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PIRBUTEROL ACETATE

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ACTIVE PHARMA INGREDIENTS

3 API Suppliers, 3 USDMF

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3 USDMF

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2 FDF Dossiers, 2 FDA Orange Book

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2 FDA Orange Book

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1 USP

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1 USP

Synopsis

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Chemistry

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Also known as: 65652-44-0, Maxair, Pirbuterol acetate [usan], Spirolair, Pirbuterol monoacetate, Cp-24,314-14

Molecular Formula

C₁₄H₂₄N₂O₅

Molecular Weight

300.35 g/mol

InChI Key

QSXMZJGGEWYVCN-UHFFFAOYSA-N

FDA UNII

1EH73XKR9N

Pirbuterol Acetate is the acetate salt form of pirbuterol, a synthetic catecholamine and a pyridine derivative with sympathomimetic and bronchodilatory effects. Pirbuterol acetate selectively stimulates beta-2 adrenergic receptors, resulting in initiation of intracellular adenylate cyclase activity leading to increased levels of cAMP. As a result muscle relaxation (broncho- and vasodilation) occurs via cAMP-dependent signal transduction. In addition, elevated levels of cAMP inhibit release of inflammatory mediators from mast cells.

1 2D Structure

PIRBUTEROL ACETATE

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

acetic acid;6-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol

2.1.2 InChI

InChI=1S/C12H20N2O3.C2H4O2/c1-12(2,3)13-6-11(17)8-4-5-10(16)9(7-15)14-8;1-2(3)4/h4-5,11,13,15-17H,6-7H2,1-3H3;1H3,(H,3,4)

2.1.3 InChI Key

QSXMZJGGEWYVCN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(=O)O.CC(C)(C)NCC(C1=NC(=C(C=C1)O)CO)O

2.2 Other Identifiers

2.2.1 UNII

1EH73XKR9N

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-tert-butylamino Ethyl)pyridine, Dihydrochloride

2. Cp 24315-1

3. Cp-24,314-1

4. Cp-24315-1

5. Maxair

6. Pirbuterol

7. Pirbuterol Acetate Salt

8. Pirbuterol Dihydrochloride

9. Pirbuterol Sulfate

10. Pyrbuterol

2.3.2 Depositor-Supplied Synonyms

1. 65652-44-0

2. Maxair

3. Pirbuterol Acetate [usan]

4. Spirolair

5. Pirbuterol Monoacetate

6. Cp-24,314-14

7. 1eh73xkr9n

8. 65652-44-0 (acetate)

9. 2-(hydroxymethyl)-6-(1-hydroxy-2-tert-butylamino-ethyl)-pyridin-3-ol

10. Cp 24314-14; Maxair;spirolair

11. Cp-24314-14

12. Pirbuterol Acetate (usan)

13. Acetic Acid;6-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol

14. 6-(2-(tert-butylamino)-1-hydroxyethyl)-2-(hydroxymethyl)pyridin-3-ol; Acetic Acid

15. Einecs 265-862-4

16. Unii-1eh73xkr9n

17. Maxair (tn)

18. Schembl3600

19. Alpha(sup 6)-((tert-butylamino)methyl)-3-hydroxy-2,6-pyridinedimethanol Monoacetate (salt)

20. Chebi:8246

21. Chembl1200444

22. Dtxsid40984214

23. Pirbuterol Acetate [vandf]

24. Pirbuterol Acetate [mart.]

25. Pirbuterol Monoacetate [mi]

26. Pirbuterol Acetate [who-dd]

27. Alpha6-((tert-butylamino)methyl)-3-hydroxypyridine-2,6-dimethanol Monoacetate

28. Pirbuterol Acetate [orange Book]

29. 2,6-pyridinedimethanol, Alpha(sup 6)-(((1,1-dimethylethyl)amino)methyl)-3-hydroxy-, Monoacetate (salt)

30. D00686

31. Pirbuterol Acetate 100 Microg/ml In Acetonitrile

32. Pirbuterol Acetate, Vetranal(tm), Analytical Standard

33. Q27252326

34. Pirbuterol Acetate, United States Pharmacopeia (usp) Reference Standard

35. Acetic Acid--6-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol (1/1)

36. .alpha.6-((tert-butylamino)methyl)-3-hydroxy-2,6-pyridinedimethanol Monoacetate (salt)

37. 2,6-pyridinedimethanol, .alpha.6-(((1,1-dimethylethyl)amino)methyl)-3-hydroxy-, Acetate (1:1)

38. 2,6-pyridinedimethanol, .alpha.6-(((1,1-dimethylethyl)amino)methyl)-3-hydroxy-, Monoacetate (salt)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₂₄N₂O₅
Molecular Weight	300.35 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	300.16852187 g/mol
Monoisotopic Mass	300.16852187 g/mol
Topological Polar Surface Area	123 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	261
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Maxair
PubMed Health	Pirbuterol (By breathing)
Drug Classes	Bronchodilator
Drug Label	The active component of MAXAIR AUTOHALER (pirbuterol acetate) is (R,S)6-{[(1,1-dimethylethyl)amino]methyl}-3-hydroxy-2,6-pyridinedimethanol monoacetate salt, a beta-2 adrenergic bronchodilator, having the following chemical structure:Pirbuterol ace...
Active Ingredient	Pirbuterol acetate
Dosage Form	Aerosol, metered
Route	Inhalation
Strength	eq 0.2mg base/inh
Market Status	Prescription
Company	Medicis

2 of 2
Drug Name	Maxair
PubMed Health	Pirbuterol (By breathing)
Drug Classes	Bronchodilator
Drug Label	The active component of MAXAIR AUTOHALER (pirbuterol acetate) is (R,S)6-{[(1,1-dimethylethyl)amino]methyl}-3-hydroxy-2,6-pyridinedimethanol monoacetate salt, a beta-2 adrenergic bronchodilator, having the following chemical structure:Pirbuterol ace...
Active Ingredient	Pirbuterol acetate
Dosage Form	Aerosol, metered
Route	Inhalation
Strength	eq 0.2mg base/inh
Market Status	Prescription
Company	Medicis

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Bronchodilator Agents

Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)

Adrenergic beta-2 Receptor Agonists

Compounds bind to and activate ADRENERGIC BETA-2 RECEPTORS. (See all compounds classified as Adrenergic beta-2 Receptor Agonists.)

Cardiotonic Agents

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.)

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