Furazabol

Multi tool useFurazabol |
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Clinical data |
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Trade names | Frazalon, Miotalon, Qu Zhi Shu |
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Synonyms | Androfurazanol; DH-245; Furazalon; Frazalon; Pirzalon; 17α-Methyl-5α-androsta[2,3-c]furazan-17β-ol; 17β-Hydroxy-17α-methyl-5α-androstano[2,3-c]-1',2',5'-oxadiazole; 17α-Methyl-5α-androstano[2,3-c][1,2,5]oxadiazol-17β-ol |
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Routes of administration | By mouth |
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Drug class | Androgen; Anabolic steroid
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ATC code | |
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Legal status |
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Legal status |
CA: Schedule IV
US: Schedule III
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Pharmacokinetic data |
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Elimination half-life
| 4 hours[citation needed] |
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Excretion | Urine |
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Identifiers |
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IUPAC name - (1S,2S,10S,13R,14S,17S,18S)-2,17,18-Trimethyl-6-oxa-5,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4,7-dien-17-ol
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CAS Number | 1239-29-8 Y
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PubChem CID
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DrugBank | DB01514 Y
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ChemSpider | 14032 Y
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UNII | |
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ChEMBL | ChEMBL1893554 N
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ECHA InfoCard | 100.013.621  |
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Chemical and physical data |
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Formula | C20H30N2O2 |
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Molar mass | 330.47 g·mol−1 |
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3D model (JSmol) | |
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SMILES O[C@@]5([C@@]4([C@H]([C@H]3[C@@H]([C@]2(Cc1nonc1C[C@@H]2CC3)C)CC4)CC5)C)C
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InChI InChI=1S/C20H30N2O2/c1-18-11-17-16(21-24-22-17)10-12(18)4-5-13-14(18)6-8-19(2)15(13)7-9-20(19,3)23/h12-15,23H,4-11H2,1-3H3/t12-,13+,14-,15-,18-,19-,20-/m0/s1 Y
Key:RGLLOUBXMOGLDQ-IVEVATEUSA-N Y
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.mw-parser-output .noboldfont-weight:normal N Y (what is this?) (verify)
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Furazabol (INN, JAN) (brand names Frazalon, Miotalon, Qu Zhi Shu), also known as androfurazanol, is a synthetic, orally active anabolic-androgenic steroid which has been marketed in Japan since 1969.[1][2][3][4] It is a 17α-alkylated derivative of dihydrotestosterone (DHT) and is closely related structurally to stanozolol, differing from it only by having a furazan ring system instead of pyrazole.[5] Furazabol has a relatively high ratio of anabolic to androgenic activity.[4] As with other 17α-alkylated AAS, it may have a risk of hepatotoxicity.[6] The drug has been described as an antihyperlipidemic and is claimed to be useful in the treatment of atherosclerosis and hypercholesterolemia,[5] but according to William Llewellyn, such properties of furazabol are a myth.[7]
References
^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 585–. ISBN 978-1-4757-2085-3..mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 475–. ISBN 978-3-88763-075-1.
^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1725–. ISBN 978-0-8155-1856-3.
^ ab Progress in Medicinal Chemistry. Elsevier. 1 January 1979. pp. 62–63. ISBN 978-0-08-086264-4.
^ ab Fragkaki AG, Angelis YS, Koupparis M, Tsantili-Kakoulidou A, Kokotos G, Georgakopoulos C (2009). "Structural characteristics of anabolic androgenic steroids contributing to binding to the androgen receptor and to their anabolic and androgenic activities. Applied modifications in the steroidal structure". Steroids. 74 (2): 172–97. doi:10.1016/j.steroids.2008.10.016. PMID 19028512.
^ Abbate V, Kicman AT, Evans-Brown M, McVeigh J, Cowan DA, Wilson C, Coles SJ, Walker CJ (2015). "Anabolic steroids detected in bodybuilding dietary supplements - a significant risk to public health". Drug Test Anal. 7 (7): 609–18. doi:10.1002/dta.1728. PMID 25284752.
^ William Llewellyn (2007). Anabolics 2007: Anabolic Steroids Reference Manual. Body of Science. ISBN 978-0967930466.
Androgens and antiandrogens
|
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Androgens (incl. AAS) |
AR agonists
| Testosterone derivatives: Androstenediol dipropionate
- Boldenone undecylenate
- Clostebol
- Clostebol acetate
- Clostebol caproate
- Clostebol propionate
- Cloxotestosterone acetate
- Prasterone (dehydroepiandrosterone, DHEA)
- Prasterone enanthate (DHEA enanthate)
- Prasterone sulfate (DHEA sulfate)
- Quinbolone
Testosterone#
Testosterone esters (e.g., testosterone cypionate, testosterone enanthate, testosterone propionate, testosterone undecanoate, testosterone ester mixtures (Deposterona, Omnadren, Sustanon, Testoviron Depot))
Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT)
- Androstanolone esters
- Bolazine capronate
- Drostanolone propionate (dromostanolone propionate)
- Epitiostanol
- Mepitiostane
- Mesterolone
- Metenolone acetate (methenolone acetate)
- Metenolone enanthate (methenolone enanthate)
- Stenbolone acetate
19-Nortestosterone derivatives: Bolandiol dipropionate
Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)
- Norclostebol
- Norclostebol acetate
- Oxabolone cipionate (oxabolone cypionate)
- Trenbolone acetate
- Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)
17α-Alkylated testosterone derivatives: Bolasterone
- Calusterone
- Chlorodehydromethyltestosterone (CDMT)
- Fluoxymesterone
- Formebolone
- Metandienone (methandienone, methandrostenolone)
- Methandriol (methylandrostenediol)
- Methandriol bisenanthoyl acetate
- Methandriol dipropionate
- Methandriol propionate
Methyltestosterone (+esterified estrogens)
- Methyltestosterone 3-hexyl ether
- Oxymesterone
- Penmesterol
- Tiomesterone (thiomesterone)
17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
- Furazabol
- Mebolazine (dimethazine)
- Mestanolone
- Oxandrolone
- Oxymetholone
- Stanozolol
17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol
- Mibolerone
- Norethandrolone
- Normethandrone (methylestrenolone, normethisterone)
- Propetandrol (propethandrol)
17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
17α-Ethynyltestosterone derivatives: Danazol
- Gestrinone
Progestins (e.g., ethisterone (ethynyltestosterone), levonorgestrel, norgestrel, norethisterone (norethindrone), lynestrenol, norgestrienone)
- Tibolone
Progesterone derivatives: Medroxyprogesterone acetate
|
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Progonadotropins | Antiestrogens (e.g., tamoxifen, clomifene)
GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
Gonadotropins (e.g., LH, hCG)
|
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|
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Antiandrogens |
AR antagonists
| Steroidal: Abiraterone acetate
- Canrenone
- Chlormadinone acetate
- Cyproterone acetate
- Delmadinone acetate
- Dienogest
- Drospirenone
- Medrogestone
- Megestrol acetate
- Nomegestrol acetate
- Osaterone acetate
- Oxendolone
- Potassium canrenoate
- Spironolactone
Nonsteroidal: Apalutamide
- Bicalutamide
- Cimetidine
Darolutamide†
- Enzalutamide
- Flutamide
- Ketoconazole
- Nilutamide
Seviteronel†
- Topilutamide (fluridil)
|
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Steroidogenesis inhibitors |
5α-Reductase | - Alfatradiol
Dutasteride (+tamsulosin)
- Epristeride
- Finasteride
- Saw palmetto extract
|
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Others | - Abiraterone acetate
- Aminoglutethimide
- Bifluranol
- Cyproterone acetate
- Flutamide
- Ketoconazole
- Nilutamide
Seviteronel†
- Spironolactone
|
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|
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Antigonadotropins | D2 receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
Estrogens (e.g., bifluranol, diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
GnRH agonists (e.g., leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Progestogens (incl., chlormadinone acetate, cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, medroxyprogesterone acetate, megestrol acetate)
|
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Others | Androstenedione immunogens: Androvax (androstenedione albumin)
- Ovandrotone albumin (Fecundin)
|
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#WHO-EM
‡Withdrawn from market
Clinical trials:
†Phase III
§Never to phase III
- See also
- Androgen receptor modulators
- Estrogens and antiestrogens
- Progestogens and antiprogestogens
- List of androgens/anabolic steroids
|
Androgen receptor modulators
|
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AR |
Agonists | Testosterone derivatives: 4-Androstenediol
- 4-Dehydroepiandrosterone (4-DHEA)
- 4-Hydroxytestosterone
- 4,17α-Dimethyltestosterone
- 5-Androstenedione
- 11-Ketotestosterone
- 11β-Hydroxyandrostenedione
- Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
Androstenediol (5-androstenediol)
- Androstenediol 3β-acetate
- Androstenediol 17β-acetate
- Androstenediol diacetate
- Androstenediol dipropionate
- Androstenedione (4-androstenedione)
- Atamestane
Boldenone
- Boldione (1,4-androstadienedione)
Clostebol
- Clostebol acetate
- Clostebol caproate
- Clostebol propionate
Cloxotestosterone
- Cloxotestosterone acetate
- Dehydroandrosterone
DHEA (androstenolone, prasterone; 5-DHEA)
- DHEA enanthate (prasterone enanthate)
- DHEA sulfate
- Exemestane
- Formestane
- Plomestane
- Quinbolone
- Silandrone
Testosterone# (+dutasteride)
- Testosterone esters
- Polytestosterone phloretin phosphate
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
- Dihydroethisterone
- Dihydroethyltestosterone
- Dihydrofluoxymesterone
- Dihydromethylandrostenediol
Dihydrotestosterone (DHT) (androstanolone, stanolone)
- Dihydrotestosterone esters
Drostanolone
- Epiandrosterone
- Epitiostanol
- Mepitiostane
- Mesabolone
Mesterolone
- Methyldiazinol
Nisterime
- Prostanozol
Stenbolone
- Testifenon (testiphenon, testiphenone)
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
- 19-Nordehydroepiandrosterone
Bolandiol
- 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
Norclostebol
- Normethandrone (methylestrenolone, normethisterone)
Oxabolone
- Oxabolone cipionate (oxabolone cypionate)
Trenbolone
- Trenbolone acetate
- Trenbolone enanthate
- Trenbolone hexahydrobenzylcarbonate
- Trenbolone undecanoate
- Trendione
Trestolone (MENT)
- Trestolone acetate
- Trestolone enanthate
Dihydrotestosterone and 19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
- 5α-Dihydronandrolone
- 5α-Dihydronorethandrolone
- 5α-Dihydronorethisterone
- 5α-Dihydronormethandrone
- 5α-Dihydrotrestolone
- 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 (+esterified estrogens)
- Methyltestosterone 3-hexyl ether
- 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
- Dimethyldienolone
- Dimethyltrienolone
- Ethyldienolone
- Ethylestrenol
- Methyldienolone
- Methylhydroxynandrolone (MOHN, MHN)
- Metribolone
- Mibolerone
- Norboletone
- Norethandrolone
- Propetandrol
- RU-2309
- Tetrahydrogestrinone
17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
- Vinyltestosterone
17α-Ethynyltestosterone derivatives: Δ4-Tibolone
- Danazol
- Desogestrel
- Ethisterone (ethynyltestosterone)
- Etonogestrel
- Etynodiol
- Etynodiol diacetate
- Gestodene
- Gestrinone
- Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate)
- Lynestrenol
- Lynestrenol phenylpropionate
- Norethisterone
Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)
- Norgestrel
- Norgestrienone
- Quingestanol
- Quingestanol acetate
- Tibolone
Progesterone derivatives: Medroxyprogesterone acetate
- Megestrol acetate
Others/unsorted: 3-Keto-5α-abiraterone
- 5α-Androstane
- Alternariol
- Cl-4AS-1
- Drupanol
- ZM-182345
|
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Mixed (SARMs) | Nonsteroidal: 198RL26
- ACP-105
- AC-262536
- Acetothiolutamide
- Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
- BMS-564929
- DTIB
- 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
- R-1
- RAD140
- RU-59063
- S-1
- S-23
- S-40503
- S-101479
- Triclosan
Steroidal: EM-9017
- MK-0773
- TFM-4AS-1
- YK-11
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Antagonists | |
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GPRC6A |
Agonists | Cations (incl. aluminum, calcium, gadolinium, magnesium, strontium, zinc)
- Dehydroandrosterone
- Dihydrotestosterone
- Estradiol
L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine)
- Osteocalcin
- SHBG
- Testosterone
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|
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- See also
- Receptor/signaling modulators
- Androgens and antiandrogens
- Estrogen receptor modulators
- Progesterone receptor modulators
- List of androgens/anabolic steroids
|
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