FINROZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H15FN4O
Molecular Weight	322.3363
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H](CC1=CC=C(F)C=C1)[C@H](N2C=NC=N2)C3=CC=C(C=C3)C#N

InChI

InChIKey=SLJZVZKQYSKYNV-ZWKOTPCHSA-N

InChI=1S/C18H15FN4O/c19-16-7-3-13(4-8-16)9-17(24)18(23-12-21-11-22-23)15-5-1-14(10-20)2-6-15/h1-8,11-12,17-18,24H,9H2/t17-,18+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H15FN4O
Molecular Weight	322.3363
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9491826 | http://adisinsight.springer.com/drugs/800010074 | Bégué, J.-P. and Bonnet-Delpon, D. (2008) 'Bioorganic and Medicinal Chemistry of Fluorine', p.330 Retrieved from https://books.google.ru/books?id=QMVSvZ-R7I0C

Finrozole is a nonsteroidal competitive aromatase inhibitor that is being evaluated in Phase II trials for the treatment of lower urinary tract symptoms associated with reduced androgen/estrogen ratio in aging males associated with benign prostatic hyperplasia. But this research was discontinued in 2005. In dimethylbenzanthracene-induced rat mammary carcinoma model, Finrozole causes regression of more than 80% of the established tumors. The hormone-dependent mammary tumors are inhibited to a level seen in ovariectomised animals.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 19A1 39 Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9491826	Inhibitor 8297		0.18 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9491826	Primary		Preclinical	Unknown Approved Use Unknown
Benign prostatic hyperplasia 28 Sources: Bégué, J.-P. and Bonnet-Delpon, D. (2008) 'Bioorganic and Medicinal Chemistry of Fluorine', p.330 Retrieved from https://books.google.ru/books?id=QMVSvZ-R7I0C	Palliative		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
18.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11736883	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	FINROZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.88 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11736883	9 mg single, oral dose: 9 mg route of administration: Oral experiment type: SINGLE co-administered:	FINROZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.11 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11736883	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:	FINROZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
118.23 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11736883	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	FINROZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
57.68 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11736883	9 mg single, oral dose: 9 mg route of administration: Oral experiment type: SINGLE co-administered:	FINROZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
13.25 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11736883	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:	FINROZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
7.71 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11736883	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	FINROZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.85 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11736883	9 mg single, oral dose: 9 mg route of administration: Oral experiment type: SINGLE co-administered:	FINROZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.36 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11736883	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:	FINROZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
BOC Sciences	204714-56-7	http://www.bocsci.com/description.asp?cas=204714-56-7
MuseChem	M041064	https://www.musechem.com/product/M041064.html

PubMed

Title	Date	PubMed
In vitro effects of diethylstilbestrol, genistein, 4-tert-butylphenol, and 4-tert-octylphenol on steroidogenic activity of isolated immature rat ovarian follicles.	2005 Apr 1	15781295
Aflatoxin B1--a potential endocrine disruptor--up-regulates CYP19A1 in JEG-3 cells.	2011 May 10	21296134
The effects of aflatoxin B1 on transporters and steroid metabolizing enzymes in JEG-3 cells.	2013 Apr 26	23402939

Patents

Sample Use Guides

In Vivo Use Guide

100 mg single dose

Route of Administration: Oral

In Vitro Use Guide

Finrozole (1 uM) also inhibited the AFB1 related mRNA induction of CYP1A1, HSD3B1, HSD17B1 and the UGT1A-family in JEG-3 cells at the 96 h time point.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:35:47 UTC 2023` Edited by `admin` on `Fri Dec 15 17:35:47 UTC 2023`
Record UNII	40028KHQ6B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FINROZOLE

Official Name

English

BENZONITRILE, 4-((1R,2S)-3-(4-FLUOROPHENYL)-2-HYDROXY-1-(1H-1,2,4-TRIAZOL-1-YL)PROPYL)-, REL-

Common Name

English

P-((1RS,2SR)-3-(P-FLUOROPHENYL)-2-HYDROXY-1-(1H-1,2,4-TRIAZOL-1-YL)PROPYL)BENZONITRILE

Common Name

English

finrozole [INN]

Common Name

English

MPV-2213AD

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1740