U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28Cl2O4
Molecular Weight 427.361
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOMETASONE

SMILES

[H][C@@]12C[C@@H](C)[C@](O)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]3(Cl)[C@@]2([H])CCC4=CC(=O)C=C[C@]34C

InChI

InChIKey=QLIIKPVHVRXHRI-CXSFZGCWSA-N
InChI=1S/C22H28Cl2O4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1

HIDE SMILES / InChI
Molecular Formula C22H28Cl2O4
Molecular Weight 427.361
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://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019796s026lbl.pdf

Mometasone is a medium-potency synthetic corticosteroid with antiinflammatory, antipruritic, and vasoconstrictive properties. Studies in asthmatic patients have demonstrated that mometasone provides a favorable ratio of topical to systemic activity due to its primary local effect along with the extensive hepatic metabolism and the lack of active metabolites. Though effective for the treatment of asthma, glucocorticoids do not affect asthma symptoms immediately. Maximum improvement in symptoms following inhaled administration of mometasone furoate may not be achieved for 1 to 2 weeks or longer after starting treatment. When glucocorticoids are discontinued, asthma stability may persist for several days or longer. Mometasone has been shown in vitro to exhibit a binding affinity for the human glucocorticoid receptor which is approximately 12 times that of dexamethasone, 7 times that of triamcinolone acetonide, 5 times that of budesonide, and 1.5 times that of fluticasone. Mometasone inhaler is indicated for the maintenance treatment of asthma as prophylactic therapy. The nasal spray is indicated for the treatment of the nasal symptoms of seasonal allergic and perennial allergic rhinitis. ELOCON Lotion (Mometasone) is indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Originator

Approval Year

1987
111
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
ELOCON

Approved Use

ELOCON Lotion is a corticosteroid indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses in patients ≥12 years of age.

Launch Date

1987
Preventing
Approved
8429
ASMANEX

Approved Use

ASMANEX TWISTHALER is a corticosteroid indicated for: • Maintenance treatment of asthma as prophylactic therapy in patients 4 years of age and older.

Launch Date

2005
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
183 pg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26845343
320 μg 1 times / day steady-state, respiratory
dose: 320 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
MOMETASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7.56 pg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29669668
100 μg single, nasal
dose: 100 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
MOMETASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1560 pg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26845343
320 μg 1 times / day steady-state, respiratory
dose: 320 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
MOMETASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
92 pg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29669668
100 μg single, nasal
dose: 100 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
MOMETASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
19.24 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29669668
100 μg single, nasal
dose: 100 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
MOMETASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1.5%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020762s053lbl.pdf
MOMETASONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
unhealthy, 0.5 - 2 yeas
n = 63
Health Status: unhealthy
Condition: dermatoses
Age Group: 0.5 - 2 yeas
Sex: unknown
Population Size: 63
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
Other AEs: Glucocorticoid decreased, Skin and subcutaneous conditions NEC...
Other AEs:
Glucocorticoid decreased (1 patient)
Skin and subcutaneous conditions NEC (1 patient)
Skin bacterial infection (1 patient)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
unhealthy, adult
n = 812
Health Status: unhealthy
Condition: dermatoses
Age Group: adult
Sex: unknown
Population Size: 812
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
Other AEs: Pruritus, Skin atrophy...
Other AEs:
Pruritus (4.8%)
Skin atrophy (4.8%)
Tingling (4.8%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Glucocorticoid decreased 1 patient
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
unhealthy, 0.5 - 2 yeas
n = 63
Health Status: unhealthy
Condition: dermatoses
Age Group: 0.5 - 2 yeas
Sex: unknown
Population Size: 63
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
Skin and subcutaneous conditions NEC 1 patient
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
unhealthy, 0.5 - 2 yeas
n = 63
Health Status: unhealthy
Condition: dermatoses
Age Group: 0.5 - 2 yeas
Sex: unknown
Population Size: 63
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
Skin bacterial infection 1 patient
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
unhealthy, 0.5 - 2 yeas
n = 63
Health Status: unhealthy
Condition: dermatoses
Age Group: 0.5 - 2 yeas
Sex: unknown
Population Size: 63
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
Pruritus 4.8%
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
unhealthy, adult
n = 812
Health Status: unhealthy
Condition: dermatoses
Age Group: adult
Sex: unknown
Population Size: 812
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
Skin atrophy 4.8%
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
unhealthy, adult
n = 812
Health Status: unhealthy
Condition: dermatoses
Age Group: adult
Sex: unknown
Population Size: 812
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
Tingling 4.8%
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
unhealthy, adult
n = 812
Health Status: unhealthy
Condition: dermatoses
Age Group: adult
Sex: unknown
Population Size: 812
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C8
911
BCRP
561

P-gp
1537
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C8
965
 yes [IC50 0.327 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
561
 likely
P-gp
1537
 likely
CYP3A4
1737
 yes
unlikely (co-administration study)
Comment: ketoconazole 200 mg (as well as placebo) were given twice daily concomitantly on Days 4 to 9. Mometasone furoate plasma concentrations were <150 pcg/mL on Day 3 prior to coadministration of ketoconazole or placebo. Following concomitant administration of ketoconazole, 4 out of 12 subjects in the ketoconazole treatment group (n=12) had peak plasma concentrations of mometasone furoate >200 pcg/mL on Day 9 (211-324 pcg/mL)
Page: 22,23
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:6970
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6970
ZINC
ZINC000004097440
http://zinc15.docking.org/substances/ZINC000004097440
PubMed

PubMed

TitleDatePubMed
A review of the pharmacology and pharmacokinetics of inhaled fluticasone propionate and mometasone furoate.
2001 Sep
Investigation of an enhanced resolution triple quadrupole mass spectrometer for high-throughput liquid chromatography/tandem mass spectrometry assays.
2002
Divergent effect of mometasone on human eosinophil and neutrophil apoptosis.
2002 Aug 16
Efficacy of budesonide in moderate to severe asthma.
2002 Jun
Instrumental evaluation of retinoid-induced skin irritation.
2002 May
[Allergic contact eczema caused by henna tattoo].
2002 Sep-Oct
Relief of cough and nasal symptoms associated with allergic rhinitis by mometasone furoate nasal spray.
2003 Apr
Randomized, double-masked comparison of olopatadine ophthalmic solution, mometasone furoate monohydrate nasal spray, and fexofenadine hydrochloride tablets using the conjunctival and nasal allergen challenge models.
2003 Aug
Efficacy of betamethasone valerate mousse in comparison with standard therapies on scalp psoriasis: an open, multicentre, randomized, controlled, cross-over study on 241 patients.
2003 Jan
Systemic bioactivity of intranasal triamcinolone and mometasone in perennial allergic rhinitis.
2003 Mar
Intranasal steroid sprays in the treatment of rhinitis: is one better than another?
2003 Nov
Comparison of the flow properties of aqueous suspension corticosteroid nasal sprays under differing sampling conditions.
2003 Oct
Pharmaceutical characteristics that influence the clinical efficacy of inhaled corticosteroids.
2003 Oct
Significant receptor affinities of metabolites and a degradation product of mometasone furoate.
2004 Jul 22
[Elocom is the newest corticosteroid for local use].
2004 Jun
Nasal allergies and beyond: a clinical review of the pharmacology, efficacy, and safety of mometasone furoate.
2005
Sputum eosinophilia and the short term response to inhaled mometasone in chronic obstructive pulmonary disease.
2005 Mar
Alternative therapies in antibiotic-resistant infection.
2006
Antimicrobial silk clothing in the treatment of atopic dermatitis proves comparable to topical corticosteroid treatment.
2006
Novel insights into the aetiology and pathophysiology of increased airway inflammation during COPD exacerbations.
2006 May 22
Cross-reactions to desoximetasone and mometasone furoate in a patient with multiple topical corticosteroid allergies.
2006 Sep
Future therapeutic treatment of COPD: struggle between oxidants and cytokines.
2007
Inhaled corticosteroids in children with asthma: pharmacologic determinants of safety and efficacy and other clinical considerations.
2007
Pathological features and inhaled corticosteroid response of eosinophilic and non-eosinophilic asthma.
2007 Dec
Seborrhoeic dermatitis.
2007 Jul 1
Onset of action of azelastine nasal spray compared with mometasone nasal spray and placebo in subjects with seasonal allergic rhinitis evaluated in an environmental exposure chamber.
2007 Jul-Aug
Montelukast in the management of allergic rhinitis.
2007 Jun
New treatment options in allergic rhinitis: patient considerations and the role of ciclesonide.
2008 Apr
Long-term follow-up of children undergoing topical intranasal steroid therapy for adenoidal hypertrophy.
2008 Aug
Effect of allergic rhinitis on the use and cost of health services by children with asthma.
2008 Aug 30
Relative oral corticosteroid-sparing effect of 7 inhaled corticosteroids in chronic asthma: a meta-analysis.
2008 Jul
Effectiveness of twice daily azelastine nasal spray in patients with seasonal allergic rhinitis.
2008 Oct
Effect of illicit direct to consumer advertising on use of etanercept, mometasone, and tegaserod in Canada: controlled longitudinal study.
2008 Sep 2
Comparative adrenocortical suppression in dogs with otitis externa following topical otic administration of four different glucocorticoid-containing medications.
2008 Summer
Bronchial diffusing capacity of nitric oxide is increased in patients with allergic rhinitis.
2009
A double-blind randomised placebo-controlled trial of topical intranasal corticosteroids in 4- to 11-year-old children with persistent bilateral otitis media with effusion in primary care.
2009 Aug
Topical intranasal corticosteroids in 4-11 year old children with persistent bilateral otitis media with effusion in primary care: double blind randomised placebo controlled trial.
2009 Dec 16
Treatment of postviral olfactory loss with glucocorticoids, Ginkgo biloba, and mometasone nasal spray.
2009 Oct
Alitretinoin--its use in intractable hand eczema and other potential indications.
2009 Sep 21
Mapping analyses to estimate health utilities based on responses to the OM8-30 Otitis Media Questionnaire.
2010 Feb
Patents

Patents

JP4589928B2
9

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Can also be used as inhalation powder http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021067s013lbl.pdf
Apply a few drops to the affected skin areas once daily and massage lightly until it disappears.
Route of Administration: Topical
In Vitro Use Guide
Mac-1 expression and human eosinophil migration were effectively downregulated by preincubation with Mometasone at 1, 10 and 100 nM
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:45:26 GMT 2023
Edited
by admin
on Fri Dec 15 15:45:26 GMT 2023
Record UNII
8HR4QJ6DW8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MOMETASONE
INN   VANDF   WHO-DD  
INN  
Official Name English
LAS-41002
Code English
9,21-DICHLORO-11.BETA.,17-DIHYDROXY-16.ALPHA.-METHYLPREGNA-1,4-DIENE-3,20-DIONE
Systematic Name English
LAS41002
Code English
MOMETASONE [VANDF]
Common Name English
mometasone [INN]
Common Name English
(+)-MOMETASONE
Common Name English
MOMETASONE FUROATE IMPURITY G [EP IMPURITY]
Common Name English
PREGNA-1,4-DIENE-3,20-DIONE, 9,21-DICHLORO-11,17-DIHYDROXY-16-METHYL-, (11.BETA.,16.ALPHA.)-
Systematic Name English
MONOVO
Brand Name English
Mometasone [WHO-DD]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 524.957
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
NDF-RT N0000175450
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
WHO-VATC QR03BA07
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WHO-ATC D07AC13
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WHO-ATC R03AK09
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NCI_THESAURUS C211
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WHO-VATC QR01AD09
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
WHO-ATC R01AD09
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
WHO-VATC QS02CA91
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WHO-VATC QR03AK09
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
WHO-VATC QD07AC13
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NDF-RT N0000175576
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
WHO-ATC R03BA07
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
WHO-ATC D07XC03
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
CFR 21 CFR 524.1044H
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
WHO-VATC QD07XC03
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
Code System Code Type Description
MESH
C053915
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
PRIMARY
DAILYMED
8HR4QJ6DW8
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
PRIMARY
CHEBI
6970
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
PRIMARY
INN
6030
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
PRIMARY
NCI_THESAURUS
C66181
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
PRIMARY
FDA UNII
8HR4QJ6DW8
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
PRIMARY
LACTMED
Mometasone, Nasal
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
PRIMARY
PUBCHEM
441335
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PRIMARY
RXCUI
108118
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PRIMARY RxNorm
DRUG BANK
DB00764
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PRIMARY
CAS
105102-22-5
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PRIMARY
EPA CompTox
DTXSID10872412
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PRIMARY
ChEMBL
CHEMBL1161
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PRIMARY
EVMPD
SUB09045MIG
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PRIMARY
SMS_ID
100000080358
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
PRIMARY
WIKIPEDIA
MOMETASONE
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
PRIMARY
LACTMED
Mometasone, Topical
Created by admin on Fri Dec 15 15:45:26 GMT 2023 , Edited by admin on Fri Dec 15 15:45:26 GMT 2023
PRIMARY
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Related Record Type Details
Structure of MOMETASONE FUROATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of MOMETASONE FUROATE MONOHYDRATE
PARENT -> IMPURITY
Related Record Type Details
Structure of MOMETASONE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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