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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2
Molecular Weight 292.418
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMETINDENE, (S)-

SMILES

C[C@@H](C1=C(CCN(C)C)CC2=C1C=CC=C2)C3=CC=CC=N3

InChI

InChIKey=MVMQESMQSYOVGV-OAHLLOKOSA-N
InChI=1S/C20H24N2/c1-15(19-10-6-7-12-21-19)20-17(11-13-22(2)3)14-16-8-4-5-9-18(16)20/h4-10,12,15H,11,13-14H2,1-3H3/t15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H24N2
Molecular Weight 292.418
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12593665 | https://www.drugbank.ca/drugs/DB08801 | https://www.drugs.com/international/dimetindene.html

Dimethindene (+)- is one of Dimethindene enantiomer that is a subtype-selective M2 muscarinic receptor antagonist. Dimetindene (trade name Fenistil; other name dimethindene maleate) is a potent antipruritic antihistamine, characterized by the small size of its effective dose and its rapidity of action. Dimetindene is an antihistamine/anticholinergic that is a selective H1 antagonist. Its effect sets in after 20 to 60 minutes and lasts several hours. Dimetindene drops as well as Dimetindene syrup is particularly indicated in pediatric practice. Dimetindene is indicated as symptomatic treatment of allergic reactions: urticaria, allergies of the upper respiratory tract such as hay fever and perennial rhinitis, food, and drug allergies; pruritus of various origins, except pruritus due to cholestasis; insect bites. Dimetindene is also indicated for pruritus in eruptive skin diseases such as chickenpox. Dimetindene can be as an adjuvant in eczema and other pruriginous dermatoses of allergic origin.

Originator

Sources: Journal of Chromatography, Biomedical Applications (1991), 567, (1), 229-39.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Fenistil

Approved Use

Unknown
Primary
Fenistil

Approved Use

Unknown
Primary
Fenistil

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Structure-activity relationships of dimethindene derivatives as new M2-selective muscarinic receptor antagonists.
2003 Feb 27
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Drops: Infants up to 1 year, 10-30 drops; Infants of 1 to 3 years, 30-45 drops; Children over 3 years, 45-60 drops; Adults, 60-120 drops. Syrup: Infants up to 1 year, 1-3 teaspoons; Infants of 1 to 3 years, 3-4 teaspoons; Children over 3 years, 4-6 teaspoons; Adults, 6-12 teaspoons. 1 teasponful Fenistil syrup = 5ml = 0.5mg Coated tablets: Adults, 3-6 tablets.
Route of Administration: Oral
In Vitro Use Guide
Rabbit vas deferens, Rat duodenum and Guinea-pig atria were used for activity evaluation. The tissues were allowed to equilibrate for 30 min. Then, concentration-response curves to the agonists were constructed in the absence (control) and in the presence of at least three concentrations (log interval = 0.48) of antagonists (Dimethindene (+)-), allowing 30-60 rain equilibration time. Preliminary experiments indicated that these intervals were sufficient for equilibration of the antagonist concentration used. The rat duodenum was exposed to only one concentration of antagonists. Each concentration of antagonist was tested 3-5 times and the ratios of agonist molar EC50 values obtained in the presence and absence of antagonists were calculated. The ECs0 values were determined by fitting the data to a non-linear iterative curve fitting procedure.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:38:21 UTC 2023
Edited
by admin
on Sat Dec 16 10:38:21 UTC 2023
Record UNII
41H5Y15VA0
Record Status Validated (UNII)
Record Version
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Name Type Language
DIMETINDENE, (S)-
Common Name English
(S)-DIMETHINDENE
Common Name English
(S)-(+)-DIMETHINDENE
Common Name English
1H-INDENE-2-ETHANAMINE, N,N-DIMETHYL-3-(1-(2-PYRIDINYL)ETHYL)-, (S)-
Common Name English
1H-INDENE-2-ETHANAMINE, N,N-DIMETHYL-3-((1S)-1-(2-PYRIDINYL)ETHYL)-
Systematic Name English
(+)-DIMETHINDENE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID00653176
Created by admin on Sat Dec 16 10:38:22 UTC 2023 , Edited by admin on Sat Dec 16 10:38:22 UTC 2023
PRIMARY
FDA UNII
41H5Y15VA0
Created by admin on Sat Dec 16 10:38:22 UTC 2023 , Edited by admin on Sat Dec 16 10:38:22 UTC 2023
PRIMARY
PUBCHEM
6604866
Created by admin on Sat Dec 16 10:38:22 UTC 2023 , Edited by admin on Sat Dec 16 10:38:22 UTC 2023
PRIMARY
CAS
121367-05-3
Created by admin on Sat Dec 16 10:38:22 UTC 2023 , Edited by admin on Sat Dec 16 10:38:22 UTC 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER