Identification
- Summary
Isothipendyl is a 1st generation histamine H1 antagonist primarily applied topically as an antipruritic.
- Generic Name
- Isothipendyl
- DrugBank Accession Number
- DB08802
- Background
Isothipendyl is an antihistamine and anticholinergic used as an antipruritic.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Isothipendyl (DB08802)
- Weight
- Average: 285.407
Monoisotopic: 285.129968313 - Chemical Formula
- C16H19N3S
- Synonyms
- Isothipendyl
- Isothipendylum
- Isotipendilo
- External IDs
- AY 56012
- AY-56012
- D 201
- D-201
Pharmacology
- Indication
For the topical treatment of itching associated with allergic reactions.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Allergic skin reaction ••• ••• ••• - Contraindications & Blackbox Warnings
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Isothipendyl, an azaphenothiazine derivative, competitively binds to histamine (H1) receptors, resulting in inhibition of the pharmacological effects of histamines. It also has some sedative, anticholinergic and antiserotoninergic effects.
- Mechanism of action
Isothipendyl is a selective histamine H1 antagonist and binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
Target Actions Organism AHistamine H1 receptor antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
Pathway Category Isothipendyl H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAmphetamine Amphetamine may decrease the sedative activities of Isothipendyl. Benzphetamine Benzphetamine may decrease the sedative activities of Isothipendyl. Benzylpenicilloyl polylysine Isothipendyl may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent. Betahistine The therapeutic efficacy of Betahistine can be decreased when used in combination with Isothipendyl. Dextroamphetamine Dextroamphetamine may decrease the sedative activities of Isothipendyl. - Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Isothipendyl hydrochloride 953AP1LBV8 1225-60-1 RQHCFTORMXCNGP-UHFFFAOYSA-N - International/Other Brands
- Actapront (Purissimus) / Alergis Jalea (Deutsche Pharma) / Andantol (Deutsche Pharma) / Apaisyl (Merck) / Calmogel (Sanofi) / Nilergex (I.C.I.)
Categories
- ATC Codes
- R06AD09 — Isothipendyl
- R06AD — Phenothiazine derivatives
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Alkyldiarylamines
- Alternative Parents
- Diarylthioethers / Benzothiazines / Pyridines and derivatives / Imidolactams / Benzenoids / 1,4-thiazines / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds show 1 more
- Substituents
- Alkyldiarylamine / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Benzenoid / Benzothiazine / Diarylthioether / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam show 6 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- WVZ7K9P0JY
- CAS number
- 482-15-5
- InChI Key
- OQJBSDFFQWMKBQ-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H19N3S/c1-12(18(2)3)11-19-13-7-4-5-8-14(13)20-15-9-6-10-17-16(15)19/h4-10,12H,11H2,1-3H3
- IUPAC Name
- dimethyl(1-{9-thia-2,4-diazatricyclo[8.4.0.0^{3,8}]tetradeca-1(14),3(8),4,6,10,12-hexaen-2-yl}propan-2-yl)amine
- SMILES
- CC(CN1C2=CC=CC=C2SC2=C1N=CC=C2)N(C)C
References
- Synthesis Reference
U.S. Patent 2,974,139.
- General References
- Moreau A, Dompmartin A, Dubreuil A, Leroy D: Phototoxic and photoprotective effects of topical isothipendyl. Photodermatol Photoimmunol Photomed. 1995 Apr;11(2):50-4. [Article]
- External Links
- Human Metabolome Database
- HMDB0015692
- KEGG Drug
- D08091
- PubChem Compound
- 3781
- PubChem Substance
- 99445272
- ChemSpider
- 3649
- 28012
- ChEBI
- 135183
- ChEMBL
- CHEMBL2111066
- PharmGKB
- PA165958421
- Wikipedia
- Isothipendyl
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Gel Cutaneous 0.750 g Gel Cutaneous 7.5 MG/G Jelly Topical 0.750 g Syrup Oral 40.000 mg Gel Topical Solution / drops; suspension / drops Syrup Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 213-216 U.S. Patent 2,974,139. - Predicted Properties
Property Value Source Water Solubility 0.14 mg/mL ALOGPS logP 3.45 ALOGPS logP 3.66 Chemaxon logS -3.3 ALOGPS pKa (Strongest Basic) 8.91 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 19.37 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 86.66 m3·mol-1 Chemaxon Polarizability 31.9 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9928 Blood Brain Barrier + 0.9804 Caco-2 permeable + 0.808 P-glycoprotein substrate Substrate 0.7871 P-glycoprotein inhibitor I Inhibitor 0.6515 P-glycoprotein inhibitor II Non-inhibitor 0.655 Renal organic cation transporter Inhibitor 0.5198 CYP450 2C9 substrate Non-substrate 0.7399 CYP450 2D6 substrate Substrate 0.7027 CYP450 3A4 substrate Substrate 0.5135 CYP450 1A2 substrate Inhibitor 0.9167 CYP450 2C9 inhibitor Non-inhibitor 0.88 CYP450 2D6 inhibitor Inhibitor 0.7844 CYP450 2C19 inhibitor Non-inhibitor 0.8657 CYP450 3A4 inhibitor Non-inhibitor 0.8468 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5185 Ames test Non AMES toxic 0.8079 Carcinogenicity Non-carcinogens 0.9305 Biodegradation Not ready biodegradable 0.993 Rat acute toxicity 2.5794 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9751 hERG inhibition (predictor II) Inhibitor 0.7695
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 171.8856433 predictedDarkChem Lite v0.1.0 [M-H]- 158.2864 predictedDeepCCS 1.0 (2019) [M+H]+ 174.0190433 predictedDarkChem Lite v0.1.0 [M+H]+ 160.64441 predictedDeepCCS 1.0 (2019) [M+Na]+ 172.0545433 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.73756 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Moreau A, Dompmartin A, Dubreuil A, Leroy D: Phototoxic and photoprotective effects of topical isothipendyl. Photodermatol Photoimmunol Photomed. 1995 Apr;11(2):50-4. [Article]
Drug created at October 15, 2010 16:26 / Updated at December 02, 2023 06:58