Guanabenz
Identification
- Summary
Guanabenz is an alpha-2 adrenergic agonist used to treat hypertension.
- Generic Name
- Guanabenz
- DrugBank Accession Number
- DB00629
- Background
An alpha-2 selective adrenergic agonist used as an antihypertensive agent. [PubChem]
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 231.082
Monoisotopic: 230.01260169 - Chemical Formula
- C8H8Cl2N4
- Synonyms
- Guanabenz
- Guanabenzo
- Guanabenzum
- External IDs
- BR 750
- FLA 137
- GBZ
- NSC-68982
- SD 15468
- Wy 8678
- WY-8678
Pharmacology
- Indication
For management of High blood pressure
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- Pharmacodynamics
Guanabenz, a centrally acting α-2 adrenergic agonist, is indicated for treatment of hypertension.
- Mechanism of action
Guanabenz's antihypertensive effect is thought to be due to central alpha-adrenergic stimulation, which results in a decreased sympathetic outflow to the heart, kidneys, and peripheral vasculature in addition to a decreased systolic and diastolic blood pressure and a slight slowing of pulse rate. Chronic administration of guanabenz also causes a decrease in peripheral vascular resistance.
Target Actions Organism AAlpha-2A adrenergic receptor agonistHumans UAlpha-2B adrenergic receptor binderHumans - Absorption
Approximately 75% absorbed from gastrointestinal tract
- Volume of distribution
Not Available
- Protein binding
90%
- Metabolism
Hepatic
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
6 hours.
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Excessive contraction of the pupils, irritability, low blood pressure, sleepiness, slow heartbeat, sluggishness
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbaloparatide Abaloparatide may increase the hypotensive activities of Guanabenz. Abametapir The serum concentration of Guanabenz can be increased when it is combined with Abametapir. Abatacept The metabolism of Guanabenz can be increased when combined with Abatacept. Abiraterone The serum concentration of Guanabenz can be increased when it is combined with Abiraterone. Acebutolol The therapeutic efficacy of Guanabenz can be decreased when used in combination with Acebutolol. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Guanabenz Acetate 443O19GK1A 23256-50-0 MCSPBPXATWBACD-GAYQJXMFSA-N - International/Other Brands
- Lisapres (Libbs) / Rexitene (L.P.B.) / Wytens (Alfresa Pharma) / Wytensin (Wyeth)
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Guanabenz Acetate Tablet 8 mg/1 Oral IVAX Pharmaceuticals, Inc. 1995-04-07 2012-10-31 US Guanabenz Acetate Tablet 4 mg/1 Oral IVAX Pharmaceuticals, Inc. 1995-04-07 2012-08-31 US
Categories
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic alpha-2 Receptor Agonists
- Adrenergic alpha-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Amidines
- Antihypertensive Agents
- Cardiovascular Agents
- Central alpha-2 Adrenergic Agonist
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 Substrates
- Guanidines
- Neurotransmitter Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Halobenzenes
- Direct Parent
- Dichlorobenzenes
- Alternative Parents
- Aryl chlorides / Guanidines / Carboximidamides / Organopnictogen compounds / Organochlorides / Imines / Hydrocarbon derivatives
- Substituents
- 1,3-dichlorobenzene / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Carboximidamide / Guanidine / Hydrocarbon derivative / Imine / Organic nitrogen compound / Organochloride
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- GGD30112WC
- CAS number
- 5051-62-7
- InChI Key
- WDZVGELJXXEGPV-YIXHJXPBSA-N
- InChI
- InChI=1S/C8H8Cl2N4/c9-6-2-1-3-7(10)5(6)4-13-14-8(11)12/h1-4H,(H4,11,12,14)/b13-4+
- IUPAC Name
- N''-{[(2,6-dichlorophenyl)methylidene]amino}guanidine
- SMILES
- NC(N)=NN=CC1=C(Cl)C=CC=C1Cl
References
- Synthesis Reference
British Patent 1,019,120.
- General References
- Not Available
- External Links
- KEGG Drug
- D04375
- KEGG Compound
- C07034
- PubChem Compound
- 3517
- PubChem Substance
- 46505200
- ChemSpider
- 4642445
- BindingDB
- 50225293
- 5033
- ChEBI
- 5553
- ChEMBL
- CHEMBL420
- ZINC
- ZINC000000001522
- Therapeutic Targets Database
- DAP000232
- PharmGKB
- PA164774903
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Guanabenz
- FDA label
- Download (219 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Active Not Recruiting Treatment Non Alcoholic Steatohepatitis (NASH) / Nonalcoholic Fatty Liver 1 1 Terminated Treatment Multiple Sclerosis / Relapsing Remitting Multiple Sclerosis (RRMS) 1 Not Available Completed Not Available Coronavirus Disease 2019 (COVID‑19) / COVID / Hypertension 1 Not Available Terminated Treatment Bone Cancer / Metastatic Cancer 1
Pharmacoeconomics
- Manufacturers
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Sandoz inc
- Teva pharmaceuticals usa
- Watson laboratories inc
- Wyeth ayerst laboratories
- Packagers
- Ivax Pharmaceuticals
- Letco Medical Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Pharmaceutical Utilization Management Program VA Inc.
- Dosage Forms
Form Route Strength Tablet Oral 4 mg/1 Tablet Oral 8 mg/1 - Prices
Unit description Cost Unit Guanabenz acetate 8 mg tablet 2.13USD tablet Guanabenz acetate 4 mg tablet 1.07USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 225-227 British Patent 1,019,120. logP 3.2 Not Available Caco2 permeability -4.5 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.0889 mg/mL ALOGPS logP 2.25 ALOGPS logP 1.71 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 16.78 Chemaxon pKa (Strongest Basic) 6.82 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 76.76 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 58.15 m3·mol-1 Chemaxon Polarizability 21.58 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9921 Blood Brain Barrier + 0.8593 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.6838 P-glycoprotein inhibitor I Non-inhibitor 0.9248 P-glycoprotein inhibitor II Non-inhibitor 0.9857 Renal organic cation transporter Non-inhibitor 0.6424 CYP450 2C9 substrate Non-substrate 0.8798 CYP450 2D6 substrate Non-substrate 0.9003 CYP450 3A4 substrate Non-substrate 0.7563 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.925 CYP450 2D6 inhibitor Inhibitor 0.884 CYP450 2C19 inhibitor Non-inhibitor 0.9158 CYP450 3A4 inhibitor Non-inhibitor 0.9135 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8825 Ames test Non AMES toxic 0.618 Carcinogenicity Non-carcinogens 0.6862 Biodegradation Not ready biodegradable 0.9972 Rat acute toxicity 2.8555 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8927 hERG inhibition (predictor II) Non-inhibitor 0.9652
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 48956.275 Da
References
- Piletz JE, Sletten K: Nonadrenergic imidazoline binding sites on human platelets. J Pharmacol Exp Ther. 1993 Dec;267(3):1493-502. [Article]
- Bockman CS, Jeffries WB, Abel PW: Binding and functional characterization of alpha-2 adrenergic receptor subtypes on pig vascular endothelium. J Pharmacol Exp Ther. 1993 Dec;267(3):1126-33. [Article]
- Bockman CS, Gonzalez-Cabrera I, Abel PW: Alpha-2 adrenoceptor subtype causing nitric oxide-mediated vascular relaxation in rats. J Pharmacol Exp Ther. 1996 Sep;278(3):1235-43. [Article]
- Galeotti N, Bartolini A, Ghelardini C: Alpha-2 agonist-induced memory impairment is mediated by the alpha-2A-adrenoceptor subtype. Behav Brain Res. 2004 Aug 31;153(2):409-17. [Article]
- van Zwieten PA: Centrally acting antihypertensives: a renaissance of interest. Mechanisms and haemodynamics. J Hypertens Suppl. 1997 Jan;15(1):S3-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Epinephrine binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
- Gene Name
- ADRA2B
- Uniprot ID
- P18089
- Uniprot Name
- Alpha-2B adrenergic receptor
- Molecular Weight
- 49565.8 Da
References
- Uhlen S, Wikberg JE: Delineation of rat kidney alpha 2A- and alpha 2B-adrenoceptors with [3H]RX821002 radioligand binding: computer modelling reveals that guanfacine is an alpha 2A-selective compound. Eur J Pharmacol. 1991 Sep 17;202(2):235-43. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [Article]
- Clement B, Demesmaeker M: Formation of guanoxabenz from guanabenz in human liver. A new metabolic marker for CYP1A2. Drug Metab Dispos. 1997 Nov;25(11):1266-71. [Article]
- CYP1A2 cancer.gov document [File]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:53