Identification
- Generic Name
- Dichloralphenazone
- DrugBank Accession Number
- DB01495
- Background
Dichloralphenazone is a sedative composed of chloral hydrate and phenazone. It is typically found in combination products Nodolor and Midrin containing isometheptene and acetaminophen used for the relief of tension and vascular headaches. It is a US Schedule IV drug and its clinical use is limited.
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Structure
Structure for Dichloralphenazone (DB01495)
- Weight
- Average: 519.032
Monoisotopic: 515.934687938 - Chemical Formula
- C15H18Cl6N2O5
- Synonyms
- Dichloralphenazone
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to manage Tension headache Combination Product in combination with: Acetaminophen (DB00316), Isometheptene (DB06706) •••••••••••• Used in combination to manage Vascular headaches Combination Product in combination with: Isometheptene (DB06706), Acetaminophen (DB00316) •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- 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 software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Dichloralphenazone is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Dichloralphenazone. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Dichloralphenazone. Agomelatine The risk or severity of CNS depression can be increased when Dichloralphenazone is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Dichloralphenazone. - Food Interactions
- Avoid alcohol.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Active Moieties
Name Kind UNII CAS InChI Key Antipyrine unknown T3CHA1B51H 60-80-0 VEQOALNAAJBPNY-UHFFFAOYSA-N Chloral hydrate unknown 418M5916WG 302-17-0 RNFNDJAIBTYOQL-UHFFFAOYSA-N - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Isometheptene Mucate, Dichloralphenazone, and Acetaminophen Dichloralphenazone (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1) Capsule Oral Macoven Pharmaceuticals 2011-06-28 2017-12-20 US 
Isometheptene Mucate, Dichloralphenazone, and Acetaminophen Dichloralphenazone (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1) Capsule Oral Burel Pharmaceuticals, Llc 2016-04-16 2016-11-10 US Isometheptene Mucate, Dichloralphenazone, and Acetaminophen Dichloralphenazone (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1) Capsule, gelatin coated Oral Vilvet Pharmaceuticals Inc 2011-05-01 2017-10-13 US Isometheptene Mucate/Dichloralphenazone/Acetaminophen Dichloralphenazone (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1) Capsule Oral Physicians Total Care, Inc. 2007-12-04 2012-06-30 US Isometheptene Mucate/Dichloralphenazone/Acetaminophen Dichloralphenazone (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1) Capsule Oral Eci Pharmaceuticals Llc 2011-02-15 2018-03-31 US
Categories
- ATC Codes
- N05CC04 — Dichloralphenazone
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups.
- Kingdom
- Organic compounds
- Super Class
- Organohalogen compounds
- Class
- Halohydrins
- Sub Class
- Chlorohydrins
- Direct Parent
- Chlorohydrins
- Alternative Parents
- Carbonyl hydrates / Organochlorides / Hydrocarbon derivatives / Alkyl chlorides
- Substituents
- Alkyl chloride / Alkyl halide / Aromatic heteromonocyclic compound / Carbonyl hydrate / Chlorohydrin / Hydrocarbon derivative / Organic oxygen compound / Organochloride / Organooxygen compound
- Molecular Framework
- Not Available
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- YYX637R279
- CAS number
- 480-30-8
- InChI Key
- ATKXDQOHNICLQW-UHFFFAOYSA-N
- InChI
- InChI=1S/C11H12N2O.2C2H3Cl3O2/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10;2*3-2(4,5)1(6)7/h3-8H,1-2H3;2*1,6-7H
- IUPAC Name
- 1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one; bis(2,2,2-trichloroethane-1,1-diol)
- SMILES
- OC(O)C(Cl)(Cl)Cl.OC(O)C(Cl)(Cl)Cl.CN1N(C(=O)C=C1C)C1=CC=CC=C1
References
- General References
- Hindmarch I, Parrott AC: The effects of combined sedative and anxiolytic preparations on subjective aspects of sleep and objective measures of arousal and performance the morning following nocturnal medication. I: Acute doses. Arzneimittelforschung. 1980;30(6):1025-8. [Article]
- External Links
- PubChem Compound
- 10188
- PubChem Substance
- 46507898
- ChemSpider
- 9776
- 22892
- ChEMBL
- CHEMBL1697834
- Wikipedia
- Dichloralphenazone
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule, gelatin coated Oral Capsule Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 68 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 47.4 mg/mL ALOGPS logP 1.18 ALOGPS logP 1.22 Chemaxon logS -0.6 ALOGPS pKa (Strongest Basic) 0.49 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 23.55 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 56.42 m3·mol-1 Chemaxon Polarizability 20.4 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.991 Blood Brain Barrier + 0.5901 Caco-2 permeable - 0.5539 P-glycoprotein substrate Non-substrate 0.8633 P-glycoprotein inhibitor I Non-inhibitor 0.9763 P-glycoprotein inhibitor II Non-inhibitor 0.9465 Renal organic cation transporter Non-inhibitor 0.9512 CYP450 2C9 substrate Non-substrate 0.6054 CYP450 2D6 substrate Non-substrate 0.8553 CYP450 3A4 substrate Substrate 0.5661 CYP450 1A2 substrate Non-inhibitor 0.6408 CYP450 2C9 inhibitor Non-inhibitor 0.8334 CYP450 2D6 inhibitor Non-inhibitor 0.9366 CYP450 2C19 inhibitor Non-inhibitor 0.7525 CYP450 3A4 inhibitor Non-inhibitor 0.9689 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9289 Ames test Non AMES toxic 0.7272 Carcinogenicity Non-carcinogens 0.8129 Biodegradation Not ready biodegradable 0.9958 Rat acute toxicity 2.3391 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9976 hERG inhibition (predictor II) Non-inhibitor 0.8907
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 189.5342 predictedDeepCCS 1.0 (2019) [M+H]+ 191.8922 predictedDeepCCS 1.0 (2019) [M+Na]+ 198.80159 predictedDeepCCS 1.0 (2019)
Drug created at July 31, 2007 13:09 / Updated at February 21, 2021 18:51