Identification

Name
HE3286
Accession Number
DB05212
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
HE 3286 / HE-3286
International/Other Brands
Triolex
Categories
UNII
PH8858757I
CAS number
Not Available
Weight
Average: 330.468
Monoisotopic: 330.219494826
Chemical Formula
C21H30O3
InChI Key
JJKOQZHWYLMASZ-FJWDNACWSA-N
InChI
InChI=1S/C21H30O3/c1-4-21(24)10-7-16-18-15(6-9-20(16,21)3)19(2)8-5-14(22)11-13(19)12-17(18)23/h1,12,14-18,22-24H,5-11H2,2-3H3/t14-,15-,16-,17-,18+,19-,20-,21-/m0/s1
IUPAC Name
(1S,2R,5S,9R,10R,11S,14R,15S)-14-ethynyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9,14-triol
SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@]2(O)C#C)[C@@H](O)C=C1C[C@@H](O)CC[C@]31C

Pharmacology

Indication

For the treatment of rheumatoid arthritis and type 2 diabetes.

Pharmacodynamics
Not Available
Mechanism of action

Potential mechanisms of action for HE3286 include regulation of NF-kB and increasing the production of regulatory T cells (Treg cells). NF-kB is a well-known transcription factor that controls the production of inflammatory cytokines such as TNF-a and interferon-g. Treg cells are referred to in the scientific literature as the peacekeepers of the body. Their role is to keep the immune system from attacking the body itself. Recent studies of Treg cells indicate that they may play a broader role than simply preventing autoimmune conditions. Manipulation of these cells may offer new treatments for conditions ranging from diabetes and organ rejection to cancer and infectious diseases. In type II diabetes, moderate inhibition of NF-kB improves glucose tolerance. [Press Release - Hollis-Eden Pharmaceuticals]

TargetActionsOrganism
UNuclear factor NF-kappa-B p105 subunitNot AvailableHuman
UNuclear factor NF-kappa-B p100 subunitNot AvailableHuman
Absorption

Up to 25% oral bioavailability in mice.

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
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with HE3286.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with HE3286.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with HE3286.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with HE3286.
5-androstenedioneThe metabolism of HE3286 can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of HE3286 can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with HE3286.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with HE3286.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with HE3286.
AcalabrutinibThe metabolism of HE3286 can be decreased when combined with Acalabrutinib.
Food Interactions
Not Available

References

General References
  1. Auci D, Kaler L, Subramanian S, Huang Y, Frincke J, Reading C, Offner H: A new orally bioavailable synthetic androstene inhibits collagen-induced arthritis in the mouse: androstene hormones as regulators of regulatory T cells. Ann N Y Acad Sci. 2007 Sep;1110:630-40. [PubMed:17911478]
External Links
PubChem Compound
16739648
PubChem Substance
347827717
ChemSpider
20571043

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentInsulin Resistance2
1, 2CompletedTreatmentRheumatoid Arthritis1
1, 2CompletedTreatmentUlcerative Colitis (UC)1
2CompletedTreatmentType 2 Diabetes Mellitus1

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.017 mg/mLALOGPS
logP1.68ALOGPS
logP1.8ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)17.59ChemAxon
pKa (Strongest Basic)-0.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity94.39 m3·mol-1ChemAxon
Polarizability37.99 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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
7-alpha-hydroxysteroids / 3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / 17-hydroxysteroids / Delta-5-steroids / Ynones / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Polyols
show 2 more
Substituents
Androgen-skeleton / 3-hydroxy-delta-5-steroid / 3-hydroxysteroid / 7-hydroxysteroid / 7-alpha-hydroxysteroid / 17-hydroxysteroid / 3-beta-hydroxysteroid / 3-beta-hydroxy-delta-5-steroid / Hydroxysteroid / Delta-5-steroid
show 11 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcriptional repressor activity, rna polymerase ii transcription regulatory region sequence-specific binding
Specific Function
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
Gene Name
NFKB1
Uniprot ID
P19838
Uniprot Name
Nuclear factor NF-kappa-B p105 subunit
Molecular Weight
105355.175 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
Gene Name
NFKB2
Uniprot ID
Q00653
Uniprot Name
Nuclear factor NF-kappa-B p100 subunit
Molecular Weight
96748.355 Da

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Ahlem CN, Kennedy MR, Page TM, Reading CL, White SK, McKenzie JJ, Cole PI, Stickney DR, Frincke JM: Studies of the pharmacology of 17alpha-ethynyl-androst-5-ene-3beta,7beta,17beta-triol, a synthetic anti-inflammatory androstene. Int J Clin Exp Med. 2011;4(2):119-35. Epub 2011 Apr 23. [PubMed:21686136]

Drug created on October 21, 2007 16:24 / Updated on November 02, 2018 06:09