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
Thumb
Weight
Average: 242.274
Monoisotopic: 242.094294311
Chemical Formula
C15H14O3
Synonyms
Not Available
External IDs
  • ARQ 501
  • ARQ-501
  • MB-12066
  • NSC-26326
  • NSC-629749

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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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
Adverseeffects
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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.
DrugInteraction
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.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Lapachone.
Human adenovirus e serotype 4 strain cl-68578 antigenThe therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Lapachone.
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Lapachone.
Typhoid Vaccine LiveThe therapeutic efficacy of Typhoid Vaccine Live can be decreased when used in combination with Lapachone.
Varicella zoster vaccine (live/attenuated)The therapeutic efficacy of Varicella zoster vaccine (live/attenuated) can be decreased when used in combination with Lapachone.
Interactions
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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
KEGG Compound
C10367
PubChem Compound
3885
PubChem Substance
347828274
ChemSpider
3748
BindingDB
81348
ChEBI
10429
ChEMBL
CHEMBL15192
ZINC
ZINC000001531790

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedNot AvailableMalignancies1
2CompletedTreatmentAdenocarcinomas / Malignant Neoplasm of Pancreas1
2CompletedTreatmentNeoplasms, Head and Neck / Squamous Cell Carcinoma (SCC)1
2TerminatedTreatmentFatty Liver, Non-alcoholic Fatty Liver Disease, NAFLD1
1CompletedScreeningObesity (Disorder) / Syndrome, Metabolic2
1CompletedScreeningSyndrome, Metabolic1
1CompletedTreatmentCarcinoma1
1CompletedTreatmentMalignancies1
1CompletedTreatmentSolid Tumors, Advanced Solid Tumors1
1, 2CompletedTreatmentMalignancies1

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-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
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
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

Targets

Drugtargets2
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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 June 12, 2020 16:53