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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

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
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

Curator's Comment: # pfizer

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3964.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
EMETE-CON

Approved Use

Unknown

Launch Date

1974
Preventing
EMETE-CON

Approved Use

Unknown

Launch Date

1974
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
609 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
1330 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.6 h
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

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

Sample Use Guides

for prevention of cancer chemotherapy-induced vomiting: 300-500 mg benzquinamide-HCl per day.
Route of Administration: Other
In Vitro Use Guide
Curator's Comment: It was hypothesized that the benzquinamide (BZQ) would interfere with P-glycoprotein (P-gp) mediated drug transport and potentiate the effects of anticancer agents in multidrug resistant (MDR) cell lines. We show that BZQ interferes with P-gp mediated drug efflux and increases drug accumulation in MDR cells using Rho-123 as a fluorescent probe. BZQ increases the cytotoxicity of chemotherapeutic agents to both human and hamster MDR cell lines in vitro. A slight increase in cytotoxicity to chemotherapeutic agents is also observed in the parental cell lines with BZQ. BZQ increases [3H]daunorubicin accumulation and inhibits the binding of [125I]iodoaryl azidoprazosin to the P-gp in MDR cells. BZQ is a new agent to increase the cytotoxic effects of anticancer agents in MDR cells and may ultimately prove useful as an adjunct in cancer chemotherapy.
Unknown
Name Type Language
BENZQUINAMIDE HYDROCHLORIDE
MART.   ORANGE BOOK   VANDF   WHO-DD  
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
Created by admin on Fri Dec 15 16:17:10 GMT 2023 , Edited by admin on Fri Dec 15 16:17:10 GMT 2023
Code System Code Type Description
RXCUI
91272
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PRIMARY RxNorm
FDA UNII
3221WFM86J
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PRIMARY
DRUG BANK
DBSALT001425
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PRIMARY
SMS_ID
100000085020
Created by admin on Fri Dec 15 16:17:10 GMT 2023 , Edited by admin on Fri Dec 15 16:17:10 GMT 2023
PRIMARY
MESH
C100234
Created by admin on Fri Dec 15 16:17:10 GMT 2023 , Edited by admin on Fri Dec 15 16:17:10 GMT 2023
PRIMARY
NCI_THESAURUS
C77569
Created by admin on Fri Dec 15 16:17:10 GMT 2023 , Edited by admin on Fri Dec 15 16:17:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201250
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PRIMARY
PUBCHEM
76963258
Created by admin on Fri Dec 15 16:17:10 GMT 2023 , Edited by admin on Fri Dec 15 16:17:10 GMT 2023
PRIMARY
CAS
113-69-9
Created by admin on Fri Dec 15 16:17:10 GMT 2023 , Edited by admin on Fri Dec 15 16:17:10 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
ECHA (EC/EINECS)
204-033-3
Created by admin on Fri Dec 15 16:17:10 GMT 2023 , Edited by admin on Fri Dec 15 16:17:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID70920968
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PRIMARY
EVMPD
SUB00734MIG
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PRIMARY