Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Guanadrel
- DrugBank Accession Number
- DB00226
- Background
Guanadrel is an antihypertensive agent and postganglionic adrenergic blocking agent.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Guanadrel (DB00226)
- Weight
- Average: 213.2768
Monoisotopic: 213.147726867 - Chemical Formula
- C10H19N3O2
- Synonyms
- Guanadrel
- Guanadrelum
Pharmacology
- Indication
Used to treat and control hypertension.
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High blood pressure adds to the work load of the heart and arteries. If it continues for a long time, the heart and arteries may not function properly. This can damage the blood vessels of the brain, heart, and kidneys resulting in a stroke, heart failure, or kidney failure. High blood pressure may also increase the risk of heart attacks. These problems may be less likely to occur if blood pressure is controlled. Guanadrel works by controlling nerve impulses along certain nerve pathways. As a result, it relaxes the blood vessels so that blood passes through them more easily. This helps to lower blood pressure.
- Mechanism of action
Guanadrel is an adrenergic neuron inhibitor that slowly displaces norepinephrine from its storage in nerve endings. It blocks the release of norepinephrine in response to the sympathetic nerve stimulation, leading to reduced arteriolar vasoconstriction, especially the reflex increase in sympathetic tone that occurs with a change in position.
Target Actions Organism ASodium-dependent noradrenaline transporter partial agonistHumans - Absorption
Rapidly and readily absorbed from the gastrointestinal tract.
- Volume of distribution
Not Available
- Protein binding
Low, approximately 20%
- Metabolism
Primarily hepatic
- Route of elimination
Not Available
- Half-life
10 hours
- Clearance
Not Available
- Adverse Effects
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Side effects include dizziness, drowsiness, headache, constipation, diarrhea, gas pains, loss of appetite, fatigue, and nasal congestion.
- 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 Guanadrel. Acebutolol Guanadrel may increase the hypotensive activities of Acebutolol. Aceclofenac The therapeutic efficacy of Guanadrel can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Guanadrel can be decreased when used in combination with Acemetacin. Acetylsalicylic acid Acetylsalicylic acid may decrease the antihypertensive activities of Guanadrel. - Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Guanadrel sulfate MT147RMO91 22195-34-2 RTEVGQJRTFFMLL-UHFFFAOYSA-N - International/Other Brands
- Anarel (Cutter) / Hylorel (Pennwalt)
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Ethers
- Direct Parent
- Ketals
- Alternative Parents
- 1,3-dioxolanes / Guanidines / Oxacyclic compounds / Carboximidamides / Organopnictogen compounds / Imines / Hydrocarbon derivatives
- Substituents
- Aliphatic heteropolycyclic compound / Carboximidamide / Guanidine / Hydrocarbon derivative / Imine / Ketal / Meta-dioxolane / Organic nitrogen compound / Organoheterocyclic compound / Organonitrogen compound
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- guanidines, spiroketal (CHEBI:5555)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 765C9332T4
- CAS number
- 40580-59-4
- InChI Key
- HPBNRIOWIXYZFK-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H19N3O2/c11-9(12)13-6-8-7-14-10(15-8)4-2-1-3-5-10/h8H,1-7H2,(H4,11,12,13)
- IUPAC Name
- N''-({1,4-dioxaspiro[4.5]decan-2-yl}methyl)guanidine
- SMILES
- NC(N)=NCC1COC2(CCCCC2)O1
References
- Synthesis Reference
U.S. Patent 3,547,951.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014371
- KEGG Drug
- D08029
- KEGG Compound
- C07035
- PubChem Compound
- 38521
- PubChem Substance
- 46506457
- ChemSpider
- 35305
- 26296
- ChEBI
- 5555
- ChEMBL
- CHEMBL1037
- Therapeutic Targets Database
- DAP000059
- PharmGKB
- PA164745308
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Guanadrel
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Pharmacia and upjohn co
- Packagers
- Pharmaceutical Utilization Management Program VA Inc.
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 213.5-215 U.S. Patent 3,547,951. logP 0.6 Not Available - Predicted Properties
Property Value Source Water Solubility 1.93 mg/mL ALOGPS logP 0.03 ALOGPS logP 0.62 Chemaxon logS -2 ALOGPS pKa (Strongest Acidic) 19.85 Chemaxon pKa (Strongest Basic) 12.56 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 82.86 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 56.54 m3·mol-1 Chemaxon Polarizability 23.23 Å3 Chemaxon Number of Rings 2 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 + 0.8727 Blood Brain Barrier + 0.5276 Caco-2 permeable - 0.5409 P-glycoprotein substrate Non-substrate 0.6176 P-glycoprotein inhibitor I Non-inhibitor 0.9348 P-glycoprotein inhibitor II Non-inhibitor 0.8788 Renal organic cation transporter Non-inhibitor 0.5077 CYP450 2C9 substrate Non-substrate 0.8797 CYP450 2D6 substrate Non-substrate 0.6273 CYP450 3A4 substrate Non-substrate 0.7651 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9529 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9413 Ames test Non AMES toxic 0.584 Carcinogenicity Non-carcinogens 0.9459 Biodegradation Not ready biodegradable 0.9371 Rat acute toxicity 2.4799 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8914 hERG inhibition (predictor II) Non-inhibitor 0.8892
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-9400000000-3e328dd7598b02063d5a Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-1690000000-0994b8b2d8ac67d91fcf Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0290000000-c950e6516a8a347ae1eb Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-07bb-9710000000-9dba902c1e9a9048adac Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00dm-9710000000-0d968b1bb34b41f2f684 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03ec-9500000000-60ecbf63b31ba1321e22 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9400000000-4044293ac3c8b5c4ad3a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 157.7472577 predictedDarkChem Lite v0.1.0 [M-H]- 148.09538 predictedDeepCCS 1.0 (2019) [M+H]+ 158.4351577 predictedDarkChem Lite v0.1.0 [M+H]+ 150.4534 predictedDeepCCS 1.0 (2019) [M+Na]+ 158.0486577 predictedDarkChem Lite v0.1.0 [M+Na]+ 157.83679 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Partial agonist
- General Function
- Mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (PubMed:2008212, PubMed:8125921). Can also mediate sodium- and chloride-dependent transport of dopamine (PubMed:11093780, PubMed:8125921)
- Specific Function
- actin binding
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Malinow SH: Comparison of guanadrel and guanethidine efficacy and side effects. Clin Ther. 1983;5(3):284-9. [Article]
- Finnerty FA Jr, Brogden RN: Guanadrel. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in hypertension. Drugs. 1985 Jul;30(1):22-31. [Article]
- Palmer JD, Nugent CA: Guanadrel sulfate: a postganglionic sympathetic inhibitor for the treatment of mild to moderate hypertension. Pharmacotherapy. 1983 Jul-Aug;3(4):220-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 07, 2024 17:52