4-{5H,6H,7H,8H-imidazo[1,5-a]pyridin-5-yl}benzonitrile hydrochloride

• ChemBase ID: 71213
• Molecular Formular: C14H14ClN3
• Molecular Mass: 259.73406
• Monoisotopic Mass: 259.08762514
• SMILES: C(#N)c1ccc(cc1)C1CCCc2n1cnc2.Cl
• Canonical SMILES: N#Cc1ccc(cc1)C1CCCc2n1cnc2.Cl
• InChI: 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
• InChIKey: UKCVAQGKEOJTSR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{5H,6H,7H,8H-imidazo[1,5-a]pyridin-5-yl}benzonitrile hydrochloride
• IUPAC Traditional name: fadrozole hydrochloride
• Synonyms: 4-(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile hydrochloride; 4-(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-5-yl)-benzonitrile; Afema; CGS 16949A; Fadrozole hydrochloride

Database IDs

• CAS Number: 102676-31-3
• MDL Number: MFCD00866239
• PubChem SID: 162103591
• PubChem CID: 59694

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.8475752
• LogD (pH = 7.4): 2.2736917
• Log P: 2.4119077
• Molar Refractivity: 66.457 cm^3
• Polarizability: 25.045046 Å^3
• Polar Surface Area: 41.61 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: powder

Safety Information

• Storage Warning: IRRITANT
• RTECS: DI4952500
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 63-22
• Safety Statements: 36/37
• TSCA Listed: false
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H361
• GHS Precautionary statements: P281-P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H13N3·HCl

DETAILS

Sigma Aldrich - F3806

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.