U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C22H32N2O5
Molecular Weight 404.4999
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZQUINAMIDE

SMILES

[H][C@@]12C[C@@H](OC(C)=O)[C@@H](CN1CCC3=C2C=C(OC)C(OC)=C3)C(=O)N(CC)CC

InChI

InChIKey=JSZILQVIPPROJI-CEXWTWQISA-N
InChI=1S/C22H32N2O5/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/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

1.32278403E11
Preventing
EMETE-CON

Approved Use

Unknown

Launch Date

1.32278403E11
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
HSDB   INN   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
PROMECON
Brand Name English
2H-BENZO(A)QUINOLIZINE-3-CARBOXAMIDE, 2-(ACETYLOXY)-N,N-DIETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-, (2R,3R,11BS)-REL-
Systematic Name English
BENZQUINAMIDE [MI]
Common Name English
Benzquinamide [WHO-DD]
Common Name English
QUANTRIL
Brand Name English
BENZQUINAMIDE [VANDF]
Common Name English
benzquinamide [INN]
Common Name English
NSC-169193
Code English
BENZQUINAMIDE [USAN]
Common Name English
NSC-108159
Code English
P-2647
Code English
N,N-Diethyl-1,3,4,6,7,11b-hexahydro-2-hydroxy-9,10-dimethoxy-2H-benzo[a]quinolizine-3-carboxamide acetate (ester)
Common Name English
BENZQUINAMIDE [HSDB]
Common Name English
2H-BENZO(A)QUINOLIZINE-3-CARBOXAMIDE, 2-(ACETYLOXY)-N,N-DIETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-
Common Name English
EMETE-CON
Brand Name English
NSC-64375
Code English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
Code System Code Type Description
NSC
64375
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
HSDB
63-12-7
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
CAS
63-12-7
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
NSC
108159
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
WIKIPEDIA
BENZQUINAMIDE
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
EVMPD
SUB05768MIG
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
MERCK INDEX
m2392
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY Merck Index
MESH
C100234
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
RXCUI
19041
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY RxNorm
IUPHAR
7124
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
PUBCHEM
23615589
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
SMS_ID
100000086413
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
EPA CompTox
DTXSID9022657
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
FDA UNII
0475EA27Q3
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
NCI_THESAURUS
C65253
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
NSC
169193
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
DRUG CENTRAL
331
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
CAS
23844-24-8
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
INN
1402
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
DRUG BANK
DB00767
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
CHEBI
27662
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201250
Created by admin on Sat Dec 16 16:51:17 UTC 2023 , Edited by admin on Sat Dec 16 16:51:17 UTC 2023
PRIMARY