)-adrenoceptor subtypes.
2002 Jan
Epidemiology and toxicity of pediatric guanfacine exposures.
2002 Nov
Stimulation of interleukin-12 production in mouse macrophages via activation of p38 mitogen-activated protein kinase by alpha2-adrenoceptor agonists.
2003 Apr 25
Hallucinations associated with initiation of guanfacine.
2003 Dec
Growth hormone response to guanfacine in boys with attention deficit hyperactivity disorder: a preliminary study.
2003 Fall
An antihypokinesic action of alpha2-adrenoceptors upon MPTP-induced behaviour deficits in mice.
2003 Feb
Pharmacological characterization of unique prazosin-binding sites in human kidney.
2003 Jul
Pharmacotherapy of pervasive developmental disorders in children and adolescents.
2004
The alpha(2A)-adrenergic agonist guanfacine improves visuomotor associative learning in monkeys.
2004 Jan
[Centrally-acting antihypertensive drugs].
2004 Mar
Loss of glutamatergic pyramidal neurons in frontal and temporal cortex resulting from attenuation of FGFR1 signaling is associated with spontaneous hyperactivity in mice.
2004 Mar 3
Potential noradrenergic targets for cognitive enhancement in schizophrenia.
2004 May
Methylphenidate an effective treatment for ADHD?
2004 Oct
Pulse-synchronous sympathetic burst power as a new index of sympathoexcitation in patients with heart failure.
2004 Oct
Alpha2 adrenergic agonists for the management of opioid withdrawal.
2004 Oct 18
Alpha-2 adrenoceptor activation inhibits phencyclidine-induced deficits of spatial working memory in rats.
2005 Aug
Aripiprazole in children and adolescents: clinical experience.
2005 Jul
The safety of non-stimulant agents for the treatment of attention-deficit hyperactivity disorder.
2005 Mar
Central sympathetic inhibition augments sleep-related ultradian rhythm of parasympathetic tone in patients with chronic heart failure.
2005 Sep
Mechanism of action of agents used in attention-deficit/hyperactivity disorder.
2006
Tourette's Syndrome.
2006 Jun
Syncope in children with Tourette's syndrome treated with guanfacine.
2006 Mar
Differential noradrenergic influence on seizure expression in genetically Fast and Slow kindling rat strains during massed trial stimulation of the amygdala.
2007 Feb
Patents

Sample Use Guides

Usual Adult Dose for Hypertension Initial dose: 1 mg orally once a day at bedtime; may increase to 2 mg once a day if satisfactory result not achieved after 3 to 4 weeks. Usual Pediatric Dose for Attention Deficit Disorder 6 YEARS TO LESS THAN 18 YEARS: Initial dose: 1 mg orally once a day, either in the morning or evening, at approximately the same time each day; may adjust in increments of no more than 1 mg/week. Recommended target dose: 0.05 to 0.12 mg/kg/day (total daily dose between 1 and 7 mg) once a day, depending on clinical response and tolerability Maximum dose: 6 to 12 years: Doses above 4 mg/day have not been evaluated; 13 to 17 years: Doses above 7 mg/day have not been evaluated.
Route of Administration: Oral
In Vitro Use Guide
Guanfacine and clonidine at relatively high concentrations (10(-6)-10(-4) M) produced contractions of the rat vas deferens which were antagonized by prazosin.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:44:04 UTC 2023
Edited
by admin
on Wed Jul 05 22:44:04 UTC 2023
Record UNII
30OMY4G3MK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GUANFACINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
N-AMIDINO-2-(2,6-DICHLOROPHENYL)ACETAMIDE
Systematic Name English
GUANFACINE [MI]
Common Name English
GUANFACINE [VANDF]
Common Name English
ESTULIC
Brand Name English
guanfacine [INN]
Common Name English
NSC-759121
Code English
BENZENEACETAMIDE, N-(AMINOIMINOMETHYL)-2,6-DICHLORO-
Systematic Name English
Guanfacine [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175554
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
FDA ORPHAN DRUG 124199
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
NDF-RT N0000009918
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
WHO-ATC C02AC02
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
NCI_THESAURUS C270
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
FDA ORPHAN DRUG 405313
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
WHO-VATC QC02AC02
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
LIVERTOX NBK548586
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
Code System Code Type Description
LACTMED
Guanfacine
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
FDA UNII
30OMY4G3MK
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
DAILYMED
30OMY4G3MK
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
IUPHAR
522
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
ChEMBL
CHEMBL862
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
NSC
759121
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID9046944
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
DRUG BANK
DB01018
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
RXCUI
40114
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY RxNorm
CAS
29110-47-2
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
MESH
D016316
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
DRUG CENTRAL
1343
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
MERCK INDEX
M5866
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY Merck Index
INN
3999
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
ECHA (EC/EINECS)
249-442-8
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
SMS_ID
100000084474
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
EVMPD
SUB07985MIG
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
PUBCHEM
3519
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
NCI_THESAURUS
C61779
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
WIKIPEDIA
GUANFACINE
Created by admin on Wed Jul 05 22:44:04 UTC 2023 , Edited by admin on Wed Jul 05 22:44:04 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
TARGET -> AGONIST
SHORT-ACTING
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC