Ipratropium

ID: ALA1621597

Chembl Id: CHEMBL1621597

Max Phase: Approved

First Approval: 1986

Molecular Formula: C20H30NO3+

Molecular Weight: 332.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ipratropium | Ipratropium cation | Ipratropium ion

Synonyms from Alternative Forms(17): Ipratropium Bromide | Ipratropium bromide hydrate | Ipratropium bromide anhydrous | Ipratropium bromide monohydrate | NSC-759613 | SCH 1000-BR-MONOHYDRATE | SCH-1000-BR- | Atrovent | Atrovent aerocaps | Atrovent fte | Atrovent hfa | Atrovent udvs | Ipratrop | Ipratrop steripoule | Respontin | Rinatec | Tropiovent

Canonical SMILES:  CC(C)[N+]1(C)[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(CO)c1ccccc1)C2

Standard InChI:  InChI=1S/C20H30NO3/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/q+1/t16-,17+,18+,19?,21?

Standard InChI Key:  OEXHQOGQTVQTAT-BHIXFJMTSA-N

Alternative Forms

1. Alternative Forms:

   

   ALA1621597

   Ipratropium Bromide

2. Parent:

   

   ALA1621597

   IPRATROPIUM
3. 

   ALA1621597

   IPRATROPIUM BROMIDE
4. 

   ALA1621597

   Ipratropium chloride

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: No

Chirality: No

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 332.46

Molecular Weight (Monoisotopic): 332.2220

AlogP: 2.85

#Rotatable Bonds: 5

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -1.82

CX LogD: -1.82

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: 0.73

References

1. Sakatis MZ, Reese MJ, Harrell AW, Taylor MA, Baines IA, Chen L, Bloomer JC, Yang EY, Ellens HM, Ambroso JL, Lovatt CA, Ayrton AD, Clarke SE..  (2012)  Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.,  25  (10): [PMID:22931300] [10.1021/tx300075j]

2. Hendrickx R, Johansson JG, Lohmann C, Jenvert RM, Blomgren A, Börjesson L, Gustavsson L..  (2013)  Identification of novel substrates and structure-activity relationship of cellular uptake mediated by human organic cation transporters 1 and 2.,  56  (18): [PMID:23984907] [10.1021/jm400966v]

3. Jones LH, Burrows J, Feeder N, Glossop P, James K, Jones RM, Kenyon AS, Patel S, Roberts DF, Selby MD, Strang RS, Stuart EF, Trevethick MA, Watson J, Wright KN, Clarke N..  (2015)  Molecular hybridization yields triazole bronchodilators for the treatment of COPD.,  25  (22): [PMID:26471092] [10.1016/j.bmcl.2015.10.008]

4. Unpublished dataset, 

5. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

6. Armani E, Rizzi A, Capaldi C, De Fanti R, Delcanale M, Villetti G, Marchini G, Pisano AR, Pitozzi V, Pittelli MG, Trevisani M, Salvadori M, Cenacchi V, Puccini P, Amadei F, Pappani A, Civelli M, Patacchini R, Baker-Glenn CAG, Van de Poël H, Blackaby WP, Nash K, Amari G..  (2021)  Discovery of M₃ Antagonist-PDE4 Inhibitor Dual Pharmacology Molecules for the Treatment of Chronic Obstructive Pulmonary Disease.,  64  (13.0): [PMID:34142835] [10.1021/acs.jmedchem.1c00204]

7. Gebauer L, Jensen O, Brockmöller J, Dücker C..  (2022)  Substrates and Inhibitors of the Organic Cation Transporter 3 and Comparison with OCT1 and OCT2.,  65  (18.0): [PMID:36067397] [10.1021/acs.jmedchem.2c01075]

8. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• SARS-CoV-2 Screening Data 2020-21