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
SMILES
CCOC(=O)C1=C(C)NC(C)=C(C1C2=C(Cl)C(Cl)=CC=C2)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
Molecular Formula | C18H19Cl2NO4 |
Molecular Weight | 384.254 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB01023Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/felodipine.html
Sources: http://www.drugbank.ca/drugs/DB01023
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
Sources: http://www.drugbank.ca/drugs/DB01023
Curator's Comment: Animal studies have demonstrated that felodipine crosses the blood-brain barrier and the placenta.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1994 Sources: http://www.drugbank.ca/drugs/DB01023 |
0.17 µM [IC50] | ||
Target ID: Cholangiocarcinoma Mz-ChA-1 cells Sources: https://www.ncbi.nlm.nih.gov/pubmed/21179572 |
26.0 µM [IC50] | ||
Target ID: CHEMBL3721 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15601807 |
0.726 µM [IC50] | ||
Target ID: CHEMBL1940 Sources: http://www.drugbank.ca/drugs/DB01023 |
|||
Target ID: CHEMBL1919 Sources: http://www.drugbank.ca/drugs/DB01023 |
|||
Target ID: CHEMBL3317336 Sources: http://www.drugbank.ca/drugs/DB01023 |
|||
Target ID: CHEMBL4138 Sources: http://www.drugbank.ca/drugs/DB01023 |
|||
Target ID: CHEMBL3805 Sources: http://www.drugbank.ca/drugs/DB01023 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PLENDIL Approved UsePLENDIL is indicated for the treatment of hypertension, to lower blood pressure. Launch Date6.8031362E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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: |
unhealthy, 51.5 (39-68) n = 50 Health Status: unhealthy Condition: hypertension Age Group: 51.5 (39-68) Sex: M+F Population Size: 50 Sources: |
Disc. AE: Headache, Ankle edema... AEs leading to discontinuation/dose reduction: Headache (18%) Sources: Ankle edema (6%) Flushing (6%) Nausea (2%) Palpitation (2%) Vertigo (2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
unhealthy, 51.5 (39-68) n = 50 Health Status: unhealthy Condition: hypertension Age Group: 51.5 (39-68) Sex: M+F Population Size: 50 Sources: |
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: |
unhealthy, 51.5 (39-68) n = 50 Health Status: unhealthy Condition: hypertension Age Group: 51.5 (39-68) Sex: M+F Population Size: 50 Sources: |
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: |
unhealthy, 51.5 (39-68) n = 50 Health Status: unhealthy Condition: hypertension Age Group: 51.5 (39-68) Sex: M+F Population Size: 50 Sources: |
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: |
unhealthy, 51.5 (39-68) n = 50 Health Status: unhealthy Condition: hypertension Age Group: 51.5 (39-68) Sex: M+F Population Size: 50 Sources: |
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: |
unhealthy, 51.5 (39-68) n = 50 Health Status: unhealthy Condition: hypertension Age Group: 51.5 (39-68) Sex: M+F Population Size: 50 Sources: |
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: |
unhealthy, 51.5 (39-68) n = 50 Health Status: unhealthy Condition: hypertension Age Group: 51.5 (39-68) Sex: M+F Population Size: 50 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 0.726 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
Page: 6.0 |
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 |
PubMed
Title | Date | PubMed |
---|---|---|
Baroreflex control of renin release in spontaneously hypertensive rats after administration of felodipine. | 1987 |
|
Cardiovascular-risk reduction: initial diuretic therapy compared with calcium-antagonist (felodipine) therapy for primary hypertension. | 1989 Sep 4 |
|
The influence of infusion rate on the hemodynamic effects of felodipine. | 1990 Sep |
|
Felodipine in combination with a beta-adrenoceptor blocker as an effective substitute for triple therapy in severe hypertension. The Australian Felodipine Multicentre Study Group. | 1991 |
|
Long-term effects of felodipine in patients with reduced renal function. | 1992 May |
|
General toxicity of the new calcium antagonist felodipine in dogs. | 1993 Jul |
|
A multicenter comparison of isradipine and felodipine in the treatment of mild-to-moderate hypertension. The Physician's Study Group. | 1993 Mar |
|
Efficacy and tolerability of extended-release felodipine and extended-release nifedipine in patients with mild-to-moderate essential hypertension. | 1994 Jul-Aug |
|
Isradipine. An update of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy in the treatment of mild to moderate hypertension. | 1995 Apr |
|
Global efficacy and tolerability of losartan, an angiotensin II subtype 1-receptor antagonist, in the treatment of hypertension. | 1996 |
|
A comparison of nisoldipine coat-core and felodipine in the treatment of mild-to-moderate hypertension. | 1998 Jun |
|
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 Sep |
|
Losartan: a review of its use, with special focus on elderly patients. | 2000 Mar |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Optimal treatment of obesity-related hypertension: the Hypertension-Obesity-Sibutramine (HOS) study. | 2007 Apr 17 |
|
Lercanidipine in the treatment of hypertension. | 2007 Mar |
|
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle. | 2010 Feb 23 |
|
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). | 2013 Dec |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/felodipine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8713491
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:18:05 UTC 2022
by
admin
on
Fri Dec 16 16:18:05 UTC 2022
|
Record UNII |
OL961R6O2C
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C333
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
||
|
WHO-ATC |
C08CA02
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
||
|
WHO-VATC |
QC09BB05
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
||
|
WHO-VATC |
QC08CA02
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
||
|
NDF-RT |
N0000007556
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
||
|
LIVERTOX |
NBK548294
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
||
|
NDF-RT |
N0000175421
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
||
|
NDF-RT |
N0000000069
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
||
|
WHO-ATC |
C09BB05
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
760343
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
72509-76-3
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
M5257
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | Merck Index | ||
|
FELODIPINE
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
DB01023
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
1142
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
4316
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | RxNorm | ||
|
D015736
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
3333
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
DTXSID4023042
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
1269389
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
SUB11963MIG
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
Felodipine
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
4877
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
OL961R6O2C
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
585948
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
X-2
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
OL961R6O2C
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
4190
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
CHEMBL1480
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY | |||
|
C29046
Created by
admin on Fri Dec 16 16:18:05 UTC 2022 , Edited by admin on Fri Dec 16 16:18:05 UTC 2022
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
METABOLIC ENZYME -> INHIBITOR |
IC50
|
||
|
TRANSPORTER -> INHIBITOR | |||
|
BINDER->LIGAND |
BINDING
|
||
|
ENANTIOMER -> RACEMATE | |||
|
ENANTIOMER -> RACEMATE | |||
|
TARGET -> INHIBITOR | |||
|
METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
MAJOR
PLASMA
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
|
|
|||