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Identification
Name16-Bromoepiandrosterone
Accession NumberDB05107
TypeSmall Molecule
GroupsInvestigational
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 Identifiers
  • HE-2000
  • HE2000
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ImmunitinNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII9735KA370S
CAS number28507-02-0
WeightAverage: 369.336
Monoisotopic: 368.135092819
Chemical FormulaC19H29BrO2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-beta-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Halo-steroid
  • 16-halo-steroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organobromide
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl bromide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationInvestigated for use/treatment in cystic fibrosis, HIV infection, hepatitis (viral, B), and malaria.
PharmacodynamicsNot Available
Mechanism of actionHE2000 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 to provide reducing power (NADPH) and pentose phosphates for fatty acid and nucleic acid synthesis.
Gene Name:
G6PD
Uniprot ID:
P11413
Molecular Weight:
59256.31 Da
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Drug created on October 21, 2007 16:23 / Updated on August 17, 2016 12:24