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β-Lapachone

β-Lapachone structure

CAS No:
4707-32-8
Formula:
C15H14O3
Chemical Name:
β-Lapachone
Synonyms:
2H-Naphtho[1,2-b]pyran-5,6-dione,3,4-dihydro-2,2-dimethyl-;3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione;β-Lapachone;SL 11001;NSC 26326;NSC 629749;ARQ 501;MB 12066;2,2-Dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
Categories:
Biochemical Engineering > Inhibitors

Description

β-Lapachone is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression.

Beta-lapachone is a benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities. It has a role as an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is a benzochromenone and a member of orthoquinones.|Lapachone has been used in trials studying the treatment of Cancer, Carcinoma, Advanced Solid Tumors, Head and Neck Neoplasms, and Carcinoma, Squamous Cell.|Lapachone is a poorly soluble, ortho-naphthoquinone with potential antineoplastic and radiosensitizing activity. Beta-lapachone (b-lap) is bioactivated by NAD(P)H:quinone oxidoreductase-1 (NQO1), creating a futile oxidoreduction that generates high levels of superoxide. In turn, the highly reactive oxygen species (ROS) interact with DNA, thereby causing single-strand DNA breaks and calcium release from endoplasmic reticulum (ER) stores. Eventually, the extensive DNA damage causes hyperactivation of poly(ADP-ribose) polymerase-1 (PARP-1), an enzyme facilitating DNA repair, accompanied by rapid depletion of NAD+/ATP nucleotide levels. As a result, a caspase-independent and ER-stress induced mu-calpain-mediated cell death occurs in NQO1-overexpressing tumor cells. NQO1, a flavoprotein and two-electron oxidoreductase, is overexpressed in a variety of tumors.

β-Lapachone Basic Attributes

Molecular Weight：

242.27

Exact Mass：

242.27

UNII：

6N4FA2QQ6A

NSC Number：

629749|26326

DSSTox ID：

DTXSID90197019

NCI Thesaurus Code：

C28694

HScode：

2914399090

Characteristics

PSA：

43.4

XLogP3：

2.2

Density：

1.3±0.1 g/cm3

Melting Point：

124.5-125.5 °C

Boiling Point：

381.4ºC at 760 mmHg

Flash Point：

169.7±27.9 °C

Refractive Index：

1.595

Storage Conditions：

-20°C Freezer

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

RTECS Number：

QL6127400

Drug Information

MeSH：

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)|Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)|Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)

MeSH Entry Terms：

ARQ 501

β-Lapachone Use and Manufacturing

β-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae) with cancer chemopreventive properties. Induces apoptosis in HL-60 and human prostate cancer cells.

Computed Properties

Molecular Weight:242.27
XLogP3:2.2
Hydrogen Bond Acceptor Count:3
Exact Mass:242.094294304
Monoisotopic Mass:242.094294304
Topological Polar Surface Area:43.4
Heavy Atom Count:18
Complexity:445
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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