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Details

Stereochemistry RACEMIC
Molecular Formula C20H24N2
Molecular Weight 292.4187
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMETHINDENE

SMILES

CC(c1ccccn1)C2=C(CCN(C)C)Cc3ccccc32

InChI

InChIKey=MVMQESMQSYOVGV-UHFFFAOYSA-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

HIDE SMILES / InChI

Molecular Formula C20H24N2
Molecular Weight 292.4187
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
Are hypotension and rash after atracurium really caused by histamine release?
1994 May
[Antipruritic effect of antihistaminic and local anesthetic topical agents after iontophoretic histamine stimulation].
1996 May
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
Effects of dimethindene maleate nasal spray on the quality of life in seasonal allergic rhinitis.
2003 Sep
Influence of methanol on the enantioresolution of antihistamines with carboxymethyl-beta-cyclodextrin in capillary electrophoresis.
2004 Aug
Premedication with H1 and H2 blocking agents reduces the incidence of postoperative nausea and vomiting.
2004 Aug
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
[Dimethindene determination in various dosage forms by means of capillary isotachophoresis].
2005 Sep
Safety of hydroxocobalamin in healthy volunteers in a randomized, placebo-controlled study.
2006
[Separation of dimetinden enantiomers in drugs by means of capillary isotachophoresis].
2006 Jan
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
[Aso an inspection of the family dog is warrented here].
2006 Oct 19
Determination of dimethindene enantiomers in pharmaceuticals by capillary electrophoresis with carboxyethyl-beta-cyclodextrin.
2007 Jan
[Quincke's edema: diagnosis and management of 102 patients with sudden upper airway obstruction].
2007 Jun
Chiral separation of alkylamine antihistamines in pharmaceuticals by capillary isotachophoresis with charged cyclodextrin.
2007 Nov
Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells.
2008 Jun 6
Treating common problems of the nose and throat in pregnancy: what is safe?
2008 May
Analytical method for simultaneously measuring ex vivo drug receptor occupancy and dissociation rate: application to (R)-dimethindene occupancy of central histamine H1 receptors.
2009
Prevention of postoperative adhesion formation by individual and combined administration of 4 per cent icodextrin and dimetindene maleate.
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
Permeability alterations after surgical trauma in normal rabbit peritoneum.
2010
Immunoglobulin E-mediated anaphylaxis to rabeprazole.
2010
Garlic-induced severe anaphylaxis in a nonatopic patient.
2010
Differential roles of M2 and M3 muscarinic receptor subtypes in modulation of bladder afferent activity in rats.
2010 Apr
10-year-old girl with severe edema caused by adder bite.
2010 Dec
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
Urticaria, angioedema and dyspnoea in adjuvant therapy of melanoma with interferon alpha-2b.
2010 May
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 Sat Jun 26 07:49:12 UTC 2021
Edited
by admin
on Sat Jun 26 07:49:12 UTC 2021
Record UNII
661FH77Z3P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIMETHINDENE
MI  
Common Name English
2-(1-(2-(2-DIMETHYLAMINOETHYL)INDEN-3-YL)ETHYL)PYRIDINE
Systematic Name English
2-(1-(2-(2-(DIMETHYLAMINO)ETHYL)INDEN-3-YL)ETHYL)PYRIDINE
Systematic Name English
3-(.ALPHA.-(2'-PYRIDYL)ETHYL)-2-(.BETA.-DIMETHYLAMINOETHYL)INDENE
Common Name English
FENIALLERG
Common Name English
DIMETINDENE [INN]
Common Name English
DIMETHINDENE [MI]
Common Name English
1H-INDENE-2-ETHANAMINE, N,N-DIMETHYL-3-(1-(2-PYRIDINYL)ETHYL)-
Systematic Name English
FORHISTAL
Common Name English
N,N-DIMETHYL-3-(1-(2-PYRIDINYL)ETHYL)-1H-INDENE-2-ETHANAMINE
Systematic Name English
DIMETINDENE [WHO-DD]
Common Name English
DIMETINDENE
INN   WHO-DD  
INN  
Official Name English
DIMETHPYRINDENE
Common Name English
(+/-)-DIMETHINDENE
Common Name English
PYRIDINE, 2-(1-(2-(2-(DIMETHYLAMINO)ETHYL)INDEN-3-YL)ETHYL)-
Systematic Name English
Classification Tree Code System Code
WHO-ATC D04AA13
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
WHO-ATC R06AB03
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
WHO-VATC QD04AA13
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
WHO-VATC QR06AB03
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
Code System Code Type Description
DRUG CENTRAL
903
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
MESH
D004115
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
NCI_THESAURUS
C83675
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
WIKIPEDIA
Dimetindene
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
PUBCHEM
21855
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
CAS
5636-83-9
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
EVMPD
SUB07179MIG
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
MERCK INDEX
M4508
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY Merck Index
FDA UNII
661FH77Z3P
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
INN
1403
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
DRUG BANK
DB08801
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
EPA CompTox
5636-83-9
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
ChEMBL
CHEMBL22108
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
RXCUI
3449
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
227-083-8
Created by admin on Sat Jun 26 07:49:12 UTC 2021 , Edited by admin on Sat Jun 26 07:49:12 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY