Guanabenz
Explore a selection of our essential drug information below, or:
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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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
- Not Available
Interactions
- Drug Interactions
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Coronavirus Disease 2019 (COVID‑19) / COVID / Hypertension 1 somestatus stop reason just information to hide Not Available Terminated Treatment Bone Cancer / Metastatic Cancer 1 somestatus stop reason just information to hide 2 Unknown Status Treatment Nonalcoholic Fatty Liver / Steatohepatitis, Nonalcoholic 1 somestatus stop reason just information to hide 1 Terminated Treatment Multiple Sclerosis / Relapsing Remitting Multiple Sclerosis (RRMS) 1 somestatus stop reason just information to hide
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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General 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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
- Specific Function
- alpha-1B adrenergic receptor binding
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 50646.17 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
- 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 > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
- Specific Function
- alpha2-adrenergic receptor activity
- Gene Name
- ADRA2B
- Uniprot ID
- P18089
- Uniprot Name
- Alpha-2B adrenergic receptor
- Molecular Weight
- 49953.145 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
- Specific Function
- aromatase activity
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58406.915 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 October 29, 2024 18:18