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Hexoprenaline

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Chemistry

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Also known as: Gynipral, Bronalin, Etoscol, 32266-10-7, Leanol, 30117-45-4

Molecular Formula

C₂₂H₃₄N₂O₁₀S

Molecular Weight

518.6 g/mol

InChI Key

GTDCHGNGVGRHQY-UHFFFAOYSA-N

FDA UNII

U851S9102C

Stimulant of adrenergic beta 2 receptors. It is used as a bronchodilator, antiasthmatic agent, and tocolytic agent.

1 2D Structure

Hexoprenaline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[2-[6-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino]hexylamino]-1-hydroxyethyl]benzene-1,2-diol;sulfuric acid

2.1.2 InChI

InChI=1S/C22H32N2O6.H2O4S/c25-17-7-5-15(11-19(17)27)21(29)13-23-9-3-1-2-4-10-24-14-22(30)16-6-8-18(26)20(28)12-16;1-5(2,3)4/h5-8,11-12,21-30H,1-4,9-10,13-14H2;(H2,1,2,3,4)

2.1.3 InChI Key

GTDCHGNGVGRHQY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=C(C=C1C(CNCCCCCCNCC(C2=CC(=C(C=C2)O)O)O)O)O)O.OS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

U851S9102C

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ginipral

2. Gynipral

3. Hexoprenaline

4. Ipradol

5. St 1512

6. St-1512

7. St1512

8. Sulfate, Hexoprenaline

2.3.2 Depositor-Supplied Synonyms

1. Gynipral

2. Bronalin

3. Etoscol

4. 32266-10-7

5. Leanol

6. 30117-45-4

7. Delaprem

8. Hexoprenaline Sulphate

9. Nsc-292266

10. St1512/so4

11. 4,4'-[hexane-1,6-diylbis[imino(1-hydroxyethylene)]]dipyrocatechol Sulphate

12. Dsstox_cid_26688

13. Dsstox_rid_81822

14. Dsstox_gsid_46688

15. Hexoprenaline Sulfate (usan)

16. Hexoprenalinesulphate

17. Hexoprenaline Sulfate [usan]

18. 4,4'-(hexane-1,6-diylbis(imino(1-hydroxyethylene)))dipyrocatechol Sulphate

19. 4-[2-[6-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino]hexylamino]-1-hydroxyethyl]benzene-1,2-diol;sulfuric Acid

20. Cas-32266-10-7

21. U851s9102c

22. Ncgc00167522-01

23. Delaprem (tn)

24. Einecs 250-057-2

25. 1,2-benzenediol, 4,4'-(1,6-hexanediylbis(imino(1-hydroxy-2,1-ethanediyl)))bis-, Sulfate (1:1) (salt)

26. Schembl598186

27. Chembl2104813

28. Dtxsid6046688

29. Chebi:31670

30. Hexoprenaline Sulfate [mi]

31. Hexoprenaline Sulfate [jan]

32. St-1512/so4

33. Tox21_112519

34. Nsc292266

35. Hexoprenaline Sulfate [mart.]

36. Hexoprenaline Sulfate [who-dd]

37. Tox21_112519_1

38. Ncgc00167522-02

39. D02396

40. Q27290818

41. 1, 4,4'-[1,6-hexanediylbis[imino(1-hydroxy-2,1-ethanediyl)]]bis-, Sulfate (1:1) (salt)

42. (+/-)-.alpha.,.alpha.'-(hexamethylenebis(iminomethylene))bis(3,4-dihydroxybenzyl Alcohol) Sulfate (1:1) (salt)

43. (+/-)-.alpha.,.alpha.'-(hexamethylenebis(iminomethylene))bis(3,4-dihydroxybenzyl Alcohol) Sulphate (1:1) (salt)

44. 1,2-benzenediol, 4,4'-(1,6-hexanediylbis(imino(1-hydroxy-2,1-ethanediyl)))bis-, Sulphate (1:1) (salt)

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₃₄N₂O₁₀S
Molecular Weight	518.6 g/mol
Hydrogen Bond Donor Count	10
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	13
Exact Mass	518.19341646 g/mol
Monoisotopic Mass	518.19341646 g/mol
Topological Polar Surface Area	228 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	499
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 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.)

Tocolytic Agents

Drugs that prevent preterm labor and immature birth by suppressing uterine contractions (TOCOLYSIS). Agents used to delay premature uterine activity include magnesium sulfate, beta-mimetics, oxytocin antagonists, calcium channel inhibitors, and adrenergic beta-receptor agonists. The use of intravenous alcohol as a tocolytic is now obsolete. (See all compounds classified as Tocolytic Agents.)

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