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16-Bromoepiandrosterone
Identification
- Name
- 16-Bromoepiandrosterone
- Accession Number
- DB05107
- 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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for 16-Bromoepiandrosterone (DB05107)
- Weight
- Average: 369.336
Monoisotopic: 368.135092819 - Chemical Formula
- C19H29BrO2
- Synonyms
- 16alpha-bromoepiandrosterone
- External IDs
- HE-2000
- HE2000
Pharmacology
- Indication
Investigated for use/treatment in cystic fibrosis, HIV infection, hepatitis (viral, B), and malaria.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism UGlucose-6-phosphate 1-dehydrogenase Not Available 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
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataBeclomethasone dipropionate The risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Beclomethasone dipropionate. Betamethasone The risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Betamethasone. Betamethasone phosphate The risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Betamethasone phosphate. Budesonide The risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Budesonide. Ciclesonide The risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Ciclesonide. Clobetasol The risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Clobetasol. Clobetasol propionate The risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Clobetasol propionate. Corticotropin The risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Corticotropin. Cortisone acetate The risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Cortisone acetate. Deflazacort The risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Deflazacort. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- International/Other Brands
- Immunitin
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 16-halo-steroid / 17-oxosteroid / 3-beta-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl bromide / Alkyl halide / Alpha-haloketone / Androgen-skeleton
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- 9735KA370S
- CAS number
- 28507-02-0
- 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][[email protected]@]12C[[email protected]@H](Br)C(=O)[[email protected]@]1(C)CC[[email protected]@]1([H])[[email protected]@]2([H])CC[[email protected]@]2([H])C[[email protected]@H](O)CC[[email protected]]12C
References
- General References
- 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]
- 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]
- 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]
- Authors unspecified: HE2000 corrects immune system dysregulation in HIV-positive patients. AIDS Read. 2000 May;10(5):282. [PubMed:10851716]
- 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
- ZINC
- ZINC000003975381
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Treatment Human Immunodeficiency Virus (HIV) Infections 1
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
Property Value Source Water Solubility 0.00209 mg/mL ALOGPS logP 4.45 ALOGPS logP 4.44 ChemAxon logS -5.2 ALOGPS pKa (Strongest Acidic) 17.86 ChemAxon pKa (Strongest Basic) -1.4 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 37.3 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 91.34 m3·mol-1 ChemAxon Polarizability 37.98 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9825 Caco-2 permeable + 0.8006 P-glycoprotein substrate Substrate 0.5669 P-glycoprotein inhibitor I Non-inhibitor 0.6611 P-glycoprotein inhibitor II Non-inhibitor 0.7795 Renal organic cation transporter Non-inhibitor 0.7902 CYP450 2C9 substrate Non-substrate 0.8133 CYP450 2D6 substrate Non-substrate 0.8886 CYP450 3A4 substrate Substrate 0.7282 CYP450 1A2 substrate Non-inhibitor 0.7876 CYP450 2C9 inhibitor Non-inhibitor 0.7726 CYP450 2D6 inhibitor Non-inhibitor 0.938 CYP450 2C19 inhibitor Non-inhibitor 0.9056 CYP450 3A4 inhibitor Non-inhibitor 0.7977 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9292 Ames test Non AMES toxic 0.8898 Carcinogenicity Non-carcinogens 0.9022 Biodegradation Not ready biodegradable 0.9964 Rat acute toxicity 2.2317 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9501 hERG inhibition (predictor II) Inhibitor 0.5
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- 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
Drug created on October 21, 2007 16:23 / Updated on June 12, 2020 10:52
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