Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H30NO3 |
Molecular Weight | 332.4571 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 4 / 5 |
E/Z Centers | 0 |
Charge | 1 |
SHOW SMILES / InChI
SMILES
CC(C)[N@+]1(C)[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@@H](CO)C3=CC=CC=C3
InChI
InChIKey=OEXHQOGQTVQTAT-VQCHGODESA-N
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?/m0/s1
Molecular Formula | C20H29NO3 |
Molecular Weight | 331.4492 |
Charge | 0 |
Count |
|
Stereochemistry | EPIMERIC |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68009241
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68009241
Ipratropium (ipratropium bromide, ATROVENT® HFA) is a muscarinic antagonist structurally related to atropine but often considered safer and more effective for inhalation use. It is indicated for the maintenance treatment of bronchospasm associated with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. Ipratropium (ipratropium bromide, ATROVENT® HFA) is an anticholinergic (parasympatholytic) agent which, based on animal studies, appears to inhibit vagally-mediated reflexes by antagonizing the action of acetylcholine, the transmitter agent released at the neuromuscular junctions in the lung. Anticholinergics prevent the increases in intracellular concentration of Ca2+ which is caused by interaction of acetylcholine with the muscarinic receptors on bronchial smooth muscle.
CNS Activity
Sources: https://books.google.ru/books?id=ZyGsBAAAQBAJ&dq
Curator's Comment: Raeburn, David, Giembycz, Mark A. (2012). Rhinitis: Immunopathology and Pharmacotherapy. Springer. p. 133:
"Topical intranasal ipratropium bromide has limited central nervous system penetration".
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL216 |
0.49 nM [Ki] | ||
Target ID: CHEMBL211 |
1.5 nM [Ki] | ||
Target ID: CHEMBL245 |
0.51 nM [Ki] | ||
Target ID: CHEMBL1821 |
0.66 nM [Ki] | ||
Target ID: CHEMBL2035 |
1.7 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ATROVENT HFA Approved UseATROVENT HFA Inhalation Aerosol is indicated as a bronchodilator for maintenance treatment of bronchospasm associated with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. Launch Date2004 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33.5 pg/mL |
20 μg 4 times / day multiple, respiratory dose: 20 μg route of administration: Respiratory experiment type: MULTIPLE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
31.7 pg/mL |
20 μg 4 times / day steady-state, respiratory dose: 20 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
|
35.4 pg/mL |
20 μg 4 times / day steady-state, respiratory dose: 20 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.04 pg × h/mL |
20 μg 4 times / day multiple, respiratory dose: 20 μg route of administration: Respiratory experiment type: MULTIPLE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
123 pg × h/mL |
20 μg 4 times / day steady-state, respiratory dose: 20 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
|
131 pg × h/mL |
20 μg 4 times / day steady-state, respiratory dose: 20 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 h |
20 μg 4 times / day multiple, respiratory dose: 20 μg route of administration: Respiratory experiment type: MULTIPLE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
95.5% |
20 μg 4 times / day multiple, respiratory dose: 20 μg route of administration: Respiratory experiment type: MULTIPLE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 18 - 75 years n = 96 Health Status: unhealthy Condition: perennial allergic rhinitis Age Group: 18 - 75 years Sex: M+F Population Size: 96 Sources: |
Disc. AE: Nasal disorder NOS, Nasal dryness... AEs leading to discontinuation/dose reduction: Nasal disorder NOS (17%) Sources: Nasal dryness (2%) Epistaxis (2%) |
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 43 Health Status: unhealthy Condition: common colds Age Group: 2 - 5 years Sex: M+F Population Size: 43 Sources: |
Disc. AE: Epistaxis... AEs leading to discontinuation/dose reduction: Epistaxis (1 patient) Sources: |
84 ug 3 times / day steady, respiratory Highest studied dose Dose: 84 ug, 3 times / day Route: respiratory Route: steady Dose: 84 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 187 Health Status: unhealthy Condition: allergies Age Group: 2 - 5 years Sex: M+F Population Size: 187 Sources: |
Disc. AE: Epistaxis, Upper respiratory tract infection... AEs leading to discontinuation/dose reduction: Epistaxis (1 patient) Sources: Upper respiratory tract infection (1 patient) Ear infection (1 patient) Exacerbation of asthma (1 patient) |
200 ug single, respiratory Highest studied dose Dose: 200 ug Route: respiratory Route: single Dose: 200 ug Sources: |
unhealthy, mean 40.7 years n = 20 Health Status: unhealthy Condition: stable chronic asthma Age Group: mean 40.7 years Sex: M+F Population Size: 20 Sources: |
Disc. AE: Nausea and vomiting... AEs leading to discontinuation/dose reduction: Nausea and vomiting (1 patient) Sources: |
42 ug 1 times / day steady, respiratory Recommended Dose: 42 ug, 1 times / day Route: respiratory Route: steady Dose: 42 ug, 1 times / day Sources: |
unhealthy, mean 42.6 years n = 99 Health Status: unhealthy Condition: rhinorrhea Age Group: mean 42.6 years Sex: M+F Population Size: 99 Sources: |
Other AEs: Nasal disorder NOS... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nasal disorder NOS | 17% Disc. AE |
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 18 - 75 years n = 96 Health Status: unhealthy Condition: perennial allergic rhinitis Age Group: 18 - 75 years Sex: M+F Population Size: 96 Sources: |
Epistaxis | 2% Disc. AE |
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 18 - 75 years n = 96 Health Status: unhealthy Condition: perennial allergic rhinitis Age Group: 18 - 75 years Sex: M+F Population Size: 96 Sources: |
Nasal dryness | 2% Disc. AE |
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 18 - 75 years n = 96 Health Status: unhealthy Condition: perennial allergic rhinitis Age Group: 18 - 75 years Sex: M+F Population Size: 96 Sources: |
Epistaxis | 1 patient Disc. AE |
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 43 Health Status: unhealthy Condition: common colds Age Group: 2 - 5 years Sex: M+F Population Size: 43 Sources: |
Ear infection | 1 patient Disc. AE |
84 ug 3 times / day steady, respiratory Highest studied dose Dose: 84 ug, 3 times / day Route: respiratory Route: steady Dose: 84 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 187 Health Status: unhealthy Condition: allergies Age Group: 2 - 5 years Sex: M+F Population Size: 187 Sources: |
Epistaxis | 1 patient Disc. AE |
84 ug 3 times / day steady, respiratory Highest studied dose Dose: 84 ug, 3 times / day Route: respiratory Route: steady Dose: 84 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 187 Health Status: unhealthy Condition: allergies Age Group: 2 - 5 years Sex: M+F Population Size: 187 Sources: |
Exacerbation of asthma | 1 patient Disc. AE |
84 ug 3 times / day steady, respiratory Highest studied dose Dose: 84 ug, 3 times / day Route: respiratory Route: steady Dose: 84 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 187 Health Status: unhealthy Condition: allergies Age Group: 2 - 5 years Sex: M+F Population Size: 187 Sources: |
Upper respiratory tract infection | 1 patient Disc. AE |
84 ug 3 times / day steady, respiratory Highest studied dose Dose: 84 ug, 3 times / day Route: respiratory Route: steady Dose: 84 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 187 Health Status: unhealthy Condition: allergies Age Group: 2 - 5 years Sex: M+F Population Size: 187 Sources: |
Nausea and vomiting | 1 patient Disc. AE |
200 ug single, respiratory Highest studied dose Dose: 200 ug Route: respiratory Route: single Dose: 200 ug Sources: |
unhealthy, mean 40.7 years n = 20 Health Status: unhealthy Condition: stable chronic asthma Age Group: mean 40.7 years Sex: M+F Population Size: 20 Sources: |
Nasal disorder NOS | 19 patients | 42 ug 1 times / day steady, respiratory Recommended Dose: 42 ug, 1 times / day Route: respiratory Route: steady Dose: 42 ug, 1 times / day Sources: |
unhealthy, mean 42.6 years n = 99 Health Status: unhealthy Condition: rhinorrhea Age Group: mean 42.6 years Sex: M+F Population Size: 99 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 6,21 |
yes [IC50 17.4 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 6,21 |
yes [IC50 2.5 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 6,21 |
yes [IC50 3.6 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 6,21 |
yes [IC50 30.5 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 6,21 |
yes [IC50 62.8 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 7,21 |
strong | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 7,21 |
strong | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 7,21 |
strong | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 7,21 |
strong | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 7,21 |
strong | |||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Styrofoam cup, ipratropium bromide, and anisocoria. | 1999 May |
|
Blurred vision from ipratropium bromide inhalation. | 1999 May 1 |
|
Asthma medications and their potential adverse effects in the elderly: recommendations for prescribing. | 2001 |
|
Anticholinergic therapy for bronchiectasis. | 2001 |
|
[Effect of ipratropium bromide on histamine-induced bronchoconstriction in subjects with chronic airway obstruction]. | 2001 |
|
An economic overview of chronic obstructive pulmonary disease. | 2001 |
|
Inhaled salmeterol: a review of its efficacy in chronic obstructive pulmonary disease. | 2001 |
|
Inhaled short-acting beta2-agonists versus ipratropium for acute exacerbations of chronic obstructive pulmonary disease. | 2001 |
|
Is exercise tolerance limited by the heart or the lungs? | 2001 Apr |
|
Use of a long-acting inhaled beta2-adrenergic agonist, salmeterol xinafoate, in patients with chronic obstructive pulmonary disease. | 2001 Apr |
|
The role of domiciliary nebulizers in managing patients with severe COPD. | 2001 Apr |
|
Antimuscarinic treatment for lung diseases from research to clinical practice. | 2001 Apr 27 |
|
Management of acute exacerbations of chronic obstructive pulmonary disease. | 2001 Aug |
|
Effect of ipratropium bromide on airway and pulmonary muscarinic receptors in a rat model of chronic obstructive pulmonary disease. | 2001 Jan |
|
Analyses of quaternary ammonium drugs in horse urine by capillary electrophoresis-mass spectrometry. | 2001 Jul |
|
Decreased bronchodilating effect of salbutamol in relieving methacholine induced moderate to severe bronchoconstriction during high dose treatment with long acting beta2 agonists. | 2001 Jul |
|
Effectiveness of salmeterol versus ipratropium bromide on exertional dyspnoea in COPD. | 2001 Jun |
|
Does the mode of inhalation affect the bronchodilator response in patients with severe COPD? | 2001 Jun |
|
Bronchodilatory effects of salbutamol, ipratropium bromide, and their combination: double-blind, placebo-controlled crossover study in cystic fibrosis. | 2001 Jun |
|
A retrospective study of risk factors for repeated admissions for asthma in a rural/suburban university hospital. | 2001 May |
|
Clozapine and sialorrhea: update. | 2001 May |
|
Function of pulmonary neuronal M(2) muscarinic receptors in stable chronic obstructive pulmonary disease. | 2001 May |
|
In patients with COPD, treatment with a combination of formoterol and ipratropium is more effective than a combination of salbutamol and ipratropium : a 3-week, randomized, double-blind, within-patient, multicenter study. | 2001 May |
|
Ipratropium bromide nasal spray for treatment of rhinorrhea in the laryngectomized patient: a pilot study. | 2001 May-Jun |
|
Does adding ipratropium to salbutamol (albuterol) help children with asthma? | 2001 Nov |
|
Ipratropium bromide hydrofluoroalkane inhalation aerosol is safe and effective in patients with COPD. | 2001 Oct |
|
Graphical model checking with correlated response data. | 2001 Oct 15 |
|
Alternative methods for assessing bronchodilator reversibility in chronic obstructive pulmonary disease. | 2001 Sep |
|
[Asthma follow-up after treatment of status asthmaticus in ICU Pneumonology Department in Warsaw Medical University]. | 2002 |
|
Heliox for treatment of exacerbations of chronic obstructive pulmonary disease. | 2002 |
|
Histochemical and biochemical studies on the secretory mechanisms of some glands of guinea-pigs treated with histamine. | 2002 |
|
Tiotropium bromide. | 2002 |
|
[Pharmacodynamics of inhalation broncholytic agents introduced in a single dose by nebulizer in patients with severe exacerbation of bronchial asthma]. | 2002 |
|
Differential response of wheezes and ruttles to anticholinergics. | 2002 Apr |
|
Intravenous versus oral corticosteroids for treatment of acute asthma exacerbations. | 2002 Apr |
|
Airways reactivity in patients with CF. | 2002 Aug |
|
Hospitalizations and mortality in the Lung Health Study. | 2002 Aug 1 |
|
24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139]. | 2002 Aug 5 |
|
Clinical review: severe asthma. | 2002 Feb |
|
Randomized, double-blind, placebo-controlled trial of intravenous salbutamol and nebulized ipratropium bromide in early management of severe acute asthma in children presenting to an emergency department. | 2002 Feb |
|
Other option in bronchiolitis. | 2002 Feb |
|
Emergency department asthma: compliance with an evidence-based management algorithm. | 2002 Jul |
|
Understanding and use of inhaler medication by asthmatics in specialty care in Trinidad: a study following development of Caribbean guidelines for asthma management and prevention. | 2002 Jun |
|
In children hospitalized for asthma exacerbations, does adding ipratropium bromide to albuterol and corticosteroids improve outcome? | 2002 Mar |
|
[Effect of ipratropium bromide on calcium activated potassium channel in tracheal smooth muscle cells from chronically hypoxic rats]. | 2002 May |
|
What is the optimal treatment strategy for chronic obstructive pulmonary disease exacerbations? | 2002 May |
Sample Use Guides
The usual starting dose of ATROVENT® HFA is two inhalations four times a day. Patients may take additional inhalations as required; however, the total number of inhalations should not exceed 12 in 24 hours.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7952627
Ba 679 BR, atropine, and ipratropium bromide inhibited electrical field stimulation (EFS)-induced contraction with IC50 values of 0.17, 0.74, and 0.58 nM, respectively, in guinea pig trachea. Ba 679 BR had a slower onset and longer duration of action than atropine or ipratropium bromide (the times required to attain 50% of the maximum response were 34.8, 3.8, and 7.6 min, respectively, and the times required for 50% recovery of the response were 540, 31.6, and 81.2 min, respectively).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:38:39 GMT 2023
by
admin
on
Fri Dec 15 16:38:39 GMT 2023
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Record UNII |
GR88G0I6UL
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29704
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NDF-RT |
N0000175574
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WHO-ATC |
R01AX03
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NDF-RT |
N0000175370
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LIVERTOX |
NBK548667
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NCI_THESAURUS |
C319
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WHO-ATC |
R03BB01
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WHO-ATC |
R03AL02
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WHO-ATC |
R03AL01
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Code System | Code | Type | Description | ||
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Ipratropium
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PRIMARY | |||
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D009241
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7213
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ALTERNATIVE | |||
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C61794
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1475
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60205-81-4
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5956
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325
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GR88G0I6UL
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100000091672
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SUB02767MIG
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DB00332
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DTXSID9048437
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Ipratropium
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1546373
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GR88G0I6UL
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |