Identification

Name
16-Bromoepiandrosterone
Accession Number
DB05107
Type
Small Molecule
Groups
Investigational
Description

16-Bromoepiandrosterone is an injectable formulation of a compound called alpha-epi-bromide. It is a chemical relative of DHEA which was selected for development after it showed antiretroviral activity in laboratory tests.

Structure
Thumb
Synonyms
  • 16alpha-bromoepiandrosterone
External IDs
HE-2000 / HE2000
International/Other Brands
Immunitin
Categories
UNII
9735KA370S
CAS number
28507-02-0
Weight
Average: 369.336
Monoisotopic: 368.135092819
Chemical Formula
C19H29BrO2
InChI Key
CWVMWSZEMZOUPC-JUAXIXHSSA-N
InChI
InChI=1S/C19H29BrO2/c1-18-7-5-12(21)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(20)17(19)22/h11-16,21H,3-10H2,1-2H3/t11-,12-,13+,14-,15-,16+,18-,19-/m0/s1
IUPAC Name
(1S,2S,5S,7S,10R,11S,13R,15S)-13-bromo-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one
SMILES
[H][C@@]12C[C@@H](Br)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C

Pharmacology

Indication

Investigated for use/treatment in cystic fibrosis, HIV infection, hepatitis (viral, B), and malaria.

Pharmacodynamics
Not Available
Mechanism of action

HE2000 interacts with certain enzymes, including G6PDH (glucose 6 phosphate dehydrogenase); these enzymes could be involved in the mechanism. Also, the compound is in the steroid hormone series, and involved in control mechanisms in our cells that are much more complex, interacting with receptors and therefore changing the biochemistry of cells. This compound may have many modes of action; we are trying to understand what they may be.

TargetActionsOrganism
UGlucose-6-phosphate 1-dehydrogenaseNot AvailableHuman
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
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with 16-Bromoepiandrosterone.
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when 16-Bromoepiandrosterone is combined with 1,10-Phenanthroline.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with 16-Bromoepiandrosterone.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with 16-Bromoepiandrosterone.
AlclofenacThe risk or severity of adverse effects can be increased when Alclofenac is combined with 16-Bromoepiandrosterone.
AlclometasoneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Alclometasone.
AlfuzosinThe metabolism of 16-Bromoepiandrosterone can be decreased when combined with Alfuzosin.
AlmasilateThe bioavailability of 16-Bromoepiandrosterone can be decreased when combined with Almasilate.
AlminoprofenThe risk or severity of adverse effects can be increased when Alminoprofen is combined with 16-Bromoepiandrosterone.
AloglutamolThe bioavailability of 16-Bromoepiandrosterone can be decreased when combined with Aloglutamol.
Food Interactions
Not Available

References

General References
  1. Frincke JM, Stickney DR, Onizuka-Handa N, Garsd A, Reading C, Krudsood S, Wilairatana P, Looareesuwan S: Reduction of parasite levels in patients with uncomplicated malaria by treatment with HE2000. Am J Trop Med Hyg. 2007 Feb;76(2):232-6. [PubMed:17297029]
  2. Reading C, Dowding C, Schramm B, Garsd A, Onizuka-Handa N, Stickney D, Frincke J: Improvement in immune parameters and human immunodeficiency virus-1 viral response in individuals treated with 16alpha-bromoepiandrosterone (HE2000). Clin Microbiol Infect. 2006 Nov;12(11):1082-8. [PubMed:17002607]
  3. Frincke J: HE2000 begins clinical trials: interview with James Frincke, Ph.D. Interview by John S. James. AIDS Treat News. 1999 Jun 4;(No 320):4-7. [PubMed:11366467]
  4. Authors unspecified: HE2000 corrects immune system dysregulation in HIV-positive patients. AIDS Read. 2000 May;10(5):282. [PubMed:10851716]
  5. Authors unspecified: HE2000 shows efficacy. AIDS Patient Care STDS. 1999 Jun;13(6):375. [PubMed:10842861]
External Links
PubChem Compound
71613
PubChem Substance
175426947
ChemSpider
64682
BindingDB
50388517
ChEMBL
CHEMBL445472

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1

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 Solubility0.00209 mg/mLALOGPS
logP4.45ALOGPS
logP4.44ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)17.86ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity91.34 m3·mol-1ChemAxon
Polarizability37.98 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9825
Caco-2 permeable+0.8006
P-glycoprotein substrateSubstrate0.5669
P-glycoprotein inhibitor INon-inhibitor0.6611
P-glycoprotein inhibitor IINon-inhibitor0.7795
Renal organic cation transporterNon-inhibitor0.7902
CYP450 2C9 substrateNon-substrate0.8133
CYP450 2D6 substrateNon-substrate0.8886
CYP450 3A4 substrateSubstrate0.7282
CYP450 1A2 substrateNon-inhibitor0.7876
CYP450 2C9 inhibitorNon-inhibitor0.7726
CYP450 2D6 inhibitorNon-inhibitor0.938
CYP450 2C19 inhibitorNon-inhibitor0.9056
CYP450 3A4 inhibitorNon-inhibitor0.7977
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9292
Ames testNon AMES toxic0.8898
CarcinogenicityNon-carcinogens0.9022
BiodegradationNot ready biodegradable0.9964
Rat acute toxicity2.2317 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9501
hERG inhibition (predictor II)Inhibitor0.5
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 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
Halogenated steroids / 3-beta-hydroxysteroids / 17-oxosteroids / Alpha-haloketones / Secondary alcohols / Cyclic alcohols and derivatives / Organobromides / Organic oxides / Hydrocarbon derivatives / Alkyl bromides
Substituents
Androgen-skeleton / 3-hydroxysteroid / 16-halo-steroid / Halo-steroid / Hydroxysteroid / 17-oxosteroid / Oxosteroid / 3-beta-hydroxysteroid / Cyclic alcohol / Alpha-haloketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Catalyzes the rate-limiting step of the oxidative pentose-phosphate pathway, which represents a route for the dissimilation of carbohydrates besides glycolysis. The main function of this enzyme is ...
Gene Name
G6PD
Uniprot ID
P11413
Uniprot Name
Glucose-6-phosphate 1-dehydrogenase
Molecular Weight
59256.31 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

Drug created on October 21, 2007 16:23 / Updated on August 02, 2018 05:29