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
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-
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 |
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 |
---|---|---|
[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 |
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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
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
by
admin
on
Edited
Fri Dec 15 16:47:30 GMT 2023
by
admin
on
Fri Dec 15 16:47:30 GMT 2023
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Record UNII |
6LL60J9E0O
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Record Status |
Validated (UNII)
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Record Version |
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C29578
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258334
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ACTIVE MOIETY |