DANIQUIDONE

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=C3C=CC=C4

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 8297
DNA topoisomerase I 59 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17942930 \| https://www.ncbi.nlm.nih.gov/pubmed/23912694	Inhibitor 8297

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 428	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23912694 https://www.ncbi.nlm.nih.gov/pubmed/25274659	Primary		Phase I 428	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	substrate 1037 inhibitor 1767	substrate 1217 inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2A6 543 CYP1B1 92 CYP1A2 1054 CYP1A1 349 CYP2E1 667 CYP2C19 991 NAT2 2 NAT1 2 CYP2C8 693 CYP2B6 664 P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=170466457	yes [IC50 0.9522 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466457	yes [IC50 1.6933 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=170466457	yes [IC50 4.2534 uM]

Drug as victim

Target	Modality	Activity	Metabolite
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major	N-acetylbatracylin 1
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major	N-acetylbatracylin 1
CYP1B1 92	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major
CYP1B1 92	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major	N-acetylbatracylin 1
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	major	N-acetylbatracylin 1
NAT1 2	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10460792/	minor
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetykbatracylin 1
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27441096/	no	N-acetylbatracylin 1
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8996611/	no
NAT2 2	substrate 3367 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
HongKong Chemhere	SCA46667
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
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
mcule	MCULE-4551032130	https://mcule.com/MCULE-4551032130/

PubMed

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

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 `Fri Dec 15 16:37:11 GMT 2023` Edited by `admin` on `Fri Dec 15 16:37:11 GMT 2023`
Record UNII	E780TX33D2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DANIQUIDONE

Official Name

English

NSC-320846

Code

English

daniquidone [INN]

Common Name

English

BAY-H-2049

Code

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