This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
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
Structure for Lapachone (DB11948)
- 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
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ADNA topoisomerase 1 modulatorHumans URetinol-binding protein 3 Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAdenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Lapachone. Anthrax vaccine The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Lapachone. Bacillus calmette-guerin substrain connaught live antigen The 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 antigen The 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 antigen The 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
- External Links
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2 Completed Not Available Cancer 1 somestatus stop reason just information to hide 2 Completed Treatment Adenocarcinomas / Pancreatic Cancer 1 somestatus stop reason just information to hide 2 Completed Treatment Head and Neck Neoplasms / Squamous Cell Carcinoma (SCC) 1 somestatus stop reason just information to hide 2 Completed Treatment Primary Sclerosing Cholangitis (PSC) 1 somestatus stop reason just information to hide 2 Terminated Treatment Fatty Liver, Non-alcoholic Fatty Liver Disease, NAFLD 1 somestatus stop reason just information to hide
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
Property Value Source Water Solubility 0.0563 mg/mL ALOGPS logP 2.82 ALOGPS logP 2.63 Chemaxon logS -3.6 ALOGPS pKa (Strongest Basic) -4.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 43.37 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 69.09 m3·mol-1 Chemaxon Polarizability 25.65 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 162.5745103 predictedDarkChem Lite v0.1.0 [M-H]- 162.3376103 predictedDarkChem Lite v0.1.0 [M-H]- 157.9904 predictedDeepCCS 1.0 (2019) [M+H]+ 162.9265103 predictedDarkChem Lite v0.1.0 [M+H]+ 163.1363103 predictedDarkChem Lite v0.1.0 [M+H]+ 160.34842 predictedDeepCCS 1.0 (2019) [M+Na]+ 162.5055103 predictedDarkChem Lite v0.1.0 [M+Na]+ 162.7208103 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.44154 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Releases the supercoiling and torsional tension of DNA introduced during the DNA replication and transcription by transiently cleaving and rejoining one strand of the DNA duplex. Introduces a single-strand break via transesterification at a target site in duplex DNA. The scissile phosphodiester is attacked by the catalytic tyrosine of the enzyme, resulting in the formation of a DNA-(3'-phosphotyrosyl)-enzyme intermediate and the expulsion of a 5'-OH DNA strand. The free DNA strand then rotates around the intact phosphodiester bond on the opposing strand, thus removing DNA supercoils. Finally, in the religation step, the DNA 5'-OH attacks the covalent intermediate to expel the active-site tyrosine and restore the DNA phosphodiester backbone (By similarity). Regulates the alternative splicing of tissue factor (F3) pre-mRNA in endothelial cells. Involved in the circadian transcription of the core circadian clock component BMAL1 by altering the chromatin structure around the ROR response elements (ROREs) on the BMAL1 promoter
- Specific Function
- ATP binding
- Gene Name
- TOP1
- Uniprot ID
- P11387
- Uniprot Name
- DNA topoisomerase 1
- Molecular Weight
- 90725.19 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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
- Specific Function
- retinal binding
- 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 August 26, 2024 19:23