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
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
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 |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22711801 |
3964.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | EMETE-CON Approved UseUnknown Launch Date1974 |
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Preventing | EMETE-CON Approved UseUnknown Launch Date1974 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
T1/2
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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1362504
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.
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NCI_THESAURUS |
C66883
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91272
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DBSALT001425
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C100234
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C77569
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CHEMBL1201250
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113-69-9
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204-033-3
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DTXSID70920968
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SUB00734MIG
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ACTIVE MOIETY
SUBSTANCE RECORD