Identification

Name
Prasterone sulfate
Accession Number
DB05804
Type
Small Molecule
Groups
Investigational
Description

DHEA sulfate is the major steroid of the fetal adrenal. DHEA-S is the principal adrenal androgen and is secreted together with cortisol under the control of ACTH and prolactin. DHEA-S is elevated with hyperprolactinemia.

Structure
Thumb
Synonyms
  • (3-beta)-3-(Sulfooxy)androst-5-en-17-one
  • 17-Ketoandrost-5-en-3beta-yl sulfate
  • 17-oxoandrost-5-en-3β-yl hydrogen sulphate
  • 3-O-Sulfodehydroepiandrosterone
  • 3beta-Hydroxyandrost-5-en-17-one 3-sulfate
  • Androst-5-en-17-on-3beta-yl sulfuric acid
  • Dehydroepiandrosterone 3-sulfate
  • Dehydroepiandrosterone monosulfate
  • Dehydroepiandrosterone sulfate
  • Dehydroepiandrosterone sulphate
  • Dehydroisoandrosterone sulfate
  • Dehydroisoandrosterone-3-sulfate
  • DHEA sulfate
  • DHEA sulphate
  • DHEA-S
  • Prasterone sulphate
International/Other Brands
Inflarest
Categories
UNII
57B09Q7FJR
CAS number
651-48-9
Weight
Average: 368.488
Monoisotopic: 368.165744696
Chemical Formula
C19H28O5S
InChI Key
CZWCKYRVOZZJNM-USOAJAOKSA-N
InChI
InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1
IUPAC Name
[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonic acid
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O

Pharmacology

Indication

Investigated for use/treatment in asthma and burns and burn infections.

Pharmacodynamics
Not Available
Mechanism of action

The low levels of dehydroepiandrosterone sulfate(DHEA-S)is associated with unfavorable levels of several strong cardiovascular disease risk factors, such as lipids and blood pleasure, which are components of the metabolic syndrome, and insulin levels. DHEA-S deficiency is risk factors of obesity and insulin resistance, but it is not clear, whether this possible influence is independent.

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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Androgen and Estrogen MetabolismMetabolic
17-beta Hydroxysteroid Dehydrogenase III DeficiencyDisease
Aromatase DeficiencyDisease
Androgen and Estrogen MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Prasterone sulfate.
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Prasterone sulfate is combined with 1,10-Phenanthroline.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Prasterone sulfate.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Prasterone sulfate.
AlclofenacThe risk or severity of adverse effects can be increased when Alclofenac is combined with Prasterone sulfate.
AlclometasoneThe risk or severity of edema formation can be increased when Prasterone sulfate is combined with Alclometasone.
AlmasilateThe bioavailability of Prasterone sulfate can be decreased when combined with Almasilate.
AlminoprofenThe risk or severity of adverse effects can be increased when Alminoprofen is combined with Prasterone sulfate.
AloglutamolThe bioavailability of Prasterone sulfate can be decreased when combined with Aloglutamol.
AloxiprinThe risk or severity of adverse effects can be increased when Aloxiprin is combined with Prasterone sulfate.
Food Interactions
Not Available

References

General References
  1. Altman R, Motton DD, Kota RS, Rutledge JC: Inhibition of vascular inflammation by dehydroepiandrosterone sulfate in human aortic endothelial cells: roles of PPARalpha and NF-kappaB. Vascul Pharmacol. 2008 Feb-Mar;48(2-3):76-84. doi: 10.1016/j.vph.2007.12.002. Epub 2007 Dec 15. [PubMed:18255343]
  2. Rabijewski M, Papierska L, Kozakowski J, Zgliczynski W: [The relationship between androgens concentrations (testosterone and dehydroepiandrosterone sulfate) and metabolic syndrome in non-obese elderly men]. Endokrynol Pol. 2007 Nov-Dec;58(6):496-504. [PubMed:18205106]
  3. Geyer J, Doring B, Meerkamp K, Ugele B, Bakhiya N, Fernandes CF, Godoy JR, Glatt H, Petzinger E: Cloning and functional characterization of human sodium-dependent organic anion transporter (SLC10A6). J Biol Chem. 2007 Jul 6;282(27):19728-41. Epub 2007 May 9. [PubMed:17491011]
External Links
Human Metabolome Database
HMDB0001032
KEGG Compound
C04555
PubChem Compound
12594
PubChem Substance
175427036
ChemSpider
12074
BindingDB
50375559
ChEBI
16814
ChEMBL
CHEMBL259898
Wikipedia
Dehydroepiandrosterone_sulfate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3CompletedTreatmentMinor burns1
3SuspendedTreatmentPlasmodium Infections1

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
PropertyValueSource
Water Solubility0.00806 mg/mLALOGPS
logP0.49ALOGPS
logP3.42ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.65 m3·mol-1ChemAxon
Polarizability39.86 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.996
Blood Brain Barrier+0.9388
Caco-2 permeable-0.6601
P-glycoprotein substrateNon-substrate0.507
P-glycoprotein inhibitor IInhibitor0.6926
P-glycoprotein inhibitor IINon-inhibitor0.9548
Renal organic cation transporterNon-inhibitor0.7909
CYP450 2C9 substrateNon-substrate0.8322
CYP450 2D6 substrateNon-substrate0.8338
CYP450 3A4 substrateSubstrate0.6799
CYP450 1A2 substrateNon-inhibitor0.8203
CYP450 2C9 inhibitorNon-inhibitor0.84
CYP450 2D6 inhibitorNon-inhibitor0.882
CYP450 2C19 inhibitorNon-inhibitor0.8117
CYP450 3A4 inhibitorNon-inhibitor0.9481
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7575
Ames testNon AMES toxic0.5802
CarcinogenicityNon-carcinogens0.586
BiodegradationNot ready biodegradable0.9519
Rat acute toxicity2.4168 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5859
hERG inhibition (predictor II)Inhibitor0.5409
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Sulfated steroids
Direct Parent
Sulfated steroids
Alternative Parents
Androstane steroids / 17-oxosteroids / Delta-5-steroids / Sulfuric acid monoesters / Alkyl sulfates / Ketones / Organic oxides / Hydrocarbon derivatives
Substituents
Sulfated steroid skeleton / Androstane-skeleton / 17-oxosteroid / Oxosteroid / Delta-5-steroid / Sulfuric acid ester / Alkyl sulfate / Sulfuric acid monoester / Sulfate-ester / Organic sulfuric acid or derivatives
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
steroid sulfate, 17-oxo steroid (CHEBI:16814) / sulfates, C19 steroids (androgens) and derivatives, Androgens (C04555) / Sulfates (LMST05020010)

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Jones ME, Boon WC, McInnes K, Maffei L, Carani C, Simpson ER: Recognizing rare disorders: aromatase deficiency. Nat Clin Pract Endocrinol Metab. 2007 May;3(5):414-21. [PubMed:17452968]
  2. ElBeltagy K, Honda K, Ozaki K, Misugi T, Tokuyama O, Kimura M, Kira Y, Ishiko O: In vitro effect of dehydroepiandrosterone sulfate on steroid receptors, aromatase, cyclooxygenase-2 expression, and steroid hormone production in preovulatory human granulosa cells. Fertil Steril. 2007 Oct;88(4 Suppl):1135-42. Epub 2007 Jun 4. [PubMed:17548088]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Bacsi K, Kosa JP, Borgulya G, Balla B, Lazary A, Nagy Z, Horvath C, Speer G, Lakatos P: CYP3A7*1C polymorphism, serum dehydroepiandrosterone sulfate level, and bone mineral density in postmenopausal women. Calcif Tissue Int. 2007 Mar;80(3):154-9. Epub 2007 Mar 3. [PubMed:17334880]
  2. Smit P, van Schaik RH, van der Werf M, van den Beld AW, Koper JW, Lindemans J, Pols HA, Brinkmann AO, de Jong FH, Lamberts SW: A common polymorphism in the CYP3A7 gene is associated with a nearly 50% reduction in serum dehydroepiandrosterone sulfate levels. J Clin Endocrinol Metab. 2005 Sep;90(9):5313-6. Epub 2005 Jun 28. [PubMed:15985487]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. ElBeltagy K, Honda K, Ozaki K, Misugi T, Tokuyama O, Kimura M, Kira Y, Ishiko O: In vitro effect of dehydroepiandrosterone sulfate on steroid receptors, aromatase, cyclooxygenase-2 expression, and steroid hormone production in preovulatory human granulosa cells. Fertil Steril. 2007 Oct;88(4 Suppl):1135-42. Epub 2007 Jun 4. [PubMed:17548088]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [PubMed:11306713]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-dependent organic anion transmembrane transporter activity
Specific Function
Transports sulfoconjugated steroid hormones, as well as taurolithocholic acid-3-sulfate and sulfoconjugated pyrenes in a sodium-dependent manner.
Gene Name
SLC10A6
Uniprot ID
Q3KNW5
Uniprot Name
Solute carrier family 10 member 6
Molecular Weight
41258.24 Da
References
  1. Geyer J, Doring B, Meerkamp K, Ugele B, Bakhiya N, Fernandes CF, Godoy JR, Glatt H, Petzinger E: Cloning and functional characterization of human sodium-dependent organic anion transporter (SLC10A6). J Biol Chem. 2007 Jul 6;282(27):19728-41. Epub 2007 May 9. [PubMed:17491011]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]

Drug created on November 18, 2007 11:27 / Updated on August 15, 2018 09:53