Fadrozole

Fadrozole
Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	℞ (Prescription only)
Identifiers
IUPAC name 4-(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile
CAS Number	102676-31-3^Y
PubChem (CID)	59693
ChemSpider	53850^N
UNII	H3988M64PU^N
KEGG	D02451^Y
ChEMBL	CHEMBL9298^N
ECHA InfoCard	100.159.562
Chemical and physical data
Formula	C₁₄H₁₃N₃
Molar mass	223.27 g/mol
3D model (Jmol)	Interactive image
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

ER agonists	Steroidal: Alfatradiol Certain androgenic-anabolic steroids (e.g., testosterone, testosterone esters, nandrolone, methyltestosterone, metandienone) (via estrogenic metabolites) Certain progestins (e.g., norethisterone, noretynodrel, etynodiol diacetate, tibolone) Clomestrone Cloxestradiol acetate Conjugated equine estrogens/esterified estrogens (Premarin) 8,9-Dehydroestrone sulfate 17α-Dihydroequilenin sulfate 17α-Dihydroequilin sulfate 17β-Dihydroequilenin sulfate 17β-Dihydroequilin sulfate Equilenin sulfate Equilin sulfate Emmenin Epiestriol Epimestrol Estetrol^† Estradiol Estradiol acetate Estradiol benzoate Estradiol butyrylacetate Estradiol cypionate^# Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol glucuronide Estradiol hemihydrate Estradiol hemisuccinate (estradiol succinate) Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol palmitate Estradiol phenylpropionate Estradiol pivalate (trimethyl estradiol acetate) Estradiol propoxyphenylpropionate Estradiol stearate Estradiol sulfate Estradiol undecylate Estradiol valerate Polyestradiol phosphate Estramustine Estriol Estriol diacetate benzoate Estriol glucuronide Estriol succinate Estriol sulfate Estriol sulfate glucuronide Estriol tripropionate Estrone Estrone acetate Estrone glucuronide Estrone sulfate Estropipate (piperazine estrone sulfate) Estrone tetraacetylglucoside Ethinyl estradiol^# Ethinyl estradiol sulfonate Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Nilestriol Progynon Promestriene Quinestradol Quinestrol Non-steroidal: Benzestrol Bifluranol Chlorotrianisene Dienestrol Dienestrol diacetate Diethylstilbestrol (stilbestrol) Diethylstilbestrol diacetate Diethylstilbestrol dilaurate Diethylstilbestrol dipalmitate (stilpalmitate) Diethylstilbestrol dipropionate Diethylstilbestrol disulfate Diethylstilbestrol monobenzyl ether Dimestrol (diethylstilbestrol dimethyl ether) Fosfestrol (diethylstilbestrol diphosphate) Mestilbol (diethylstilbestrol monomethyl ether) Doisynoestrol (fenocycline) Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate Methallenestril Methestrol dipropionate (promethestrol dipropionate) Paroxypropione Quadrosilan Zeranol

Progonadotropins	Antiandrogens (e.g., bicalutamide) GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin) Gonadotropins (e.g., FSH, LH)

Antiestrogens

ER antagonists (incl. SERMs/SERDs)	Acolbifene^† Anordrin Bazedoxifene (+conjugated equine estrogens) Broparestrol Clomifene^# Cyclofenil Enclomifene^† Epitiostanol Etacstil ^§ Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen^# Toremifene Exclusively antagonistic: Fulvestrant

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

Antigonadotropins	Androgens/anabolic steroids (e.g., testosterone, testosterone esters, nandrolone, oxandrolone, fluoxymesterone) D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride) GnRH agonists (e.g., leuprorelin, goserelin) GnRH antagonists (e.g., cetrorelix) Progestogens (e.g., chlormadinone acetate, cyproterone acetate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone acetate, megestrol acetate)

Others	Mixed mechanism of action: Danazol Gestrinone

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

See also: Androgens and antiandrogens • Progestogens and antiprogestogens • Glucocorticoids and antiglucocorticoids • Mineralocorticoids and antimineralocorticoids • Gonadotropins and GnRH

Androgen receptor modulators

Agonists	Testosterone derivatives: 4-Androstenediol 4-Androstenedione 4-Dehydroepiandrosterone (4-DHEA) 4-Hydroxytestosterone 5-Androstenediol 5-Androstenedione 11-Ketotestosterone 11β-Hydroxyandrostenedione Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione) Atamestane Boldenone Boldenone undecylenate Boldione (1,4-androstadienedione) Clostebol Clostebol acetate Clostebol caproate Clostebol propionate Cloxotestosterone Cloxotestosterone acetate DHEA (androstenolone, prasterone; 5-DHEA) DHEA enanthate (prasterone enanthate) DHEA sulfate Exemestane Formestane Plomestane Quinbolone Silandrone Testosterone^# Testosterone acetate Testosterone acetate butyrate Testosterone acetate propionate Testosterone benzoate Testosterone butyrate Testosterone buciclate Testosterone capropate Testosterone cyclohexylpropionate Testosterone cypionate Testosterone decanoate Testosterone diacetate Testosterone dipropionate Testosterone enanthate Testosterone formate Testosterone furoate Testosterone hexahydrobenzoate Testosterone hexahydrobenzylcarbonate Testosterone hexyloxyphenylpropionate Testosterone isobutyrate Testosterone isocaproate Testosterone isovalerate Testosterone ketolaurate Testosterone nicotinate Testosterone palmitate Testosterone phenylacetate Testosterone phenylbutyrate Testosterone phenylpropionate Testosterone phosphate Testosterone propionate Testosterone stearate Testosterone sulfate Testosterone undecanoate Testosterone valerate Dihydrotestosterone derivatives: 1-Androstenediol 1-Androstenedione 1-Androsterone (1-andro, 1-DHEA) 1-Testosterone 3α-Androstanediol 5α-Androst-2-en-17-one 7β-Hydroxyepiandrosterone 11-Ketodihydrotestosterone Androsterone Bolazine Bolazine capronate Dihydrotestosterone (androstanolone, stanolone) Dihydrotestosterone acetate Dihydrotestosterone benzoate Dihydrotestosterone butyrate Dihydrotestosterone enanthate Dihydrotestosterone formate Dihydrotestosterone propionate Dihydrotestosterone valerate Drostanolone Drostanolone propionate Epiandrosterone Epitiostanol Mepitiostane Mesabolone Mesterolone Nisterime Nisterime acetate Prostanozol Stenbolone Stenbolone acetate 19-Nortestosterone derivatives: 7α-Methyl-19-norandrostenedione (MENT dione, trestione) 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione Bolandiol Bolandiol dipropionate Bolandione (19-nor-4-androstenedione) Bolmantalate (nandrolone adamantoate) Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate LS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate) Methoxydienone (methoxygonadiene) Nandrolone Nandrolone acetate Nandrolone caproate Nandrolone cypionate Nandrolone cyclohexanecarboxylate Nandrolone cyclohexylpropionate Nandrolone cyclotate Nandrolone decanoate Nandrolone formate Nandrolone furylpropionate Nandrolone hexyloxyphenylpropionate Nandrolone hydrogen succinate Nandrolone laurate Nandrolone phenylpropionate Nandrolone propionate Nandrolone sulfate Nandrolone sulfate sodium Nandrolone undecanoate Norclostebol Norclostebol acetate Normethandrone (methylestrenolone, normethisterone) Oxabolone Oxabolone cipionate (oxabolone cypionate) Trenbolone Trenbolone acetate Trenbolone enanthate Trenbolone hexahydrobenzylcarbonate Trestolone (MENT) Trestolone acetate Dihydrotestosterone and 19-nortestosterone derivatives: 5α-Dihydronandrolone 19-Norandrosterone 17α-Alkylated testosterone derivatives: Bolasterone Calusterone Chlorodehydromethylandrostenediol (CDMA) Chlorodehydromethyltestosterone (CDMT) Chloromethylandrostenediol (CMA) Enestebol Ethyltestosterone Fluoxymesterone Formebolone Hydroxystenozole Metandienone (methandrostenolone) Methandriol (methylandrostenediol) Methandriol bisenanthoyl acetate Methandriol diacetate Methandriol dipropionate Methandriol propionate Methylclostebol (chloromethyltestosterone) Methyltestosterone Oxymesterone Penmesterol Tiomesterone 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole Desoxymethyltestosterone Furazabol Mebolazine (dimethazine) Mestanolone Metenolone Metenolone acetate Metenolone enanthate Methasterone Methyl-1-testosterone Methylepitiostanol Methylstenbolone Oxandrolone Oxymetholone Stanozolol 17α-Alkylated 19-nortestosterone derivatives: Bolenol Dimethyltrienolone (7α-methylmetribolone, 7α,17α-dimethyltrenbolone) Ethyldienolone Ethylestrenol Methyldienolone Methylhydroxynandrolone (MOHN, MHN) Metribolone Mibolerone Norboletone Norethandrolone Propetandrol Tetrahydrogestrinone 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone) Vinyltestosterone 17α-Ethynyltestosterone derivatives: Δ^4-Tibolone Chloroethynyl norgestrel Danazol Desogestrel Ethisterone (ethynyltestosterone) Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel butanoate Lynestrenol Norethisterone Norethisterone acetate Norethisterone acetate oxime Norethisterone enanthate Norgestrel Norgestrienone Quingestanol Quingestanol acetate Tibolone Progesterone derivatives: Medroxyprogesterone acetate Others/unsorted: Cl-4AS-1

Mixed (SARMs)	Non-steroidal: 198RL26 ACP-105 AC-262,356 Acetothiolutamide Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4) BMS-564,929 Enobosarm (ostarine, MK-2866, GTx-024, S-22) FTBU-1 GSK-4336A GSK-8698 LG-121071 (LGD-121071) LGD-2226 LGD-2941 (LGD-122941) LGD-3303 LGD-4033 JNJ-26146900 JNJ-28330835 JNJ-37654032 ORM-11984 RAD140 R-1 R-2 R-3 S-1 S-23 S-40503 S-101479 Steroidal: MK-0773 TFM-4AS-1 YK-11

Antagonists	Steroidal: 3α-Hydroxytibolone 3β-Hydroxytibolone 9,11-Dehydrocortexolone 17α-butyrate (CB-03-04) 11α-Hydroxyprogesterone 15β-Hydroxycyproterone acetate Abiraterone acetate Allyltestosterone Benorterone BOMT Canrenoic acid Canrenone Chlormadinone acetate Clometerone Cortexolone 17α-propionate (CB-03-01) Cyproterone Cyproterone acetate Delanterone Dienogest Drospirenone Edogestrone Epitestosterone Galeterone Guggulsterone Medrogestone Megestrol acetate Mespirenone Metogest Mexrenone Mifepristone Nomegestrol acetate Nordinone Osaterone Osaterone acetate Oxendolone Potassium canrenoate Prorenone Rosterolone SC-5233 (spirolactone) Spironolactone Spirorenone Topterone Trimethyltrienolone (R-2956) Zanoterone Non-steroidal: AA560 Apalutamide Atraric acid AZD-3514 BAY-1024767 Bicalutamide Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S) BMS-641,988 Cimetidine Cioteronel Darolutamide DDT (via metabolite p,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 EPI-506 Fenarimol Flutamide Hydroxyflutamide Inocoterone Inocoterone acetate Ketoconazole Lavender oil LG-105 LG-120907 Linuron Methiocarb N-Butylbenzenesulfonamide N-Desmethylenzalutamide Nilutamide ONC1-13B ORM-15341 Pentomone PF-998425 Phenothrin Prochloraz Procymidone RU-22930 RU-58642 RU-58841 Seviteronel Thalidomide Topilutamide (fluridil) Valproic acid Vinclozolin

GPRC6A

Agonists	Cations (incl. aluminum, calcium, gadolinium, magnesium, strontium) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin Testosterone

See also: Estrogenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators • List of androgens/anabolic steroids

Estrogen receptor modulators

Agonists	Steroidal: 3α-Androstanediol 3β-Androstanediol 3α-Hydroxytibolone 3β-Hydroxytibolone 4-Androstenediol 4-Androstenedione 4-Hydroxyestradiol 4-Hydroxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodo-E2 16α-LE2 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17β-Dihydroequilenin 17β-Dihydroequilin Abiraterone Abiraterone acetate 17α-Estradiol (alfatradiol) Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate DHEA DHEA-S Digitoxin (digitalis) Diosgenin Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin Estetrol Estradiol Estradiol 3-propionate Estradiol acetate Estradiol benzoate Estradiol butyrate benzoate Estradiol butyrylacetate Estradiol cyclooctyl acetate Estradiol cypionate Estradiol decanoate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol glucuronide Estradiol hemihydrate Estradiol hemisuccinate (estradiol succinate) Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol mustard Estradiol palmitate Estradiol pivalate (trimethyl estradiol acetate) Estradiol propoxyphenylpropionate Estradiol stearate Estradiol sulfate Estradiol undecylate Estradiol valerate Lipoidal estradiol Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol acetate benzoate Estriol glucuronide Estriol sodium succinate Estriol succinate Estriol sulfate Estriol sulfate glucuronide Estriol triacetate Estriol tripropionate Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone glucuronide Estrone sulfate Estrone tetraacetylglucoside Estropipate Etamestrol (eptamestrol) Ethinyl estradiol Ethinyl estradiol sulfonate Ethinyl estriol Etynodiol diacetate Guggulsterone Hexolame Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Noretynodrel Orestrate Pentolame Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate Prodiame Prolame Promestriene Quinestradol Quinestrol Non-steroidal: (R,R)-THC (S,S)-THC 1-Keto-1,2,3,4-tetrahydrophenanthrene 2,8-DHHHC Allenoic acid Alternariol Anethole Anol Benzestrol Bifluranol Biochanin A Bisdehydrodoisynolic acid Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Coumestans (e.g., coumestrol, psoralidin) Deoxymiroestrol Dianethole Dianol Diarylpropionitrile Dieldrin Dienestrol Dienestrol acetate Diethylstilbestrol Diethylstilbestrol diacetate Diethylstilbestrol dilaurate Diethylstilbestrol dipalmitate Diethylstilbestrol dipropionate Diethylstilbestrol disulfate Diethylstilbestrol monobenzyl ether Dimestrol (dianisylhexene) Dimethylallenolic acid Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Endosulfan ERB-196 (WAY-202196) Estrobin (DBE) 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 (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate ICI-85966 (Stilbostat) Lavender oil Lignans (e.g., enterodiol, enterolactone) Mestilbol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Methiocarb Methoxychlor Miroestrol Nyasol (cis-hinokiresinol) Paroxypropione Pentafluranol Phenestrol Photoanethole Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol)) Quadrosilan SC-4289 SKF-82,958 Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Terfluranol WAY-166818 WAY-200070 Triphenylchlorethylene Triphenylmethylethylene WAY-214156

Mixed (SERMs)	2-Hydroxyestradiol 2-Hydroxyestrone 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordrin Anordriol Arzoxifene Bazedoxifene Brilanestrant Broparestrol Elacestrant Chlorotrianisene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Epitiostanol Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LY-117018 Menerba Mepitiostane Methylepitiostanol Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Phenytoin Pipendoxifene Raloxifene SS1010 Tamoxifen TAS-108 (SR-16234) Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene

Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Cytestrol acetate Fulvestrant (ICI-182780) ICI-164384 Methylpiperidinopyrazole MIBE PHTPP Prochloraz RU-58668 SS1020 TAS-108 (SR-16234) XCT-790 ZK-164015 ZK-191703

GPER

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Equol Estradiol Ethinyl estradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol Tamoxifen Tectoridin Zearalanone Zearalenol Zearalenone Zeranol (zearalanol))

Antagonists	CCL18 Estriol G-15 G-36 MIBE

See also: Androgenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators

Steroid hormone metabolism modulators

HMGCR	Inhibitors: Atorvastatin Cerivastatin Fluvastatin Lovastatin Mevastatin Pitavastatin Pravastatin Rosuvastatin Simvastatin

FPS	Inhibitors: Alendronic acid Clodronic acid Etidronic acid Ibandronic acid Incadronic acid Pamidronic acid Risedronic acid Tiludronic acid Zoledronic acid

24-DHCR24	20,25-Diazacholesterol Clomifene Triparanol

20,22-Desmolase (P450scc)	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 Δ⁴-Abiraterone Abiraterone Abiraterone acetate Amphenone Bifluranol Bifonazole Canrenone CFG-920 Clotrimazole Cyanoketone Cyproterone acetate Danazol Econazole Flutamide Galeterone Gestrinone Isoconazole Ketoconazole L-39 Levoketoconazole Liarozole LY-207,320 MDL-27,302 Miconazole Mifepristone Nilutamide Orteronel Pioglitazone Prochloraz Rosiglitazone Seviteronel Spironolactone Stanozolol SU-9055 SU-10603 TGF-β Tioconazole Troglitazone VN/87-1 YM116

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

3β-HSD	Inhibitors: 4-MA Δ⁴-Abiraterone Abiraterone Abiraterone acetate Azastene Cyanoketone Cyproterone acetate Danazol Epostane Genistein Gestrinone Medrogestone Medroxyprogesterone acetate Metyrapone Norethisterone Oxymetholone Pioglitazone Rosiglitazone Trilostane Troglitazone

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

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

11β-Hydroxylase	Inhibitors: Δ⁴-Abiraterone Abiraterone Abiraterone acetate Aminoglutethimide Canrenone Etomidate Fadrozole FETO Ketoconazole Levoketoconazole Metomidate Metyrapol Metyrapone Mitotane Potassium canrenoate Spironolactone Trilostane

18-Hydroxylase	Inhibitors: 18-Ethynylprogesterone (18-ethinylprogesterone) 18-Vinylprogesterone Aminoglutethimide Canrenone FAD286 Fadrozole Ketoconazole LCI699 Metyrapone Mespirenone Potassium canrenoate Spironolactone

17β-HSD	Inhibitors: Danazol Simvastatin

5α-Reductase	Inhibitors: 22-Oxime Δ⁴-Abiraterone Abiraterone Abiraterone acetate 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 Gestodene Izonsteride L-39 Lapisteride Oxendolone Saw palmetto TFM-4AS-1 Turosteride Vitamin B6 Zinc

Aromatase	Inhibitors: 4-AT 4-Cyclohexylaniline 4-Hydroxytestosterone 5α-DHNET 20α-Dihydroprogesterone Abyssinone II Aminoglutethimide Anastrozole Ascorbic acid (vitamin C) Atamestane ATD Bifonazole CGP-45,688 CGS-47,645 Chalconoids (e.g., isoliquiritigenin) Clotrimazole Corynesidone A Coumestrol 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)

SST/EST	4′OH-CB79 6-Hydroxyflavone 2,6-Dichloro-4-nitrophenol (DCNP) Equol Galangin Genistein Parabens (e.g., butylparaben) Pentachlorophenol (PCP) Triclosan

STS	AHBS Danazol Estrone-3-O-sulfamate (EMATE) Irosustat (STX64, 667 Coumate, BN-83495) KW-2581 Progestogens SR-16157 STX213 STX681 STX1938

27-Hydroxylase	Inhibitors: Anastrozole Bicalutamide Dexmedetomidine Fadrozole Posaconazole Ravuconazole

Others	Inhibitors: Inhibit estradiol degradation: Cimetidine

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

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