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

• ChemBase编号: 71213
• 分子式: C14H14ClN3
• 平均质量: 259.73406
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-{5H,6H,7H,8H-imidazo[1,5-a]pyridin-5-yl}benzonitrile hydrochloride
• IUPAC传统名: fadrozole hydrochloride
• 别名: 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

登记号

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

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.8475752
• LogD (pH = 7.4): 2.2736917
• Log P: 2.4119077
• 摩尔折射率: 66.457 cm^3
• 极化性: 25.045046 Å^3
• 极化表面积: 41.61 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >20 mg/mL
• 外观: powder

安全信息

• 保存注意事项: IRRITANT
• RTECS编号: DI4952500
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 2
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 63-22
• 安全公开号: 36/37
• TSCA收录: false
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H361
• GHS警示性声明: P281-P301 + P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: room temp

产品相关信息

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

详细说明

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.