PINAFIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H17N3O4
Molecular Weight	339.3453
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+](=O)C1=CC2=C3C(=CC=C2)C(=O)N(CCN4CCCC4)C(=O)C3=C1

InChI

InChIKey=GBOQUHPYCRYKGV-UHFFFAOYSA-N

InChI=1S/C18H17N3O4/c22-17-14-5-3-4-12-10-13(21(24)25)11-15(16(12)14)18(23)20(17)9-8-19-6-1-2-7-19/h3-5,10-11H,1-2,6-9H2

HIDE SMILES / InChI

Molecular Formula	C18H17N3O4
Molecular Weight	339.3453
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/22619121 | https://www.ncbi.nlm.nih.gov/pubmed/3582420 | https://www.ncbi.nlm.nih.gov/pubmed/28106753 | Elks, J. (2014) The Dictionary of Drugs: Chemical Data, page 983, retrieved from: https://books.google.ru/books?id=0vXTBwAAQBAJ

Pinafide is a rodenticide and anti-protozoal agent. Pinafide shows strong cytostatic activity against both HeLa and KB cells and is moderately toxic to both mice and rats. It has been proved active against experimental tumors and shown to be inhibitor of two DNA viruses. Pinafide blocks cell growth by inhibiting DNA and RNA synthesis. It has been shown to bind to double-helical DNA by intercalation. Pinafide inhibited the activity of M. tuberculosis NAD⁺-dependent DNA ligase A at concentrations of 50 uM. At the chemical screening was found that pinafide inhibited B-Myb transcriptional activity in luciferase assays. The cross placental-barrier studies showed that 3H-pinafide was present in the 14-day fetuses.

Approval Year

PubMed

Title	Date	PubMed
The pharmacokinetics, tissue distribution, and biotransformation of a new class of antitumor agents: mitonafide and pinafide.	1986 Oct-Dec	3582420
Fluorescence of chromatin DNA induced by antitumoral naphthalimides.	1997 May-Jun	9232898
A chemical screen identifies the chemotherapeutic drug topotecan as a specific inhibitor of the B-MYB/MYCN axis in neuroblastoma.	2012 May	22619121
Naphthalimides Selectively Inhibit the Activity of Bacterial, Replicative DNA Ligases and Display Bactericidal Effects against Tubercle Bacilli.	2017 Jan 17	28106753

Patents

Sample Use Guides

In Vivo Use Guide

Single dose - 20 mg/kg

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:36:16 GMT 2023` Edited by `admin` on `Fri Dec 15 15:36:16 GMT 2023`
Record UNII	1OZ94FI615
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PINAFIDE

Official Name

English

pinafide [INN]

Common Name

English

3-NITRO-N-(2-(1-PYRROLIDINYL)-ETHYL)NAPHTHALIMIDE

Common Name

English

NSC-300289

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C582