Identification
- Summary
Prasterone is a steroid formulated as a vaginal insert indicated for the treatment of moderate to severe dyspareunia associated with menopausal vulvar and vaginal atrophy.
- Brand Names
- Intrarosa
- Generic Name
- Prasterone
- DrugBank Accession Number
- DB01708
- Background
Prasterone, also known as dehydroepiandrosterone (DHEA) is a major C19 steroid produced by the adrenal cortex. It is also produced in small quantities in the testis and the ovary. Dehydroepiandrosterone (DHEA) can be converted to testosterone; androstenedione; estradiol; and estrone. Most of DHEA is sulfated (dehydroepiandrosterone sulfate) before secretion.
In the United States, DHEA or DHEAS have been advertised with claims that they may be beneficial for a wide variety of ailments. DHEA and DHEAS are readily available in the United States, where they are marketed as over-the-counter dietary supplements. In November 2016, DHEA was approved (as Intrarosa) to treat women experiencing moderate to severe pain during sexual intercourse (dyspareunia), a symptom of vulvar and vaginal atrophy (VVA), due to menopause.
In Canada, a prescription is required to buy DHEA.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Nutraceutical
- Structure
Structure for Prasterone (DB01708)
- Weight
- Average: 288.4244
Monoisotopic: 288.20893014 - Chemical Formula
- C19H28O2
- Synonyms
- 3-beta-hydroxy-5-androsten-17-one
- 3beta-hydroxyandrost-5-en-17-one
- 3β-hydroxyandrost-5-en-17-one
- Dehydroandrosterone
- Dehydroepiandrosterone
- Dehydroisoandrosterone
- DHEA
- Prasterone
Pharmacology
- Indication
DHEA is taken as a supplement for a variety of unsubstantiated indications. The following indications have shown promise and are backed up by some scientific evidence: schizophrenia (DHEA may be more effective in women than men); improving the appearance of older people’s skin (taking DHEA by mouth seems to increase skin thickness and moisture, and decrease facial “age spots” in elderly men and women); improving ability to achieve an erection in men with sexual dysfunction. Additionally, DHEA has shown promise in improving symptoms of lupus (SLE). Taking DHEA by mouth along with conventional treatment may help reduce the number of times symptoms flare up and may allow a reduction in the dose of prescription drugs needed. DHEA may also help SLE symptoms such as muscle ache and mouth ulcers. DHEA also seems to strengthen bones in SLE patients being treated with high-dose steroids (corticosteroids). DHEA also shows promise in the treatment of osteoporosis. Taking DHEA by mouth daily seems to improve bone mineral density (BMD) in older women and men with osteoporosis or osteopenia (pre-osteoporosis). DHEA may also increase BMD in young women with the eating disorder called anorexia nervosa. DHEA is often prescribed in India for the induction of ovulation to improve chances of pregnancy.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Moderate dyspareunia •••••••••••• •••••• Treatment of Severe dyspareunia •••••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
DHEA is naturally produced from cholesterol through two cytochrome P450 enzymes. Cholesterol is converted to pregnenolone by the enzyme P450 scc (side chain cleavage); then another enzyme, CYP17A1, converts pregnenolone to 17α-Hydroxypregnenolone and then to DHEA. DHEA is increased by exercise and calorie restriction. Some theorize that the increase in endogenous DHEA brought about by calorie restriction is partially responsible for the longer life expectancy known to be associated with calorie restriction.
- Mechanism of action
DHEA can be understood as a prohormone for the sex steroids. DHEAS may be viewed as buffer and reservoir. As most DHEA is produced by the zona reticularis of the adrenal cortex, it is argued that there is a role in the immune and stress response. DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia as it is produced nearly entirely by the adrenal glands. Women with polycystic ovary syndrome tend to have elevated levels of DHEAS.
Target Actions Organism UEstrogen receptor alpha binderHumans UEstrogen receptor beta activatorHumans UGABA(A) Receptor antagonistHumans UNMDA receptor agonistHumans UAndrogen receptor agonistHumans UPeroxisome proliferator-activated receptor alpha activatorHumans USigma non-opioid intracellular receptor 1 agonistHumans UNuclear receptor subfamily 1 group I member 2 activatorHumans UNuclear receptor subfamily 1 group I member 3 activatorHumans - Absorption
Following a 50-mg DHEA PO dose in cynomolgus monkeys, systemic availability was only 3.1 +/- 0.4%. [PMID: 12970301]
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic. As shown by their high conversion ratios (in a study involving cynomolgus monkeys), the major circulating metabolites of DHEA are DHEA-S, androsterone glucuronide, and androstane-3 alpha,17 beta-diol-glucuronide. [PMID: 12970301]
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- Route of elimination
Not Available
- Half-life
12 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Acute oral toxicity (LD50): >10000 mg/kg [Rat]. Lowest Published Toxic Dose (TDL) [Man] - Route: Oral; Dose: 10 mg/kg/2W intermittent.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Prasterone can be increased when it is combined with Abametapir. Apalutamide The serum concentration of Prasterone can be decreased when it is combined with Apalutamide. Avanafil The serum concentration of Avanafil can be increased when it is combined with Prasterone. Bosutinib The serum concentration of Bosutinib can be increased when it is combined with Prasterone. Capmatinib The serum concentration of Capmatinib can be increased when it is combined with Prasterone. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Biolaif / Fidelin (Paladin) / OVIGYN-D (Alembic Pharmaceuicals Ltd)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Intrarosa 6.5 mg Endoceutics S.A. 2020-12-22 Not applicable EU 
Intrarosa Insert 6.5 mg/1 Vaginal AMAG Pharmaceuticals, Inc. 2017-07-24 Not applicable US 
Intrarosa Insert 6.5 mg/1 Vaginal Millicent US, Inc. 2020-11-01 Not applicable US Intrarosa Insert 6.5 mg/1 Vaginal Endoceutics Inc. 2017-07-19 2017-07-19 US Intrarosa Insert 6.5 mg/1 Vaginal Millicent US, Inc. 2020-11-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Prastera Prasterone (200 mg/1) + Ibuprofen (400 mg/1) Kit Oral Health Science Funding, Llc 2014-04-04 Not applicable US
Categories
- ATC Codes
- G03EA03 — Prasterone and estrogen
- G03EA — Androgens and estrogens
- G03E — ANDROGENS AND FEMALE SEX HORMONES IN COMBINATION
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- G03XX — Other sex hormones and modulators of the genital system
- G03X — OTHER SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- 17-Ketosteroids
- Adjuvants, Immunologic
- Adrenal Cortex Hormones
- Alimentary Tract and Metabolism
- Anabolic Agents for Systemic Use
- Anabolic Steroids
- Androgens and Estrogens
- Androstan Derivatives
- Androstanes
- Androstenes
- Androstenols
- BCRP/ABCG2 Substrates
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates (strength unknown)
- Cytochrome P-450 CYP3A7 Inhibitors
- Cytochrome P-450 CYP3A7 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Gonadal Hormones
- Gonadal Steroid Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Immunologic Factors
- Ketosteroids
- OATP1B1/SLCO1B1 Substrates
- OATP1B3 substrates
- OATP2B1/SLCO2B1 substrates
- Sex Hormones and Modulators of the Genital System
- Steroids
- Testosterone Congeners
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Androstane steroids
- Direct Parent
- Androgens and derivatives
- Alternative Parents
- 3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / 17-oxosteroids / Delta-5-steroids / Secondary alcohols / Ketones / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
- Substituents
- 17-oxosteroid / 3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / 3-hydroxy-delta-5-steroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Carbonyl group / Cyclic alcohol
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 3beta-hydroxy steroid, 17-oxo steroid, androstanoid (CHEBI:28689) / C19 steroids (androgens) and derivatives, Androstane and derivatives, Androgens (C01227) / C19 steroids (androgens) and derivatives (LMST02020021)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 459AG36T1B
- CAS number
- 53-43-0
- InChI Key
- FMGSKLZLMKYGDP-USOAJAOKSA-N
- 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
- IUPAC Name
- (3aS,3bR,7S,9aR,9bS,11aS)-7-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-one
- SMILES
- [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@]([H])(O)CC[C@]12C
References
- Synthesis Reference
Isao Sugimoto, Yoko Sawase, "Stable preparation of water-soluble salts of dehydroepiandrosterone sulfate for parenteral administration." U.S. Patent US4061744, issued January, 1977.
US4061744- General References
- Baker WL, Karan S, Kenny AM: Effect of dehydroepiandrosterone on muscle strength and physical function in older adults: a systematic review. J Am Geriatr Soc. 2011 Jun;59(6):997-1002. doi: 10.1111/j.1532-5415.2011.03410.x. Epub 2011 Jun 7. [Article]
- Alkatib AA, Cosma M, Elamin MB, Erickson D, Swiglo BA, Erwin PJ, Montori VM: A systematic review and meta-analysis of randomized placebo-controlled trials of DHEA treatment effects on quality of life in women with adrenal insufficiency. J Clin Endocrinol Metab. 2009 Oct;94(10):3676-81. doi: 10.1210/jc.2009-0672. Epub 2009 Sep 22. [Article]
- Arlt W: Dehydroepiandrosterone and ageing. Best Pract Res Clin Endocrinol Metab. 2004 Sep;18(3):363-80. [Article]
- Wallace MB, Lim J, Cutler A, Bucci L: Effects of dehydroepiandrosterone vs androstenedione supplementation in men. Med Sci Sports Exerc. 1999 Dec;31(12):1788-92. [Article]
- Grimley Evans J, Malouf R, Huppert F, van Niekerk JK: Dehydroepiandrosterone (DHEA) supplementation for cognitive function in healthy elderly people. Cochrane Database Syst Rev. 2006 Oct 18;(4):CD006221. [Article]
- Fuller SJ, Tan RS, Martins RN: Androgens in the etiology of Alzheimer's disease in aging men and possible therapeutic interventions. J Alzheimers Dis. 2007 Sep;12(2):129-42. [Article]
- Thijs L, Fagard R, Forette F, Nawrot T, Staessen JA: Are low dehydroepiandrosterone sulphate levels predictive for cardiovascular diseases? A review of prospective and retrospective studies. Acta Cardiol. 2003 Oct;58(5):403-10. [Article]
- Barrett-Connor E, Khaw KT, Yen SS: A prospective study of dehydroepiandrosterone sulfate, mortality, and cardiovascular disease. N Engl J Med. 1986 Dec 11;315(24):1519-24. [Article]
- Arnlov J, Pencina MJ, Amin S, Nam BH, Benjamin EJ, Murabito JM, Wang TJ, Knapp PE, D'Agostino RB Sr, Bhasin S, Vasan RS: Endogenous sex hormones and cardiovascular disease incidence in men. Ann Intern Med. 2006 Aug 1;145(3):176-84. [Article]
- Crosbie D, Black C, McIntyre L, Royle PL, Thomas S: Dehydroepiandrosterone for systemic lupus erythematosus. Cochrane Database Syst Rev. 2007 Oct 17;(4):CD005114. [Article]
- Mattison JA, Lane MA, Roth GS, Ingram DK: Calorie restriction in rhesus monkeys. Exp Gerontol. 2003 Jan-Feb;38(1-2):35-46. [Article]
- Roberts E: The importance of being dehydroepiandrosterone sulfate (in the blood of primates): a longer and healthier life? Biochem Pharmacol. 1999 Feb 15;57(4):329-46. [Article]
- Leblanc M, Labrie C, Belanger A, Candas B, Labrie F: Bioavailability and pharmacokinetics of dehydroepiandrosterone in the cynomolgus monkey. J Clin Endocrinol Metab. 2003 Sep;88(9):4293-302. [Article]
- Casson PR, Lindsay MS, Pisarska MD, Carson SA, Buster JE: Dehydroepiandrosterone supplementation augments ovarian stimulation in poor responders: a case series. Hum Reprod. 2000 Oct;15(10):2129-32. [Article]
- Chang DM, Lan JL, Lin HY, Luo SF: Dehydroepiandrosterone treatment of women with mild-to-moderate systemic lupus erythematosus: a multicenter randomized, double-blind, placebo-controlled trial. Arthritis Rheum. 2002 Nov;46(11):2924-7. [Article]
- The NIH National Library of Medicine [Link]
- INTRAROSA™ FDA Label [Link]
- External Links
- Human Metabolome Database
- HMDB0000077
- KEGG Drug
- D08409
- KEGG Compound
- C01227
- PubChem Compound
- 5881
- PubChem Substance
- 46508824
- ChemSpider
- 5670
- BindingDB
- 50223368
- 3143
- ChEBI
- 28689
- ChEMBL
- CHEMBL90593
- ZINC
- ZINC000003807917
- Therapeutic Targets Database
- DNC001146
- PharmGKB
- PA451993
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- AND
- Wikipedia
- Dehydroepiandrosterone
- PDB Entries
- 1coy / 1e3r / 1j99 / 1q22 / 3dhe / 7xkd / 7xke / 7xkf
- MSDS
- Download (19.8 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Other Atrophy of vulva / Breast Cancer / Genitourinary Syndrome of Menopause (GSM) 1 4 Completed Treatment Infertility 1 4 Completed Treatment Painful Intercourse 1 4 Recruiting Treatment Breast Cancer / Vulvo Vaginal Atrophy 1 4 Recruiting Treatment Genitourinary Syndrome of Menopause (GSM) / Vulvo Vaginal Atrophy 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Insert Vaginal 6.5 mg Insert Vaginal 6.5 mg/1 Kit Oral - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8268806 No 2012-09-18 2031-03-19 US US8629129 No 2014-01-14 2028-08-07 US US8957054 No 2015-02-17 2028-08-07 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 140-141 °C PhysProp water solubility 63.5 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 3.23 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.0438 mg/mL ALOGPS logP 3.53 ALOGPS logP 3.36 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 18.2 Chemaxon pKa (Strongest Basic) -1.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 84.66 m3·mol-1 Chemaxon Polarizability 34.1 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9611 Caco-2 permeable + 0.8816 P-glycoprotein substrate Substrate 0.6176 P-glycoprotein inhibitor I Inhibitor 0.6272 P-glycoprotein inhibitor II Non-inhibitor 0.9014 Renal organic cation transporter Non-inhibitor 0.7596 CYP450 2C9 substrate Non-substrate 0.8415 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.7404 CYP450 1A2 substrate Non-inhibitor 0.9313 CYP450 2C9 inhibitor Non-inhibitor 0.9672 CYP450 2D6 inhibitor Non-inhibitor 0.9476 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8399 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9013 Ames test Non AMES toxic 0.9382 Carcinogenicity Non-carcinogens 0.947 Biodegradation Not ready biodegradable 0.8998 Rat acute toxicity 1.5214 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8861 hERG inhibition (predictor II) Non-inhibitor 0.7176
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 176.9786819 predictedDarkChem Lite v0.1.0 [M-H]- 177.7842819 predictedDarkChem Lite v0.1.0 [M-H]- 176.9476819 predictedDarkChem Lite v0.1.0 [M-H]- 171.50917 predictedDeepCCS 1.0 (2019) [M+H]+ 177.5253819 predictedDarkChem Lite v0.1.0 [M+H]+ 178.4732819 predictedDarkChem Lite v0.1.0 [M+H]+ 177.5613819 predictedDarkChem Lite v0.1.0 [M+H]+ 173.59688 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.0259819 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.2582819 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.9559819 predictedDarkChem Lite v0.1.0 [M+Na]+ 179.57912 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- Chen F, Knecht K, Birzin E, Fisher J, Wilkinson H, Mojena M, Moreno CT, Schmidt A, Harada S, Freedman LP, Reszka AA: Direct agonist/antagonist functions of dehydroepiandrosterone. Endocrinology. 2005 Nov;146(11):4568-76. Epub 2005 Jun 30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
- Gene Name
- ESR2
- Uniprot ID
- Q92731
- Uniprot Name
- Estrogen receptor beta
- Molecular Weight
- 59215.765 Da
References
- Chen F, Knecht K, Birzin E, Fisher J, Wilkinson H, Mojena M, Moreno CT, Schmidt A, Harada S, Freedman LP, Reszka AA: Direct agonist/antagonist functions of dehydroepiandrosterone. Endocrinology. 2005 Nov;146(11):4568-76. Epub 2005 Jun 30. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Sousa A, Ticku MK: Interactions of the neurosteroid dehydroepiandrosterone sulfate with the GABA(A) receptor complex reveals that it may act via the picrotoxin site. J Pharmacol Exp Ther. 1997 Aug;282(2):827-33. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Voltage-gated cation channel activity
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
Components:
References
- Compagnone NA, Mellon SH: Dehydroepiandrosterone: a potential signalling molecule for neocortical organization during development. Proc Natl Acad Sci U S A. 1998 Apr 14;95(8):4678-83. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 98987.9 Da
References
- Chen F, Knecht K, Birzin E, Fisher J, Wilkinson H, Mojena M, Moreno CT, Schmidt A, Harada S, Freedman LP, Reszka AA: Direct agonist/antagonist functions of dehydroepiandrosterone. Endocrinology. 2005 Nov;146(11):4568-76. Epub 2005 Jun 30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Zinc ion binding
- Specific Function
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
- Gene Name
- PPARA
- Uniprot ID
- Q07869
- Uniprot Name
- Peroxisome proliferator-activated receptor alpha
- Molecular Weight
- 52224.595 Da
References
- Kohalmy K, Tamasi V, Kobori L, Sarvary E, Pascussi JM, Porrogi P, Rozman D, Prough RA, Meyer UA, Monostory K: Dehydroepiandrosterone induces human CYP2B6 through the constitutive androstane receptor. Drug Metab Dispos. 2007 Sep;35(9):1495-501. Epub 2007 Jun 25. [Article]
- Tamasi V, Miller KK, Ripp SL, Vila E, Geoghagen TE, Prough RA: Modulation of receptor phosphorylation contributes to activation of peroxisome proliferator activated receptor alpha by dehydroepiandrosterone and other peroxisome proliferators. Mol Pharmacol. 2008 Mar;73(3):968-76. Epub 2007 Dec 13. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma m...
- Gene Name
- SIGMAR1
- Uniprot ID
- Q99720
- Uniprot Name
- Sigma non-opioid intracellular receptor 1
- Molecular Weight
- 25127.52 Da
References
- Waterhouse RN, Chang RC, Atuehene N, Collier TL: In vitro and in vivo binding of neuroactive steroids to the sigma-1 receptor as measured with the positron emission tomography radioligand [18F]FPS. Synapse. 2007 Jul;61(7):540-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- Kohalmy K, Tamasi V, Kobori L, Sarvary E, Pascussi JM, Porrogi P, Rozman D, Prough RA, Meyer UA, Monostory K: Dehydroepiandrosterone induces human CYP2B6 through the constitutive androstane receptor. Drug Metab Dispos. 2007 Sep;35(9):1495-501. Epub 2007 Jun 25. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Zinc ion binding
- Specific Function
- Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital re...
- Gene Name
- NR1I3
- Uniprot ID
- Q14994
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 3
- Molecular Weight
- 39942.145 Da
References
- Kohalmy K, Tamasi V, Kobori L, Sarvary E, Pascussi JM, Porrogi P, Rozman D, Prough RA, Meyer UA, Monostory K: Dehydroepiandrosterone induces human CYP2B6 through the constitutive androstane receptor. Drug Metab Dispos. 2007 Sep;35(9):1495-501. Epub 2007 Jun 25. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Torimoto N, Ishii I, Toyama K, Hata M, Tanaka K, Shimomura H, Nakamura H, Ariyoshi N, Ohmori S, Kitada M: Helices F-G are important for the substrate specificities of CYP3A7. Drug Metab Dispos. 2007 Mar;35(3):484-92. doi: 10.1124/dmd.106.011304. Epub 2006 Dec 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Testosterone dehydrogenase (nad+) activity
- Specific Function
- Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
- Gene Name
- HSD17B1
- Uniprot ID
- P14061
- Uniprot Name
- Estradiol 17-beta-dehydrogenase 1
- Molecular Weight
- 34949.715 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Hilborn E, Stal O, Jansson A: Estrogen and androgen-converting enzymes 17beta-hydroxysteroid dehydrogenase and their involvement in cancer: with a special focus on 17beta-hydroxysteroid dehydrogenase type 1, 2, and breast cancer. Oncotarget. 2017 May 2;8(18):30552-30562. doi: 10.18632/oncotarget.15547. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sulfotransferase activity
- Specific Function
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
- Gene Name
- SULT2A1
- Uniprot ID
- Q06520
- Uniprot Name
- Bile salt sulfotransferase
- Molecular Weight
- 33779.57 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Dawson PA, Setchell KDR: Will the real bile acid sulfotransferase please stand up? Identification of Sult2a8 as a major hepatic bile acid sulfonating enzyme in mice. J Lipid Res. 2017 Jun;58(6):1033-1035. doi: 10.1194/jlr.C077420. Epub 2017 Apr 28. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid sulfotransferase activity
- Specific Function
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulf...
- Gene Name
- SULT2B1
- Uniprot ID
- O00204
- Uniprot Name
- Sulfotransferase family cytosolic 2B member 1
- Molecular Weight
- 41307.32 Da
References
- Alherz FA, El Daibani AA, Abunnaja MS, Bairam AF, Rasool MI, Sakakibara Y, Suiko M, Kurogi K, Liu MC: Effect of SULT2B1 genetic polymorphisms on the sulfation of dehydroepiandrosterone and pregnenolone by SULT2B1b allozymes. Mol Cell Endocrinol. 2019 Oct 1;496:110535. doi: 10.1016/j.mce.2019.110535. Epub 2019 Aug 7. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid delta-isomerase activity
- Specific Function
- 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system pl...
- Gene Name
- HSD3B1
- Uniprot ID
- P14060
- Uniprot Name
- 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1
- Molecular Weight
- 42251.25 Da
References
- Dumont M, Luu-The V, Dupont E, Pelletier G, Labrie F: Characterization, expression, and immunohistochemical localization of 3 beta-hydroxysteroid dehydrogenase/delta 5-delta 4 isomerase in human skin. J Invest Dermatol. 1992 Oct;99(4):415-21. [Article]
- Lorence MC, Murry BA, Trant JM, Mason JI: Human 3 beta-hydroxysteroid dehydrogenase/delta 5----4isomerase from placenta: expression in nonsteroidogenic cells of a protein that catalyzes the dehydrogenation/isomerization of C21 and C19 steroids. Endocrinology. 1990 May;126(5):2493-8. [Article]
- Kind
- Protein
- Organism
- Brevibacterium sterolicum
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid delta-isomerase activity
- Specific Function
- Catalyzes the oxidation and isomerization of cholesterol to cholestenone (4-cholesten-3-one), which is an initial step in the cholesterol degradation process.
- Gene Name
- choB
- Uniprot ID
- P22637
- Uniprot Name
- Cholesterol oxidase
- Molecular Weight
- 59357.765 Da
References
- Pollegioni L, Piubelli L, Molla G: Cholesterol oxidase: biotechnological applications The Febs Journal. 2009 Nov 16;276(23):6857-6870. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Product of
- General Function
- Steroid 17-alpha-monooxygenase activity
- Specific Function
- Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation ...
- Gene Name
- CYP17A1
- Uniprot ID
- P05093
- Uniprot Name
- Steroid 17-alpha-hydroxylase/17,20 lyase
- Molecular Weight
- 57369.995 Da
References
- Guengerich FP, Wilkey CJ, Glass SM, Reddish MJ: Conformational selection dominates binding of steroids to human cytochrome P450 17A1. J Biol Chem. 2019 Jun 28;294(26):10028-10041. doi: 10.1074/jbc.RA119.008860. Epub 2019 May 9. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Cho E, Montgomery RB, Mostaghel EA: Minireview: SLCO and ABC transporters: a role for steroid transport in prostate cancer progression. Endocrinology. 2014 Nov;155(11):4124-32. doi: 10.1210/en.2014-1337. Epub 2014 Aug 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Cho E, Montgomery RB, Mostaghel EA: Minireview: SLCO and ABC transporters: a role for steroid transport in prostate cancer progression. Endocrinology. 2014 Nov;155(11):4124-32. doi: 10.1210/en.2014-1337. Epub 2014 Aug 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Cho E, Montgomery RB, Mostaghel EA: Minireview: SLCO and ABC transporters: a role for steroid transport in prostate cancer progression. Endocrinology. 2014 Nov;155(11):4124-32. doi: 10.1210/en.2014-1337. Epub 2014 Aug 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Cho E, Montgomery RB, Mostaghel EA: Minireview: SLCO and ABC transporters: a role for steroid transport in prostate cancer progression. Endocrinology. 2014 Nov;155(11):4124-32. doi: 10.1210/en.2014-1337. Epub 2014 Aug 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Transporter activity
- Specific Function
- Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
- Gene Name
- ABCC1
- Uniprot ID
- P33527
- Uniprot Name
- Multidrug resistance-associated protein 1
- Molecular Weight
- 171589.5 Da
References
- Cho E, Montgomery RB, Mostaghel EA: Minireview: SLCO and ABC transporters: a role for steroid transport in prostate cancer progression. Endocrinology. 2014 Nov;155(11):4124-32. doi: 10.1210/en.2014-1337. Epub 2014 Aug 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- Cho E, Montgomery RB, Mostaghel EA: Minireview: SLCO and ABC transporters: a role for steroid transport in prostate cancer progression. Endocrinology. 2014 Nov;155(11):4124-32. doi: 10.1210/en.2014-1337. Epub 2014 Aug 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Atpase activity, coupled to transmembrane movement of substances
- Specific Function
- May be an organic anion pump relevant to cellular detoxification.
- Gene Name
- ABCC4
- Uniprot ID
- O15439
- Uniprot Name
- Multidrug resistance-associated protein 4
- Molecular Weight
- 149525.33 Da
References
- Cho E, Montgomery RB, Mostaghel EA: Minireview: SLCO and ABC transporters: a role for steroid transport in prostate cancer progression. Endocrinology. 2014 Nov;155(11):4124-32. doi: 10.1210/en.2014-1337. Epub 2014 Aug 22. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 21, 2024 02:33