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Details

Stereochemistry ACHIRAL
Molecular Formula C15H14ClN3O6
Molecular Weight 367.741
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LODOXAMIDE ETHYL

SMILES

CCOC(=O)C(=O)NC1=CC(=CC(NC(=O)C(=O)OCC)=C1Cl)C#N

InChI

InChIKey=BNTAPIYHWPPFBW-UHFFFAOYSA-N
InChI=1S/C15H14ClN3O6/c1-3-24-14(22)12(20)18-9-5-8(7-17)6-10(11(9)16)19-13(21)15(23)25-4-2/h5-6H,3-4H2,1-2H3,(H,18,20)(H,19,21)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24113750 | https://www.ncbi.nlm.nih.gov/pubmed/7033581 | https://www.ncbi.nlm.nih.gov/pubmed/7358942

Lodoxamide ethyl, diethyl N,N'-(2-chloro-5-cyano-m-phenylene) dioxamate, is an orally active candidate for the treatment of asthma and other allergic diseases. Lodoxamide ethyl prevents mast cell mediator release during allergic reactions in rats, guinea pigs, and monkeys at doses well below toxic levels. Lodoxamide ethyl does not interfere with antigen-antibody interaction, does not antagonize the effects of histamine or slow-reacting substance of anaphylaxis, and does not have direct antiinflammatory effects. Lodoxamide ethyl has been proven capable of preventing bronchospasm in humans when the subject was given 1, 3, or 10 mg of the drug orally prior to challenge with an antigen.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
N,N'-(Phenylene)dioxamic acids and their esters as antiallergy agents.
1978 Sep
Patents

Patents

Sample Use Guides

1- or 3-mg capsules, PO
Route of Administration: Oral
In Vitro Use Guide
Mast cells were removed from 250-gram rats by peritoneal lavage with 15 ml of Hank’s BSS containing 50 units/ml of heparin USP. The cells were washed twice in the above buffer by centrifugation at 750 g for 10 min and resuspended in Tyrode’s buffer, pH 7.4, containing 2°/o heat-inactivated normal rat scrum. These cells were then layered and centrifuged 150 g for 15 min on Ficoll gradients prepared by gradients of 4 ml of 30% Ficoll over 2 ml of 40% Ficoll. The Ficoll was made up in Tyrode’s buffer, pH 7.4. The cells were again washed twice in Tyrode’s buffer and rat serum to remove the Ficoll. 2-4 X 10^5 cells/ml mast cells were then incubated with the drugs before addition of compound 48/80, 0.2 mkg/ml (Burroughs-Welcome, Tuckahoe, N.Y.) after which they were placed in a 37 °C bath for 5 min. The cells were spun out at 750 g for 10 min and the supernatant made 0.4 N with respect to HC104. After an additional spin, the histamine released into the supernatant was assayed by an automated Technicon modification of the fluorimetric assay. 10 mkCi 45CaCI2 was added to 1-2 X 10^7 cells suspended in 5.0 ml of Tyrode’s buffer. When U-42,585E (LODOXAMIDE ETHYL) was present, it was added immediately before addition of the ionophore. The ionophore (A23,187) was made up in 100% DMSO at 10 mg/ml and diluted out to an appropriate concentration in Tyrode's buffer.
Name Type Language
LODOXAMIDE ETHYL
MART.   USAN  
USAN  
Official Name English
U-42,718
Code English
LODOXAMIDE DIETHYL ESTER
MI  
Common Name English
LODOXAMIDE DIETHYL ESTER [MI]
Common Name English
U-42718
Code English
LODOXAMIDE ETHYL [USAN]
Common Name English
ACETIC ACID, 2,2'-((2-CHLORO-5-CYANO-1,3-PHENYLENE)DIIMINO)-, BIS 2-OXO-, DIETHYL ESTER
Common Name English
LODOXAMIDE ETHYL [MART.]
Common Name English
Code System Code Type Description
NCI_THESAURUS
C170124
Created by admin on Fri Dec 15 15:14:14 UTC 2023 , Edited by admin on Fri Dec 15 15:14:14 UTC 2023
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ChEMBL
CHEMBL2107161
Created by admin on Fri Dec 15 15:14:14 UTC 2023 , Edited by admin on Fri Dec 15 15:14:14 UTC 2023
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CAS
53882-13-6
Created by admin on Fri Dec 15 15:14:14 UTC 2023 , Edited by admin on Fri Dec 15 15:14:14 UTC 2023
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FDA UNII
TQY1B8145B
Created by admin on Fri Dec 15 15:14:14 UTC 2023 , Edited by admin on Fri Dec 15 15:14:14 UTC 2023
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PUBCHEM
40915
Created by admin on Fri Dec 15 15:14:14 UTC 2023 , Edited by admin on Fri Dec 15 15:14:14 UTC 2023
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EPA CompTox
DTXSID90202137
Created by admin on Fri Dec 15 15:14:14 UTC 2023 , Edited by admin on Fri Dec 15 15:14:14 UTC 2023
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MERCK INDEX
m6883
Created by admin on Fri Dec 15 15:14:14 UTC 2023 , Edited by admin on Fri Dec 15 15:14:14 UTC 2023
PRIMARY Merck Index