Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H24N2 |
Molecular Weight | 292.418 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C1=C(CCN(C)C)CC2=C1C=CC=C2)C3=CC=CC=N3
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
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 | ( + / - ) |
DescriptionSources: https://www.drugbank.ca/drugs/DB08801
Sources: https://www.drugbank.ca/drugs/DB08801
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12593665 |
0.692 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: http://pcm.me/fenistil-%C2%AE/ |
Primary | Fenistil Approved UseUnknown |
||
Sources: http://pcm.me/fenistil-%C2%AE/ |
Primary | Fenistil Approved UseUnknown |
||
Sources: http://pcm.me/fenistil-%C2%AE/ |
Primary | Fenistil Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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: |
PubMed
Title | Date | PubMed |
---|---|---|
[Antipruritic effect of antihistaminic and local anesthetic topical agents after iontophoretic histamine stimulation]. | 1996 May |
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Neuronal soma-dendritic and prejunctional M1-M4 receptors in gastrointestinal and genitourinary smooth muscle. | 1999 |
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Immune changes in patients with advanced breast cancer undergoing chemotherapy with taxanes. | 2002 Jul 1 |
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Anti-inflammatory efficacy of topical preparations with 10% hamamelis distillate in a UV erythema test. | 2002 Mar-Apr |
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Histamine release in mesenteric traction syndrome during abdominal aortic aneurysm surgery: prophylaxis with H1 and H2 antihistamines. | 2002 Oct |
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[Mesenteric traction syndrome during the operation of aneurysms of the abdominal aorta--histamine release and prophylaxis with antihistaminics]. | 2003 |
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Influence of peak measurement parameters on the quality of chiral electrophoretic separations. | 2003 Aug |
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Structure-activity relationships of dimethindene derivatives as new M2-selective muscarinic receptor antagonists. | 2003 Feb 27 |
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Pruritic urticarial papules and plaques of pregnancy (PUPPP)--a case report. | 2003 May-Jun |
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Effects of dimethindene maleate nasal spray on the quality of life in seasonal allergic rhinitis. | 2003 Sep |
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Influence of methanol on the enantioresolution of antihistamines with carboxymethyl-beta-cyclodextrin in capillary electrophoresis. | 2004 Aug |
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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 |
|
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 |
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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 |
|
Anaphylactic shock caused by buffalo's mozzarella cheese. | 2008 Jul |
|
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 |
|
Glioblastoma cells express functional cell membrane receptors activated by daily used medical drugs. | 2009 Dec |
|
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 |
|
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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://pcm.me/fenistil-%C2%AE/
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6832322
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
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admin
on
Edited
Fri Dec 15 15:11:24 UTC 2023
by
admin
on
Fri Dec 15 15:11:24 UTC 2023
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Record UNII |
661FH77Z3P
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
D04AA13
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WHO-ATC |
R06AB03
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WHO-VATC |
QD04AA13
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QR06AB03
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NCI_THESAURUS |
C29578
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903
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D004115
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C83675
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Dimetindene
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21855
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5636-83-9
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SUB07179MIG
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m4508
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100000082645
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661FH77Z3P
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661FH77Z3P
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1403
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DB08801
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DTXSID9022942
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CHEMBL22108
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3449
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227-083-8
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |