Arformoterol Tartrate

Synopsis, Chemistry

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Also known as: 200815-49-2, Brovana, (r,r)-arformoterol tartrate, Arformoterol tartrate [usan], 5p8vj2i235, Arformoterol tartrate (usan)

Molecular Formula

C₂₃H₃₀N₂O₁₀

Molecular Weight

494.5 g/mol

InChI Key

FCSXYHUNDAXDRH-OKMNHOJOSA-N

FDA UNII

5P8VJ2I235

Arformoterol Tartrate is the tartrate salt of arformoterol, the (R,R)-enantiomer of formoterol and a long-acting beta-2 adrenergic agonist with bronchodilator activity. Arformoterol selectively binds to and activates beta-2 adrenergic receptors in bronchiolar smooth muscle, thereby causing stimulation of adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3',5'-adenosine monophosphate (cAMP). Increased intracellular cAMP levels cause relaxation of bronchial smooth muscle and lead to an inhibition of release of inflammatory mediators from mast cells. This may eventually lead to an improvement of airway function.

1 2D Structure

Arformoterol Tartrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R)-2,3-dihydroxybutanedioic acid;N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide

2.1.2 InChI

InChI=1S/C19H24N2O4.C4H6O6/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22;5-1(3(7)8)2(6)4(9)10/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22);1-2,5-6H,(H,7,8)(H,9,10)/t13-,19+;1-,2-/m11/s1

2.1.3 InChI Key

FCSXYHUNDAXDRH-OKMNHOJOSA-N

2.1.4 Canonical SMILES

CC(CC1=CC=C(C=C1)OC)NCC(C2=CC(=C(C=C2)O)NC=O)O.C(C(C(=O)O)O)(C(=O)O)O

2.1.5 Isomeric SMILES

C[C@H](CC1=CC=C(C=C1)OC)NC[C@@H](C2=CC(=C(C=C2)O)NC=O)O.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O

2.2 Other Identifiers

2.2.1 UNII

5P8VJ2I235

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 200815-49-2

2. Brovana

3. (r,r)-arformoterol Tartrate

4. Arformoterol Tartrate [usan]

5. 5p8vj2i235

6. Arformoterol Tartrate (usan)

7. Formamide, N-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-, (2r,3r)-2,3-dihydroxybutanedioate (1:1)

8. (r,r)-formoterol Tartrate

9. (-)-n-(2-hydroxy-5-((1r)-1-hydroxy-2-(((1r)-2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)phenyl)formamide Hydrogen (2r,3r)-2,3-dihydroxybutanedioate (salt)

10. Formamide, N-(2-hydroxy-5-((1r)-1-hydroxy-2-(((1r)-2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)phenyl)-, (2r,3r)-2,3-dihydroxybutanedioate (1:1) (salt)

11. N-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-formamide (2r,3r)-2,3-dihydroxybutanedioate (1:1) (salt)

12. Brovana Inhalation Solution

13. Unii-5p8vj2i235

14. Brovana (tn)

15. Arformotero Ltartrate

16. Dtxsid80173903

17. Arformoterol Tartrate [vandf]

18. S5217

19. Arformoterol Tartrate [mart.]

20. Akos005145740

21. Arformoterol Tartrate [who-dd]

22. Ccg-269651

23. Arformoterol Tartrate, >=98% (hplc)

24. Ba171831

25. Bs-42158

26. Arformoterol Tartrate [orange Book]

27. Formoterol R,r-form L-tartrate [mi]

28. D02981

29. 815f492

30. Q-101035

31. Q27262686

32. (2r,3r)-2,3-dihydroxybutanedioic Acid;n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide

33. (r,r)-formoterol Tartrate; N-(2-hydroxy-5-((1r)-1-hydroxy-2-(((1r)-2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)phenyl)formamide (2r,3r)-2,3-dihydroxybutanedioate (1:1)

34. [(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]-[(2r)-1-(4-methoxyphenyl)propan-2-yl]azanium;(2r,3r)-2,3,4-trihydroxy-4-oxobutanoate

35. N-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide (2r,3r)-2,3-dihydroxybutane Dioate

36. N-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide (2r,3r)-2,3-dihydroxybutanedioate

37. N-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide L-tartrate

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₃₀N₂O₁₀
Molecular Weight	494.5 g/mol
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	11
Exact Mass	494.19004516 g/mol
Monoisotopic Mass	494.19004516 g/mol
Topological Polar Surface Area	206 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	521
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
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	Brovana
PubMed Health	Arformoterol (By breathing)
Drug Classes	Bronchodilator
Active Ingredient	Arformoterol tartrate
Dosage Form	Solution
Route	Inhalation
Strength	eq 0.015mg base/2ml
Market Status	Prescription
Company	Sunovion

2 of 2
Drug Name	Brovana
PubMed Health	Arformoterol (By breathing)
Drug Classes	Bronchodilator
Active Ingredient	Arformoterol tartrate
Dosage Form	Solution
Route	Inhalation
Strength	eq 0.015mg base/2ml
Market Status	Prescription
Company	Sunovion