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Chemistry

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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

Ipratropium Bromide
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 Bromide

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 Weight 412.4 g/mol
Molecular Formula C20H30BrNO3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Exact Mass411.14091 g/mol
Monoisotopic Mass411.14091 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count25
Formal Charge0
Complexity430
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameAtrovent
PubMed HealthIpratropium (Into the nose)
Drug ClassesNasal Agent
Drug LabelThe 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 IngredientIpratropium bromide
Dosage FormSpray, metered
RouteNasal
Strength0.042mg/spray; 0.021mg/spray
Market StatusPrescription
CompanyBoehringer Ingelheim

2 of 4  
Drug NameIpratropium bromide
PubMed HealthIpratropium
Drug ClassesBronchodilator, Nasal Agent
Drug LabelThe 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 IngredientIpratropium bromide
Dosage FormSpray, metered; Solution
RouteNasal; Inhalation
Strength0.042mg/spray; 0.02%; 0.021mg/spray
Market StatusPrescription
CompanyRitedose; Nephron; Mylan Speclt; Roxane; Watson Labs; Bausch And Lomb; Landela Pharm

3 of 4  
Drug NameAtrovent
PubMed HealthIpratropium (Into the nose)
Drug ClassesNasal Agent
Drug LabelThe 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 IngredientIpratropium bromide
Dosage FormSpray, metered
RouteNasal
Strength0.042mg/spray; 0.021mg/spray
Market StatusPrescription
CompanyBoehringer Ingelheim

4 of 4  
Drug NameIpratropium bromide
PubMed HealthIpratropium
Drug ClassesBronchodilator, Nasal Agent
Drug LabelThe 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 IngredientIpratropium bromide
Dosage FormSpray, metered; Solution
RouteNasal; Inhalation
Strength0.042mg/spray; 0.02%; 0.021mg/spray
Market StatusPrescription
CompanyRitedose; 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


API SUPPLIERS

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Vamsi Labs

India

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LGM Pharma

U.S.A

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Jai Radhe Sales

India

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Aarti Pharmalabs

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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Virtual BoothAarti Pharmalabs is a partner of choice for APIs & Intermediates and the largest Indian manufacturer of Xanthine Derivatives.

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Neuland Laboratories

India

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Boehringer Ingelheim GmbH

Germany

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Boehringer Ingelheim GmbH

Germany

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Sifavitor srl

Italy

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Sifavitor srl

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Amphastar Pharmaceuticals

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Amphastar Pharmaceuticals

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Lusochimica

Italy

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Lusochimica

Italy

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Derivados Quimicos SAU

Spain

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Derivados Quimicos SAU

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API Reference Price

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12-Jan-2021
24-Oct-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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INTERMEDIATES SUPPLIERS

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01

Vamsi Labs

India
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothVamsi Labs is one of the major manufacturers of Anti-asthmatic, Anti-migraine & Anti-psychotic APIs.

CAS Number : 710-11-2

End Use API : Ipratropium Bromide

About The Company : Vamsi Labs, established in 1991, is a leading Indian API manufacturer. Specializing in anti-asthmatic, anti-migraine & anti-psychotic APIs, it caters to domesti...

Vamsi Labs

02

Vamsi Labs

India
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothVamsi Labs is one of the major manufacturers of Anti-asthmatic, Anti-migraine & Anti-psychotic APIs.

CAS Number : 1209437-82-0

End Use API : Ipratropium Bromide

About The Company : Vamsi Labs, established in 1991, is a leading Indian API manufacturer. Specializing in anti-asthmatic, anti-migraine & anti-psychotic APIs, it caters to domesti...

Vamsi Labs

03

Vamsi Labs

India
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothVamsi Labs is one of the major manufacturers of Anti-asthmatic, Anti-migraine & Anti-psychotic APIs.

CAS Number : 3423-25-4

End Use API : Ipratropium Bromide

About The Company : Vamsi Labs, established in 1991, is a leading Indian API manufacturer. Specializing in anti-asthmatic, anti-migraine & anti-psychotic APIs, it caters to domesti...

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

USFDA APPLICATION NUMBER - 20393

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

USFDA APPLICATION NUMBER - 20394

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

USFDA APPLICATION NUMBER - 20950

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