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Details

Stereochemistry ACHIRAL
Molecular Formula C8H8Cl2N4.C2H4O2
Molecular Weight 291.134
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of GUANABENZ ACETATE

SMILES

CC(O)=O.NC(=N)N\N=C\C1=C(Cl)C=CC=C1Cl

InChI

InChIKey=MCSPBPXATWBACD-GAYQJXMFSA-N
InChI=1S/C8H8Cl2N4.C2H4O2/c9-6-2-1-3-7(10)5(6)4-13-14-8(11)12;1-2(3)4/h1-4H,(H4,11,12,14);1H3,(H,3,4)/b13-4+;

HIDE SMILES / InChI

Molecular Formula C8H8Cl2N4
Molecular Weight 231.082
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C2H4O2
Molecular Weight 60.052
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Guanabenz, an antihypertensive agent for oral administration-, is an aminoguanidine derivative, 2,'6-dichlorobenzylideneamina-guanidine acetate. It is white to an almost white powder having not more than a slight odor. Sparingly soluble in water and in 0.1 N hydrochloric acid; soluble in alcohol and in propylene glycol. Guanabenz is an orally active central alpha-2 adrenergic agonist. Its antihypertensive action appears to be mediated via stimulation of central alpha-adrenergic receptors, resulting in a decrease of sympathetic outflow from the brain at the bulbar level to the peripheral circulatory system. In clinical trials, guanabenz acetate, given orally to hypertensive patients, effectively controlled blood pressure without any significant effect on glomerular filtration rate, renal blood flow, body fluid volume or body weight. The Myelin Repair Foundation and the National Institutes of Health (National Institute of Neurological Disorders and Stroke) are developing guanabenz for the treatment of multiple sclerosis. Unlike the currently available treatment for multiple sclerosis that suppresses the immune system, guanabenz, an FDA approved the drug for the treatment of high blood pressure, has a potential to reduce the loss of myelin by protecting and repairing myelin-producing cells in the brain from damage. Phase I development is underway in the US.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.7 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
WYTENSIN

Approved Use

INDICATIONS AND USAGE. Guanabenz acetate tablets are indicated in the treatment of hypertension. It may be employed alone or in combination with a thiazide diuretic.

Launch Date

1982
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.4 ng/mL
16 mg single, oral
dose: 16 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GUANABENZ plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.8 ng/mL
16 mg single, oral
dose: 16 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GUANABENZ plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
19 ng × h/mL
16 mg single, oral
dose: 16 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GUANABENZ plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
97 ng × h/mL
16 mg single, oral
dose: 16 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GUANABENZ plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.3 h
16 mg single, oral
dose: 16 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GUANABENZ plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.4 h
16 mg single, oral
dose: 16 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GUANABENZ plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
11%
16 mg single, oral
dose: 16 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GUANABENZ plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
13%
16 mg single, oral
dose: 16 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GUANABENZ plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
16 mg single, oral
Recommended
Dose: 16 mg
Route: oral
Route: single
Dose: 16 mg
Sources: Page: p.S767
healthy, 22-55
Health Status: healthy
Age Group: 22-55
Sex: M
Sources: Page: p.S767
32 mg single, oral
Highest studied dose
Dose: 32 mg
Route: oral
Route: single
Dose: 32 mg
Sources: Page: p.S764
unhealthy, 39-65
n = 12
Health Status: unhealthy
Condition: hypertension
Age Group: 39-65
Sex: M+F
Population Size: 12
Sources: Page: p.S764
16 mg single, oral
Recommended
Dose: 16 mg
Route: oral
Route: single
Dose: 16 mg
Sources: Page: p.S764
unhealthy, 39-65
n = 12
Health Status: unhealthy
Condition: hypertension
Age Group: 39-65
Sex: M+F
Population Size: 12
Sources: Page: p.S764
Disc. AE: Hypotension...
Other AEs: Drowsiness...
AEs leading to
discontinuation/dose reduction:
Hypotension (8.35%)
Other AEs:
Drowsiness (50%)
Sources: Page: p.S764
24 mg single, oral
Recommended
Dose: 24 mg
Route: oral
Route: single
Dose: 24 mg
Sources: Page: p.S764
unhealthy, 39-65
n = 12
Health Status: unhealthy
Condition: hypertension
Age Group: 39-65
Sex: M+F
Population Size: 12
Sources: Page: p.S764
Disc. AE: Hypotension...
AEs leading to
discontinuation/dose reduction:
Hypotension (8.35%)
Sources: Page: p.S764
240 mg single, oral (max)
Overdose
Dose: 240 mg
Route: oral
Route: single
Dose: 240 mg
Sources: Page: p.787
healthy, 45
n = 1
Health Status: healthy
Age Group: 45
Sex: F
Population Size: 1
Sources: Page: p.787
Other AEs: Sinus bradycardia...
Other AEs:
Sinus bradycardia
Sources: Page: p.787
480 mg single, oral (max)
Overdose
Dose: 480 mg
Route: oral
Route: single
Dose: 480 mg
Sources: Page: p.787-788
unknown
n = 3
Health Status: unknown
Population Size: 3
Sources: Page: p.787-788
Other AEs: Somnolence, Coma...
Other AEs:
Somnolence
Coma
Hypotension
Bradycardia
Sources: Page: p.787-788
AEs

AEs

AESignificanceDosePopulation
Drowsiness 50%
16 mg single, oral
Recommended
Dose: 16 mg
Route: oral
Route: single
Dose: 16 mg
Sources: Page: p.S764
unhealthy, 39-65
n = 12
Health Status: unhealthy
Condition: hypertension
Age Group: 39-65
Sex: M+F
Population Size: 12
Sources: Page: p.S764
Hypotension 8.35%
Disc. AE
16 mg single, oral
Recommended
Dose: 16 mg
Route: oral
Route: single
Dose: 16 mg
Sources: Page: p.S764
unhealthy, 39-65
n = 12
Health Status: unhealthy
Condition: hypertension
Age Group: 39-65
Sex: M+F
Population Size: 12
Sources: Page: p.S764
Hypotension 8.35%
Disc. AE
24 mg single, oral
Recommended
Dose: 24 mg
Route: oral
Route: single
Dose: 24 mg
Sources: Page: p.S764
unhealthy, 39-65
n = 12
Health Status: unhealthy
Condition: hypertension
Age Group: 39-65
Sex: M+F
Population Size: 12
Sources: Page: p.S764
Sinus bradycardia
240 mg single, oral (max)
Overdose
Dose: 240 mg
Route: oral
Route: single
Dose: 240 mg
Sources: Page: p.787
healthy, 45
n = 1
Health Status: healthy
Age Group: 45
Sex: F
Population Size: 1
Sources: Page: p.787
Bradycardia
480 mg single, oral (max)
Overdose
Dose: 480 mg
Route: oral
Route: single
Dose: 480 mg
Sources: Page: p.787-788
unknown
n = 3
Health Status: unknown
Population Size: 3
Sources: Page: p.787-788
Coma
480 mg single, oral (max)
Overdose
Dose: 480 mg
Route: oral
Route: single
Dose: 480 mg
Sources: Page: p.787-788
unknown
n = 3
Health Status: unknown
Population Size: 3
Sources: Page: p.787-788
Hypotension
480 mg single, oral (max)
Overdose
Dose: 480 mg
Route: oral
Route: single
Dose: 480 mg
Sources: Page: p.787-788
unknown
n = 3
Health Status: unknown
Population Size: 3
Sources: Page: p.787-788
Somnolence
480 mg single, oral (max)
Overdose
Dose: 480 mg
Route: oral
Route: single
Dose: 480 mg
Sources: Page: p.787-788
unknown
n = 3
Health Status: unknown
Population Size: 3
Sources: Page: p.787-788
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Pharmacological characterization of spinal alpha adrenoceptors related to blood pressure control in rats.
1987 Jan
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Inhibitors of eIF2α dephosphorylation slow replication and stabilize latency in Toxoplasma gondii.
2013 Apr
Guanabenz interferes with ER stress and exerts protective effects in cardiac myocytes.
2014
Patents

Sample Use Guides

Dosage with guanabenz acetate tablets should be individualized. A starling dose of 4 mg twice a day is recommended, whether guanabenz acetate tablets are used alone or with a thiazide diuretic. Dosage may be increased in increments of 4 to 8 mg per day every one to two weeks, depending on the patient's response. The maximum dose studied to date has been 32 mg twice daily, but doses as high as this are rarefy needed.
Route of Administration: Oral
In Vitro Use Guide
Peptidylprolyl isomerase B (cyclophilin B) mRNA expression levels were monitored after treatment of with hsiRNA (2 --500 nM) and increasing amounts of Guanabenz (0-100mkM) in HeLa cell culture for 24 h. Guanabenz acetate is capable of markedly increasing the cellular internalization and target mRNA silencing of hydrophobically modified siRNAs (hsiRNAs), yielding a ∼100-fold decrease in hsiRNA IC50 (from 132 nM to 2.4 nM).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:20:35 GMT 2023
Edited
by admin
on Fri Dec 15 16:20:35 GMT 2023
Record UNII
443O19GK1A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GUANABENZ ACETATE
HSDB   MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
Guanabenz acetate [WHO-DD]
Common Name English
GUANABENZ MONOACETATE
MI  
Common Name English
[(2,6-Dichlorobenzylidene)amino]guanidine monoacetate
Systematic Name English
WYTENSIN
Brand Name English
GUANABENZ ACETATE [USP MONOGRAPH]
Common Name English
GUANABENZ ACETATE [USAN]
Common Name English
2-((2,6-DICHLOROPHENYL)METHYLENE)HYDRAZINECARBOXIMIDAMIDE MONOACETATE
Systematic Name English
GUANABENZ ACETATE [USP-RS]
Common Name English
GUANABENZ ACETATE [JAN]
Common Name English
GUANABENZ ACETATE [VANDF]
Common Name English
GUANABENZ ACETATE [HSDB]
Common Name English
HYDRAZINECARBOXIMIDAMIDE, 2-((2,6-DICHLOROPHENYL)METHYLENE)-, MONOACETATE
Systematic Name English
WY-8678 ACETATE
Code English
GUANABENZ ACETATE [MART.]
Common Name English
NSC-757044
Code English
N-(2,6-DICHLOROBENZYLIDENE)-N'-AMIDINOHYDRAZINE MONOACETATE
Systematic Name English
GUANABENZ MONOACETATE [MI]
Common Name English
GUANABENZ ACETATE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
NCI_THESAURUS C270
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
Code System Code Type Description
NSC
757044
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
CAS
23256-50-0
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
RXCUI
227225
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m5863
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY Merck Index
HSDB
6535
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL420
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID101017207
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
245-534-7
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
DRUG BANK
DBSALT000649
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
PUBCHEM
5702062
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
DAILYMED
443O19GK1A
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
NCI_THESAURUS
C65826
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
RS_ITEM_NUM
1301404
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
FDA UNII
443O19GK1A
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
EVMPD
SUB02423MIG
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
SMS_ID
100000086675
Created by admin on Fri Dec 15 16:20:35 GMT 2023 , Edited by admin on Fri Dec 15 16:20:35 GMT 2023
PRIMARY
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