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targets (3)
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Identification
Name Tolazoline
Accession Number DB00797 (APRD00170)
Type small molecule
Groups approved
Description

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. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Artonil
Benzazoline
Benzidazol
Benzolin
Benzylimidazoline
Dilatol Asi
Divascol
Imidalin
Imidaline
Kasimid
Lambril
Olitensol
Peripherine
Phenylmethylimidazoline
Prefaxil
Priscol
Priscoline
Tolazolin
Vasimid
Vasodil
Vasodilatan
First Prev Next Last
Brand mixtures Not Available
Categories
  • Antihypertensive Agents
  • Vasodilator Agents
  • Adrenergic alpha-Antagonists
CAS number 59-98-3
Weight Average: 160.2157
Monoisotopic: 160.100048394
Chemical Formula C10H12N2
InChI Key InChIKey=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)
Plain Text
IUPAC Name
2-benzyl-4,5-dihydro-1H-imidazole
SMILES
C(C1=NCCN1)C1=CC=CC=C1
Plain Text
Mass Spec show (8.79 KB)
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
Substructures
  • Imidazolines
  • Carboxylic Acids and Derivatives
  • Benzene and Derivatives
  • Imidazoles
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamidines
  • Imines
Pharmacology
Indication For the treatment of pulmonary artery anomalies
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.
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
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
Packagers
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 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 1.36e+00 g/l 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 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 49.07 ChemAxon
polarizability 17.94 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07147 Link_out
PubChem Compound 5504 Link_out
PubChem Substance 46505641 Link_out
ChemSpider 5303 Link_out
ChEBI 28502 Link_out
ChEMBL 28502 Link_out
Therapeutic Targets Database DAP000477 Link_out
PharmGKB PA451716 Link_out
Drug Product Database 2195887 Link_out
Wikipedia http://en.wikipedia.org/wiki/Tolazoline Link_out
ATC Codes
  • C04AB02
  • M02AX02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (73.7 KB)
Interactions
Drug Interactions
Drug Interaction
Cimetidine Anticipated loss of efficacy of tolazoline
Ranitidine Anticipated loss of efficacy of tolazoline
Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Food Interactions Not Available
Targets

1. Alpha-1A adrenergic receptor

Pharmacological action: yes
Actions: antagonist

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) proteins

Organism class: human
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed

2. Alpha-2A adrenergic receptor

Pharmacological action: unknown
Actions: antagonist

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

Organism class: human
UniProt ID: P08913 Link_out
Gene: ADRA2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed

3. Histamine H1 receptor

Pharmacological action: unknown
Actions: agonist

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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system

Organism class: human
UniProt ID: P35367 Link_out
Gene: HRH1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19