ENCIPRAZINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H32N2O6
Molecular Weight	432.51
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=CC=C1N2CCN(CC(O)COC3=CC(OC)=C(OC)C(OC)=C3)CC2

InChI

InChIKey=KSQCNASWXSCJTD-UHFFFAOYSA-N

InChI=1S/C23H32N2O6/c1-27-20-8-6-5-7-19(20)25-11-9-24(10-12-25)15-17(26)16-31-18-13-21(28-2)23(30-4)22(14-18)29-3/h5-8,13-14,17,26H,9-12,15-16H2,1-4H3

HIDE SMILES / InChI

Molecular Formula	C23H32N2O6
Molecular Weight	432.51
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2236459

Enciprazine also known as WY-48624 or, D-3112 is a GABA A receptor agonist which was in the phase III of clinical trial for the treatment of anxiety disorders. Enciprazine was well tolerated, with low levels of sedative and asthenic side effects reported. However, research was discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA A receptor 2 Target ID: GABA A receptor Sources: http://adisinsight.springer.com/drugs/800000720	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 275 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2236459	Primary		Phase III 665	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGTs 13

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466221	inconclusive [IC50 27.5404 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=170466221	inconclusive [IC50 34.6713 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=170466221	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGTs 13	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/1686125/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY567241	https://www.001chemical.com/chem/68576-86-3
ABI Chem	AC1L18OE
Ambinter	Amb15695042	http://www.ambinter.com/reference/15695042
BLD Pharm	BD127261	http://www.bldpharm.com/products/68576-86-3.html
Chemspace	CSSS00102527557	https://chem-space.com/CSSS00102527557
KeyOrganics	KE-0221
King Scientific	KS-00002WV0
Molcore	MC567241	https://www.molcore.com/product/68576-86-3
MolPort	MolPort-009-194-188	https://www.molport.com/shop/molecule-link/MolPort-009-194-188
MuseChem	I006667	https://www.musechem.com/product/I006667.html
NovoSeek	50222
Smolecule	S527115	http://www.smolecule.com/products/s527115
THE BioTek	bt-267237	https://www.thebiotek.com/product/inhibitors/bt-267237

PubMed

Title	Date	PubMed
Chemistry and pharmacology of the non-benzodiazepine anxiolytic enciprazine and related compounds.	1990-11	1977910
A placebo-controlled study of enciprazine in the treatment of generalized anxiety disorder: a preliminary report.	1990	2236459
Comparison of changes in the EEG of freely moving rats induced by enciprazine, buspirone and diazepam.	1989-08	2571102
Early phase-II semi double-blind study of the new alkaline propanolamine derivative enciprazine (short communication).	1988-06	3178922

Patents

Sample Use Guides

In Vivo Use Guide

5-week, double-blind trial comparing three dose strengths of enciprazine (5 mg t.i.d., 10 mg t.i.d., and 20 mg t.i.d.) to placebo. A dose escalation was permitted after 2 weeks of active drug treatment, which 61 percent of patients overall took advantage of.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:01:00 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:00 GMT 2025`
Record UNII	L6X660925G
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ENCIPRAZINE

Official Name

English

4-(2-METHOXYPHENYL)-A-((3,4,5-TRIMETHOXYPHENOXY)METHYL)-1-PIPERAZINEETHANOL

Preferred Name

English

(±)-4-(O-METHOXYPHENYL)-.ALPHA.-((3,4,5-TRIMETHOXYPHENOXY)METHYL)-1-PIPERAZINEETHANOL

Common Name

English

1-PIPERAZINEETHANOL, 4-(2-METHOXYPHENYL)-.ALPHA.-((3,4,5-TRIMETHOXYPHENOXY)METHYL)-, (±)-

Systematic Name

English

ENCIPRAZINE [MI]

Common Name

English

enciprazine [INN]

Common Name

English

(±)-1-(3-(3,4,5-TRIMETHOXYPHENOXY)-2-HYDROXYPROPYL)-4-(2-METHOXYPHENYL)PIPERAZINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197