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Details

Stereochemistry ACHIRAL
Molecular Formula C11H6ClN3O6.2C4H11NO3
Molecular Weight 553.905
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LODOXAMIDE TROMETHAMINE

SMILES

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

InChI

InChIKey=JJOFNSLZHKIJEV-UHFFFAOYSA-N
InChI=1S/C11H6ClN3O6.2C4H11NO3/c12-7-5(14-8(16)10(18)19)1-4(3-13)2-6(7)15-9(17)11(20)21;2*5-4(1-6,2-7)3-8/h1-2H,(H,14,16)(H,15,17)(H,18,19)(H,20,21);2*6-8H,1-3,5H2

HIDE SMILES / InChI

Molecular Formula C11H6ClN3O6
Molecular Weight 311.635
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H11NO3
Molecular Weight 121.135
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

7.4874238E11
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

7.4874238E11
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

7.4874238E11
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
Lodoxamide in vernal keratoconjunctivitis.
1996 May
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
Comparison of antiallergic drugs in an experimental model of ocular anaphylaxis.
2003 Mar-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
Cromoglycate drugs suppress eicosanoid generation in U937 cells by promoting the release of Anx-A1.
2009 Jun 15
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:49:09 UTC 2023
Edited
by admin
on Wed Jul 05 22:49:09 UTC 2023
Record UNII
50LV9A548L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LODOXAMIDE TROMETHAMINE
ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
N,N'-(2-CHLORO-5-CYANO-M-PHENYLENE)DIOXAMIC ACID COMPOUND WITH 2-AMINO-2-(HYDROXYMETHYL)-1,3-PROPANEDIOL (1:2)
Systematic Name English
Lodoxamide tromethamine [WHO-DD]
Common Name English
LODOXAMIDE TROMETHAMINE SALT [MI]
Common Name English
ALOMIDE
Brand Name English
LODOXAMIDE TROMETHAMINE [USAN]
Common Name English
LODOXAMIDE TROMETHAMINE [VANDF]
Common Name English
ACETIC ACID, 2,2'-((2-CHLORO-5-CYANO-1,3-PHENYLENE)DIIMINO)BIS 2-OXO-, COMPOUND WITH 2-AMINO-2-(HYDROXYMETHYL)-1,3-PROPANEDIOL (1:2)
Common Name English
LODOXAMIDE TROMETHAMINE SALT
MI  
Common Name English
LODOXAMIDE TROMETHAMINE [ORANGE BOOK]
Common Name English
LODOXAMIDE TROMETAMOL [MART.]
Common Name English
U-42,585E
Code English
U-42585E
Code English
LODOXAMIDE TROMETAMOL
MART.  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29714
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
FDA ORPHAN DRUG 59791
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
Code System Code Type Description
PUBCHEM
11192129
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY
DRUG BANK
DB06794
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY
EVMPD
SUB02964MIG
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY
CAS
63610-09-3
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY
FDA UNII
50LV9A548L
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY
MERCK INDEX
M6883
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY Merck Index
RXCUI
28859
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID20979825
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY
SMS_ID
100000092604
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201266
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY
MESH
C022028
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY
DAILYMED
50LV9A548L
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY
NCI_THESAURUS
C29160
Created by admin on Wed Jul 05 22:49:09 UTC 2023 , Edited by admin on Wed Jul 05 22:49:09 UTC 2023
PRIMARY
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ACTIVE MOIETY