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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H37ClO7.H2O
Molecular Weight 539.057
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BECLOMETHASONE DIPROPIONATE MONOHYDRATE

SMILES

O.CCC(=O)OCC(=O)[C@@]1(OC(=O)CC)[C@@H](C)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]12C

InChI

InChIKey=QHQJZIXSVLFOHD-LYRZEVDOSA-N
InChI=1S/C28H37ClO7.H2O/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5;/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3;1H2/t16-,19-,20-,21-,25-,26-,27-,28-;/m0./s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C28H37ClO7
Molecular Weight 521.042
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://reference.medscape.com/drug/qvar-beclomethasone-inhaled-343427

Beclometasone dipropionate or beclomethasone dipropionate is sold under the brand name Qvar among others. Beclomethasone dipropionate is a corticosteroid demonstrating potent anti-inflammatory activity. The precise mechanism of corticosteroid action on asthma is not known. Corticosteroids have been shown to have multiple anti-inflammatory effects, inhibiting both inflammatory cells (e.g., mast cells, eosinophils, basophils, lymphocytes, macrophages, and neutrophils) and release of inflammatory mediators (e.g., histamine, eicosanoids, leukotrienes, and cytokines). These anti-inflammatory actions of corticosteroids may contribute to their efficacy in asthma. Beclomethasone dipropionate is a prodrug that is rapidly activated by hydrolysis to the active monoester, 17 monopropionate (17-BMP). Beclomethasone 17 monopropionate has been shown in vitro to exhibit a binding affinity for the human glucocorticoid receptor, which is approximately 13 times that of dexamethasone, 6 times that of triamcinolone acetonide, 1.5 times that of budesonide and 25 times that of beclomethasone dipropionate. The clinical significance of these findings is unknown. Studies in patients with asthma have shown a favorable ratio between topical anti-inflammatory activity and systemic corticosteroid effects with recommended doses of QVAR. Beclometasone dipropionate was first patented in 1962 and used medically in 1972. Common side effects with the inhaled form include respiratory infections, headaches, and throat inflammation. Serious side effects include an increased risk of infection, cataracts, Cushing’s syndrome, and severe allergic reactions. Long term use of the pill form may cause adrenal insufficiency. The pills may also cause mood or personality changes. The inhaled form is generally regarded as safe in pregnancy. Beclometasone is mainly a glucocorticoid.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
QVAR® 40

Approved Use

QVAR is indicated in the maintenance treatment of asthma as prophylactic therapy in patients 5 years of age and older. QVAR is also indicated for asthma patients who require systemic corticosteroid administration, where adding QVAR may reduce or eliminate the need for the systemic corticosteroids.

Launch Date

2000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3103.4 pg/mL
160 μg single, respiratory
dose: 160 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
BECLOMETHASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6635.1 pg/mL
320 μg single, respiratory
dose: 320 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
BECLOMETHASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
88 pg/mL
320 μg single, respiratory
dose: 320 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
BECLOMETHASONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
181.95 pg/mL
320 μg single, nasal
dose: 320 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
BECLOMETHASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
262.65 pg/mL
320 μg single, nasal
dose: 320 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
BECLOMETHASONE 17-MONOPROPIONATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
283.5 pg × h/mL
160 μg single, respiratory
dose: 160 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
BECLOMETHASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
623.6 pg × h/mL
320 μg single, respiratory
dose: 320 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
BECLOMETHASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
88.23 pg × h/mL
320 μg single, nasal
dose: 320 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
BECLOMETHASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1661.53 pg × h/mL
320 μg single, nasal
dose: 320 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
BECLOMETHASONE 17-MONOPROPIONATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.57 h
160 μg single, respiratory
dose: 160 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
BECLOMETHASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.92 h
320 μg single, respiratory
dose: 320 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
BECLOMETHASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.278 h
320 μg single, nasal
dose: 320 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
BECLOMETHASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.457 h
320 μg single, nasal
dose: 320 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
BECLOMETHASONE 17-MONOPROPIONATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
13%
BECLOMETHASONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
320 ug single, respiratory
Highest studied dose
Dose: 320 ug
Route: respiratory
Route: single
Dose: 320 ug
Sources:
healthy, 18 - 45 years
Health Status: healthy
Age Group: 18 - 45 years
Sex: M
Sources:
Disc. AE: Presyncope...
Other AEs: Headache, Nausea...
AEs leading to
discontinuation/dose reduction:
Presyncope (1 patient)
Other AEs:
Headache (2 patients)
Nausea (1 patient)
Tonsillar hypertrophy (1 patient)
Cerumen impaction (1 patient)
Oropharyngeal pain (1 patient)
Anxiety (1 patient)
Sources:
40 ug 2 times / day steady, respiratory
Recommended
Dose: 40 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 40 ug, 2 times / day
Sources:
unhealthy, 5-18 years
Health Status: unhealthy
Age Group: 5-18 years
Sex: M+F
Sources:
40 ug 2 times / day steady, respiratory
Recommended
Dose: 40 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 40 ug, 2 times / day
Sources:
unhealthy, 5-18 years
Health Status: unhealthy
Age Group: 5-18 years
Sex: M+F
Sources:
320 ug 2 times / day steady, respiratory
Highest studied dose
Dose: 320 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 320 ug, 2 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Headache, Pain...
Other AEs:
Headache (25%)
Pain (5%)
Back pain (4%)
Dysphonia (4%)
Sources:
320 ug 1 times / day steady, respiratory
Dose: 320 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 320 ug, 1 times / day
Sources:
unhealthy, adults and children
Health Status: unhealthy
Age Group: adults and children
Sex: unknown
Sources:
Disc. AE: Nasal mucosal disorder NOS...
AEs leading to
discontinuation/dose reduction:
Nasal mucosal disorder NOS (17 patients)
Sources:
80 ug 1 times / day steady, respiratory
Dose: 80 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 80 ug, 1 times / day
Sources:
unhealthy, child
Health Status: unhealthy
Age Group: child
Sources:
Other AEs: Epistaxis, Pyrexia...
Other AEs:
Epistaxis (below serious, 5 patients)
Pyrexia (below serious, 5 patients)
Sources:
80 ug 1 times / day steady, respiratory
Dose: 80 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 80 ug, 1 times / day
Sources:
unhealthy, child
Health Status: unhealthy
Age Group: child
Sources:
Other AEs: Epistaxis...
Other AEs:
Epistaxis (below serious, 18 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Anxiety 1 patient
320 ug single, respiratory
Highest studied dose
Dose: 320 ug
Route: respiratory
Route: single
Dose: 320 ug
Sources:
healthy, 18 - 45 years
Health Status: healthy
Age Group: 18 - 45 years
Sex: M
Sources:
Cerumen impaction 1 patient
320 ug single, respiratory
Highest studied dose
Dose: 320 ug
Route: respiratory
Route: single
Dose: 320 ug
Sources:
healthy, 18 - 45 years
Health Status: healthy
Age Group: 18 - 45 years
Sex: M
Sources:
Nausea 1 patient
320 ug single, respiratory
Highest studied dose
Dose: 320 ug
Route: respiratory
Route: single
Dose: 320 ug
Sources:
healthy, 18 - 45 years
Health Status: healthy
Age Group: 18 - 45 years
Sex: M
Sources:
Oropharyngeal pain 1 patient
320 ug single, respiratory
Highest studied dose
Dose: 320 ug
Route: respiratory
Route: single
Dose: 320 ug
Sources:
healthy, 18 - 45 years
Health Status: healthy
Age Group: 18 - 45 years
Sex: M
Sources:
Tonsillar hypertrophy 1 patient
320 ug single, respiratory
Highest studied dose
Dose: 320 ug
Route: respiratory
Route: single
Dose: 320 ug
Sources:
healthy, 18 - 45 years
Health Status: healthy
Age Group: 18 - 45 years
Sex: M
Sources:
Presyncope 1 patient
Disc. AE
320 ug single, respiratory
Highest studied dose
Dose: 320 ug
Route: respiratory
Route: single
Dose: 320 ug
Sources:
healthy, 18 - 45 years
Health Status: healthy
Age Group: 18 - 45 years
Sex: M
Sources:
Headache 2 patients
320 ug single, respiratory
Highest studied dose
Dose: 320 ug
Route: respiratory
Route: single
Dose: 320 ug
Sources:
healthy, 18 - 45 years
Health Status: healthy
Age Group: 18 - 45 years
Sex: M
Sources:
Headache 25%
320 ug 2 times / day steady, respiratory
Highest studied dose
Dose: 320 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 320 ug, 2 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Back pain 4%
320 ug 2 times / day steady, respiratory
Highest studied dose
Dose: 320 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 320 ug, 2 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Dysphonia 4%
320 ug 2 times / day steady, respiratory
Highest studied dose
Dose: 320 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 320 ug, 2 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Pain 5%
320 ug 2 times / day steady, respiratory
Highest studied dose
Dose: 320 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 320 ug, 2 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Nasal mucosal disorder NOS 17 patients
Disc. AE
320 ug 1 times / day steady, respiratory
Dose: 320 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 320 ug, 1 times / day
Sources:
unhealthy, adults and children
Health Status: unhealthy
Age Group: adults and children
Sex: unknown
Sources:
Epistaxis below serious, 5 patients
80 ug 1 times / day steady, respiratory
Dose: 80 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 80 ug, 1 times / day
Sources:
unhealthy, child
Health Status: unhealthy
Age Group: child
Sources:
Pyrexia below serious, 5 patients
80 ug 1 times / day steady, respiratory
Dose: 80 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 80 ug, 1 times / day
Sources:
unhealthy, child
Health Status: unhealthy
Age Group: child
Sources:
Epistaxis below serious, 18 patients
80 ug 1 times / day steady, respiratory
Dose: 80 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 80 ug, 1 times / day
Sources:
unhealthy, child
Health Status: unhealthy
Age Group: child
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
On the inappropriateness of an EM algorithm based procedure for blinded sample size re-estimation.
2002-01-30
Inhaled steroids for children's acute asthma exacerbations?
2002-01
Duration of steroid therapy determines dose-response effect.
2002-01
Initial improvements in lung function and bronchial hyperresponsiveness are maintained during 5 years of treatment with inhaled beclomethasone dipropionate and terbutaline.
2002-01
Evaluation of an asthma management program for Chinese children with mild-to-moderate asthma in Hong Kong.
2002-01
Growth factors in idiopathic pulmonary fibrosis: relative roles.
2002
Autocrine regulation of asthmatic airway inflammation: role of airway smooth muscle.
2002
Cost analysis of the use of inhaled corticosteroids in the treatment of asthma: a 1-year follow-up.
2001-12
Effects of theophylline withdrawal in well-controlled asthmatics treated with inhaled corticosteroid.
2001-12
Inhaled beclomethasone dipropionate improves acoustic measures of voice in patients with asthma.
2001-12
Electro-hydrodynamic atomization of drug solutions for inhalation purposes.
2001-12
Beclomethasone, budesonide and fluticasone propionate inhibit human neutrophil apoptosis.
2001-11-23
Apoptosis of airway epithelial cells induced by corticosteroids.
2001-11-15
[Difficulties in diagnosis and treatment of asthma in the elderly].
2001-11
Effect of salmeterol and salmeterol plus beclomethasone on saliva flow and IgA in patients with moderate-persistent chronic asthma.
2001-11
Effects of inhaled corticosteroid and short courses of oral corticosteroids on bone mineral density in asthmatic patients : a 4-year longitudinal study.
2001-11
Decreased osteocalcin levels in patients with chronic obstructive pulmonary disease using long-term inhaled beclomethasone dipropionate.
2001-11
Effects of 2 inhaled corticosteroids on growth: results of a randomized controlled trial.
2001-11
Chronic asthma.
2001-10-27
Evaluation of quality of life in children and teenagers with allergic rhinitis: adaptation and validation of the Rhinoconjunctivitis Quality of Life Questionnaire (RQLQ).
2001-10-25
Systematic review of clinical effectiveness of pressurised metered dose inhalers versus other hand held inhaler devices for delivering corticosteroids in asthma.
2001-10-20
Asthma stability after oral prednisone: a clinical model for comparing inhaled steroid potency.
2001-10-01
[Inhaled corticosteroid therapy in childhood asthma].
2001-10
[Recent advance in inhaled corticosteroid therapy].
2001-10
[Inhaled corticosteroids: first-line therapy in asthma].
2001-10
What's new: newly approved drugs for children.
2001-10
Beclomethasone diproprionate reduced airway inflammation without adrenal suppression in young children with cystic fibrosis: a pilot study.
2001-10
Symptomatic adrenal insufficiency during inhaled corticosteroid treatment.
2001-10
Exhaled nitric oxide and hydrogen peroxide in patients with chronic obstructive pulmonary disease: effects of inhaled beclomethasone.
2001-09-15
Long-acting inhaled beta(2)-agonist therapy in asthma.
2001-09-15
Treatment update: nonallergic rhinitis.
2001-09-13
Improved safety with equivalent asthma control in adults with chronic severe asthma on high-dose fluticasone propionate.
2001-09
Effect of seasonal allergen exposure on mucosal IL-16 and CD4+ cells in patients with allergic rhinitis.
2001-09
Dose-response relation of inhaled fluticasone propionate in adolescents and adults with asthma: meta-analysis.
2001-08-04
Effects of withdrawal of inhaled steroids in men with severe irreversible airflow obstruction.
2001-08-01
The anti-IgE antibody omalizumab reduces exacerbations and steroid requirement in allergic asthmatics.
2001-08
Effects of pranlukast, a cysteinyl leukotriene receptor 1 antagonist, combined with inhaled beclomethasone in patients with moderate or severe asthma.
2001-08
Antibacterial activity of apical surface fluid from the human airway cell line Calu-3: pharmacologic alteration by corticosteroids and beta(2)-agonists.
2001-08
Treatment of childhood asthma with anti-immunoglobulin E antibody (omalizumab).
2001-08
[Tracheobronchopathia osteochondroplastica].
2001-07
Improved asthma control after changing from low-to-medium doses of other inhaled corticosteroids to low-dose fluticasone propionate.
2001-06-08
A comparison of clinical use of fluticasone propionate and beclomethasone dipropionate in pediatric asthma.
2001-06
[Effect of FP inhalation and airway inflammation assessed by ECP in asthma].
2001-06
Influence of respiratory spacer devices on aerodynamic particle size distribution and fine particle mass of beclomethasone from metered-dose inhalers.
2001
Oral montelukast versus inhaled beclomethasone in 6- to 11-year-old children with asthma: results of an open-label extension study evaluating long-term safety, satisfaction, and adherence with therapy.
2001
Small airway inflammation in asthma.
2001
Comparison of hydrofluoroalkane-beclomethasone dipropionate Autohaler with budesonide Turbuhaler in asthma control.
2001
Oral steroids for bronchiectasis (stable and acute exacerbations).
2001
Aerosol characterization of nebulized intranasal glucocorticoid formulations.
2001
Comparison of beclomethasone dipropionate delivery by easyhaler dry powder inhaler and pMDI plus large volume spacer.
2001
Patents

Sample Use Guides

Administer QVAR (beclomethasone dipropionate HFA 40 ug) by the orally inhaled route only. Patients should prime QVAR by actuating into the air twice before using for the first time or if QVAR has not been used for over 10 days.
Route of Administration: Other
Incubation of challenged rings (bronchial rings from nonatopic humans) for 3 h with 3 x 10(-6) M beclomethasone dipropionate (BDP) restored the relaxant effect, suggesting reversal of beta(2)-AR pathway dysfunction.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:13:17 GMT 2025
Edited
by admin
on Mon Mar 31 18:13:17 GMT 2025
Record UNII
4H7L9AI22I
Record Status Validated (UNII)
Record Version
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Name Type Language
BECLOMETASONE DIPROPIONATE MONOHYDRATE
EP   WHO-DD  
Preferred Name English
BECLOMETHASONE DIPROPIONATE MONOHYDRATE
ORANGE BOOK  
Common Name English
BECLOMETASONE DIPROPIONATE MONOHYDRATE [EP IMPURITY]
Common Name English
BECLOMETASONE DIPROPIONATE MONOHYDRATE [EP MONOGRAPH]
Common Name English
Beclometasone dipropionate monohydrate [WHO-DD]
Common Name English
BECLOMETHASONE DIPROPIONATE MONOHYDRATE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
Code System Code Type Description
CAS
77011-63-3
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID00227831
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
PRIMARY
RXCUI
253156
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
PRIMARY RxNorm
DAILYMED
4H7L9AI22I
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL1200500
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
PRIMARY
FDA UNII
4H7L9AI22I
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
PRIMARY
SMS_ID
100000089858
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
PRIMARY
PUBCHEM
16052009
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
PRIMARY
EVMPD
SUB26308
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
PRIMARY
DRUG BANK
DBSALT001373
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
PRIMARY
NCI_THESAURUS
C61644
Created by admin on Mon Mar 31 18:13:17 GMT 2025 , Edited by admin on Mon Mar 31 18:13:17 GMT 2025
PRIMARY
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