PRASTERONE

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Search structure


Trade Names	INTRAROSA
Synonyms	Biolaif Dehydroandrosterone Dehydroepiandrosterone Dehydroisoandrosterone Dhea EM-760 Enzymatic therapy Intrarosa NSC-9896 Natrol dhea Prasterone Vaginorm
Status
Molecule Category	UNKNOWN
ATC	A14AA07 G03XX01
UNII	459AG36T1B
EPA CompTox	DTXSID4020379


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	FMGSKLZLMKYGDP-USOAJAOKSA-N
Smiles	C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
InChI	InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H28O2
Molecular Weight	288.43
AlogP	3.88
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	0.0
Polar Surface Area	37.3
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	21.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of LPS-induced TNFalpha production in mouse J774A.1 cells	Mus musculus	141.0 nM
Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding globulin	Homo sapiens	14.45 nM
Inhibition of G6PD-mediated NADPH production in mouse 3T3-L1 cells at above 100 umol/L	Mus musculus	40.0 %
Neuroprotective activity in rat PC12 cells assessed as inhibition of serum deprivation-induced apoptosis after 24 hrs by APO Percentage apoptosis assay	Rattus norvegicus	0.29 nM
Displacement of [3H]DHEA from DHEA-binding site in rat PC12 cell membranes by gamma-scintillation counting	Rattus norvegicus	1.65 nM
Inhibition of human 17beta-HSD7 expressed in HEK293 cells assessed as inhibition of reduction of [14C]estrone into [14C]estradiol at 0.3 uM after 7 hrs	Homo sapiens	5.7 %
Inhibition of human 17beta-HSD7 expressed in HEK293 cells assessed as inhibition of reduction of [14C]estrone into [14C]estradiol at 3 uM after 7 hrs	Homo sapiens	12.1 %
Antiinflammatory activity in LPS-stimulated mouse BV2 cells assessed as inhibition of NO production at 40 uM after 24 hrs by Griess method relative to control	Mus musculus	55.3 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	13.56 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	2.6 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	10.09 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	11.37 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	27.01 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	14.47 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	2.55 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-0.69 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	6.528 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.01 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.01 %

Related Entries

Cross References

Resources	Reference
ChEBI	28689
ChEMBL	CHEMBL90593
DrugBank	DB01708
DrugCentral	795
FDA SRS	459AG36T1B
Human Metabolome Database	HMDB0000077
Guide to Pharmacology	2370
KEGG	C01227
PDB	AND
PharmGKB	PA451993
PubChem	5881
SureChEMBL	SCHEMBL24156
ZINC	ZINC000003807917

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).