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(OCC(O)CN2CCN(CC2)C3=C(OC)C=CC=C3)=CC(OC)=C1OC

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 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2236459	Primary		Phase III 656	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGTs 13

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466221	inconclusive [IC50 27.5404 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=170466221	inconclusive [IC50 34.6713 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=170466221	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGTs 13	substrate 3367 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
MolPort	MolPort-009-194-188	https://www.molport.com/shop/molecule-link/MolPort-009-194-188
Molcore	MC567241	https://www.molcore.com/product/68576-86-3
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
Early phase-II semi double-blind study of the new alkaline propanolamine derivative enciprazine (short communication).	1988 Jun	3178922
Comparison of changes in the EEG of freely moving rats induced by enciprazine, buspirone and diazepam.	1989 Aug	2571102
Chemistry and pharmacology of the non-benzodiazepine anxiolytic enciprazine and related compounds.	1990 Nov	1977910

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 `Fri Dec 15 15:33:18 UTC 2023` Edited by `admin` on `Fri Dec 15 15:33:18 UTC 2023`
Record UNII	L6X660925G
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ENCIPRAZINE

Official 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

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

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197