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Tolazoline

Tolazoline structure

CAS No:
59-98-3
Formula:
C10H12N2
Chemical Name:
Tolazoline
Synonyms:
1H-Imidazole,4,5-dihydro-2-(phenylmethyl)-;2-Imidazoline,2-benzyl-;Imidazoline,2-benzyl-;4,5-Dihydro-2-(phenylmethyl)-1H-imidazole;Artonil;Benzazoline;Benzidazol;2-Benzyl-4,5-imidazoline;2-Benzyl-2-imidazoline;Divascol;Imidalin;Kasimid;Lambril;Olitensol;Peripherine;Phenylmethylimidazoline;Prefaxil;Priscol;Priscoline;Tolazoline;Vasimid;Vasodil;Benzylimidazoline;2-Benzylimidazoline;Benzolin (vasodilator);Benzolin;Dilatol ASI;Tolazolin;Imidaline;2-Benzyl-4,5-dihydro-1H-imidazole;NSC 35110
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

Tolazoline(NSC35110; Imidaline) is a non-selective competitive α-adrenergic receptor antagonist.IC50 value:Target: α-adrenoceptor antagonistTolazoline can be synthesized by the heterocyclation of the ethyl ester of iminophenzylacetic acid with ethylene diamine, which forms the desired product. The structure of tolazoline is strikingly similar to α-adrenergic agonists, which are antiedema sympathomimetics.

Solid

Tolazoline is a member of the class of imidazoles that is 4,5-dihydro-1H-imidazole substituted by a benzyl group. It has a role as an alpha-adrenergic antagonist, an antihypertensive agent and a vasodilator agent.|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.

Tolazoline Basic Attributes

Molecular Weight：

160.22

Exact Mass：

160.22

EC Number：

200-448-9

UNII：

CHH9H12AQ3

NSC Number：

35110

DSSTox ID：

DTXSID3023683

ATC Code：

C - Cardiovascular system|M - Musculo-skeletal system

HScode：

2933290090

Characteristics

PSA：

24.4

XLogP3：

1.5

Appearance：

Solid

Density：

1.1±0.1 g/cm3

Melting Point：

174 °C

Boiling Point：

147 °C @ Press: 9 Torr

Flash Point：

158.3±22.1 °C

Refractive Index：

1.596

Water Solubility：

alcohol: freely soluble

Storage Conditions：

2-8°C

Toxicity：

Oral-Mouse LD50: 350 mg/kg; Abdominal cavity-mouse LD50: 160 mg/kg

Flammability characteristics：

Flammable; emit toxic nitrogen oxide gas when heated

PKA：

10.3None

Dissociation Constants：

10.3

Safety Information

wgk germany：

hazard class code：

20/21/22-36/37/38

safety instructions：

26-28-36/37/39-45

RTECS Number：

NJ1925000

Marks：

Storage features：

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 128 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

highly toxic

Drug Information

Drug Indication：

For the treatment of pulmonary artery anomalies

Pharmacology：

Tolazoline is a pulmonary vasodilator indicated used to decrease pulmonary vascular resistance (PVR) in persistent pulmonary hypertension of the newborn (PPHN).

MeSH：

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)|Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)|Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma. (See all compounds classified as Adrenergic alpha-Antagonists.)

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.

MeSH Entry Terms：

Benzalolin

Tolazoline Use and Manufacturing

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:160.22
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:160.100048391
Monoisotopic Mass:160.100048391
Topological Polar Surface Area:24.4
Heavy Atom Count:12
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes