68P

(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile

Created:	2016-02-17
Last modified:	2016-04-13

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4 entries where 68P is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	45
Chiral Atom Count	1
Bond Count	47
Aromatic Bond Count	12

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Chemical Component Summary
Name	(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
Systematic Name (OpenEye OEToolkits)	(1~{S})-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3~{H}-2-benzofuran-5-carbonitrile
Formula	C₂₀ H₂₁ F N₂ O
Molecular Weight	324.392
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	c1(ccc(cc1)F)C3(OCc2c3ccc(C#N)c2)CCCN(C)C
SMILES	CACTVS	3.385	CN(C)CCC[C]1(OCc2cc(ccc12)C#N)c3ccc(F)cc3
SMILES	OpenEye OEToolkits	2.0.4	CN(C)CCCC1(c2ccc(cc2CO1)C#N)c3ccc(cc3)F
Canonical SMILES	CACTVS	3.385	CN(C)CCC[C@]1(OCc2cc(ccc12)C#N)c3ccc(F)cc3
Canonical SMILES	OpenEye OEToolkits	2.0.4	CN(C)CCC[C@@]1(c2ccc(cc2CO1)C#N)c3ccc(cc3)F
InChI	InChI	1.03	InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1
InChIKey	InChI	1.03	WSEQXVZVJXJVFP-FQEVSTJZSA-N

Drug Info: DrugBank

DrugBank ID	DB01175
Name	Escitalopram
Groups	approved
Description	Escitalopram is a selective serotonin re-uptake inhibitor (SSRI) and the S-enantiomer of racemic [citalopram].[A185420] It is used to restore serotonergic function in the treatment of depression and anxiety.[L8513,L8516,L8522] Escitalopram is approximately 150 times more potent than citalopram’s R-enantiomer and is responsible for the vast majority of citalopram’s clinical activity, with some evidence suggesting that the R-enantiomer of racemic citalopram actively dampens the activity of escitalopram rather than existing simply as an inactive enantiomer.[A39738,A185819] Amongst SSRIs, escitalopram exerts the highest degree of selectivity for the serotonin transporter (SERT) relative to other off-targets which may explain its lower rates of adverse effects as compared to other agents in this class.[A185726] Escitalopram also differentiates itself from other SSRIs via allosteric action on its target - this may be the mechanism responsible for its observed superior efficacy and faster onset compared to other SSRIs.[A185825,A185726,A185822]
Synonyms	Escitalopramum Escitalopram oxalate (+)-Citalopram S(+)-Citalopram Escitalopram S-(+)-Citalopram (S)-Citalopram
Brand Names	Escitalopram oxalate Lexapro PMS-escitalopram PramLyte Riva-escitalopram Cipralex -20mg Cipralex -10mg Apo-escitalopram Ipg-escitalopram Nra-escitalopram Mint-escitalopram Cipralex -5mg Kye-escitalopram M-escitalopram Cipralex Meltz Pmsc-escitalopram Auro-escitalopram Escitalopram Tablets Ag-escitalopram Tablets Sandoz Escitalopram Taro-escitalopram Escitalopram Oral Solution Mar-escitalopram Cipralex -15mg Nat-escitalopram Ach-escitalopram Act Escitalopram Bio-escitalopram Ag-escitalopram Teva-escitalopram Mylan-escitalopram Act Escitalopram ODT Escitalopram Oxalate Jamp Escitalopram Escitalopram
Indication	Escitalopram is indicated for the acute and maintenance treatment of major depressive disorder (MDD) in adults and pediatric patients 12 years old and older and for the acute treatment of generalized anxiety disorder (GAD) in adults and pediatric patients 7 years old and older.[L8513,L8513] It is additionally indicated for symptomatic relief of obsessive-compulsive disorder (OCD) in Canada.[L8516]
Categories	Amines Anticholinergic Agents Antidepressive Agents Antidepressive Agents Indicated for Depression Antidepressive Agents, Second-Generation Benzofurans Central Nervous System Agents Central Nervous System Depressants Combined Inhibitors of Serotonin/Norepinephrine Reuptake Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Heterocyclic Compounds, Fused-Ring Highest Risk QTc-Prolonging Agents Hypoglycemia-Associated Agents Membrane Transport Modulators Monoamine Oxidase A Substrates Muscarinic Antagonists Nervous System Neurotransmitter Agents Neurotransmitter Uptake Inhibitors Nitriles P-glycoprotein substrates Photosensitizing Agents Propylamines Psychoanaleptics Psychotropic Drugs QTc Prolonging Agents Selective Serotonin Reuptake Inhibitors Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome Serotonin Agents Serotonin Modulators
ATC-Code	N06AB10
CAS number	128196-01-0

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Sodium-dependent serotonin transporter	METTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAV...	unknown	inhibitor
Muscarinic acetylcholine receptor M1	MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISF...	unknown	inhibitor
Histamine H1 receptor	MSLPNSSCLLEDKMCEGNKTTMASPQLMPLVVVLSTICLVTVGLNLLVLY...	unknown	inhibitor
5-hydroxytryptamine receptor 1A	MDVLSPGQGNNTTSPPAPFETGGNTTGISDVTVSYQVITSLLLGTLIFCA...	unknown	inhibitor
5-hydroxytryptamine receptor 2A	MDILCEENTSLSSTTNSLMQLNDDTRLYSNDFNSGEANTSDAFNWTVDSE...	unknown	inhibitor
Alpha-1 adrenergic receptors	MVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILS...	unknown	inhibitor
5-hydroxytryptamine receptor 2C	MVNLRNAVHSFLVHLIGLLVWQCDISVSPVAAIVTDIFNTSDGGRFKFPD...	unknown	inhibitor
Alpha-2 adrenergic receptors	MGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLTLVCLAGLLMLLTVFG...	unknown	inhibitor
Dopamine D2 receptor	MDPLNLSWYDDDLERQNWSRPFNGSDGKADRPHYNYYATLLTLLIAVIVF...	unknown	inhibitor
Sodium-dependent noradrenaline transporter	MLLARMNPQVQPENNGADTGPEQPLRARKTAELLVVKERNGVQCLLAPRD...	unknown	inhibitor
Sodium-dependent dopamine transporter	MSKSKCSVGLMSSVVAPAKEPNAVGPKEVELILVKEQNGVQLTSSTLTNP...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate,inhibitor
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	substrate
Amine oxidase [flavin-containing] A	MENQEKASIAGHMFDVVVIGGGISGLSAAKLLTEYGVSVLVLEARDRVGG...	unknown	substrate
Amine oxidase [flavin-containing] B	MSNKCDVVVVGGGISGMAAAKLLHDSGLNVVVLEARDRVGGRTYTLRNQK...	unknown	substrate
Aldehyde oxidase	MDRASELLFYVNGRKVIEKNVDPETMLLPYLRKKLRLTGTKYGCGGGGCG...	unknown	substrate
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682