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F3806

Sigma-Aldrich

Fadrozole hydrochloride

≥98% (HPLC)

Synonym(s):

4-(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-5-yl)-benzonitrile, Afema, CGS 16949A

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About This Item

Empirical Formula (Hill Notation):
C14H13N3·HCl
CAS Number:
102676-31-3
Molecular Weight:
259.73
MDL number:
MFCD00866239
UNSPSC Code:
51111800
PubChem Substance ID:
329799706
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: >20 mg/mL

originator

Novartis

storage temp.

room temp

SMILES string

Cl.N#Cc1ccc(cc1)C2CCCc3cncn23

InChI

1S/C14H13N3.ClH/c15-8-11-4-6-12(7-5-11)14-3-1-2-13-9-16-10-17(13)14;/h4-7,9-10,14H,1-3H2;1H

InChI key

UKCVAQGKEOJTSR-UHFFFAOYSA-N

Biochem/physiol Actions

Fadrozole is a nonsteroidal aromatase inhibitor. Fadrozole is a very potent and highly selective inhibitor of the aromatase enzyme system in vitro and estrogen biosynthesis in vivo. It inhibited the conversion of [4-14C]androstenedione to [4-14C]estrone by human placental microsomes in a competitive manner (Ki = 1.6 nM). At a substrate concentration 3-fold the Km, Fadrozole was 180 times more potent, as an inhibitor, than aminoglutethimide (Cat. No. A9657), exhibiting half-maximal inhibition at 1.7 nM as compared to 0.3 μM. In vivo, Fadrozole lowered ovarian estrogen synthesis by gonadotropin-primed, androstenedione treated, immature rats by 90% at a dose of 260 μg/kg (PO). In vivo, Fadrozole leads to sequelae of estrogen deprivation (e.g. regression of DMBA-induced mammary tumors) without causing adrenal hypertrophy in adult rats. It blocked aromatase by 50% in human breast cancer homogenates, live breast cancer cells, human placental microsomes, and porcine ovarian microsomes at concentrations of 0.008 to 0.02 μM.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H361

Hazard Classifications

Acute Tox. 3 Oral - Repr. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kazuyoshi Motomura et al.
Oncology, 79(1-2), 55-61 (2010-11-13)
Aromatase inhibitor (AI) is widely used as an endocrine treatment in postmenopausal patients with hormone receptor-positive breast cancer. To identify useful prognostic factors for patients with metastatic breast cancer treated with AI therapy, we investigated the association between several hormone
Dean F Rigel et al.
The Journal of pharmacology and experimental therapeutics, 334(1), 232-243 (2010-04-01)
Aldosterone synthase (CYP11B2) inhibitors (ASIs) represent an attractive therapeutic approach for mitigating the untoward effects of aldosterone. We characterized the pharmacokinetic/pharmacodynamic relationships of a prototypical ASI, (+)-(5R)-4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl]benzonitrile hydrochloride (CGS020286A, FAD286, FAD) and compared these profiles to those of the 11beta-hydroxylase
Bing S Huang et al.
American journal of physiology. Heart and circulatory physiology, 299(2), H422-H430 (2010-06-01)
An increase in plasma ANG II causes neuronal activation in hypothalamic nuclei and a slow pressor response, presumably by increasing sympathetic drive. We evaluated whether the activation of a neuromodulatory pathway, involving aldosterone and "ouabain," is involved in these responses.
K J Ralston-Hooper et al.
Environmental science & technology, 47(2), 1091-1100 (2012-11-28)
Although two-dimensional electrophoresis (2D-GE) remains the basis for many ecotoxicoproteomic analyses, newer non-gel-based methods are beginning to be applied to overcome throughput and coverage limitations of 2D-GE. The overall objective of our research was to apply a comprehensive, liquid chromatography-tandem
M Gust et al.
Chemosphere, 79(1), 47-53 (2010-02-16)
The freshwater prosobranch Potamopyrgus antipodarum (Molluska, Hydrobiidea, Smith 1889) has been proposed as a suitable species to assess the impact of endocrine disrupting compounds (EDC) in aquatic ecosystems. Steroid hormone biosynthesis pathway is potentially an important target for EDC, and
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