Caroxazone

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Caroxazone
Accession Number
DB09254
Type
Small Molecule
Groups
Withdrawn
Description

Caroxazone (Surodil, Timostenil) is an antidepressant which was formerly used for the treatment of depression but is now no longer marketed. It acts as a reversible monoamine oxidase inhibitor (MAOI) of both MAO-A and MAO-B subtypes, with five-fold preference for the latter.

Structure
Thumb
Synonyms
Not Available
External IDs
F.I. 6654
International/Other Brands
Surodil / Timostenil
Categories
UNII
807N226MNL
CAS number
18464-39-6
Weight
Average: 206.201
Monoisotopic: 206.06914219
Chemical Formula
C10H10N2O3
InChI Key
KYCBWEZLKCTALM-UHFFFAOYSA-N
InChI
InChI=1S/C10H10N2O3/c11-9(13)6-12-5-7-3-1-2-4-8(7)15-10(12)14/h1-4H,5-6H2,(H2,11,13)
IUPAC Name
2-(2-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)acetamide
SMILES
NC(=O)CN1CC2=CC=CC=C2OC1=O

Pharmacology

Indication

For the treatment of depression.

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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Caroxazone.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Caroxazone.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Caroxazone.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Caroxazone.
4-MethoxyamphetamineCaroxazone may increase the hypertensive activities of 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Caroxazone.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineCaroxazone may increase the hypertensive activities of 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbediterolThe risk or severity of adverse effects can be increased when Caroxazone is combined with Abediterol.
AcarboseCaroxazone may increase the hypoglycemic activities of Acarbose.
AcebutololCaroxazone may increase the hypotensive activities of Acebutolol.
Food Interactions
Not Available

References

General References
  1. Cecchini S, Petri P, Ardito R, Bareggi SR, Torriti A: A comparative double-blind trial of the new antidepressant caroxazone and amitriptyline. J Int Med Res. 1978;6(5):388-94. [PubMed:359383]
  2. Moretti A, Caccia C, Martini A, Bonollo L, Amico A, Sega R, Nicolella V, Nicolis FB: Effect of caroxazone, a new antidepressant drug, on monoamine oxidases in healthy volunteers. Br J Clin Pharmacol. 1981 May;11(5):511-5. [PubMed:7272163]
External Links
PubChem Compound
29083
PubChem Substance
310265157
ChemSpider
27057
ChEBI
134867
ChEMBL
CHEMBL2104164
Wikipedia
Caroxazone

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.9 mg/mLALOGPS
logP-0.25ALOGPS
logP0.12ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)15.42ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.63 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.12 m3·mol-1ChemAxon
Polarizability19.9 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzoxazines
Sub Class
Not Available
Direct Parent
Benzoxazines
Alternative Parents
Alpha amino acids and derivatives / Benzenoids / Carbamate esters / Primary carboxylic acid amides / Organic carbonic acids and derivatives / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
Alpha-amino acid or derivatives / Benzoxazine / Benzenoid / Carbamic acid ester / Carboxamide group / Carbonic acid derivative / Primary carboxylic acid amide / Carboxylic acid derivative / Azacycle / Oxacycle
show 9 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on October 23, 2015 22:21 / Updated on August 02, 2018 06:16