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Details

Stereochemistry RACEMIC
Molecular Formula C13H21NO3.ClH
Molecular Weight 275.772
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALBUTEROL HYDROCHLORIDE

SMILES

Cl.CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1

InChI

InChIKey=OWNWYCOLFIFTLK-UHFFFAOYSA-N
InChI=1S/C13H21NO3.ClH/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15;/h4-6,12,14-17H,7-8H2,1-3H3;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C13H21NO3
Molecular Weight 239.3107
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Albuterol is a short acting beta2-adrenergic receptor agonist. Albuterol effectively alleviates bronchospasm due to bronchial asthma, chronic bronchitis, and other chronic bronchopulmonary disorders such as COPD. In vitro studies and in vivo pharmacologic studies have demonstrated that albuterol has a preferential effect on beta2-adrenergic receptors compared with isoproterenol. While it is recognized that beta2-adrenergic receptors are the predominant receptors in bronchial smooth muscle, data indicate that there is a population of beta2-receptors in the human heart existing in a concentration between 10% and 50%. The precise function of these receptors has not been established. The pharmacologic effects of beta-adrenergic agonist drugs, including albuterol, are at least in part attributable to stimulation through beta-adrenergic receptors of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3',5'- adenosine monophosphate (cyclic AMP). Increased cyclic AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells. Albuterol has been shown in most controlled clinical trials to have more effect on the respiratory tract, in the form of bronchial smooth muscle relaxation, than isoproterenol at comparable doses while producing fewer cardiovascular effects. Albuterol is longer acting than isoproterenol in most patients by any route of administration because it is not a substrate for the cellular uptake processes for catecholamines nor for catechol-O-methyl transferase.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rat. Human data not available Intravenous studies in rats with Albuterol sulfate have demonstrated that Albuterol crosses the blood brain barrier and reaches brain concentrations amounting to approximately 5% of the plasma concentrations.

Originator

Curator's Comment: On arriving at Allen and Hanburys in 1961 as Research Director, David set himself the task of finding a more selective bronchodilator than isoprenaline, the non-selective ß-adrenoceptor agonist, which was widely in use at the time but caused unwanted effects on the heart at doses that caused bronchodilation, even when inhaled. This led to the discovery of salbutamol, as the first selective ß2-adrenoceptor agonist for the treatment of bronchospasm associated with airway diseases such as asthma

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROVENTIL-HFA

Approved Use

Albuterol sulfate inhalation solution is indicated for the relief of bronchospasm in patients 2 years of age and older with reversible obstructive airway disease and acute attacks of bronchospasm.

Launch Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.12 ng/mL
10 mg single, respiratory
dose: 10 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(R)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
10.06 ng/mL
10 mg single, respiratory
dose: 10 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(S)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.84 ng/mL
2.5 mg single, respiratory
dose: 2.5 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(R)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.77 ng/mL
2.5 mg single, respiratory
dose: 2.5 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(S)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
13 ng/mL
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALBUTEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
14.7 ng/mL
4 mg 4 times / day steady-state, oral
dose: 4 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
15.1 ng/mL
4 mg 4 times / day multiple, oral
dose: 4 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1469 pg/mL
180 μg single, respiratory
dose: 180 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
15.97 ng × h/mL
10 mg single, respiratory
dose: 10 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(R)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
74.46 ng × h/mL
10 mg single, respiratory
dose: 10 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(S)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.61 ng × h/mL
2.5 mg single, respiratory
dose: 2.5 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(R)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
11.66 ng × h/mL
2.5 mg single, respiratory
dose: 2.5 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(S)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3239 μg × min/L
1.5 mg single, intravenous
dose: 1.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ALBUTEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3677 μg × min/L
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALBUTEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
72.6 ng × h/mL
4 mg 4 times / day steady-state, oral
dose: 4 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
77.4 ng × h/mL
4 mg 4 times / day multiple, oral
dose: 4 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4268 pg × h/mL
180 μg single, respiratory
dose: 180 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
10 mg single, respiratory
dose: 10 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(R)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.75 h
10 mg single, respiratory
dose: 10 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(S)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.52 h
2.5 mg single, respiratory
dose: 2.5 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(R)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.29 h
2.5 mg single, respiratory
dose: 2.5 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
(S)-ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3.9 h
400 μg single, intravenous
dose: 400 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
237 min
1.5 mg single, intravenous
dose: 1.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ALBUTEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.5 h
4 mg 4 times / day multiple, oral
dose: 4 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.4 h
180 μg single, respiratory
dose: 180 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
92%
ALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status:
Doses

Doses

DosePopulationAdverse events​
6 mg single, oral
MTD
Dose: 6 mg
Route: oral
Route: single
Dose: 6 mg
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
DLT: Tremor...
Dose limiting toxicities:
Tremor
Sources:
180 ug 4 times / day multiple, respiratory
Studied dose
Dose: 180 ug, 4 times / day
Route: respiratory
Route: multiple
Dose: 180 ug, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Disc. AE: Pancreatic carcinoma, Gastrointestinal carcinoma...
AEs leading to
discontinuation/dose reduction:
Pancreatic carcinoma (0.6%)
Gastrointestinal carcinoma (0.6%)
Papillary thyroid cancer (0.6%)
Asthma exacerbation (0.6%)
Sources:
1.9 mg/kg single, oral
Overdose
Dose: 1.9 mg/kg
Route: oral
Route: single
Dose: 1.9 mg/kg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
Other AEs: Hypoglycemia, Hypokalemia...
Other AEs:
Hypoglycemia
Hypokalemia (grade 1)
Restlessness
Sinus tachycardia
Agitation
Tremor NEC
Sources:
AEs

AEs

AESignificanceDosePopulation
Tremor DLT
6 mg single, oral
MTD
Dose: 6 mg
Route: oral
Route: single
Dose: 6 mg
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Asthma exacerbation 0.6%
Disc. AE
180 ug 4 times / day multiple, respiratory
Studied dose
Dose: 180 ug, 4 times / day
Route: respiratory
Route: multiple
Dose: 180 ug, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Gastrointestinal carcinoma 0.6%
Disc. AE
180 ug 4 times / day multiple, respiratory
Studied dose
Dose: 180 ug, 4 times / day
Route: respiratory
Route: multiple
Dose: 180 ug, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Pancreatic carcinoma 0.6%
Disc. AE
180 ug 4 times / day multiple, respiratory
Studied dose
Dose: 180 ug, 4 times / day
Route: respiratory
Route: multiple
Dose: 180 ug, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Papillary thyroid cancer 0.6%
Disc. AE
180 ug 4 times / day multiple, respiratory
Studied dose
Dose: 180 ug, 4 times / day
Route: respiratory
Route: multiple
Dose: 180 ug, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Agitation
1.9 mg/kg single, oral
Overdose
Dose: 1.9 mg/kg
Route: oral
Route: single
Dose: 1.9 mg/kg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
Hypoglycemia
1.9 mg/kg single, oral
Overdose
Dose: 1.9 mg/kg
Route: oral
Route: single
Dose: 1.9 mg/kg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
Restlessness
1.9 mg/kg single, oral
Overdose
Dose: 1.9 mg/kg
Route: oral
Route: single
Dose: 1.9 mg/kg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
Sinus tachycardia
1.9 mg/kg single, oral
Overdose
Dose: 1.9 mg/kg
Route: oral
Route: single
Dose: 1.9 mg/kg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
Tremor NEC
1.9 mg/kg single, oral
Overdose
Dose: 1.9 mg/kg
Route: oral
Route: single
Dose: 1.9 mg/kg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
Hypokalemia grade 1
1.9 mg/kg single, oral
Overdose
Dose: 1.9 mg/kg
Route: oral
Route: single
Dose: 1.9 mg/kg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: M
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
beta-adrenergic receptor stimulation selectively inhibits IL-12p40 release in microglia.
2001-04-27
Effect of polymorphism of the beta(2)-adrenergic receptor on response to regular use of albuterol in asthma.
2001-04-18
A combination of fluticasone and salmeterol for asthma.
2001-04-16
Up-regulation of uncoupling proteins by beta-adrenergic stimulation in L6 myotubes.
2001-04-13
Salmeterol and fluticasone propionate given as a combination. Lack of systemic pharmacodynamic and pharmacokinetic interactions.
2001-04-11
Requirement of additional adenylate cyclase activation for the inhibition of human eosinophil degranulation by phosphodiesterase IV inhibitors.
2001-04-06
The diagnosis and treatment of cough.
2001-04-05
Profile of ligand binding to the porcine beta2-adrenergic receptor.
2001-04
Pharmacokinetics and systemic beta2-adrenoceptor-mediated responses to inhaled salbutamol.
2001-04
Use of a long-acting inhaled beta2-adrenergic agonist, salmeterol xinafoate, in patients with chronic obstructive pulmonary disease.
2001-04
The role of domiciliary nebulizers in managing patients with severe COPD.
2001-04
Comparative efficiency of commercial and improvised spacer device in acute bronchial asthma.
2001-04
The utility of peak flow, symptom scores, and beta-agonist use as outcome measures in asthma clinical research.
2001-04
Evaluation of salmeterol or montelukast as second-line therapy for asthma not controlled with inhaled corticosteroids.
2001-04
Comparative in vivo lung delivery of hydrofluoroalkane-salbutamol formulation via metered-dose inhaler alone, with plastic spacer, or with cardboard tube.
2001-04
Fluticasone propionate/salmeterol combination.
2001-04
Efficacy of nebulized epinephrine versus salbutamol in hospitalized infants with bronchiolitis.
2001-04
Interethnic variability in human drug responses.
2001-04
Genetic variation in beta-adrenergic receptors and their relationship to susceptibility for asthma and therapeutic response.
2001-04
Permeability of endothelial monolayers to albumin is increased by bradykinin and inhibited by prostaglandins.
2001-04
Nebivolol and airway responsiveness in the rabbit.
2001-03-23
Functional properties of atypical beta-adrenoceptors on the guinea pig duodenum.
2001-03-23
Solubility prediction of salmeterol xinafoate in water--dioxane mixtures.
2001-03-23
Hyperosmolar diabetic non-ketotic coma, hyperkalaemia and an unusual near death experience.
2001-03
Towards evidence based emergency medicine: best BETs from the Manchester Royal Infirmary. Salbutamol and ipratropium in COPD.
2001-03
Assessment of forearm vasodilator responses to acetylcholine and albuterol by strain gauge plethysmography: reproducibility and influence of strain gauge placement.
2001-03
Switching from Ventolin CFC to Ventolin HFA is well tolerated and effective in patients with asthma.
2001-03
Clinical predictors of health-related quality of life depend on asthma severity.
2001-03
The effect of salmeterol on markers of airway inflammation following segmental allergen challenge.
2001-03
Albuterol delivery in a neonatal ventilated lung model: Nebulization versus chlorofluorocarbon- and hydrofluoroalkane-pressurized metered dose inhalers.
2001-03
The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: the role of potassium channels and vasoactive intestinal peptide receptors.
2001-03
Effect of salmeterol on allergen-induced airway inflammation in mild allergic asthma.
2001-03
Single-isomer beta-agonists.
2001-03
Chronic systemic administration of salmeterol to rats promotes pulmonary beta(2)-adrenoceptor desensitization and down-regulation of G(s alpha).
2001-03
Salmeterol and conventional asthma therapy.
2001-03
Effectiveness and safety of salmeterol in nonspecialist practice settings.
2001-03
Low-dose fluticasone propionate compared with montelukast for first-line treatment of persistent asthma: a randomized clinical trial.
2001-03
[Bronchial asthma. A combination preparation improves patient compliance].
2001-02-22
[Salmeterol plus fluticasone--a powerful team. New combined preparation improves compliance].
2001-02-08
Respiratory and cardiovascular effects of WP-934 in guinea pigs.
2001-02
Some behavioural effects of antidepressant drugs are time-dependent.
2001-02
Quantitative determination of clenbuterol, salbutamol and tulobuterol enantiomers by capillary electrophoresis.
2001-02
Pediatric pre-hospital advanced life support care in an urban setting.
2001-02
Mometasone furoate: efficacy and safety in moderate asthma compared with beclomethasone dipropionate.
2001-02
Effects of therapeutic doses of albuterol on beta2-adrenergic receptor density and metabolic changes.
2001-02
Beta2-agonist exerts differential effects on the development of cord blood T cells but not on peripheral blood T cells.
2001-02
Effect of inspiratory flow rate on beta2-agonist induced bronchodilation in mechanically ventilated COPD patients.
2001-01
Nocturnal asthma uncontrolled by inhaled corticosteroids: theophylline or long-acting beta2 agonists?
2001
The effect of acute alteration in oxygen tension on the bronchodilator response to salbutamol in vitro and in vivo in man.
2001
Zafirlukast: an update of its pharmacology and therapeutic efficacy in asthma.
2001
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Albuterol also supplied as 2 mg tablets: usual dosage - 2 or 4 mg three or four times a day. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=87b8cd3c-2849-4b50-b63e-9ea379165c07 Intravenous salbutamol is commonly used to treat children with severe asthma unresponsive to inhaled β2-agonist therapy, usual dose is 4ug/kg. https://www.drugs.com/uk/ventolin-injection-500mcg-1ml-leaflet.html
Two inhalations repeated every 4 to 6 hours (aerosol, metered)
Route of Administration: Respiratory
In Vitro Use Guide
Curator's Comment: albuterol at 7.25 mg/L (concentrations, mimicking those in the bronchial tree) could modulate pneumococcal biofilm development and antibiotic action using an in vitro model.
7.25 mg/L, pneumococcal biofilm in vitro model.
Substance Class Chemical
Created
by admin
on Tue Apr 01 17:06:57 GMT 2025
Edited
by admin
on Tue Apr 01 17:06:57 GMT 2025
Record UNII
P12862PDAK
Record Status Validated (UNII)
Record Version
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Name Type Language
ALBUTEROL HYDROCHLORIDE
Common Name English
1,3-BENZENEDIMETHANOL, .ALPHA.1-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-4-HYDROXY-, HYDROCHLORIDE (±)-SALBUTAMOL HYDROCHLORIDE
Preferred Name English
SALBUTAMOL HYDROCHLORIDE
Common Name English
1,3-BENZENEDIMETHANOL, .ALPHA.1-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-4-HYDROXY-, HYDROCHLORIDE (1:1)
Systematic Name English
DL-SALBUTAMOL HYDROCHLORIDE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID80965587
Created by admin on Tue Apr 01 17:06:57 GMT 2025 , Edited by admin on Tue Apr 01 17:06:57 GMT 2025
PRIMARY
SMS_ID
100000181252
Created by admin on Tue Apr 01 17:06:57 GMT 2025 , Edited by admin on Tue Apr 01 17:06:57 GMT 2025
PRIMARY
PUBCHEM
6452399
Created by admin on Tue Apr 01 17:06:57 GMT 2025 , Edited by admin on Tue Apr 01 17:06:57 GMT 2025
PRIMARY
FDA UNII
P12862PDAK
Created by admin on Tue Apr 01 17:06:57 GMT 2025 , Edited by admin on Tue Apr 01 17:06:57 GMT 2025
PRIMARY
CAS
51293-66-4
Created by admin on Tue Apr 01 17:06:57 GMT 2025 , Edited by admin on Tue Apr 01 17:06:57 GMT 2025
PRIMARY
CAS
39006-83-2
Created by admin on Tue Apr 01 17:06:57 GMT 2025 , Edited by admin on Tue Apr 01 17:06:57 GMT 2025
SUPERSEDED
Related Record Type Details
PARENT -> SALT/SOLVATE