DANIQUIDONE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H11N3O
Molecular Weight	249.2673
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=CC=C2N=C3N(CC2=C1)C(=O)C4=CC=CC=C34

InChI

InChIKey=SRIOCKJKFXAKHK-UHFFFAOYSA-N

InChI=1S/C15H11N3O/c16-10-5-6-13-9(7-10)8-18-14(17-13)11-3-1-2-4-12(11)15(18)19/h1-7H,8,16H2

HIDE SMILES / InChI

Molecular Formula	C15H11N3O
Molecular Weight	249.2673
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/23912694 | https://www.ncbi.nlm.nih.gov/pubmed/25274659 | https://www.ncbi.nlm.nih.gov/pubmed/17942930

Daniquidone, also known as Batracylin, is a water-insoluble heterocyclic amide with potential antineoplastic activity. Daniquidone inhibits topoisomerases I and II, thereby inhibiting DNA replication and repair, and RNA and protein synthesis. Batracylin advanced as an anticancer agent to Phase I clinical trials where dose limiting hemorrhagic cystitis (bladder inflammation and bleeding) was observed.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17942930 \| https://www.ncbi.nlm.nih.gov/pubmed/22830346 \| https://www.ncbi.nlm.nih.gov/pubmed/23912694	Inhibitor 8504
DNA topoisomerase I 60 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17942930 \| https://www.ncbi.nlm.nih.gov/pubmed/23912694	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Lymphomas 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23912694 https://www.ncbi.nlm.nih.gov/pubmed/25274659	Primary		Phase I 438	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23912694 https://www.ncbi.nlm.nih.gov/pubmed/25274659	Primary		Phase I 438	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193 inhibitor 2438	substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2A6 626 CYP1B1 104 CYP1A2 1197 CYP1A1 389 CYP2E1 729 CYP2C19 1119 NAT2 2 NAT1 2 CYP2C8 810 CYP2B6 776 P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=170466457	yes [IC50 0.9522 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466457	yes [IC50 1.6933 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=170466457	yes [IC50 4.2534 uM]

Drug as victim

Target	Modality	Activity	Metabolite
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major	N-acetylbatracylin 1
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major	N-acetylbatracylin 1
CYP1B1 104	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major
CYP1B1 104	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major	N-acetylbatracylin 1
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major	N-acetylbatracylin 1
NAT1 2	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10460792/	minor
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetykbatracylin 1
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8996611/	no
NAT2 2	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23912694/	yes

Sourcing

Vendor/Aggregator	ID	URL
BOC Sciences	67199-66-0	http://www.bocsci.com/description.asp?cas=67199-66-0
eMolecules	49802803	https://orderbb.emolecules.com/search/#?query=49802803
eNovation Chemicals	K08102	https://www.enovationchem.com/Products.asp?SEARCHTEXT=K08102&searchbtn.x=0&searchbtn.y=0
HongKong Chemhere	SCA46667
mcule	MCULE-4551032130	https://mcule.com/MCULE-4551032130/
MuseChem	I006259	https://www.musechem.com/product/I006259.html
NCI Plated 2007	320846
SynQuest	103452	http://www.synquestlabs.com/search-result.html?q=103452
SynQuest	4H48-1-8S	http://www.synquestlabs.com/search-result.html?q=4H48-1-8S

PubMed

Title	Date	PubMed
Pharmacogenetically driven patient selection for a first-in-human phase I trial of batracylin in patients with advanced solid tumors and lymphomas.	2013-10	23912694
Structural simplification of bioactive natural products with multicomponent synthesis. 3. Fused uracil-containing heterocycles as novel topoisomerase-targeting agents.	2011-04-14	21388138

Patents

Sample Use Guides

In Vivo Use Guide

Advanced refractory solid tumors or lymphomas: the starting dose was 5 mg/day for 7 days in 28-day cycles. Dose escalation followed accelerated titration design 4B, with restaging performed every 2 cycles. Dose escalation was stopped at 400 mg/day due to grade 1 and 2 hemorrhagic cystitis.

Route of Administration: Oral

In Vitro Use Guide

Using a colony formation assay, the IC50 of batracylin was established to be 10 umol/L after a 6-h pulse exposure in the human colon carcinoma cell line, HT29. Treatment with 100 umol/L of batracylin for 3 h produced DNA single-strand breaks under deproteinizing conditions.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:32:49 GMT 2025` Edited by `admin` on `Mon Mar 31 18:32:49 GMT 2025`
Record UNII	E780TX33D2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BAY-H-2049

Preferred Name

English

DANIQUIDONE

Official Name

English

NSC-320846

Code

English

daniquidone [INN]

Common Name

English

BATRACYLIN

Common Name

English

8-AMINOISOINDOLO(1,2-B)QUINAZOLIN-12(10H)-ONE

Systematic Name

English

BAY H 2049

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1968