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Isoproterenol

Isoproterenol structure

Isoproterenol 

structure
  • CAS No:

    7683-59-2

  • Formula:

    C11H17NO3

  • Chemical Name:

    Isoproterenol

  • Synonyms:

    1,2-Benzenediol,4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]-;Benzyl alcohol,3,4-dihydroxy-α-[(isopropylamino)methyl]-;4-[1-Hydroxy-2-[(1-methylethyl)amino]ethyl]-1,2-benzenediol;Isoproterenol;Isoprenaline;Isopropylarterenol;Isopropylnoradrenaline;Isopropylnorepinephrine;N-Isopropylnorepinephrine;Aludrine;3,4-Dihydroxy-α-[(isopropylamino)methyl]benzyl alcohol;α-(Isopropylaminomoethyl)protocatechuyl alcohol;Isopropylaminomethyl(3,4-dihydroxyphenyl)carbinol;N-Isopropyl-β-dihydroxyphenyl-β-hydroxyethylamine;N-Isopropylnoradrenaline;Aludrin;Norisodrine;Asiprenol;Asmalar;Lomupren;Isopropydrin;Assiprenol;Respifral;Bellasthman;1-(3,4-Dihydroxyphenyl)-2-(isopropylamino)ethanol;Isoprenalin;ICI 46399;(±)-Isoproterenol;(±)-Isoprenaline;dl-Isoprenaline;Racemic isoprenaline;dl-Isopropylnoradrenaline;dl-N-Isopropylnoradrenaline;DL-Isopropylnorepinephrine;dl-Isadrine;Racemic isoproterenol;DL(±)-Isoproterenol;DL-Isoproterenol;dl-Isoproterenol;Isorenin;Isupren;Epinephrine isopropyl homolog;Vapo-N-Iso;Neo-Epinine;Neodrenal;Isonorin;A 21;NSC 33791;NSC 9975;149-53-1;46388-38-9

  • Categories:

    Active Pharmaceutical Ingredients  >  Respiratory Drugs

Description

ChEBI: A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hy rochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.


Solid


Isoprenaline is a secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders. It has a role as a sympathomimetic agent, a beta-adrenergic agonist, a bronchodilator agent and a cardiotonic drug. It is a member of catechols, a secondary amino compound and a secondary alcohol.|Isopropyl analog of epinephrine; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.|Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.

Isoproterenol Basic Attributes

211.26

211.26

231-687-7

33791|9975

DTXSID4023175

C01CA02|C - Cardiovascular system|R - Respiratory system

Characteristics

72.7

1.4

Solid

1.32 g/cm3

170.5 °C

417.5±40.0 °C at 760 mmHg

179.7±17.9 °C

1.579

5.86e+00 g/L

149.4 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|150 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated]

Safety Information

DO1750000

Drug Information

For the treatment of mild or transient episodes of heart block that do not require electric shock or pacemaker therapy also used in management of asthma and chronic bronchitis|FDA Label

Isoproterenol is a relatively selective beta2-adrenergic bronchodilator. Isoproterenol is indicated for the relief of bronchospasm associated with chronic obstructive pulmonary disease. The pharmacologic effects of beta adrenergic agonist drugs, including Isoproterenol, are at least in part attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (ATP) to cyclic- 3',5'- adenosine monophosphate (c-AMP). Increased c-AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)|Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)|Drugs that selectively bind to and activate beta-adrenergic receptors. (See all compounds classified as Adrenergic beta-Agonists.)|Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)

Excretion following inhalation administration is primarily renal and the major metabolite is the sulfate conjugate of isoproterenol.

The pharmacologic effects of isoproterenol are at least in part attributable to stimulation through beta-adrenergic receptors of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic AMP. Increased cyclic AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.

4-(1-Hydroxy-2-((1-methylethyl)amino)ethyl)-1,2-benzenediol

Isoproterenol Use and Manufacturing

Uses

This product is an anti-shock vasoactive drug. It has the functions of strengthening the heart, dilating peripheral blood vessels and bronchial tubes. The effect of relaxing bronchial smooth muscle and alleviating bronchospasm is about 10 times that of epinephrine, which enhances myocardial contractility, accelerates heart rate and accelerates conduction. Isoproterenol hydrochloride oral LD50 in rats was 2221±93mg/kg.

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

Computed Properties

Molecular Weight:211.26
XLogP3:-0.6
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:211.12084340
Monoisotopic Mass:211.12084340
Topological Polar Surface Area:72.7
Heavy Atom Count:15
Complexity:187
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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