BENZQUINAMIDE HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H32N2O5.ClH
Molecular Weight	440.961
Optical Activity	( + / - )
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of BENZQUINAMIDE HYDROCHLORIDE

Structure Search

SMILES

Cl.[H][C@@]12C[C@@H](OC(C)=O)[C@@H](CN1CCC3=CC(OC)=C(OC)C=C23)C(=O)N(CC)CC

InChI

InChIKey=KZLNXGBVFTWMPS-CVEUAIMDSA-N

InChI=1S/C22H32N2O5.ClH/c1-6-23(7-2)22(26)17-13-24-9-8-15-10-20(27-4)21(28-5)11-16(15)18(24)12-19(17)29-14(3)25;/h10-11,17-19H,6-9,12-13H2,1-5H3;1H/t17-,18+,19-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C22H32N2O5
Molecular Weight	404.4999
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Description
Sources: http://www.druglib.com/activeingredient/benzquinamide/ | https://www.ncbi.nlm.nih.gov/pubmed/22711801

Benzquinamide also known as BZQ; Emete-con, Emetico, is an antiemetic drug, which was discontinued. That drug was used to prevent and treat nausea and vomiting associated with anesthesia and surgery, administered intramuscularly or intravenously. The mechanism of action is not known, but was made predictions which shown, that in spite of benzquinamide did bind to the α2A, α2B, and α2C adrenergic receptors (α2-AR). It was known, that this activity may partially explain the anxiolytic activity effect of the drug. But the dopamine D2 receptor, which by ligand-set similarity resembles α2-AR is an accepted target for emesis. Then benzquinamide was tested towards to the D2, D3, and D4 receptors. Notwithstanding the fact that the α2-AR values are lower than the D2 values, it was predicted, that D2 activity may be the most relevant for emesis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22711801	Modulator 828		3964.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vomiting 38 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13992595	Preventing		Approved 8429	EMETE-CON Approved Use Unknown Launch Date 1.32278403E11
Nausea 63 Sources: http://www.druglib.com/activeingredient/benzquinamide/	Preventing		Approved 8429	EMETE-CON Approved Use Unknown Launch Date 1.32278403E11

C_max

Value	Dose	Co-administered	Analyte	Population
609 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/581593/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		BENZQUINAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1330 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/581593/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		BENZQUINAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/581593/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		BENZQUINAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S1368764617300432	yes

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific	SYN5517
AOBIOUS INC	AOB5327
AbovChem LLC	HY-U00244
BOC Sciences	23352
Compound Cloud	2342
Hangzhou Yuhao Chemical Technology	RT3338
KeyOrganics	AS-16851
MolPort	MolPort-006-167-629
MuseChem	R050177
Sigma Aldrich	PH003157
Sigma Aldrich	PH003157\|ALDRICH
Toronto Research Chemicals	B209900
ZINC	ZINC000137804425	http://zinc15.docking.org/substances/ZINC000137804425
eMolecules	35864747
eMolecules	36757027
mcule	MCULE-2957619994
mcule	MCULE-3629676711

PubMed

Title	Date	PubMed
Specific therapeutic actions of acetophenazine, perphenazine, and benzquinamide in newly admitted schizophrenic patients.	1967 Mar-Apr	5336562
Identifying mechanism-of-action targets for drugs and probes.	2012 Jul 10	22711801

Patents

Sample Use Guides

In Vivo Use Guide

for prevention of cancer chemotherapy-induced vomiting: 300-500 mg benzquinamide-HCl per day.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:17:10 UTC 2023` Edited by `admin` on `Fri Dec 15 16:17:10 UTC 2023`
Record UNII	3221WFM86J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZQUINAMIDE HYDROCHLORIDE

Common Name

English

Benzquinamide hydrochloride [WHO-DD]

Common Name

English

BENZQUINAMIDE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

BENZQUINAMIDE HYDROCHLORIDE [VANDF]

Common Name

English

BENZQUINAMIDE HCL

Common Name

English

BENZQUINAMIDE HYDROCHLORIDE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66883