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FADROZOLE HYDROCHLORIDE

Product Name
FADROZOLE HYDROCHLORIDE
CAS No.
102676-31-3
Chemical Name
FADROZOLE HYDROCHLORIDE
Synonyms
CS-356;D02451;Fadrazole;CGS-16949A;Fadrozole HCl;FADROZOLE HYDROCHLORIDE;Fadrozole HCl (CGS-16949A);Fadrozole hydrochloride (usan);FADROZOLE (HYDROCHLORIDE);CGS 16949A;4-(5,6,7,8-TETRAHYDROIMIDAZO[1,5-A]PYRIDIN-5-YL)BENZONITRILE(WXC09920)
CBNumber
CB41504066
Molecular Formula
C14H13N3.ClH
Formula Weight
259.739
MOL File
102676-31-3.mol
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FADROZOLE HYDROCHLORIDE Property

Melting point:
231-233℃
storage temp. 
room temp
solubility 
DMSO: >20mg/mL
form 
powder
color 
Pale Beige to Pale Yellow
Stability:
Hygroscopic
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Safety

Hazard Codes 
Xn
Risk Statements 
63-22
Safety Statements 
36/37
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
2
RTECS 
DI4952500
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
F3806
Product name
Fadrozole hydrochloride
Purity
≥98% (HPLC)
Packaging
10mg
Price
$131
Updated
2024/03/01
Sigma-Aldrich
Product number
F3806
Product name
Fadrozole hydrochloride
Purity
≥98% (HPLC)
Packaging
50mg
Price
$522
Updated
2024/03/01
Cayman Chemical
Product number
24272
Product name
Fadrozole (hydrochloride)
Purity
≥98%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
24272
Product name
Fadrozole (hydrochloride)
Purity
≥98%
Packaging
5mg
Price
$63
Updated
2024/03/01
Cayman Chemical
Product number
24272
Product name
Fadrozole (hydrochloride)
Purity
≥98%
Packaging
10mg
Price
$109
Updated
2024/03/01
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FADROZOLE HYDROCHLORIDE Chemical Properties,Usage,Production

Description

Fadrozole hydrochloride is a non-steroidal imidazole derivative launched for the treatment of post-menopausal breast cancer. Fadrozole is a potent and specific aromatase inhibitor with neither androgenic nor estrogenic activities due to its structural novelty. Fadrozole exerts its action by coordinating with the iron of the porphyrin nucleus, presumably through the imidazole moiety. This strong binding competes with the binding of molecular oxygen to iron and reversibly inactivates the enzyme. An excellent clinical response rate has been reported for fadrozole with no significant side effects.

Originator

Ciba-Geigy (Switzerland)

Uses

Fadrozole hydrochloride is a very potent and selective inhibitory effect of the aromatase enzyme system.

Uses

Antineoplastic.

Definition

ChEBI: Fadrozole hydrochloride is an imidazopyridine.

Manufacturing Process

5-p-Cyanophenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine hydrochloride:
A solution of 2.0 g of 4-(4-chloro-4-p-cyanophenyl-n-butyl)-1H-imidazole in 50 ml of chloroform is refluxed for 4 hours under nitrogen, cooled and evaporated to yield the 5-p-cyanophenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine hydrochloride; melting point 231-233°C (from 2-propanol).
Preparation of the starting materials:
A solution of 1.82 g of 4-(3-ethoxycarbonylpropyl)-1H-imidazole in 30 ml of tetrahydrofuran under nitrogen is treated with 0.5 g of sodium hydride (50% oil dispersion) at 0°C for 30 min and 1.45 ml of trimethylsilyl chloride at 0°C for 3 hours. The reaction mixture is washed with cold 0.5 N sodium bicarbonate solution, dried over sodium sulfate and evaporated to dryness. The oil is redissolved in 100 ml of methylene chloride at -78°C under nitrogen and 12.82 ml of diisobutylaluminum hydride (1.56 M) is added dropwise. The reaction mixture is stirred for 5 min at -78°C, quenched with 1 ml of methanol followed by 10 ml of water and filtered through Celite?. The organic phase is separated, dried over sodium sulfate and evaporated to yield the title compound (a).
(b) 4-(4-p-t-Butylaminocarbonylphenyl-4-hydroxy-n-butyl)-1-trimethylsilylim idazole:6.95 g of p-tert-butylaminocarbonylbromobenzene is dissolved in 175 ml of tetrahydrofuran at -70°C under nitrogen and 20.1 ml of a solution of n-butyl lithium (2.7 m) in hexane is added dropwise. After reacting 30 min, a solution of 5.69 g of 4-(3-formyl-n-propyl)-1-trimethylsilyl imidazole in 10 ml of tetrahydrofuran is added slowly. The reaction mixture is allowed to warm slowly to room temperature and 20 ml of ammonium chloride is added. The organic layer is separated, dried over sodium sulfate and evaporated to yield the title compound (b).
(c) 4-(4-Chloro-4-p-cyanophenyl-n-butyl)-1H-imidazole:
A solution of 4.5 g of 4-(4-p-t-butylaminocarbonylphenyl-4-hydroxy-n-butyl)- 1-trimethylsilylimidazole in 50 ml of thionyl chloride is refluxed for 1 hour, cooled and evaporated. The residue is partitioned between methylene chloride and aqueous sodium bicarbonate solution. The organic phase is separated, dried over sodium sulfate and evaporated to yield the title compound (c).
5-p-Cyanophenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine:
A solution of 2.0 g of 4-(4-chloro-4-p-cyanophenyl-n-butyl)-1H-imidazole in 50 ml of chloroform is refluxed for 4 hours under nitrogen, cooled and evaporated to yield the 5-p-cyanophenyl-5,6,7,8-tetrahydroimidazo[1,5- a]pyridine.

brand name

Afema

Therapeutic Function

Antineoplastic

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.

FADROZOLE HYDROCHLORIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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FADROZOLE HYDROCHLORIDE Suppliers

LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
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Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
9387
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ShangHai Caerulum Pharma Discovery Co., Ltd.
Tel
18149758185 18149758185
Email
sales-cpd@caerulumpharma.com
Country
China
ProdList
3466
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Nantong MYBio-pharm. Co., Ltd.
Tel
0513-66921823 18662920231
Fax
86-513-85012876
Email
sales@minyanmedical.com
Country
China
ProdList
3405
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58
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51456
Advantage
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Shenzhen Regent Biochemical Technology Co., Ltd.
Tel
0755-0755-85201366 18938635012
Fax
0755-85201366
Email
sales@regentsciences.com
Country
China
ProdList
9357
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Capot Chemical Co.,Ltd.
Tel
+86-(0)57185586718 +86-13336195806
Fax
+86-571-85864795
Email
sales@capot.com
Country
China
ProdList
29791
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Aikon International Limited
Tel
025-58859352 18068836627
Fax
02557626880
Email
sales01@aikonchem.com
Country
China
ProdList
15084
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Twochem Co.Ltd.
Tel
021-58111628 15800915896
Fax
QQ 3285589261
Email
sales@twochem.com
Country
China
ProdList
1788
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58
Shanghai Jizhi Biochemical Technology Co. Ltd.
Tel
4009004166/18616739031 18616739031
Email
3007523370@qq.com
Country
China
ProdList
52693
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58

102676-31-3, FADROZOLE HYDROCHLORIDERelated Search:


  • FADROZOLE HYDROCHLORIDE
  • CGS-16949A
  • Fadrazole
  • D02451
  • Fadrozole hydrochloride (usan)
  • 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(WXC09920)
  • Fadrozole HCl
  • +-5-(p-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine hydrochloride
  • CS-356
  • FADROZOLE (HYDROCHLORIDE);CGS 16949A
  • Benzonitrile, 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)-, hydrochloride (1:1)
  • Fadrozole HCl (CGS-16949A)
  • P-450,(Rac)-FAD286,Aromatase,spontaneous tumour,Fadrozole hydrochloride,Fadrozole,Inhibitor,Estrogen,progesterone,inhibit
  • 102676-31-3
  • C14H13N3ClH