NAV

Dichloralphenazone

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
Similar Structures
Weight
Average: 519.032
Monoisotopic: 515.934687938
Chemical Formula
C15H18Cl6N2O5
Synonyms
  • Dichloralphenazone
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Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageTension headacheCombination Product in combination with: Acetaminophen (DB00316), Isometheptene (DB06706)••••••••••••
Used in combination to manageVascular headachesCombination Product in combination with: Isometheptene (DB06706), Acetaminophen (DB00316)••••••••••••
Contraindications & Blackbox Warnings
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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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Dichloralphenazone is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Dichloralphenazone.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Dichloralphenazone.
AgomelatineThe risk or severity of CNS depression can be increased when Dichloralphenazone is combined with Agomelatine.
AlfentanilThe risk or severity of CNS depression can be increased when Alfentanil is combined with Dichloralphenazone.
Food Interactions
  • Avoid alcohol.

Products

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Active Moieties
NameKindUNIICASInChI Key
AntipyrineunknownT3CHA1B51H60-80-0VEQOALNAAJBPNY-UHFFFAOYSA-N
Chloral hydrateunknown418M5916WG302-17-0RNFNDJAIBTYOQL-UHFFFAOYSA-N
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Isometheptene Mucate, Dichloralphenazone, and AcetaminophenDichloralphenazone (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1)CapsuleOralMacoven Pharmaceuticals2011-06-282017-12-20US flag
Isometheptene Mucate, Dichloralphenazone, and AcetaminophenDichloralphenazone (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1)CapsuleOralBurel Pharmaceuticals, Llc2016-04-162016-11-10US flag
Isometheptene Mucate, Dichloralphenazone, and AcetaminophenDichloralphenazone (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1)Capsule, gelatin coatedOralVilvet Pharmaceuticals Inc2011-05-012017-10-13US flag
Isometheptene Mucate/Dichloralphenazone/AcetaminophenDichloralphenazone (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1)CapsuleOralEci Pharmaceuticals Llc2011-02-152018-03-31US flag
Isometheptene Mucate/Dichloralphenazone/AcetaminophenDichloralphenazone (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1)CapsuleOralPhysicians Total Care, Inc.2007-12-042012-06-30US flag

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
  1. 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]
PubChem Compound
10188
PubChem Substance
46507898
ChemSpider
9776
RxNav
22892
ChEMBL
CHEMBL1697834
Wikipedia
Dichloralphenazone

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule, gelatin coatedOral
CapsuleOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)68 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility47.4 mg/mLALOGPS
logP1.18ALOGPS
logP1.22Chemaxon
logS-0.6ALOGPS
pKa (Strongest Basic)0.49Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area23.55 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity56.42 m3·mol-1Chemaxon
Polarizability20.4 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.991
Blood Brain Barrier+0.5901
Caco-2 permeable-0.5539
P-glycoprotein substrateNon-substrate0.8633
P-glycoprotein inhibitor INon-inhibitor0.9763
P-glycoprotein inhibitor IINon-inhibitor0.9465
Renal organic cation transporterNon-inhibitor0.9512
CYP450 2C9 substrateNon-substrate0.6054
CYP450 2D6 substrateNon-substrate0.8553
CYP450 3A4 substrateSubstrate0.5661
CYP450 1A2 substrateNon-inhibitor0.6408
CYP450 2C9 inhibitorNon-inhibitor0.8334
CYP450 2D6 inhibitorNon-inhibitor0.9366
CYP450 2C19 inhibitorNon-inhibitor0.7525
CYP450 3A4 inhibitorNon-inhibitor0.9689
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9289
Ames testNon AMES toxic0.7272
CarcinogenicityNon-carcinogens0.8129
BiodegradationNot ready biodegradable0.9958
Rat acute toxicity2.3391 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9976
hERG inhibition (predictor II)Non-inhibitor0.8907
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-189.5342
predicted
DeepCCS 1.0 (2019)
[M+H]+191.8922
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.80159
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:09 / Updated at February 21, 2021 18:51