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Details

Stereochemistry RACEMIC
Molecular Formula C20H24N2.C4H4O4
Molecular Weight 408.4901
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DIMETHINDENE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CC(C1=C(CCN(C)C)CC2=C1C=CC=C2)C3=CC=CC=N3

InChI

InChIKey=SWECWXGUJQLXJF-BTJKTKAUSA-N
InChI=1S/C20H24N2.C4H4O4/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;5-3(6)1-2-4(7)8/h4-10,12,15H,11,13-14H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C20H24N2
Molecular Weight 292.418
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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 chicken-pox. Dimetindene can be as an adjuvant in eczema and other pruriginous dermatoses of allergic origin.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.692 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Fenistil

Approved Use

Unknown
Primary
Fenistil

Approved Use

Unknown
Primary
Fenistil

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14.6 ng/mL
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIMETHINDENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
101.3 ng × h/mL
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIMETHINDENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.41 h
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIMETHINDENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.28 mg 2 times / day multiple, intranasal
Recommended
Dose: 0.28 mg, 2 times / day
Route: intranasal
Route: multiple
Dose: 0.28 mg, 2 times / day
Sources:
unhealthy, 18 -69
n = 76
Health Status: unhealthy
Condition: seasonal allergic rhinitis
Age Group: 18 -69
Sex: M+F
Population Size: 76
Sources:
0.1 % 1 times / day single, topical
Highest studied dose
Dose: 0.1 %, 1 times / day
Route: topical
Route: single
Dose: 0.1 %, 1 times / day
Sources:
healthy, 33 (21-54)
n = 24
Health Status: healthy
Age Group: 33 (21-54)
Sex: M+F
Population Size: 24
Sources:
6 mg 1 times / day single, oral
Highest studied dose
Dose: 6 mg, 1 times / day
Route: oral
Route: single
Dose: 6 mg, 1 times / day
Sources:
healthy, adult
n = 60
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 60
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
yes [IC50 32.5 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
[Antimycobacterial antihistaminics].
1989 Aug
Neuronal soma-dendritic and prejunctional M1-M4 receptors in gastrointestinal and genitourinary smooth muscle.
1999
Immune changes in patients with advanced breast cancer undergoing chemotherapy with taxanes.
2002 Jul 1
Anti-inflammatory efficacy of topical preparations with 10% hamamelis distillate in a UV erythema test.
2002 Mar-Apr
Histamine release in mesenteric traction syndrome during abdominal aortic aneurysm surgery: prophylaxis with H1 and H2 antihistamines.
2002 Oct
[Mesenteric traction syndrome during the operation of aneurysms of the abdominal aorta--histamine release and prophylaxis with antihistaminics].
2003
Effects of dimethindene maleate nasal spray on the quality of life in seasonal allergic rhinitis.
2003 Sep
Anaphylaxis to intravenous sinistrin.
2004 Dec
[Prescription and safety of dimethindene maleate micropellet capsules in Hungary].
2004 Feb 15
Differential effects of organic modifiers on the enantioseparation of dimetindene maleate with carboxymethyl-beta-cyclodextrin in capillary electrophoresis.
2004 Jan
[Systemic mastocytosis. Classification, symptoms, therapy].
2004 Mar 15
Antimuscarinic agents exhibit local inhibitory effects on muscarinic receptors in bladder-afferent pathways.
2005 Feb
Acute ST-segment elevation myocardial infarction after amoxycillin-induced anaphylactic shock in a young adult with normal coronary arteries: a case report.
2005 Feb 25
A simplified premedication schedule for 1-hour paclitaxel administration.
2005 Jan-Feb
Safety of hydroxocobalamin in healthy volunteers in a randomized, placebo-controlled study.
2006
Spectrophotometric determination of some antihistaminic drugs using 7,7,8,8-tetracyanoquinodimethane (TCNQ).
2006 Jan-Feb
Comparison of capillary zone electrophoresis and isotachophoresis determination of dimethindene enantiomers in pharmaceuticals using charged carboxyethyl-beta-cyclodextrin as a chiral selector.
2006 Nov
A simplified premedication protocol for one-hour paclitaxel infusion in various combinations.
2006 Nov
Analysis of enantiomers in biological matrices by charged cyclodextrin-mediated capillary zone electrophoresis in column-coupling arrangement with capillary isotachophoresis.
2006 Nov 15
[Aso an inspection of the family dog is warrented here].
2006 Oct 19
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.
2007 Apr 20
[Quincke's edema: diagnosis and management of 102 patients with sudden upper airway obstruction].
2007 Jun
Rituximab therapy in Greek patients with rheumatoid arthritis.
2008 Dec
Analytical method for simultaneously measuring ex vivo drug receptor occupancy and dissociation rate: application to (R)-dimethindene occupancy of central histamine H1 receptors.
2009
Glioblastoma cells express functional cell membrane receptors activated by daily used medical drugs.
2009 Dec
Induction of anti-tumor immunity by trifunctional antibodies in patients with peritoneal carcinomatosis.
2009 Feb 14
Evaluation of the paclitaxel-ifosfamide-cisplatin (TIP) combination in relapsed and/or metastatic cervical cancer.
2009 Oct 6
Characterization of novel selective H1-antihistamines for clinical evaluation in the treatment of insomnia.
2009 Sep 10
Differential roles of M2 and M3 muscarinic receptor subtypes in modulation of bladder afferent activity in rats.
2010 Apr
Prevention of postoperative adhesion formation by individual and combined administration of 4 per cent icodextrin and dimetindene maleate (Br J Surg 2009; 96: 1476-1483).
2010 Mar
Identification of a novel selective H1-antihistamine with optimized pharmacokinetic properties for clinical evaluation in the treatment of insomnia.
2010 Oct 1
CD203c-based basophil activation test in allergy diagnosis: characteristics and differences to CD63 upregulation.
2010 Sep
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
Experiments were carried out on isolated right ventricular papillary muscle of cat and guinea-pig, and on left atrial muscle of guinea-pig. The animals were anesthetized with ether, and the muscles were dissected from the heart as quickly as possible and mounted in an organ chamber. The preparations were driven electrically at 2.0 or 0.5 Hz. The transmembrane potentials were recorded by means of conventional glass microelectrode technique. The slow response APs were elicited with histamine (10^-5 M) ) or caffeine (2 mM) in partially depolarized (up to -40 mV) left atrial and right ventricular.myocardium of guinea-pigs. The membrane was depolarized by means of elevated K + (26 mM)-Krebs solution. Dimetindene was freshly dissolved and added to the organ chamber containing Krebs solution (composition in mM): NaC1 118, KCl 4.7, CaC12 2.5, NaH2PO4 1.0, MgC12 1.2, NaHCO3 24.9, glucose 11.5, which was gassed with 95% 02 and 5% CO2 and kept at 37C
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:47:30 GMT 2023
Edited
by admin
on Fri Dec 15 16:47:30 GMT 2023
Record UNII
6LL60J9E0O
Record Status Validated (UNII)
Record Version
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Name Type Language
DIMETHINDENE MALEATE
MI   USAN  
USAN  
Official Name English
DIMETHINDENE MALEATE [USAN]
Common Name English
DIMETINDENE MALEATE [MART.]
Common Name English
2-[1-[2-[2-(Dimethylamino)ethyl]inden-3-yl]ethyl]pyridine maleate (1:1)
Systematic Name English
DIMETINDENE MALEATE
EP   JAN   MART.   WHO-DD  
Common Name English
DIMETINDENE MALEATE [EP MONOGRAPH]
Common Name English
DIMETHINDENE MALEATE [MI]
Common Name English
DIMETINDENE MALEATE [JAN]
Common Name English
SU-6518
Code English
FORHISTAL MALEATE
Brand Name English
1H-INDENE-2-ETHANAMINE, N,N-DIMETHYL-3-(1-(2-PYRIDINYL)ETHYL)-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
DIMETHPYRINDENE MALEATE
Common Name English
NSC-107677
Code English
Dimetindene maleate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
Code System Code Type Description
NSC
107677
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY
RXCUI
258334
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL22108
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY
ECHA (EC/EINECS)
222-789-2
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY
FDA UNII
6LL60J9E0O
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY
CAS
3614-69-5
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY
NCI_THESAURUS
C76674
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY
DRUG BANK
DBSALT000908
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY
MERCK INDEX
m4508
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY Merck Index
PUBCHEM
5282414
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY
SMS_ID
100000087512
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY
EVMPD
SUB01754MIG
Created by admin on Fri Dec 15 16:47:31 GMT 2023 , Edited by admin on Fri Dec 15 16:47:31 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY