Identification

Name
Formebolone
Accession Number
DB01569
Type
Small Molecule
Groups
Experimental, Illicit
Description

Formebolone, a derivative of androstane [1], is an anabolic androgenic steroid. It is on the list of substances prohibited by the Word Anti-Doping Agency, and is regularly screened for in athletes. It is also classified by the US Drug Enforcement Administration as Schedule III drug in the Controlled Substances Act. It has been used experimentally in the treatment of growth retardation, and has been noted to increase bone mass. [1] Additionally, it has been patented for use in development of novel transdermal delivery systems for enhanced drug delivery.

Structure
Thumb
Synonyms
  • 11-alpha,17-beta-Dihydroxy-17-methyl-3-oxoandrosta-1,4-diene-2-carboxaldehyde
  • 2-Formyl-11-alpha-hydroxy-delta(sup 1)-methyltestosterone
  • 2-formyl-11α-hydroxy-17α-methyl-δ1-testosterone
  • 2-Formyl-17-alpha-methylandrosta-1,4-diene-11-alpha,17-beta-diol-3-one
  • Esiclene
  • Formebolona
  • Formebolonum
  • Formyldienolone
External IDs
DEA No. 4000
International/Other Brands
Esiclene / Hubernol / Metanor
Categories
UNII
Z2MMV08KUQ
CAS number
2454-11-7
Weight
Average: 344.4446
Monoisotopic: 344.198759384
Chemical Formula
C21H28O4
InChI Key
AMVODTGMYSRMNP-GNIMZFFESA-N
InChI
InChI=1S/C21H28O4/c1-19-9-12(11-22)16(23)8-13(19)4-5-14-15-6-7-21(3,25)20(15,2)10-17(24)18(14)19/h8-9,11,14-15,17-18,24-25H,4-7,10H2,1-3H3/t14-,15-,17+,18+,19-,20-,21-/m0/s1
IUPAC Name
(1S,2R,10S,11S,14S,15S,17R)-14,17-dihydroxy-2,14,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-4-carbaldehyde
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C(C=O)=C[C@]12C

Pharmacology

Indication

No approve indications. Studied experimentally as a treatment for non-pituitary growth retardation [1].

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCorticosteroid 11-beta-dehydrogenase isozyme 2
inhibitor
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Formebolone.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Formebolone.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Formebolone.
AbciximabThe therapeutic efficacy of Abciximab can be increased when used in combination with Formebolone.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Formebolone.
Acetylsalicylic acidThe therapeutic efficacy of Acetylsalicylic acid can be increased when used in combination with Formebolone.
AlteplaseThe therapeutic efficacy of Alteplase can be increased when used in combination with Formebolone.
AmediplaseThe therapeutic efficacy of Amediplase can be increased when used in combination with Formebolone.
AnagrelideThe therapeutic efficacy of Anagrelide can be increased when used in combination with Formebolone.
AncrodThe therapeutic efficacy of Ancrod can be increased when used in combination with Formebolone.
Food Interactions
Not Available

References

Synthesis Reference

Canonica, Luigi; Jommi, Giancarlo; Pelizzoni, Francesca; Scolastico, Carlo. 1,11-Oxido steroids. I. 1a,11a-Oxidoandrostanes. Gazzetta Chimica Italiana (1965), 95(3), 138-50.

General References
  1. Cuatrecasas Membrado JM, Bosch Banyeres JM: [Study of non-hypophysiary growth retardation treated with formebolone]. An Esp Pediatr. 1985 Jan;22(1):27-32. [PubMed:3985494]
External Links
Human Metabolome Database
HMDB0004631
PubChem Compound
17150
PubChem Substance
46508967
ChemSpider
16234
ChEBI
135456
ChEMBL
CHEMBL2107419
Wikipedia
Formebolone

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)210.5 °CPhysProp
boiling point (°C)543.6 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0605 mg/mLALOGPS
logP2.59ALOGPS
logP1.76ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.39ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity96.9 m3·mol-1ChemAxon
Polarizability38.13 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9964
Blood Brain Barrier+0.9575
Caco-2 permeable+0.6357
P-glycoprotein substrateSubstrate0.7668
P-glycoprotein inhibitor INon-inhibitor0.7709
P-glycoprotein inhibitor IINon-inhibitor0.793
Renal organic cation transporterNon-inhibitor0.8094
CYP450 2C9 substrateNon-substrate0.8477
CYP450 2D6 substrateNon-substrate0.9066
CYP450 3A4 substrateSubstrate0.7647
CYP450 1A2 substrateNon-inhibitor0.8748
CYP450 2C9 inhibitorNon-inhibitor0.8936
CYP450 2D6 inhibitorNon-inhibitor0.9646
CYP450 2C19 inhibitorNon-inhibitor0.9333
CYP450 3A4 inhibitorNon-inhibitor0.8312
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9428
Ames testNon AMES toxic0.9233
CarcinogenicityNon-carcinogens0.9452
BiodegradationNot ready biodegradable0.9741
Rat acute toxicity3.2193 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.925
hERG inhibition (predictor II)Non-inhibitor0.8035
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-oxo delta-1,4-steroids / 17-hydroxysteroids / 11-alpha-hydroxysteroids / Delta-1,4-steroids / Tertiary alcohols / Secondary alcohols / Cyclic ketones / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Androgen-skeleton / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Hydroxysteroid / Oxosteroid / 11-alpha-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / Delta-1,4-steroid / Cyclic alcohol
show 12 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid binding
Specific Function
Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation...
Gene Name
HSD11B2
Uniprot ID
P80365
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 2
Molecular Weight
44126.06 Da
References
  1. Furstenberger C, Vuorinen A, Da Cunha T, Kratschmar DV, Saugy M, Schuster D, Odermatt A: The anabolic androgenic steroid fluoxymesterone inhibits 11beta-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation. Toxicol Sci. 2012 Apr;126(2):353-61. doi: 10.1093/toxsci/kfs022. Epub 2012 Jan 23. [PubMed:22273746]

Drug created on July 31, 2007 07:10 / Updated on November 02, 2018 05:03