Ipratropium

Synopsis, Chemistry

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168 Dossiers, 41 FDA Orange Book, 65 Europe, 17 Canada, 7 Australia, 23 South Africa, 15 Listed Dossiers

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SPRAY, METERED;NASAL - 0.021MG/SPRAY **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, SPRAY, METERED;NASAL - 0.042MG/SPRAY **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, SOLUTION;INHALATION - EQ 0.083% BASE;0.017% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

SPRAY, METERED;NASAL - 0.021MG/SPRAY **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
SPRAY, METERED;NASAL - 0.042MG/SPRAY **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
SOLUTION;INHALATION - EQ 0.083% BASE;0.017% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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Suppliers, 5 Actylis, 1 Nanjing Well Pharmaceutical, 1 Finar

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5 Parenteral, 2 Solubilizers

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16 US Medicaid Prescriptions, 40 Finished Drug Prices

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4 EDQM Standards, 4 USP Standards, 9 Other Ref. Standards

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Also known as: 22254-24-6, Atrovent, Itrop, Ipratropiumbromid, Bromure d'ipratropium, Bromuro de ipratropio

Molecular Formula

C₂₀H₃₀BrNO₃

Molecular Weight

412.4 g/mol

InChI Key

LHLMOSXCXGLMMN-CLTUNHJMSA-M

FDA UNII

VJV4X1P2Z1

A muscarinic antagonist structurally related to ATROPINE but often considered safer and more effective for inhalation use. It is used for various bronchial disorders, in rhinitis, and as an antiarrhythmic.

1 2D Structure

Ipratropium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1S,5R)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;bromide

2.1.2 InChI

InChI=1S/C20H30NO3.BrH/c1-14(2)21(3)16-9-10-17(21)12-18(11-16)24-20(23)19(13-22)15-7-5-4-6-8-15;/h4-8,14,16-19,22H,9-13H2,1-3H3;1H/q+1;/p-1/t16-,17+,18?,19?,21?;

2.1.3 InChI Key

LHLMOSXCXGLMMN-CLTUNHJMSA-M

2.1.4 Canonical SMILES

CC(C)[N+]1(C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3)C.[Br-]

2.1.5 Isomeric SMILES

CC(C)[N+]1([C@@H]2CC[C@H]1CC(C2)OC(=O)C(CO)C3=CC=CC=C3)C.[Br-]

2.2 Other Identifiers

2.2.1 UNII

VJV4X1P2Z1

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (endo,syn)-(+-)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo(3.2.1)octane

2. Atrovent

3. Ipratropium

4. Ipratropium Bromide Anhydrous

5. Ipratropium Bromide Monohydrate

6. Ipratropium Bromide, (endo,anti)-isomer

7. Ipratropium Bromide, (exo,syn)-isomer

8. Ipratropium Bromide, Endo-isomer

9. Itrop

10. N Isopropylatropine

11. N-isopropylatropine

12. Sch 1000

13. Sch 1178

14. Sch-1000

15. Sch-1178

16. Sch1000

17. Sch1178

2.3.2 Depositor-Supplied Synonyms

1. 22254-24-6

2. Atrovent

3. Itrop

4. Ipratropiumbromid

5. Bromure D'ipratropium

6. Bromuro De Ipratropio

7. Sch 1000

8. 8-isopropylnoratropine Methobromide

9. Ipratropium Bromide [inn]

10. Ipratropium Bromide'

11. Ipratropii Bromidum

12. N-isopropylnoratropinium Bromomethylate

13. Ipratropium Bromide Anhydrous

14. Vjv4x1p2z1

15. Mls000069557

16. 60251-88-9

17. Ipratropiumbromide

18. Smr000058764

19. (1r,5s)-3-((3-hydroxy-2-phenylpropanoyl)oxy)-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium Bromide

20. 24358-20-1

21. Ipratropium Bromide Monohydrate

22. 8-azoniabicyclo[3.2.1]octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, Bromide (1:1), (3-exo,8-syn)-

23. Rel-(1r,3r,5s,8r)-3-((3-hydroxy-2-phenylpropanoyl)oxy)-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium Bromide

24. Atem

25. 66985-17-9

26. Ipratropiumbromid [german]

27. Unii-vjv4x1p2z1

28. Ipratropii Bromidum [inn-latin]

29. Prestwick_279

30. Bromure D'ipratropium [inn-french]

31. Einecs 244-873-8

32. Einecs 261-098-0

33. Einecs 262-128-5

34. Bromuro De Ipratropio [inn-spanish]

35. Opera_id_1621

36. Schembl3852

37. Schembl3854

38. Schembl107906

39. (1s,3s,5r)-3-tropyloxy-8-isopropyltropanium Bromide

40. Ipratropium Bromide (anhydrous)

41. Chembl1464005

42. Ipratropium Bromide [mi]

43. Regid_for_cid_657308

44. Schembl16762661

45. Chebi:46659

46. Dtxsid10860753

47. Dtxsid60858923

48. Hms2234j05

49. Einecs 246-197-9

50. Bdbm50021892

51. Ipratropium Bromide [who-dd]

52. Mfcd00069291

53. Akos015895324

54. Akos030485952

55. (8r)-3-alpha-hydroxy-8-isopropyl-1-alpha-h,5-alpha-h-tropiumbromide-(+-)-tropate

56. 3-alpha-hydroxy-8-isopropyl-1-alpha-h,5-alpha-h-tropanium Bromide (+-)-tropate

57. (endo,anti)-(1)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-isopropyl-8-methyl-8-azoniabicyclo(3.2.1)octane Bromide

58. (exo,syn)-(1)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-isopropyl-8-methyl-8-azoniabicyclo(3.2.1)octane Bromide

59. Bi164579

60. N-isopropylnortropine Tropate Methobromide

61. C74140

62. T72808

63. Q424294

64. 3alpha-hydroxy-8-isopropyl-1alphah,5alphah-tropanium Bromide (+-)-tropate

65. 1-alpha-h,5-alpha-h-tropanium, 3-alpha-hydroxy-8-isopropyl-, Bromide, (+-)-tropate

66. (1r,3r,5s)-3-(3-hydroxy-2-phenylpropanoyloxy)-8-isopropyl-8-methyl-8-azoniabicyclo[3.2.1]octane Bromide

67. (3-endo,8-syn)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-isopropyl-8-methyl-8-azoniabicyclo[3.2.1]octane Bromide

68. (endo,syn)-(+-)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo[3.2.1]octane Bromide

69. 8-azoniabicyclo(3.2.1)octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, Bromide, Endo-

70. Endo-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-isopropyl-8-methyl-8-azoniabicyclo(3.2.1)octane Bromide

71. Rel-(1r,3r,5s,8s)-3-((3-hydroxy-2-phenylpropanoyl)oxy)-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium Bromide

2.4 Create Date

2005-06-29

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₀BrNO₃
Molecular Weight	412.4 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	411.14091 g/mol
Monoisotopic Mass	411.14091 g/mol
Topological Polar Surface Area	46.5 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	430
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 4
Drug Name	Atrovent
PubMed Health	Ipratropium (Into the nose)
Drug Classes	Nasal Agent
Drug Label	The active ingredient in ATROVENT Nasal Spray is ipratropium bromide (as the monohydrate). It is an anticholinergic agent chemically described as 8-azoniabicyclo[3.2.1]octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, bromide m...
Active Ingredient	Ipratropium bromide
Dosage Form	Spray, metered
Route	Nasal
Strength	0.042mg/spray; 0.021mg/spray
Market Status	Prescription
Company	Boehringer Ingelheim

2 of 4
Drug Name	Ipratropium bromide
PubMed Health	Ipratropium
Drug Classes	Bronchodilator, Nasal Agent
Drug Label	The active ingredient in Ipratropium Bromide Nasal Solution 0.03% (Nasal Spray) is ipratropium bromide monohydrate. It is an anticholinergic agent chemically described as 8-azoniabicyclo [3.2.1] octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-...
Active Ingredient	Ipratropium bromide
Dosage Form	Spray, metered; Solution
Route	Nasal; Inhalation
Strength	0.042mg/spray; 0.02%; 0.021mg/spray
Market Status	Prescription
Company	Ritedose; Nephron; Mylan Speclt; Roxane; Watson Labs; Bausch And Lomb; Landela Pharm

3 of 4
Drug Name	Atrovent
PubMed Health	Ipratropium (Into the nose)
Drug Classes	Nasal Agent
Drug Label	The active ingredient in ATROVENT Nasal Spray is ipratropium bromide (as the monohydrate). It is an anticholinergic agent chemically described as 8-azoniabicyclo[3.2.1]octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, bromide m...
Active Ingredient	Ipratropium bromide
Dosage Form	Spray, metered
Route	Nasal
Strength	0.042mg/spray; 0.021mg/spray
Market Status	Prescription
Company	Boehringer Ingelheim

4 of 4
Drug Name	Ipratropium bromide
PubMed Health	Ipratropium
Drug Classes	Bronchodilator, Nasal Agent
Drug Label	The active ingredient in Ipratropium Bromide Nasal Solution 0.03% (Nasal Spray) is ipratropium bromide monohydrate. It is an anticholinergic agent chemically described as 8-azoniabicyclo [3.2.1] octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-...
Active Ingredient	Ipratropium bromide
Dosage Form	Spray, metered; Solution
Route	Nasal; Inhalation
Strength	0.042mg/spray; 0.02%; 0.021mg/spray
Market Status	Prescription
Company	Ritedose; Nephron; Mylan Speclt; Roxane; Watson Labs; Bausch And Lomb; Landela Pharm

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.)

Cholinergic Antagonists

Drugs that bind to but do not activate CHOLINERGIC RECEPTORS, thereby blocking the actions of ACETYLCHOLINE or cholinergic agonists. (See all compounds classified as Cholinergic Antagonists.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Cholinergic Antagonists [MoA]; Anticholinergic [EPC]

5.3 ATC Code

R03BB01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

R - Respiratory system

R01 - Nasal preparations

R01A - Decongestants and other nasal preparations for topical use

R01AX - Other nasal preparations

R01AX03 - Ipratropium bromide

R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03B - Other drugs for obstructive airway diseases, inhalants

R03BB - Anticholinergics

R03BB01 - Ipratropium bromide

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Ipratropium

Ipratropium

Synopsis

Chemistry

APIs // Active Pharmaceutical Ingredients

26 API Suppliers

8 USDMF

8 CEP/COS

1 JDMF

5 EU WC

9 KDMF

15 NDC API

21 Listed Suppliers

PRICE INFORMATION

API Reference Price

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INTERMEDIATES

3 Suppliers

DOSSIERs // Finished Dosage Formulations

168 Dossiers

41 FDA Orange Book

65 Europe

17 Canada

7 Australia

23 South Africa

15 Listed Dossiers

DRUG PRODUCT COMPOSITION

SPRAY, METERED;NASAL - 0.021MG/SPRAY **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

SPRAY, METERED;NASAL - 0.042MG/SPRAY **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

SOLUTION;INHALATION - EQ 0.083% BASE;0.017% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

RELATED EXCIPIENT COMPANIES

Suppliers

5 Actylis

1 Nanjing Well Pharmaceutical

1 Finar

EXCIPIENTS BY APPLICATIONS

5 Parenteral

2 Solubilizers

GLOBAL SALES INFORMATION

16 US Medicaid Prescriptions

40 Finished Drug Prices

MARKET PLACE

10 APIs

5 DOSSIERS // FDF

1 EXCIPIENTS

PATENTS

7 US Patents

1 Health Canada Patents

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4 EDQM Standards

4 USP Standards

9 Other Ref. Standards

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12 News

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API REF. PRICE (USD / KG)

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SPRAY, METERED;NASAL - 0.021MG/SPRAY Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons

SPRAY, METERED;NASAL - 0.042MG/SPRAY Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons

SOLUTION;INHALATION - EQ 0.083% BASE;0.017% Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons