FPL-64176

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 Search

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

Molecular Formula	C22H21NO3
Molecular Weight	347.407
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12842134

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

Primary Target	Pharmacology	Condition	Potency
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12842134	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
The calcium channel ligand FPL 64176 enhances L-type but inhibits N-type neuronal calcium currents.	2003 Aug	12842134
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	12914927
Combined activation of L-type Ca2+ channels and synaptic transmission is sufficient to induce striatal long-term depression.	2007 Jun 20	17581965
Arrhythmogenic actions of the Ca2+ channel agonist FPL-64716 in Langendorff-perfused murine hearts.	2009 Feb	18978037
Endocannabinoid-dependent plasticity at GABAergic and glutamatergic synapses in the striatum is regulated by synaptic activity.	2009 Jan	19120438
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	19351867
Acute ethanol treatment prevents endocannabinoid-mediated long-lasting disinhibition of striatal output.	2010 Mar-Apr	20026138
Ionic currents in intimal cultured synoviocytes from the rabbit.	2010 Nov	20720182

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:59:31 UTC 2023` Edited by `admin` on `Fri Dec 15 17:59:31 UTC 2023`
Record UNII	UU89L306PO
Record Status	`Validated (UNII)`
Record Version

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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