| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H29BrO2 |
| Molecular Weight | 369.336 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](O)CC[C@]34C)[C@@H]1C[C@@H](Br)C2=O
InChI
InChIKey=CWVMWSZEMZOUPC-JUAXIXHSSA-N
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
16alpha-Bromoepiandrosterone (HE2000) is a synthetic steroid that limits non-productive inflammation, enhances protective immunity and improves survival in clinical studies of patients with human immunodeficiency virus (HIV), malaria and tuberculosis infections. HE 2000 had also shown activity in vitro against cytomegalovirus, polio, hepatitis B and C and influenza virus. 16alpha-Bromoepiandrosterone inhibits glucose-6-phosphate dehydrogenase (G6PD) and cell proliferation. HE 2000 was in phase II development for the Hepatitis B in Malaysia and Singapore, but it was suspended.
Originator
Approval Year
Sourcing
PubMed
Sample Use Guides
Mice: 16alpha-Bromoepiandrosterone (HE2000) or vehicle (0.1 ml) was delivered by various routes (s.c. injection, oral gavage or buccal administration) 24 h before and 1 h after bacterial challenge. When mice (three to five per group) treated orally with HE2000 (40 mg/kg given) were challenged with LPS, the numbers of infiltrating cells in BAL at 48 h were reduced significantly. HE2000 (120 mg/kg) increased significantly numbers of lymphocytes in the PLN 7 days after the footpad was injected with the compound and a nonsensitizing
dose of TNP–OVA.
Route of Administration:
Other
16alpha-Bromoepiandrosterone (HE2000) inhibits nitric oxide production by LPS-stimulated RAW 264·7 cells. HE2000 (0.03–3 uM) had no significant
effect on either cell proliferation or NO production by resting (unstimulated) RAW264·7 cells. HE2000 alone did not effect cell proliferation in LPS-stimulated cultures. When HE2000 was cultured with LPS-stimulated RAW264·7 cells for 6, 28 h or 48 h, a dose-dependent inhibition of NO production was observed. Optimal inhibition was observed at the 24-h time point. HE2000 appears to
limit NO production with an inhibitory concentration 50% (IC50) of approximately 1 uM.
ACTIVE MOIETY
