Details of the Drug

General Information of Drug (ID: DMUHCF1)

• Drug Name: Fluoxymesterone
• Synonyms: Androfluorene; Androfluorone; Androsterolo; Fluossimesterone; Fluosterone; Fluotestin; Fluoximesteron; Fluoximesterona; Fluoximesterone; Fluoximesteronum; Fluoxymesteronum; Fluoxymestrone; Flusteron; Flutestos; Halotestin; Oralsterone; Oratestin; Testoral; Ultandren; Ultandrene; Component of Halodrin; Fluossimesterone [DCIT]; Ora Testryl; U 6040; Anadroid-F; Android-f; Fluoximesterona [INN-Spanish]; Fluoxymesteronum [INN-Latin]; Halotestin (TN); Neo-Ormonal; Ora-Testryl; Fluoxymesterone [INN:BAN:JAN]; Fluoxymesterone (JP15/USP/INN); Fluoro-9-alpha dihydroxy-11-beta,17-beta methyl-17-alpha androstene-4 one-3; Fluoro-9-alpha dihydroxy-11-beta,17-beta methyl-17-alpha androstene-4 one-3 [French]; Androst-4-en-3-one, 9-fluoro-11beta,17beta-dihydroxy-17-methyl-(VAN); Androst-4-en-3-one, 9-fluoro-11beta,17beta-dihydroxy-17-methyl-(VAN) (8CI); (11beta,17beta)-9-fluoro-11,17-dihydroxy-17-methylandrost-4-en-3-one; (8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one; 11-beta,17-beta-Dihydroxy-9-alpha-fluoro-17-alpha-methyl-4-androster-3-one; 11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androsten-3-one; 11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androster-3-one; 17-alpha-Methyl-9-alpha-fluoro-11-beta-hydroxytesterone; 17alpha-Methyl-9alpha-fluoro-11beta-hydroxytesterone; 9-Fluoro-11-beta,17-beta-dihydroxy-17-methylandrost-4-en-3-one; 9-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one; 9-alpha-Fluoro-11-beta,17-beta-dihydroxy-17-alpha-methyl-4-androstene-3-one; 9-alpha-Fluoro-11-beta-hydroxy-17-methyltestosterone; 9-alpha-Fluoro-17-alpha-methyl-11-beta,17-dihydroxy-4-androsten-3-one;9-fluoro-11beta,17beta-dihydroxy-17alpha-methylandrost-4-en-3-one; 9.alpha.-Fluoro-11.beta.,17.beta.-dihydroxy-17.alpha.-methyl-4-androstene-3-one; 9.alpha.-Fluoro-11.beta.-hydroxy-17-methyltestosterone; 9alpha-Fluoro-11beta,17beta-dihydroxy-17alpha-methyl-4-androstene-3-one; 9alpha-Fluoro-11beta,17beta-dihydroxy-17alpha-methylandrost-4-en-3-one; 9alpha-Fluoro-11beta-hydroxy-17-methyltestosterone; 9alpha-Fluoro-11beta-hydroxy-17alpha-methyltestosterone; 9alpha-Fluoro-17alpha-methyl-11beta,17-dihydroxy-4-androsten-3-one

Indication

Disease Entry	ICD 11	Status	REF
Breast cancer	2C60-2C65	Approved	[1]
Myotonia congenita, autosomal dominant	N.A.	Approved	[2]
Noonan syndrome	N.A.	Approved	[2]
Hypogonadism, male	N.A.	Investigative	[2]

• Therapeutic Class: Anabolic Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 336.4
  Logarithm of the Partition Coefficient (xlogp); 2.4
  Rotatable Bond Count (rotbonds); 0
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 4
• ADMET Property:
  Bioavailability: The bioavailability of drug is 44% []
  Half-life: The concentration or amount of drug in body reduced by one-half in 9.2 hours [3]
  Metabolism: The drug is metabolized via the hepatic []
• Chemical Identifiers:
  Formula: C20H29FO3
  IUPAC Name: (8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
  Canonical SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@]2([C@H](C[C@]4([C@H]3CC[C@]4(C)O)C)O)F
  InChI: InChI=1S/C20H29FO3/c1-17-8-6-13(22)10-12(17)4-5-15-14-7-9-19(3,24)18(14,2)11-16(23)20(15,17)21/h10,14-16,23-24H,4-9,11H2,1-3H3/t14-,15-,16-,17-,18-,19-,20-/m0/s1
  InChIKey: YLRFCQOZQXIBAB-RBZZARIASA-N
• Cross-matching ID:
  PubChem CID: 6446
  ChEBI ID: CHEBI:5120
  CAS Number: 76-43-7
  DrugBank ID: DB01185
  TTD ID: D0L2LS
  INTEDE ID: DR1767
  ACDINA ID: D00284
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Androgen receptor (AR)	TTS64P2	ANDR_HUMAN	Agonist	[4]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4) Main DME	DE4LYSA	CP3A4_HUMAN	Substrate	[5]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
11-beta-hydroxysteroid dehydrogenase type 2 (HSD11B2)	OTHF4H9U	DHI2_HUMAN	Gene/Protein Processing	[6]

Molecular Expression Atlas of This Drug

• The Studied Disease: Breast cancer
• ICD Disease Classification: 2C60-2C65

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Androgen receptor (AR)	DTT	AR	2.13E-01	-0.07	-0.11
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	7.93E-02	-8.20E-02	-8.93E-01

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Fluoxymesterone (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Fluoxymesterone and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[7]
Insulin-glulisine	DMQI0FU	Moderate	Increased risk of hypoglycemia by the combination of Fluoxymesterone and Insulin-glulisine.	Acute diabete complication [5A2Y]	[8]
Insulin-aspart	DMX7V28	Moderate	Increased risk of hypoglycemia by the combination of Fluoxymesterone and Insulin-aspart.	Acute diabete complication [5A2Y]	[9]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Fluoxymesterone and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[10]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Fluoxymesterone and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[11]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Fluoxymesterone and Cannabidiol.	Epileptic encephalopathy [8A62]	[12]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Fluoxymesterone and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[13]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Fluoxymesterone and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[14]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Fluoxymesterone and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[15]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Fluoxymesterone and Idelalisib.	Mature B-cell leukaemia [2A82]	[16]
Carfilzomib	DM48K0X	Major	Additive thrombogenic effects by the combination of Fluoxymesterone and Carfilzomib.	Multiple myeloma [2A83]	[7]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Fluoxymesterone and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[12]
Insulin-detemir	DMOA4VW	Moderate	Increased risk of hypoglycemia by the combination of Fluoxymesterone and Insulin-detemir.	Type-1/2 diabete [5A10-5A11]	[8]
Insulin degludec	DMPL395	Moderate	Increased risk of hypoglycemia by the combination of Fluoxymesterone and Insulin degludec.	Type-1/2 diabete [5A10-5A11]	[8]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
FD&C blue no. 1	E00263	19700	Colorant
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Carmellose sodium	E00625	Not Available	Disintegrant
Magnesium stearate	E00208	11177	lubricant

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Fluoxymesterone 10 mg tablet	10 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2861).
• [2] Fluoxymesterone FDA Label
• [3] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [4] An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73.
• [5] Effect of dexamethasone on cytochrome P-450 mediated metabolism of 2-acetylaminofluorene in cultured rat hepatocytes. Biochem Pharmacol. 1987 Jan 15;36(2):237-43.
• [6] The anabolic androgenic steroid fluoxymesterone inhibits 11beta-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation. Toxicol Sci. 2012 Apr;126(2):353-61.
• [7] Cerner Multum, Inc. "Australian Product Information.".
• [8] Abad S, Moachon L, Blanche P, Bavoux F, Sicard D, Salmon-Ceron D "Possible interaction between glicazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia." Br J Clin Pharmacol 52 (2001): 456-7. [PMID: 11678792]
• [9] Asplund K, Wiholm BE, Lithner F "Glibenclamide-associated hypoglycaemia: a report on 57 cases." Diabetologia 24 (1983): 412-7. [PMID: 6411511]
• [10] Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
• [11] Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
• [12] Cerner Multum, Inc. "UK Summary of Product Characteristics.".
• [13] Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
• [14] Canadian Pharmacists Association.
• [15] Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
• [16] Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.