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

Details

Stereochemistry ACHIRAL
Molecular Formula C22H21NO3
Molecular Weight 347.407
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FPL-64176

SMILES

COC(=O)C1=C(C)NC(C)=C1C(=O)C2=CC=CC=C2CC3=CC=CC=C3

InChI

InChIKey=MDMWHKZANMNXTF-UHFFFAOYSA-N
InChI=1S/C22H21NO3/c1-14-19(20(15(2)23-14)22(25)26-3)21(24)18-12-8-7-11-17(18)13-16-9-5-4-6-10-16/h4-12,23H,13H2,1-3H3

HIDE SMILES / InChI
FPL 64176 is a nondihydropyridine L-type calcium channel activator with high efficacy properties. It is being used as a tool for studying the physiological roles and disorders of L-type channels, identification of L-type currents within the mix of channel subtypes and for increasing the contractility of smooth and cardiac muscle.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The calcium channel ligand FPL 64176 enhances L-type but inhibits N-type neuronal calcium currents.
2003 Aug
DHP-insensitive L-type-like Ca channel of ascidian acquires sensitivity to DHP with single amino acid change in domain III P-region.
2003 Aug 14
Facilitation of L-type Ca2+ channels in dendritic spines by activation of beta2 adrenergic receptors.
2004 Sep 29
Combined activation of L-type Ca2+ channels and synaptic transmission is sufficient to induce striatal long-term depression.
2007 Jun 20
Arrhythmogenic actions of the Ca2+ channel agonist FPL-64716 in Langendorff-perfused murine hearts.
2009 Feb
Activity-dependent modulation of limbic dopamine D3 receptors by CaMKII.
2009 Feb 12
Endocannabinoid-dependent plasticity at GABAergic and glutamatergic synapses in the striatum is regulated by synaptic activity.
2009 Jan
The intracellular II-III loops of Cav1.2 and Cav1.3 uncouple L-type voltage-gated Ca2+ channels from glucagon-like peptide-1 potentiation of insulin secretion in INS-1 cells via displacement from lipid rafts.
2009 Jul
Acute ethanol treatment prevents endocannabinoid-mediated long-lasting disinhibition of striatal output.
2010 Mar-Apr
Ionic currents in intimal cultured synoviocytes from the rabbit.
2010 Nov
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
The pharmacological, radioligand binding and electrophysiological properties of FPL 64176 were studied in rat tail artery, cardiac membranes, and A7r5 smooth muscle cells. FPL 64176 induced a contractile response, with an EC50 value of 2.11 x 10(-7) M. The maximum tension response to FPL 64176 was approximately 2-fold higher than that to (S)-Bay K 8644. FPL 64176 showed no significant inhibitory activity at concentrations up to 10(-5) M. The Ca2+ channel antagonists nifedipine, verapamil and diltiazem noncompetitively antagonized and completely relaxed the responses induced by FPL 64176. FPL 64176 weakly inhibited (+)-[3H]PN 200-110, [3H]D888, and [3H]TA-3090 binding in rat cardiac membranes, with IC50 values of 1.04 x 10(-5) M and 7.03 x 10(-6) M for inhibition of (+)-[3H]PN 200-110 and [3H]TA-3090 binding, respectively, and with 23% inhibition of [3H]D888 binding at a FPL 64176 concentration of 1 x 10(-5) M. The results suggested that FPL 64176 had a mechanism and site of action that is distinct from those for (S)-Bay K 8644.
Name Type Language
FPL-64176
Common Name English
1H-PYRROLE-3-CARBOXYLIC ACID, 2,5-DIMETHYL-4-(2-(PHENYLMETHYL)BENZOYL)-, METHYL ESTER
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID40153064
Created by admin on Fri Dec 15 17:59:31 GMT 2023 , Edited by admin on Fri Dec 15 17:59:31 GMT 2023
PRIMARY
CHEBI
249982
Created by admin on Fri Dec 15 17:59:31 GMT 2023 , Edited by admin on Fri Dec 15 17:59:31 GMT 2023
PRIMARY
CAS
120934-96-5
Created by admin on Fri Dec 15 17:59:31 GMT 2023 , Edited by admin on Fri Dec 15 17:59:31 GMT 2023
PRIMARY
PUBCHEM
3423
Created by admin on Fri Dec 15 17:59:31 GMT 2023 , Edited by admin on Fri Dec 15 17:59:31 GMT 2023
PRIMARY
FDA UNII
UU89L306PO
Created by admin on Fri Dec 15 17:59:31 GMT 2023 , Edited by admin on Fri Dec 15 17:59:31 GMT 2023
PRIMARY