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Details

Stereochemistry ACHIRAL
Molecular Formula C11H6ClN3O6
Molecular Weight 311.635
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LODOXAMIDE

SMILES

OC(=O)C(=O)NC1=CC(=CC(NC(=O)C(O)=O)=C1Cl)C#N

InChI

InChIKey=RVGLGHVJXCETIO-UHFFFAOYSA-N
InChI=1S/C11H6ClN3O6/c12-7-5(14-8(16)10(18)19)1-4(3-13)2-6(7)15-9(17)11(20)21/h1-2H,(H,14,16)(H,15,17)(H,18,19)(H,20,21)

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB06794 http://www.rxlist.com/alomide-drug.htm

Lodoxamide is a mast-cell stabilizer for topical administration into the eye. This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. Lodoxamide inhibits the in vivo Type I immediate hypersensitivity reaction. In vitro, Lodoxamide stabilizes mast cells and prevents antigen-stimulated release of histamine. In addition, Lodoxamide prevents the release of other mast cell inflammatory mediators and inhibits eosinophil chemotaxis. Although Lodoxamide's precise mechanism of action is unknown, the drug has been reported to prevent calcium influx into mast cells upon antigen stimulation. Among side effects to Lodoxamide, the most frequently reported ocular adverse experiences were transient burning, stinging, or discomfort upon instillation. Nonocular events reported were headache and heat sensation, dizziness, somnolence, nausea, stomach discomfort, sneezing, dry nose, and rash.

Originator

Curator's Comment: Additional resources: http://www.google.ch/patents/US3993679 http://www.drugfuture.com/chemdata/lodoxamide.html http://www.ncbi.nlm.nih.gov/pubmed/102796 https://books.google.ru/books?id=0vXTBwAAQBAJ&pg=PA737&lpg=PA737&dq=N,N%E2%80%99-++%282-chloro-5-cyano-m-phenylene%29dioxamic++acid&source=bl&ots=6ITmv3Yzuw&sig=F7WQDCB_NG3dR476ZXvS5xZqkg4&hl=ru&sa=X&ved=0ahUKEwipi6e05NnLAhVnYpoKHQOHDSkQ6AEIKzAC#v=onepage&q=N%2CN%E2%80%99-%20%20%282-chloro-5-cyano-m-phenylene%29dioxamic%20%20acid&f=false

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ALOMIDE

Approved Use

ALOMIDE® (lodoxamide tromethamine ophthalmic solution) 0.1% is indicated in the treatment of the ocular disorders referred to by the terms vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis.

Launch Date

1993
Curative
ALOMIDE

Approved Use

ALOMIDE® (lodoxamide tromethamine ophthalmic solution) 0.1% is indicated in the treatment of the ocular disorders referred to by the terms vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis.

Launch Date

1993
Curative
ALOMIDE

Approved Use

ALOMIDE® (lodoxamide tromethamine ophthalmic solution) 0.1% is indicated in the treatment of the ocular disorders referred to by the terms vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis.

Launch Date

1993
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.5 h
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LODOXAMIDE unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 % 4 times / day multiple, ophthalmic
Highest studied dose
Dose: 1 %, 4 times / day
Route: ophthalmic
Route: multiple
Dose: 1 %, 4 times / day
Sources:
unknown, unknown
Health Status: unknown
Condition: conjunctivitis
Age Group: unknown
Sex: unknown
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Mechanisms and comparison of anti-allergic efficacy of topical lodoxamide and cromolyn sodium treatment in vernal keratoconjunctivitis.
2000 Jul
Lodoxamide as adjuvant therapy in patients with dry eye.
2001
[Evaluation of efficacy and safety of sterile solution of lodoxamide in patients with ocular allergy].
2001
Comparison of lodoxamide 0.1% ophthalmic solution and levocabastine 0.05% ophthalmic suspension in vernal keratoconjunctivitis.
2001 Apr-Jun
[Evaluation of the efficacy and safety of lodoxamide in patients with allergic eye diseases].
2002
Effects of ketotifen 0.025% and lodoxamide 0.1% on eosinophil infiltration into the guinea pig conjunctiva in a model of allergic conjunctivitis.
2003 Apr
Vernal keratoconjunctivitis in Thailand.
2003 Mar
Comparison of antiallergic drugs in an experimental model of ocular anaphylaxis.
2003 Mar-Apr
Topical treatments for seasonal allergic conjunctivitis: systematic review and meta-analysis of efficacy and effectiveness.
2004 Jun
Efficacy and tolerability of newer antihistamines in the treatment of allergic conjunctivitis.
2005
Cardiac mast cell-derived renin promotes local angiotensin formation, norepinephrine release, and arrhythmias in ischemia/reperfusion.
2006 Apr
A clinicopathological analysis of the efficacy of lodoxamide 0.1% eye drops on the conjunctiva of patients with vernal keratoconjunctivitis seen at Guinness Eye Centre, Lagos University Teaching Hospital.
2006 Mar
Immediate hypersensitivity elicits renin release from cardiac mast cells.
2008
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: The dose for adults and children greater than two years of age is one to two drops in each affected eye four times daily for up to 3 months.
1-2 drops in each affected eye four times daily
Route of Administration: Other
In Vitro Use Guide
Lodoxamide exerts dose-dependent inhibitory effects on human eosinophil chemotactic response to fMLP, reaching more than 60% inhibition at 100 ng/ml and 80% inhibition for 10 ug/ml lodoxamide.
Name Type Language
LODOXAMIDE
INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
N,N'-(2-CHLORO-5-CYANO-M-PHENYLENE)DIOXAMATE
Systematic Name English
LODOXAMIDE [VANDF]
Common Name English
Lodoxamide [WHO-DD]
Common Name English
ACETIC ACID, 2,2'-((2-CHLORO-5-CYANO-1,3-PHENYLENE)DIIMINO)-, BIS 2-OXO-
Common Name English
lodoxamide [INN]
Common Name English
LODOXAMIDE [MART.]
Common Name English
LODOXAMIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29714
Created by admin on Fri Dec 15 15:56:30 GMT 2023 , Edited by admin on Fri Dec 15 15:56:30 GMT 2023
WHO-VATC QS01GX05
Created by admin on Fri Dec 15 15:56:30 GMT 2023 , Edited by admin on Fri Dec 15 15:56:30 GMT 2023
NDF-RT N0000175628
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WHO-ATC S01GX05
Created by admin on Fri Dec 15 15:56:30 GMT 2023 , Edited by admin on Fri Dec 15 15:56:30 GMT 2023
NDF-RT N0000175630
Created by admin on Fri Dec 15 15:56:30 GMT 2023 , Edited by admin on Fri Dec 15 15:56:30 GMT 2023
Code System Code Type Description
INN
4351
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PRIMARY
ChEMBL
CHEMBL1201266
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DRUG BANK
DB06794
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DRUG CENTRAL
3325
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CAS
53882-12-5
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RXCUI
52151
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PRIMARY RxNorm
EPA CompTox
DTXSID9057767
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PRIMARY
DAILYMED
SPU695OD73
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PRIMARY
NCI_THESAURUS
C61813
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PRIMARY
ChEMBL
CHEMBL2107161
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PRIMARY
WIKIPEDIA
LODOXAMIDE
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PRIMARY
LACTMED
Lodoxamide
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SMS_ID
100000081998
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PRIMARY
EVMPD
SUB08553MIG
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PRIMARY
FDA UNII
SPU695OD73
Created by admin on Fri Dec 15 15:56:30 GMT 2023 , Edited by admin on Fri Dec 15 15:56:30 GMT 2023
PRIMARY
MESH
C021702
Created by admin on Fri Dec 15 15:56:30 GMT 2023 , Edited by admin on Fri Dec 15 15:56:30 GMT 2023
PRIMARY
PUBCHEM
44564
Created by admin on Fri Dec 15 15:56:30 GMT 2023 , Edited by admin on Fri Dec 15 15:56:30 GMT 2023
PRIMARY
MERCK INDEX
m6883
Created by admin on Fri Dec 15 15:56:30 GMT 2023 , Edited by admin on Fri Dec 15 15:56:30 GMT 2023
PRIMARY Merck Index