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Details

Stereochemistry RACEMIC
Molecular Formula C18H19Cl2NO4
Molecular Weight 384.254
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FELODIPINE

SMILES

CCOC(=O)C1=C(C)NC(C)=C(C1C2=CC=CC(Cl)=C2Cl)C(=O)OC

InChI

InChIKey=RZTAMFZIAATZDJ-UHFFFAOYSA-N
InChI=1S/C18H19Cl2NO4/c1-5-25-18(23)14-10(3)21-9(2)13(17(22)24-4)15(14)11-7-6-8-12(19)16(11)20/h6-8,15,21H,5H2,1-4H3

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/felodipine.html

Felodipine is a long-acting 1,4-dihydropyridine calcium channel blocker (CCB)b. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, felodipine prevents calcium-dependent myocyte contraction and vasoconstriction. Felodipine is the most potent CCB in use and is unique in that it exhibits fluorescent activity. In addition to binding to L-type calcium channels, felodipine binds to a number of calcium-binding proteins, exhibits competitive antagonism of the mineralcorticoid receptor, inhibits the activity of calmodulin-dependent cyclic nucleotide phosphodiesterase, and blocks calcium influx through voltage-gated T-type calcium channels. Felodipine is used to treat mild to moderate essential hypertension.

CNS Activity

CNS Penetrant
2588
Curator's Comment: Animal studies have demonstrated that felodipine crosses the blood-brain barrier and the placenta.

Originator

Approval Year

1991
122
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 0.17 µM [IC50]
Cholangiocarcinoma Mz-ChA-1 cells
1
Target ID: Cholangiocarcinoma Mz-ChA-1 cells
Inhibitor
8504
 26.0 µM [IC50]
Inhibitor
8504
 0.726 µM [IC50]
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
PLENDIL

Approved Use

PLENDIL is indicated for the treatment of hypertension, to lower blood pressure.

Launch Date

1991
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
23.1 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2015166/
10 mg 2 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FELODIPINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: FASTED
35.6 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2015166/
10 mg 2 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DEHYDROFELODIPINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.2 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3396260/
5 mg 2 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FELODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
17.1 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3396260/
5 mg 2 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FELODIPINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
100.9 nM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2015166/
10 mg 2 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FELODIPINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: FASTED
142 nM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2015166/
10 mg 2 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DEHYDROFELODIPINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: FASTED
33.7 nM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3396260/
5 mg 2 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FELODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
87.5 nM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3396260/
5 mg 2 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FELODIPINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
23.1 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2015166/
10 mg 2 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FELODIPINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: FASTED
14.1 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3396260/
5 mg 2 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FELODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
27.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3396260/
5 mg 2 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FELODIPINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
20 mg 1 times / day multiple, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
unhealthy, 51.5 (39-68)
Health Status: unhealthy
Age Group: 51.5 (39-68)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
Disc. AE: Headache, Ankle edema...
AEs leading to
discontinuation/dose reduction:
Headache (18%)
Ankle edema (6%)
Flushing (6%)
Nausea (2%)
Palpitation (2%)
Vertigo (2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
AEs

AEs

AESignificanceDosePopulation
Headache 18%
Disc. AE
20 mg 1 times / day multiple, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
unhealthy, 51.5 (39-68)
Health Status: unhealthy
Age Group: 51.5 (39-68)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
Nausea 2%
Disc. AE
20 mg 1 times / day multiple, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
unhealthy, 51.5 (39-68)
Health Status: unhealthy
Age Group: 51.5 (39-68)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
Palpitation 2%
Disc. AE
20 mg 1 times / day multiple, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
unhealthy, 51.5 (39-68)
Health Status: unhealthy
Age Group: 51.5 (39-68)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
Vertigo 2%
Disc. AE
20 mg 1 times / day multiple, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
unhealthy, 51.5 (39-68)
Health Status: unhealthy
Age Group: 51.5 (39-68)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
Ankle edema 6%
Disc. AE
20 mg 1 times / day multiple, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
unhealthy, 51.5 (39-68)
Health Status: unhealthy
Age Group: 51.5 (39-68)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
Flushing 6%
Disc. AE
20 mg 1 times / day multiple, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
unhealthy, 51.5 (39-68)
Health Status: unhealthy
Age Group: 51.5 (39-68)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2475701/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C8
1057
P-gp
2052

CYP1A2
1197
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C8
1117
 yes [IC50 0.726 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1197
 yes
P-gp
2052
 yes
CYP3A4
1946
 yes
yes (co-administration study)
Comment: Co-administration of another extended release formulation of felodipine with itraconazole resulted in approximately 8-fold increase in the AUC, more than 6-fold increase in the Cmax, and 2-fold prolongation in the half-life of felodipine.
Page: 6.0
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:585948
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:585948
ChemicalBook
CB4300661
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4300661
ChemicalBook
CB6411200
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6411200
eMolecules
538533
https://www.emolecules.com/cgi-bin/more?vid=538533
MolPort
MolPort-002-801-136
https://www.molport.com/shop/molecule-link/MolPort-002-801-136
Selleck Chemicals
Felodipine(Plendil)
http://www.selleckchem.com/products/Felodipine(Plendil).html
PubMed

PubMed

TitleDatePubMed
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013-12
Evaluation of in vitro cytochrome P450 induction and inhibition activity of deoxyelephantopin, a sesquiterpene lactone from Elephantopus scaber L.
2013-10
Cystic fibrosis: a new target for 4-Imidazo[2,1-b]thiazole-1,4-dihydropyridines.
2011-06-09
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle.
2010-02-23
Chloride channels as drug targets.
2009-02
Felodipine reduces cardiac expression of IL-18 and perivascular fibrosis in fructose-fed rats.
2008-02-25
Molecular mechanisms of felodipine suppressing atherosclerosis in high-cholesterol-diet apolipoprotein E-knockout mice.
2008-02
Structure-activity relationship of 1,4-dihydropyridines as potentiators of the cystic fibrosis transmembrane conductance regulator chloride channel.
2007-07
Optimal treatment of obesity-related hypertension: the Hypertension-Obesity-Sibutramine (HOS) study.
2007-04-17
Lercanidipine in the treatment of hypertension.
2007-03
Improved tolerability of felodipine compared with amlodipine in elderly hypertensives: a randomised, double-blind study in 535 patients, focusing on vasodilatory adverse events. The International Study Group.
1998-09
Influence of felodipine on experimental seizures and activity of different antiepileptic drugs in mice.
1998-07-15
Significance of blood pressure levels achieved with felodipine anti-hypertensive treatment on cardiovascular structure and function changes.
1998-07
A comparison of nisoldipine coat-core and felodipine in the treatment of mild-to-moderate hypertension.
1998-06
Effect of the calcium antagonist felodipine as supplementary vasodilator therapy in patients with chronic heart failure treated with enalapril: V-HeFT III. Vasodilator-Heart Failure Trial (V-HeFT) Study Group.
1997-08-05
Cardiovascular effects of a low-dose combination of ramipril and felodipine in spontaneously hypertensive rats.
1997-06
Calcium antagonists, a useful additional therapy in treatment resistant hypertension: comparison of felodipine ER and nifedipine Retard by 24-h ambulatory blood pressure monitoring.
1997-01
Felodipine in the treatment of severe refractory hypertension.
1996-09
Losartan potassium: a review of its pharmacology, clinical efficacy and tolerability in the management of hypertension.
1996-05
Global efficacy and tolerability of losartan, an angiotensin II subtype 1-receptor antagonist, in the treatment of hypertension.
1996
Isradipine. An update of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy in the treatment of mild to moderate hypertension.
1995-04
Efficacy and tolerability of extended-release felodipine and extended-release nifedipine in patients with mild-to-moderate essential hypertension.
1994-07-01
Mono- and combination therapy with felodipine or enalapril in elderly patients with systolic hypertension.
1994-03
Comparison of effects of felodipine versus hydrochlorothiazide on arterial diameter and pulse-wave velocity in essential hypertension.
1993-10-01
General toxicity of the new calcium antagonist felodipine in dogs.
1993-07
A multicenter comparison of isradipine and felodipine in the treatment of mild-to-moderate hypertension. The Physician's Study Group.
1993-03
Felodipine clinical pharmacokinetics.
1991-12
Felodipine: a new dihydropyridine calcium-channel antagonist.
1991-11
Acute effects on exercise tolerance of felodipine and diltiazem, alone and in combination, in stable effort angina.
1991-01
Extended release felodipine in essential hypertension. Variations in blood pressure during whole-day continuous ambulatory recording.
1991-01
Felodipine ER formulation in the treatment of mild hypertension: efficacy and tolerability vs placebo.
1990-10
The influence of infusion rate on the hemodynamic effects of felodipine.
1990-09
The efficacy and tolerability of long-term felodipine treatment in hypertension. The Scandinavian Multicenter Group.
1990-06
Cardiovascular-risk reduction: initial diuretic therapy compared with calcium-antagonist (felodipine) therapy for primary hypertension.
1989-09-04
Felodipine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in hypertension.
1988-10
Antihypertensive effect of felodipine or hydralazine when added to beta-blocker therapy.
1988-07
A double-blind comparison of felodipine and hydrochlorothiazide added to metoprolol to control hypertension.
1988
Catecholamines, renin-angiotensin-aldosterone, and cardiovascular response during exercise following acute and long-term calcium antagonism with felodipine in essential hypertension.
1987-10
Baroreflex control of renin release in spontaneously hypertensive rats after administration of felodipine.
1987
Felodipine, a new calcium antagonist, as monotherapy in mild or moderate hypertension. Cooperative study group.
1987
Monotherapy with felodipine, a new calcium antagonist, in mild and moderate hypertension.
1987
Felodipine compared to nifedipine as "third-line drug" in resistant hypertension.
1986-11
Felodipine can replace minoxidil in the treatment of refractory hypertension.
1985-12
Renal and antihypertensive effects of felodipine in hypertensive patients.
1985-12
Renal and cardiovascular effects of acute and chronic administration of felodipine to SHR.
1985-07-11
Haemodynamic effects of single-dose felodipine in normal man.
1985
Effects of felodipine on resistance and capacitance vessels in patients with essential hypertension.
1985
Comparative trial of felodipine and nifedipine in refractory hypertension.
1985
Antihypertensive effect of felodipine combined with beta-blockade. A comparison between 2 and 3 daily dosages.
1985
Hemodynamic effects of felodipine at rest and during exercise in exertional angina pectoris.
1983-09-01
Patents

Patents

06268377
3
JP2009526755A
475
JP2011529101A
67

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Hypertension Initial dose: 5 mg orally once a day Maintenance dose: 2.5 to 10 mg orally once a day
Route of Administration: Oral
In Vitro Use Guide
the maximum contraction to NA in rat vessels exposed to felodipine (0.1 umol/L) was reduced by 37%, and the contraction to K+ (62 mmol/L) was reduced by 84% compared with vehicle-treated arteries.
Name Type Language
C08CA02
Preferred Name English
FELODIPINE
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
PLENDIL
Brand Name English
FELODIPINE [USP-RS]
Common Name English
FELODIPINE [MART.]
Common Name English
NSC-760343
Code English
FELODIPINE [VANDF]
Common Name English
Felodipine [WHO-DD]
Common Name English
3,5-PYRIDINEDICARBOXYLIC ACID 4-(2,3-DICHLOROPHENYL)-1,4-DIHYDRO-2,6-DIMETHYL-, ETHYL METHYL ESTER, (±)-
Common Name English
FELODIPINE [ORANGE BOOK]
Common Name English
FELODIPINE [USAN]
Common Name English
FELODIPINE [EP MONOGRAPH]
Common Name English
FELODIPINE [USP MONOGRAPH]
Common Name English
FELODIPINE [MI]
Common Name English
LEXXEL COMPONENT FELODIPINE
Common Name English
H 154/82
Code English
felodipine [INN]
Common Name English
(±)-ETHYL METHYL 4-(2,3-DICHLOROPHENYL)-1,4-DIHYDRO-2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLATE
Systematic Name English
FELODIPINE [USP IMPURITY]
Common Name English
FELODIPINE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C333
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
WHO-ATC C08CA02
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
WHO-VATC QC09BB05
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WHO-VATC QC08CA02
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
NDF-RT N0000007556
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LIVERTOX NBK548294
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NDF-RT N0000175421
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NDF-RT N0000000069
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
WHO-ATC C09BB05
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
Code System Code Type Description
NSC
760343
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PRIMARY
CAS
72509-76-3
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PRIMARY
MERCK INDEX
m5257
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PRIMARY Merck Index
WIKIPEDIA
FELODIPINE
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PRIMARY
DRUG BANK
DB01023
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PRIMARY
DRUG CENTRAL
1142
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PRIMARY
RXCUI
4316
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PRIMARY RxNorm
MESH
D015736
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PRIMARY
PUBCHEM
3333
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PRIMARY
EPA CompTox
DTXSID4023042
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PRIMARY
RS_ITEM_NUM
1269389
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PRIMARY
EVMPD
SUB11963MIG
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PRIMARY
LACTMED
Felodipine
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PRIMARY
INN
4877
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PRIMARY
DAILYMED
OL961R6O2C
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PRIMARY
CHEBI
585948
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PRIMARY
USAN
X-2
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PRIMARY
FDA UNII
OL961R6O2C
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PRIMARY
IUPHAR
4190
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PRIMARY
SMS_ID
100000089989
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PRIMARY
ChEMBL
CHEMBL1480
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PRIMARY
NCI_THESAURUS
C29046
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of FELODIPINE
METABOLITE (PARENT)
Structure of DEHYDROFELODIPINE
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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