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Details

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
Structure of 16.ALPHA.-BROMOANDROSTERONE

SMILES

[H][C@@]12C[C@@H](Br)C(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])C[C@H](O)CC[C@]34C

InChI

InChIKey=CWVMWSZEMZOUPC-LLIWRYSGSA-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

HIDE SMILES / InChI

Molecular Formula C19H29BrO2
Molecular Weight 369.336
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Reduction of parasite levels in patients with uncomplicated malaria by treatment with HE2000.
2007 Feb
16alpha-Bromoepiandrosterone (HE2000) limits non-productive inflammation and stimulates immunity in lungs.
2009 Dec
A new parasiticidal compound in T. solium cysticercosis.
2013
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Humans: patients with malaria were hospitalized and given seven consecutive daily 100-mg doses of HE2000 without concomitant anti-malarial drugs. Intramuscular injections were given as one or two injections in different locations in the deltoid muscle. Buccomucosal dosing was administered with four tablets (25 mg each) inserted between the lower gingival surfaces of the gum and buccal mucosa of the cheek. https://www.ncbi.nlm.nih.gov/pubmed/17297029
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:20:50 GMT 2023
Edited
by admin
on Sat Dec 16 10:20:50 GMT 2023
Record UNII
VZN6G84SJQ
Record Status Validated (UNII)
Record Version
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Name Type Language
16.ALPHA.-BROMOANDROSTERONE
Common Name English
ANDROSTAN-17-ONE, 16-BROMO-3-HYDROXY-, (3.ALPHA.,5.ALPHA.,16.ALPHA.)-
Systematic Name English
ANDROSTERONE, 16.ALPHA.-BROMO-
Common Name English
Code System Code Type Description
FDA UNII
VZN6G84SJQ
Created by admin on Sat Dec 16 10:20:50 GMT 2023 , Edited by admin on Sat Dec 16 10:20:50 GMT 2023
PRIMARY
PUBCHEM
69872672
Created by admin on Sat Dec 16 10:20:50 GMT 2023 , Edited by admin on Sat Dec 16 10:20:50 GMT 2023
PRIMARY
CAS
59462-53-2
Created by admin on Sat Dec 16 10:20:50 GMT 2023 , Edited by admin on Sat Dec 16 10:20:50 GMT 2023
PRIMARY