NAV

Lapachone

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

Identification

Generic Name
Lapachone
DrugBank Accession Number
DB11948
Background

Lapachone has been used in trials studying the treatment of Cancer, Carcinoma, Advanced Solid Tumors, Head and Neck Neoplasms, and Carcinoma, Squamous Cell.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 242.274
Monoisotopic: 242.094294311
Chemical Formula
C15H14O3
Synonyms
Not Available
External IDs
  • ARQ 501
  • ARQ-501
  • HK-660S
  • MB-12066
  • NSC-26326
  • NSC-629749
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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
URetinol-binding protein 3Not 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 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.
DrugInteraction
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interactions in your software
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Lapachone.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Lapachone.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Lapachone.
Bacillus calmette-guerin substrain russian BCG-I live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Lapachone.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Lapachone.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Naphthopyrans
Sub Class
Naphthopyranones
Direct Parent
Naphthopyranones
Alternative Parents
Naphthoquinones / Quinones / Aryl ketones / Pyrans / Vinylogous esters / Oxacyclic compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aromatic heteropolycyclic compound / Aryl ketone / Benzenoid / Carbonyl group / Hydrocarbon derivative / Ketone / Naphthalene / Naphthopyranone / Naphthoquinone / Organic oxide
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinone, benzochromenone (CHEBI:10429)
Affected organisms
Not Available

Chemical Identifiers

UNII
6N4FA2QQ6A
CAS number
4707-32-8
InChI Key
QZPQTZZNNJUOLS-UHFFFAOYSA-N
InChI
InChI=1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3
IUPAC Name
2,2-dimethyl-2H,3H,4H,5H,6H-naphtho[1,2-b]pyran-5,6-dione
SMILES
CC1(C)CCC2=C(O1)C1=CC=CC=C1C(=O)C2=O

References

General References
Not Available
Human Metabolome Database
HMDB0249138
KEGG Compound
C10367
PubChem Compound
3885
PubChem Substance
347828274
ChemSpider
3748
BindingDB
81348
ChEBI
10429
ChEMBL
CHEMBL15192
ZINC
ZINC000001531790

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedNot AvailableCancer1
2CompletedTreatmentAdenocarcinomas / Pancreatic Cancer1
2CompletedTreatmentHead and Neck Neoplasms / Squamous Cell Carcinoma (SCC)1
2CompletedTreatmentPrimary Sclerosing Cholangitis (PSC)1
2TerminatedTreatmentFatty Liver, Non-alcoholic Fatty Liver Disease, NAFLD1

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0563 mg/mLALOGPS
logP2.82ALOGPS
logP2.63Chemaxon
logS-3.6ALOGPS
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area43.37 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity69.09 m3·mol-1Chemaxon
Polarizability25.65 Å3Chemaxon
Number of Rings3Chemaxon
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-MSsplash10-03di-4980000000-93a44e3902f7e083ce89
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSsplash10-004i-0490000000-9dbf4ce893a2feaca176
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0090000000-4a26146991318c5f1e1c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0950000000-fc19149826e6662b522d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-052r-0900000000-47530e7c0f8b6bf3c398
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-bc6b197a7ba33ff3caf9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-9b23674b37357d81e688
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-006y-0950000000-88e0179d41c7b1b42752
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-f01418e7272228b40df6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0950000000-f1723260062183bfb179
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0190000000-4029bc1d24c2c1fae86c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0cdi-3920000000-0120eeec915dfd5e1957
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0229-0940000000-e704cf5bbb5a86d631f2
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]-162.5745103
predicted
DarkChem Lite v0.1.0
[M-H]-162.3376103
predicted
DarkChem Lite v0.1.0
[M-H]-157.9904
predicted
DeepCCS 1.0 (2019)
[M+H]+162.9265103
predicted
DarkChem Lite v0.1.0
[M+H]+163.1363103
predicted
DarkChem Lite v0.1.0
[M+H]+160.34842
predicted
DeepCCS 1.0 (2019)
[M+Na]+162.5055103
predicted
DarkChem Lite v0.1.0
[M+Na]+162.7208103
predicted
DarkChem Lite v0.1.0
[M+Na]+166.44154
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Retinol-binding protein 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine-type peptidase activity
Specific Function
IRBP shuttles 11-cis and all trans retinoids between the retinol isomerase in the pigment epithelium and the visual pigments in the photoreceptor cells of the retina.
Gene Name
RBP3
Uniprot ID
P10745
Uniprot Name
Retinol-binding protein 3
Molecular Weight
135361.46 Da

Drug created at October 20, 2016 21:03 / Updated at September 26, 2023 22:59