Levoketoconazole

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

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
Levoketoconazole
Accession Number
DB05667
Type
Small Molecule
Groups
Investigational
Description

Levoketoconazole is a cortisol synthesis inhibitor that is being developed as a therapy for glucose and cholesterol control in patients with type 2 diabetes mellitus.

Structure
Thumb
Synonyms
Not Available
External IDs
COR-003 / COR003 / DIO-902
Categories
Not Available
UNII
2DJ8R0NT7K
CAS number
142128-57-2
Weight
Average: 531.431
Monoisotopic: 530.148760818
Chemical Formula
C26H28Cl2N4O4
InChI Key
XMAYWYJOQHXEEK-ZEQKJWHPSA-N
InChI
InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m1/s1
IUPAC Name
1-[4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
SMILES
CC(=O)N1CCN(CC1)C1=CC=C(OC[C@@H]2CO[C@](CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1

Pharmacology

Indication

Investigated for use/treatment in diabetes mellitus type 2.

Pharmacodynamics
Not Available
Mechanism of action

Preliminary data suggests that DIO-902 increases insulin sensitivity by lowering cortisol levels. The primary mechanism of action is via inhibition of the 11-β-hydroxylase enzyme, the terminal step in cortisol synthesis in the adrenal gland. DIO-902 has also been shown to lower total and LDL-cholesterol by inhibiting 14-α-demethylase, a key enzyme in cholesterol synthesis. In combination with a typical glucose-lowering agent, such as metformin, DIO-902 may enhance glucose control and improve total and LDL-cholesterol. [DiObex Press Release]

TargetActionsOrganism
UCytochrome P450 11B1, mitochondrialNot AvailableHumans
ULanosterol 14-alpha demethylaseNot 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
Toxicity
Not Available
Affected organisms
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

References

General References
  1. Link [Link]
External Links
Human Metabolome Database
HMDB0012242
ChemSpider
43284
BindingDB
31768
ChEBI
47518
ChEMBL
CHEMBL295698
PharmGKB
PA450146
HET
KLN
Wikipedia
Levoketoconazole
PDB Entries
2jjp / 2v0m

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedOtherHealthy Volunteers2
1, 2CompletedTreatmentType 2 Diabetes Mellitus1
2TerminatedTreatmentType 2 Diabetes Mellitus1
2, 3TerminatedTreatmentType 2 Diabetes Mellitus1
3CompletedTreatmentEndogenous Cushing's Syndrome1
3RecruitingTreatmentCushing's Disease / Cushing's Syndrome1
3RecruitingTreatmentEndogenous Cushing's Syndrome1

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 Solubility0.00931 mg/mLALOGPS
logP4.3ALOGPS
logP4.19ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)6.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.06 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity138.07 m3·mol-1ChemAxon
Polarizability54.67 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-3530190000-a2b05a2498270bcd4a7e

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazinanes
Sub Class
Piperazines
Direct Parent
Phenylpiperazines
Alternative Parents
N-arylpiperazines / Aminophenyl ethers / Phenoxy compounds / Aniline and substituted anilines / Dialkylarylamines / Dichlorobenzenes / Alkyl aryl ethers / Ketals / Aryl chlorides / N-substituted imidazoles
show 12 more
Substituents
Phenylpiperazine / N-arylpiperazine / Aminophenyl ether / 1,3-dichlorobenzene / Phenol ether / Tertiary aliphatic/aromatic amine / Phenoxy compound / Dialkylarylamine / Aniline or substituted anilines / Alkyl aryl ether
show 34 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
cis-1-acetyl-4-(4-\{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy\}phenyl)piperazine (CHEBI:47518)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid 11-beta-monooxygenase activity
Specific Function
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochro...
Gene Name
CYP11B1
Uniprot ID
P15538
Uniprot Name
Cytochrome P450 11B1, mitochondrial
Molecular Weight
57572.44 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sterol 14-demethylase activity
Specific Function
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name
CYP51A1
Uniprot ID
Q16850
Uniprot Name
Lanosterol 14-alpha demethylase
Molecular Weight
56805.26 Da

Drug created on November 18, 2007 11:26 / Updated on September 02, 2019 18:15