Identification
- Summary
Tolazoline is a vasodilator used to treat pulmonary artery anomalies.
- Generic Name
- Tolazoline
- DrugBank Accession Number
- DB00797
- Background
A vasodilator that apparently has direct actions on blood vessels and also increases cardiac output. Tolazoline can interact to some degree with histamine, adrenergic, and cholinergic receptors, but the mechanisms of its therapeutic effects are not clear. It is used in treatment of persistent pulmonary hypertension of the newborn.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Tolazoline (DB00797)
- Weight
- Average: 160.2157
Monoisotopic: 160.100048394 - Chemical Formula
- C10H12N2
- Synonyms
- 2-Benzyl-2-imidazoline
- 2-Benzyl-4,5-imidazoline
- 2-Benzylimidazoline
- 4,5-Dihydro-2-(phenylmethyl)-1H-imidazole
- Benzazoline
- Tolazolin
- Tolazolina
- Tolazoline
- Tolazolinum
- External IDs
- Ciba 3259
Pharmacology
- Indication
For the treatment of pulmonary artery anomalies
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
Tolazoline is a pulmonary vasodilator indicated used to decrease pulmonary vascular resistance (PVR) in persistent pulmonary hypertension of the newborn (PPHN).
- Mechanism of action
Vasodilation by means of a direct effect on peripheral vascular smooth muscle and indirect effects produced, in part, by release of endogenous histamine; tolazoline has moderate alpha-adrenergic blocking activity and has histamine agonist activity. Tolazoline usually reduces pulmonary arterial pressure and vascular resistance.
Target Actions Organism AAlpha-1A adrenergic receptor antagonistHumans UAlpha-2A adrenergic receptor antagonistHumans UHistamine H1 receptor agonistHumans UHistamine H2 receptor agonistHumans UAlpha-2C adrenergic receptor binderHumans UAlpha-2B adrenergic receptor binderHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- 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
Not Available
- 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 The risk or severity of adverse effects can be increased when Tolazoline is combined with Abaloparatide. Acebutolol Acebutolol may increase the orthostatic hypotensive activities of Tolazoline. Aceclofenac The therapeutic efficacy of Tolazoline can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Tolazoline can be decreased when used in combination with Acemetacin. Acetylsalicylic acid Acetylsalicylic acid may decrease the antihypertensive activities of Tolazoline. - 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 Tolazoline hydrochloride E669Z6S1JG 59-97-2 RHTNTTODYGNRSP-UHFFFAOYSA-N - International/Other Brands
- Divascol (VUAB Pharma) / Imidalin (Astellas Pharma) / Tolazine
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Priscoline hydrochloride Injection, solution 25 mg/1mL Intravenous Novartis 1948-03-17 2008-08-18 US 
Categories
- ATC Codes
- M02AX02 — Tolazoline
- M02AX — Other topical products for joint and muscular pain
- M02A — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M02 — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M — MUSCULO-SKELETAL SYSTEM
- Drug Categories
- Adrenergic Agents
- Adrenergic alpha-1 Receptor Antagonists
- Adrenergic alpha-Antagonists
- Adrenergic Antagonists
- Agents that produce hypertension
- Antihypertensive Agents
- Cardiovascular Agents
- Hypotensive Agents
- Imidazoles
- Imidazoline Derivatives
- Imidazolines
- Musculo-Skeletal System
- Neurotransmitter Agents
- Peripheral alpha-1 blockers
- Peripheral Vasodilators
- Topical Products for Joint and Muscular Pain
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Not Available
- Direct Parent
- Benzene and substituted derivatives
- Alternative Parents
- Imidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- 2-imidazoline / Amidine / Aromatic heteromonocyclic compound / Azacycle / Carboximidamide / Carboxylic acid amidine / Hydrocarbon derivative / Imidolactam / Monocyclic benzene moiety / Organic 1,3-dipolar compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- imidazoles (CHEBI:28502)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- CHH9H12AQ3
- CAS number
- 59-98-3
- InChI Key
- JIVZKJJQOZQXQB-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H12N2/c1-2-4-9(5-3-1)8-10-11-6-7-12-10/h1-5H,6-8H2,(H,11,12)
- IUPAC Name
- 2-benzyl-4,5-dihydro-1H-imidazole
- SMILES
- C(C1=NCCN1)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014935
- KEGG Compound
- C07147
- PubChem Compound
- 5504
- PubChem Substance
- 46505641
- ChemSpider
- 5303
- BindingDB
- 55436
- 10634
- ChEBI
- 28502
- ChEMBL
- CHEMBL770
- ZINC
- ZINC000000125006
- Therapeutic Targets Database
- DAP000477
- PharmGKB
- PA451716
- Wikipedia
- Tolazoline
- MSDS
- Download (73.7 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
Pharmacoeconomics
- Manufacturers
- Novartis pharmaceuticals corp
- Packagers
- Novartis AG
- Dosage Forms
Form Route Strength Injection, solution Intravenous 25 mg/1mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 174 °C PhysProp water solubility 373 mg/L Not Available logP 2.65 SANGSTER (1993) pKa 10.3 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 1.36 mg/mL ALOGPS logP 2.05 ALOGPS logP 1.2 Chemaxon logS -2.1 ALOGPS pKa (Strongest Basic) 10.25 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 24.39 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 49.07 m3·mol-1 Chemaxon Polarizability 17.94 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9821 Blood Brain Barrier + 0.9334 Caco-2 permeable - 0.5062 P-glycoprotein substrate Substrate 0.6249 P-glycoprotein inhibitor I Non-inhibitor 0.9707 P-glycoprotein inhibitor II Non-inhibitor 0.9188 Renal organic cation transporter Inhibitor 0.7923 CYP450 2C9 substrate Non-substrate 0.8404 CYP450 2D6 substrate Substrate 0.6912 CYP450 3A4 substrate Non-substrate 0.8088 CYP450 1A2 substrate Non-inhibitor 0.6013 CYP450 2C9 inhibitor Non-inhibitor 0.9629 CYP450 2D6 inhibitor Inhibitor 0.7446 CYP450 2C19 inhibitor Non-inhibitor 0.9844 CYP450 3A4 inhibitor Non-inhibitor 0.9738 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9644 Ames test Non AMES toxic 0.8569 Carcinogenicity Non-carcinogens 0.9492 Biodegradation Not ready biodegradable 0.9824 Rat acute toxicity 2.5351 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7268 hERG inhibition (predictor II) Non-inhibitor 0.8357
Spectra
- Mass Spec (NIST)
- Download (8.79 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 138.4537882 predictedDarkChem Lite v0.1.0 [M-H]- 138.5958882 predictedDarkChem Lite v0.1.0 [M-H]- 130.39632 predictedDeepCCS 1.0 (2019) [M+H]+ 139.2109882 predictedDarkChem Lite v0.1.0 [M+H]+ 139.1818882 predictedDarkChem Lite v0.1.0 [M+H]+ 133.23268 predictedDeepCCS 1.0 (2019) [M+Na]+ 138.7690882 predictedDarkChem Lite v0.1.0 [M+Na]+ 138.7572882 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.09726 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- Molecular Weight
- 51486.005 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]
- Teskin O, Uydes-Dogan BS, Enc Y, Alp FI, Kaleli D, Keser S, Iyigun T, Bilgen F, Dagsali S, Ozdemir O: Comparative effects of tolazoline and nitroprusside on human isolated radial artery. Ann Thorac Surg. 2006 Jan;81(1):125-31. [Article]
- Song W, Zhang Y, Xia L, Liu G: [Effects of some mexiletine derivatives on alpha 1-adrenoceptors]. Yao Xue Xue Bao. 1998;33(2):102-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- 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
- Song W, Zhang Y, Xia L, Liu G: [Effects of some mexiletine derivatives on alpha 1-adrenoceptors]. Yao Xue Xue Bao. 1998;33(2):102-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Roll C, Hanssler L: [Interaction of tolazoline and cimetidine in persistent fetal circulation of the newborn infant]. Monatsschr Kinderheilkd. 1993 Apr;141(4):297-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Histamine receptor activity
- Specific Function
- The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and diff...
- Gene Name
- HRH2
- Uniprot ID
- P25021
- Uniprot Name
- Histamine H2 receptor
- Molecular Weight
- 40097.65 Da
References
- Ward RM: Pharmacology of tolazoline. Clin Perinatol. 1984 Oct;11(3):703-13. [Article]
- Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [Article]
- Roll C, Hanssler L: [Interaction of tolazoline and cimetidine in persistent fetal circulation of the newborn infant]. Monatsschr Kinderheilkd. 1993 Apr;141(4):297-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Protein homodimerization activity
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
- Gene Name
- ADRA2C
- Uniprot ID
- P18825
- Uniprot Name
- Alpha-2C adrenergic receptor
- Molecular Weight
- 49521.585 Da
References
- Trendelenburg AU, Sutej I, Starke K: Presynaptic alpha 2A/D-autoreceptors in the brain cortex of Cercopithecus aethiops. Naunyn Schmiedebergs Arch Pharmacol. 1997 Mar;355(3):341-6. [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
- Trendelenburg AU, Sutej I, Starke K: Presynaptic alpha 2A/D-autoreceptors in the brain cortex of Cercopithecus aethiops. Naunyn Schmiedebergs Arch Pharmacol. 1997 Mar;355(3):341-6. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:59