NAV

Carboxin

Identification

Generic Name
Carboxin
DrugBank Accession Number
DB04657
Background

A systemic agricultural fungicide and seed treatment agent.

Type
Small Molecule
Groups
Approved, Experimental
Structure
3D
Similar Structures
Weight
Average: 235.302
Monoisotopic: 235.066699355
Chemical Formula
C12H13NO2S
Synonyms
  • 2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiin
  • 2,3-Dihydro-6-methyl-1,4-oxathiin-5-carboxanilide
  • 2,3-Dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiin
  • 5-Carboxanilido-2,3-dihydro-6-methyl-1,4-oxathiin
  • 5,6-Dihydro-2-methyl-1,4-oxathiin-3-carboxanilide
  • 5,6-Dihydro-2-methyl-3-carboxanilido-1,4-oxathiin
  • 5,6-Dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide
  • Carbathiin
  • Carboxine
  • Oxatin
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USuccinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrialNot AvailableHumans
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
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.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Kisvax / Vitavax

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Anilides
Alternative Parents
N-arylamides / Oxathiins / Vinylogous esters / Thioenol ethers / Secondary carboxylic acid amides / Oxacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
1,4-oxathiin / Anilide / Aromatic heteromonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / N-arylamide / Organic nitrogen compound / Organic oxide
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
anilide (CHEBI:41412) / Amide fungicides (C11255) / an amide (CPD0-1366)
Affected organisms
Not Available

Chemical Identifiers

UNII
5A8K850HDE
CAS number
5234-68-4
InChI Key
GYSSRZJIHXQEHQ-UHFFFAOYSA-N
InChI
InChI=1S/C12H13NO2S/c1-9-11(16-8-7-15-9)12(14)13-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,13,14)
IUPAC Name
2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide
SMILES
CC1=C(SCCO1)C(=O)NC1=CC=CC=C1

References

General References
Not Available
KEGG Compound
C11255
PubChem Compound
21307
PubChem Substance
46507275
ChemSpider
20027
ChEBI
3405
ChEMBL
CHEMBL1231667
ZINC
ZINC000000043478
PDBe Ligand
CBE
PDB Entries
2fbw / 2wdq / 2wp9 / 2wqy / 2ws3 / 2wu2 / 2wu5

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)91.5 °CPhysProp
water solubility147 mg/L (at 20 °C)TOMLIN,C (2003)
logP2.14HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.536 mg/mLALOGPS
logP1.65ALOGPS
logP1.51Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)13.24Chemaxon
pKa (Strongest Basic)-2.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area38.33 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity69.1 m3·mol-1Chemaxon
Polarizability24.85 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9794
Blood Brain Barrier+0.9764
Caco-2 permeable+0.6035
P-glycoprotein substrateNon-substrate0.6547
P-glycoprotein inhibitor IInhibitor0.5183
P-glycoprotein inhibitor IINon-inhibitor0.9174
Renal organic cation transporterNon-inhibitor0.7344
CYP450 2C9 substrateNon-substrate0.655
CYP450 2D6 substrateNon-substrate0.7929
CYP450 3A4 substrateSubstrate0.5503
CYP450 1A2 substrateInhibitor0.6498
CYP450 2C9 inhibitorInhibitor0.5784
CYP450 2D6 inhibitorNon-inhibitor0.8963
CYP450 2C19 inhibitorInhibitor0.7341
CYP450 3A4 inhibitorNon-inhibitor0.8503
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8491
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8705
BiodegradationReady biodegradable0.6897
Rat acute toxicity2.7064 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9405
hERG inhibition (predictor II)Non-inhibitor0.8196
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Mass Spectrum (Electron Ionization)MSsplash10-000f-9620000000-9a851c11b79664d86a44
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0006-4901000000-ccaeb7005f3f1f68e10a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-4901000000-ccaeb7005f3f1f68e10a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000f-1930000000-72e2c2ef3bb724ab723c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0309-7910000000-d711e8d2e16d0f391110
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ko-6920000000-4063d5770a61435fded6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-030c-9300000000-9c5070ca7e7b48910acf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9100000000-e02b120c0c3c8d7cb0aa
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ukd-8910000000-4ea53635e4f790789b94
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.4397833
predicted
DarkChem Lite v0.1.0
[M-H]-157.1840833
predicted
DarkChem Lite v0.1.0
[M-H]-149.20845
predicted
DeepCCS 1.0 (2019)
[M+H]+156.8456833
predicted
DarkChem Lite v0.1.0
[M+H]+155.4847833
predicted
DarkChem Lite v0.1.0
[M+H]+151.56645
predicted
DeepCCS 1.0 (2019)
[M+Na]+157.6071833
predicted
DarkChem Lite v0.1.0
[M+Na]+157.1072833
predicted
DarkChem Lite v0.1.0
[M+Na]+157.85115
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Succinate dehydrogenase activity
Specific Function
Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate ...
Gene Name
SDHA
Uniprot ID
P31040
Uniprot Name
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
Molecular Weight
72690.975 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52