Fadrozole

Fadrozole
Systematic (IUPAC) name

4-(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile
Clinical data
Routes of administration	Oral
Legal status	℞ (Prescription only)
Identifiers
CAS Number	102676-31-3^Y
ATC code	none
PubChem	CID 59693
ChemSpider	53850^N
UNII	H3988M64PU^N
KEGG	D02451^Y
ChEMBL	CHEMBL9298^N
Chemical data
Formula	C₁₄H₁₃N₃
Molar mass	223.27 g/mol
SMILES C1CC(N2C=NC=C2C1)C3=CC=C(C=C3)C#N
InChI InChI=1S/C14H13N3/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^N Key:CLPFFLWZZBQMAO-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

Fadrozole (INN, marketed as Afema by Novartis) is a selective^[1] aromatase inhibitor^[2] that has been introduced in Japan for the treatment of breast cancer.

References

↑ Browne LJ, Gude C, Rodriguez H, Steele RE, Bhatnager A (February 1991). "Fadrozole hydrochloride: a potent, selective, nonsteroidal inhibitor of aromatase for the treatment of estrogen-dependent disease". J. Med. Chem. 34 (2): 725–36. doi:10.1021/jm00106a038. PMID 1825337.
↑ Raats JI, Falkson G, Falkson HC (January 1992). "A study of fadrozole, a new aromatase inhibitor, in postmenopausal women with advanced metastatic breast cancer". J. Clin. Oncol. 10 (1): 111–6. PMID 1530798.

Estrogens and antiestrogens

Estrogens

Steroidal: Alfatradiol
Conjugated estrogens (Premarin)
Epimestrol
Esterified estrogens
Estetrol
Estradiol
- Cloxestradiol acetate
- Estradiol acetate
- Estradiol benzoate
- Estradiol butyrylacetate
- Estradiol cypionate^#
- Estradiol dipropionate
- Estradiol diundecylate
- Estradiol enanthate
- Estradiol furoate
- Estradiol hemihydrate
- Estradiol hemisuccinate
- Estradiol hexahydrobenzoate
- Estradiol monopropionate
- Estradiol palmitate
- Estradiol propoxyphenylpropionate
- Estradiol stearate
- Estradiol undecylate
- Estradiol valerate
- Estramustine
- Polyestradiol phosphate
- Trimethyl estradiol acetate
Estriol
- Estriol diacetate benzoate
- Estriol sodium succinate
- Estriol succinate
- Estriol triproprionate
- Quinestradol
Estrone
- Estrone acetate
- Estrone sulfate
  - Estropipate
- Estrone tetraacetylglucoside
Ethinyl estradiol^#
Etynodiol diacetate
Methylestradiol
Noretynodrel
Paroxypropione
Promestriene
Tibolone

Non-steroidal: Benzestrol
Dienestrol
Dienestrol acetate
Diethylstilbestrol
Diethylstilbestrol dipropionate
Doisynoestrol (fenocycline)
Hexestrol
Fosfestrol
Methallenestril
Methestrol dipropionate (promethestrol dipropionate)
Quadrosilan
Zeranol

Antiestrogens

SERMs / antagonists	SERMs: Anordrin Bazedoxifene Broparestrol Chlorotrianisene Clomifene citrate^# Cyclofenil Lasofoxifene Ormeloxifene Raloxifene Tamoxifen^# Toremifene Antagonists: Fulvestrant

Aromatase inhibitors	Non-selective: Aminoglutethimide Testolactone Selective: Anastrozole Exemestane Fadrozole Formestane Letrozole

Antigonadotropins	Androgens/anabolic steroids (e.g., testosterone, nandrolone, oxandrolone) GnRH agonists (e.g., leuprorelin) GnRH antagonists (e.g., cetrorelix) Progestogens (incl. allylestrenol, chlormadinone acetate, cyproterone acetate, delmadinone acetate, dydrogesterone, medroxyprogesterone acetate, megestrol acetate, nomegestrol acetate, norethisterone acetate, progesterone, spironolactone)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Androgenics

Receptor
(ligands)

Agonists	4-Chlordehydromethyltestosterone 4-Hydroxytestosterone 5α-Androst-1-ene-3,17-dione 7β-Hydroxyepiandrosterone 11-Ketotestosterone 17-((1-Oxoheptyl)oxy)androstan-3-one 17-((1-Oxopentyl)oxy)androstan-3-one 17-(1-Oxopropoxy)androstan-3-one 17β-Hydroxyandrost-2-ene-2-carbonitrile 19-Norandrostenediol 19-Norandrostenedione 19-Norandrosterone 19-Nordehydrotestosterone Δ¹-Androstenediol Δ¹-Testosterone Δ^1,4-Androstenedione Δ⁴-Androstenediol Δ⁴-Androstenedione Δ^4-Tibolone Δ⁴-Androstenediol Δ⁴-Androstenedione Adrenosterone Androisoxazole Androstanolone Bolandiol Bolasterone Bolazine Boldenone Boldione Bolenol Bolmantalate Calusterone Cl-4AS-1 Clostebol Cloxotestosterone Cortexolone 17α-propionate Danazol Desogestrel Desoxymethyltestosterone DHEA DHEA sulfate Dihydrotestosterone Drostanolone Enestebol Epitiostanol Ethisterone Ethyldienolone Ethylestrenol Fluoxymesterone Formebolone Furazabol Hexabolan Hydroxystenozole Levonorgestrel Mebolazine Medroxyprogesterone acetate Mepitiostane Mesabolone Mestanolone Mesterolone Metandienone/Methandrostenolone Metenolone Metenolone acetate Metenolone enanthate Methandriol Methandriol propionate Methasterone Methylestrenolone Methyltestosterone Metribolone Mibolerone Nandrolone Nandrolone caproate Nandrolone cypionate Nandrolone cyclohexane carboxylate Nandrolone cyclohexylpropionate Nandrolone cyclotate Nandrolone decanoate Nandrolone furylpropionate Nandrolone hexyloxyphenylpropionate Nandrolone hydrogen succinate Nandrolone laurate Nandrolone phenylpropionate Nandrolone propionate Nandrolone undecyclate Norboletone Norclostebol Norethandrolone Norethisterone Norgestrel Oxabolone Oxabolone cypionate Oxandrolone Oxendolone Oxymesterone Oxymetholone Penmesterol Propetandrol Quinbolone Quingestanol acetate Roxibolone Silandrone Stanozolol Stenbolone Stenbolone acetate Testolactone Testosterone Testosterone acetate Testosterone capropate Testosterone cypionate Testosterone decanoate Testosterone enanthate Testosterone isocaproate Testosterone ketolaurate Testosterone nicotinate Testosterone phenylpropionate Testosterone propionate Testosterone undecanoate Tetrahydrogestrinone Thiomesterone Tibolone Tiomesterone Trenboloneca Trenbolone acetate Trestolone

Mixed (SARMs)	AC-262,356 Andarine BMS-564,929 Enobosarm (ostarine) LGD-2226 LGD-3303 LGD-4033 RAD140 S-23 S-40503 TFM-4AS-1

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Abiraterone Abiraterone acetate Apalutamide AZD-3514 Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S) Benorterone Bicalutamide BMS-641,988 BOMT Canrenoic acid Canrenone Chlormadinone acetate Cimetidine Cioteronel Clometerone Cyproterone Cyproterone acetate Delanterone DDT (via metabolite p,p’-DDE) Dieldrin Dienogest Drospirenone Endosulfan Enzalutamide EPI-001 Epitestosterone Fenarimol Flutamide Galeterone Guggulsterone Hydroxyflutamide Inocoterone Ketoconazole Lavender oil Linuron Megestrol acetate Mespirenone Methiocarb Metogest Mifepristone Nilutamide Nomegestrol Nordinone Norgestimate ODM-201 ONC1-13B ORM-15341 Osaterone Oxendolone PF-998425 Potassium canrenoate Prochloraz Procymidone R-2956 Rosterolone RU-58642 RU-58841 Spironolactone Topilutamide (fluridil) Topterone Valproic acid Vinclozolin VT-464 Zanoterone

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase).

Others

Precursors/prohormones	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycortisol (cortodoxone) DHEA DHEA sulfate Δ⁵-Androstenediol Δ⁴-Androstenedione

Indirect	Antigonadotropins (e.g., estrogens, progestogens, prolactin) GnRH agonists (e,g, GnRH, leuprorelin) GnRH antagonists (e.g., cetrorelix) Gonadotropins (e.g., FSH, hCG, LH) Kisspeptin Plasma proteins (ABP, albumin, SHBG)

See also: Estrogenics • Glucocorticoids • Mineralocorticoids • Progestogenics

Estrogenics

Receptor
(ligands)

ER (α, β)

Agonists	(R)-DPN (S)-DPN (R,R)-THC (S,S)-THC 2,8-DHHHC 3α-Androstanediol 3β-Androstanediol 3α-Hydroxytibolone 3β-Hydroxytibolone 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8β-VE₂ 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-IE₂ 16α-LE₂ (Cpd1471) Δ⁴-Androstenedione Δ⁵-Androstenediol 17α-Estradiol (alfatradiol) 17β-Estradiol (estradiol) Alestramustine Almestrone Anabolic steroids (prodrugs; e.g., testosterone, metandienone (methandrostenolone), others) Anethole Anol Atrimustine Benzestrol Bifluranol Bisdehydrodoisynolic acid Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Cloxestradiol Conjugated equine estrogens (e.g., sodium equilin sulfate, sodium equilenin sulfate) Coumestans (e.g., coumestrol, psoralidin) DHEA DHEA-S Deoxymiroestrol Dianethole Dianol Diarylpropionitrile Dieldrin Dienestrol Dienestrol acetate Diethylstilbestrol Diethylstilbestrol dipropionate Diosgenin Doisynoestrol (fenocycline) Doisynolic acid DY-131 (GSK-9089) Endosulfan Epiestriol Epimestrol ERB-196 (WAY-202196) Esterified estrogens (e.g., estrone sulfate, equilin sulfate, equilenin sulfate) Estetrol Estradiol benzoate Estradiol butyrylacetate Estradiol cypionate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol hemihydrate Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol palmitate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol stearate Estradiol succinate Estradiol undecylate Estradiol valerate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol succinate Estriol tripropionate Estrobin (DBE) Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone sulfate Estrone tetraacetylglucoside Estropipate Estropronicate Etamestrol (eptamestrol) Ethinyl estradiol Ethinyl estradiol 3-isopropylsulfonate Etynodiol diacetate Fenarimol Fenestrel FERb 033 Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Fosfestrol Furostilbestrol GSK-4716 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate Hydroxyestrone diacetate Lavender oil Lignans (e.g., enterodiol, enterolactone) Mestranol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Methiocarb Methylestradiol Miroestrol Moxestrol Nilestriol Noretynodrel Orestrate Paroxypropione Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Promestriene Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranal (zearalanol)) Quadrosilan Quinestradol Quinestrol SKF-82,958 Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) WAY-166818 WAY-200070

Mixed (SERMs)	2-Hydroxyestrone 27-Hydroxycholesterol Acolbifene Afimoxifene Anordrin Anordriol Arzoxifene Bazedoxifene Broparestrol Chlorotrianisene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW5638 Idoxifene Lasofoxifene Levormeloxifene Menerba Mepitiostane Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Phenytoin Pipendoxifene Raloxifene SS1010 Sivifene Tamoxifen TAS-108 Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene

Antagonists	(R,R)-THC Fulvestrant ICI-164384 Methylpiperidinopyrazole MIBE PHTPP Prochloraz RU-58668 SS1020 XCT-790 ZK-164015 ZK-191703

GPER

Agonists	7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Equol Estradiol Fulvestrant (ICI-182,780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Nicotinamide Nonylphenol Oleuropein PCB (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol Tamoxifen Tectoridin Zearalenone

Antagonists	Estriol G-15 G-36 MIBE

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, aromatase, and 27-hydroxylase).

Others

Precursors	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycortisol (cortodoxone) DHEA DHEA sulfate 16-Hydroxy-DHEA sulfate Δ⁵-Androstenediol Δ⁴-Androstenedione 16-Hydroxyandrostenedione Testosterone

Indirect	Antigonadotropins (e.g., androgens, estrogens, progestogens, prolactin) Calcitriol (vitamin D) GnRH agonists (e,g, GnRH, leuprorelin) GnRH antagonists (e.g., cetrorelix) Gonadotropins (e.g., FSH, hCG, LH) Kisspeptin Plasma proteins (ABP, albumin, SHBG)

See also: Androgenics • Glucocorticoids • Mineralocorticoids • Progestogenics

Steroid hormone metabolism modulators

20,22-Desmolase	Inhibitors: 22-ABC 3,3′-Dimethoxybenzidine 3-Methoxybenzidine Aminoglutethimide Canrenone Cyanoketone Danazol Etomidate Ketoconazole Mitotane Spironolactone Trilostane

17α-Hydroxylase, 17,20-Lyase	Inhibitors: 22-ABC 22-Oxime Abiraterone Abiraterone acetate Bifonazole Canrenone CFG-920 Clotrimazole Cyanoketone Cyproterone acetate Danazol Econazole Galeterone Gestrinone Isoconazole Ketoconazole L-39 Liarozole LY-207,320 MDL-27,302 Miconazole Mifepristone Orteronel Pioglitazone Prochloraz Rosiglitazone Spironolactone Stanozolol SU-10,603 TGF-β Tioconazole Troglitazone VN/87-1 VT-464 YM116

3α-HSD	Inhibitors: Coumestrol Daidzein Genistein Indomethacin Medroxyprogesterone acetate Inducers: Fluoxetine Fluvoxamine Mirtazapine Paroxetine Sertraline Venlafaxine

3β-HSD	Inhibitors: 4-MA Abiraterone Abiraterone acetate Azastene Cyanoketone Cyproterone acetate Danazol Epostane Genistein Gestrinone Metyrapone Norethisterone Oxymetholone Pioglitazone Rosiglitazone Trilostane Troglitazone

11β-HSD	Inhibitors: 18α-Glycyrrhizic acid ABT-384 Acetoxolone Carbenoxolone Enoxolone (glycyrrhetinic acid) Epigallocatechin gallate Glycyrrhizin (glycyrrhizic acid)

21-Hydroxylase	Inhibitors: Aminoglutethimide Amphenone B Bifonazole Canrenone Clotrimazole Diazepam Econazole Genistein Isoconazole Ketoconazole Metyrapone Miconazole Midazolam Spironolactone Tioconazole

11β-Hydroxylase	Inhibitors: Abiraterone Abiraterone acetate Aminoglutethimide Canrenone Etomidate Fadrozole FETO Ketoconazole Metomidate Metyrapone Mitotane Potassium canrenoate Spironolactone Trilostane

18-Hydroxylase	Inhibitors: Aminoglutethimide Canrenone FAD286 Fadrozole Ketoconazole LCI699 Metyrapone Mespirenone Potassium canrenoate Spironolactone

17β-HSD	Inhibitors: Danazol Simvastatin

5α-Reductase	Inhibitors: 22-Oxime Alfatradiol Azelaic acid β-Sitosterol Bexlosteride Chlormadinone acetate Cl-4AS-1 Dutasteride Epitestosterone Epristeride Fatty acids (α-linolenic acid, linoleic acid, γ-linolenic acid, monolinolein, oleic acid) Finasteride Ganoderic acid Izonsteride L-39 Lapisteride Saw palmetto TFM-4AS-1 Turosteride Vitamin B6 Zinc

Aromatase	Inhibitors: 4-AT 4-Cyclohexylaniline 4-Hydroxytestosterone 5α-DHNET Abyssinone II Aminoglutethimide Anastrozole Ascorbic acid (vitamin C) Atamestane ATD Bifonazole CGP-45,688 CGS-47,645 Chalconoids (e.g., isoliquiritigenin) Corynesidone A Clotrimazole DHT Difeconazole Econazole Ellagitannins Endosulfan Exemestane Fadrozole Fatty acids (e.g., conjugated linoleic acid, linoleic acid, linolenic acid, palmitic acid) Fenarimol Finrozole Flavonoids (e.g., 7-hydroxyflavone, 7-hydroxyflavanone, 7,8-DHF, acacetin, apigenin, baicalein, biochanin A, chrysin, EGCG, gossypetin, hesperetin, liquiritigenin, myricetin, naringenin, pinocembrin, rotenone, quercetin, sakuranetin, tectochrysin) Formestane Imazalil Isoconazole Ketoconazole Letrozole Liarozole Melatonin MEN-11066 Miconazole Minamestane Nimorazole NKS01 Norendoxifen ORG-33,201 Penconazole Phenytoin Prochloraz PGE2 (dinoprostone) Plomestane Prochloraz Propioconazole Pyridoglutethimide Quinolinoids (e.g., berberine, casimiroin, triptoquinone A, XHN22, XHN26, XHN27) Resorcylic acid lactones (e.g., zearalenone) Rogletimide Stilbenoids (e.g., resveratrol) Talarozole Terpenoids (e.g., dehydroabietic acid, (–)-dehydrololiolide, retinol (vitamin A), Δ⁹-THC, tretinoin) Testolactone Tioconazole Triadimefon Triadimenol Troglitazone Valproic acid Vorozole Xanthones (e.g., garcinone D, garcinone E, α-mangostin, γ-mangostin, monodictyochrome A, monodictyochrome B) YM-511 Zinc Inducers: Atrazine Flavonoids (e.g., genistein, quercetin)

27-Hydroxylase	Inhibitors: Anastrozole Bicalutamide Dexmedetomidine Fadrozole Posaconazole Ravuconazole

See also: Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics

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