NAPABUCASIN

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H8O4
Molecular Weight	240.2109
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)C1=CC2=C(O1)C(=O)C3=C(C=CC=C3)C2=O

InChI

InChIKey=DPHUWDIXHNQOSY-UHFFFAOYSA-N

InChI=1S/C14H8O4/c1-7(15)11-6-10-12(16)8-4-2-3-5-9(8)13(17)14(10)18-11/h2-6H,1H3

HIDE SMILES / InChI

Molecular Formula	C14H8O4
Molecular Weight	240.2109
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28573435
Curator's Comment: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT02753127 | https://clinicaltrials.gov/ct2/show/NCT02178956 | https://clinicaltrials.gov/ct2/show/NCT02826161 | https://www.ncbi.nlm.nih.gov/pubmed/22845014 | https://www.ncbi.nlm.nih.gov/pubmed/25605917

Napabucasin (BBI608) is an orally administered small molecule that blocks stem cell activity in cancer cells by targeting the signal transducer and activator of transcription 3 pathway, which is over-activated in many types of cancer and has been shown to be an important pathway in cancer stem cell-mediated propagation of cancer. Napabucasin has already shown promising efficacy on different cancer types, both as a monotherapy and in combination with conventional chemotherapeutic agents. Early-phase trials have shown promising anti-tumor efficacy when patients are treated with napabucasin in combination with standard chemotherapy agents, and preclinical results suggest that napabucasin can synergize with chemotherapy agents, such as paclitaxel, to potentially overcome drug resistance. Encouraging phase Ib/II trial results warrant further clinical study with napabucasin and paclitaxel combination therapy, especially in malignancies where there is an urgent and unmet need for effective therapeutics, such as in patients with advanced pancreatic adenocarcinoma.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
stat3 signaling pathway 1 Target ID: stat3 signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/25605917	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Non-small cell lung cancer 211 Sources: https://clinicaltrials.gov/ct2/show/NCT02826161	Primary	Phase III 665	Unknown Approved Use Unknown
Colorectal cancer 102 Sources: https://clinicaltrials.gov/ct2/show/NCT02753127	Primary	Phase III 665	Unknown Approved Use Unknown
Gastric cancer 53 Sources: https://clinicaltrials.gov/ct2/show/NCT02178956	Primary	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
609 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34291369/	240 mg 2 times / day multiple, oral dose: 240 mg route of administration: Oral experiment type: MULTIPLE co-administered: BEVACIZUMAB	BEVACIZUMAB	NAPABUCASIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
1083 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31028219	480 mg 2 times / day multiple, oral dose: 480 mg route of administration: Oral experiment type: MULTIPLE co-administered: PACLITAXEL	PACLITAXEL	NAPABUCASIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
5249 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34291369/	240 mg 2 times / day multiple, oral dose: 240 mg route of administration: Oral experiment type: MULTIPLE co-administered: BEVACIZUMAB	BEVACIZUMAB	NAPABUCASIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
10666 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31028219	480 mg 2 times / day multiple, oral dose: 480 mg route of administration: Oral experiment type: MULTIPLE co-administered: PACLITAXEL	PACLITAXEL	NAPABUCASIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34291369/	240 mg 2 times / day multiple, oral dose: 240 mg route of administration: Oral experiment type: MULTIPLE co-administered: BEVACIZUMAB	BEVACIZUMAB	NAPABUCASIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
5.96 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31028219	480 mg 2 times / day multiple, oral dose: 480 mg route of administration: Oral experiment type: MULTIPLE co-administered: PACLITAXEL	PACLITAXEL	NAPABUCASIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00G44A	https://www.1pchem.com/search?query=1P00G44A
A2B Chem	AH51034	http://a2bchem.com/prod/AH51034
AChemBlock	M15407	http://www.achemblock.com/catalogsearch/result/?q=M15407
Ambeed	A113651	http://www.ambeed.com/search/Search.html?keyword=A113651
ApexBio Technology	B6029	https://www.apexbt.com/catalogsearch/result/?q=B6029
AstaTech	F17379	http://astatechinc.com/CPSResult.php?CRNO=F17379
Axon MedChem	2517	https://www.axonmedchem.com/product/2517
BLD Pharm	BD630883	http://www.bldpharm.com/search/Search.html?keyword=BD630883
Chem Scene	CS-1747	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1747
ChemShuttle	139057	https://www.chemshuttle.com/catalogsearch/result/?q=139057
eMolecules	49837379	https://orderbb.emolecules.com/search/#?query=49837379
Enamine	EN300-207428	https://www.enaminestore.com/catalog/EN300-207428
eNovation Chemicals	D546562	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D546562&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A1314	http://www.excenen.com/searchresultlist.php?id=EX-A1314
Hairui	NASA014	http://www.hairuichem.com/en/product/search.do?q=NASA014
KeyOrganics	AS-60519	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-60519
Lab Network	LN01341768	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01341768
mcule	MCULE-7188189426	https://mcule.com/MCULE-7188189426/
MedChem Express	HY-13919	https://www.medchemexpress.com/search.html?q=HY-13919&ft=&fa=&fp=
Molnova	M16087	https://www.molnova.com/en/serch-list.html?keywords=M16087
MolPort	MolPort-039-101-321	https://www.molport.com/shop/molecule-link/MolPort-039-101-321
MuseChem	I005003	https://www.musechem.com/product/I005003.html
Selleck Chemicals	S7977	http://www.selleckchem.com/search.html?searchDTO.searchParam=S7977
ShangHai Biochempartner	BCP07628	http://www.biochempartner.com/search_BCP07628
TargetMol	T3218	https://www.targetmol.com/search?keyword=T3218
Tocris	5522	https://www.tocris.com/search.php?Type=QuickSearch&Value=5522

PubMed

Title	Date	PubMed
Antiprotozoal activities of some constituents of Markhamia tomentosa (Bignoniaceae).	2010-07	20819307

Patents

Sample Use Guides

In Vivo Use Guide

Napabucasin will be administered in continuous 28-day cycles. The starting dose of napabucasin is 240 mg twice daily (480 mg total daily dose) with approximately 12 hours between each dose. Napabucasin should be taken with fluids either 1 hour prior to a meal or 2 hours after a meal.

Route of Administration: Oral

In Vitro Use Guide

Colo205, Dld1, Hct116, RKO, SW480, AGS, MKN-28, MKN-45, 786-0, ACHN, Huh7, Panc1, Du145, HeLa, PC3, and A431 cells were plated under cancer stem cell culture conditions on coated 96-well plates. After 72 h of culture, wells were dosed with the indicated compounds (Napabucasin). Seventy-two hours or 24 h after dosing, CellTiter-Glo 2.0 was added to each well, and the luminescence was measured as described by the manufacturer (Promega)

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:37:39 GMT 2025` Edited by `admin` on `Mon Mar 31 20:37:39 GMT 2025`
Record UNII	Z1HHM49K7O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NAPABUCASIN

Official Name

English

napabucasin [INN]

Preferred Name

English

2-Acetylnaphtho[2,3-b]furan-4,9-dione

Systematic Name

English

2-ACETYLFURO-1,4-NAPHTHOQUINONE

Common Name

English

NAPABUCASIN [USAN]

Common Name

English

BBI-608

Code

English

NAPABUCASIN [JAN]

Common Name

English

BBI608

Code

English

NAPHTHO(2,3-B)FURAN-4,9-DIONE, 2-ACETYL-

Systematic Name

English

Napabucasin [WHO-DD]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

542316