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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-20 22:13:30 UTC
Update Date2018-05-20 08:51:03 UTC
HMDB IDHMDB0001830
Secondary Accession Numbers
  • HMDB01830
Metabolite Identification
Common NameProgesterone
DescriptionThe major progestational steroid that is secreted primarily by the corpus luteum and the placenta. Progesterone acts on the uterus, the mammary glands and the brain. It is required in embryo implantation, pregnancy maintenance, and the development of mammary tissue for milk production. Progesterone, converted from pregnenolone, also serves as an intermediate in the biosynthesis of gonadal steroid hormones and adrenal corticosteroids (Pubchem). Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestagens, and is the major naturally occurring human progestagen (Wikipedia). During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine smooth muscle. The fetus metabolizes placental progesterone in the production of adrenal mineralo- and glucosteroids. A drop in progesterone levels is possibly one step that facilitates the onset of labor. In addition progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production (Wikipedia). Progesterone is found to be associated with pregnene hydroxylation deficiency, which is an inborn error of metabolism.
Structure
Thumb
Synonyms
ValueSource
(S)-4-Pregnene-3,20-dioneChEBI
(S)-Pregn-4-en-3,20-dioneChEBI
(S)-ProgesteroneChEBI
17alpha-ProgesteroneChEBI
4-Pregnene-3,20-dioneChEBI
AgolutinChEBI
AkrolutinChEBI
Corpus luteum hormoneChEBI
CrinoneChEBI
Delta(4)-Pregnene-3,20-dioneChEBI
GelbkoerperhormonChEBI
LuteohormoneChEBI
ProgesteronChEBI
17a-ProgesteroneGenerator
17α-progesteroneGenerator
δ(4)-pregnene-3,20-dioneGenerator
3,20-Pregnene-4HMDB
4-Pregnen-3,20-dioneHMDB
beta-ProgesteroneHMDB
bio-LutonHMDB
CIDRHMDB
ColprosteroneHMDB
CorlutinHMDB
CorlutinaHMDB
CorluviteHMDB
CorporinHMDB
Crinone progesterone gelHMDB
CurretabHMDB
CyclogestHMDB
CyclogesterinHMDB
D4-Pregnene-3,20-dioneHMDB
DelalutinHMDB
DuraprogenHMDB
EstimaHMDB
FlavolutanHMDB
FologenonHMDB
GesterolHMDB
Gesterol 100HMDB
Gesterol 50HMDB
GestironHMDB
GestoneHMDB
GestormoneHMDB
GestronHMDB
GlanducorpinHMDB
GynlutinHMDB
GynolutonHMDB
GynolutoneHMDB
HormoflaveineHMDB
HormolutonHMDB
Hydroxyprogesterone caproateHMDB
Hydroxyprogesterone caproic acidHMDB
LingusorbsHMDB
lipo-LutinHMDB
LucorteumHMDB
Lucorteum solHMDB
LugesteronHMDB
Luteal hormoneHMDB
Luteocrin normaleHMDB
LuteodynHMDB
LuteoganHMDB
LuteolHMDB
LuteopurHMDB
LuteosanHMDB
LuteostabHMDB
LuteovisHMDB
LuteumHMDB
LutexHMDB
LutidonHMDB
LutociclinaHMDB
Lutocuclin mHMDB
LutocyclinHMDB
Lutocyclin mHMDB
LutocylinHMDB
LutocylolHMDB
LutoformHMDB
LutogylHMDB
LutrenHMDB
LutromoneHMDB
MembrettesHMDB
MethylpregnoneHMDB
MPAHMDB
NalutronHMDB
PercutacrineHMDB
Percutacrine luteiniqueHMDB
PiapononHMDB
PranoneHMDB
Pregn-4-en-3,20-dioneHMDB
Pregn-4-ene-3,20-dioneHMDB
Pregnene-3,20-dioneHMDB
PregnenedioneHMDB
PrimolutHMDB
ProchieveHMDB
ProgeffikHMDB
ProgekanHMDB
ProgestanHMDB
ProgestasertHMDB
ProgesterolHMDB
ProgesteronumHMDB
ProgestinHMDB
ProgestogelHMDB
ProgestolHMDB
ProgestonHMDB
ProgestoneHMDB
ProgestosolHMDB
ProgestronHMDB
ProgestronolHMDB
ProjestajectHMDB
ProletsHMDB
ProlidonHMDB
ProlutinHMDB
ProlutonHMDB
ProlutoneHMDB
PrometriumHMDB
ProntogestHMDB
ProtormoneHMDB
SyngesteroneHMDB
SyngestretsHMDB
Synovex SHMDB
SyntolutanHMDB
UtrogestHMDB
UtrogestanHMDB
VitarrineHMDB
Progesterone, (13 alpha,17 alpha)-(+-)-isomerMeSH
Progesterone, (17 alpha)-isomerMeSH
Progesterone, (9 beta,10 alpha)-isomerMeSH
Chemical FormulaC21H30O2
Average Molecular Weight314.4617
Monoisotopic Molecular Weight314.224580204
IUPAC Name(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Nameprogesterone
CAS Registry Number57-83-0
SMILES
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1
InChI KeyRJKFOVLPORLFTN-LEKSSAKUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point121 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0088 mg/mL at 25 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP3.87HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0055 g/LALOGPS
logP3.58ALOGPS
logP4.15ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)18.92ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.71 m³·mol⁻¹ChemAxon
Polarizability37.15 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fbc-5910000000-422e38df6de7e8b0a4b7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fbc-5910000000-385f45345742235da8e0View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-024l-6923000000-639c7405f69825de7f90View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0229-2941000000-1e075d8489b79cf4e34aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0229-3963000000-f35e3d9faf6b2ee87465View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fbc-5910000000-422e38df6de7e8b0a4b7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fbc-5910000000-385f45345742235da8e0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6x-2910000000-1baafb91a3e0b988caa7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000g-1590000000-3ebb52b90c541e38c0b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-1009000000-0f8b7c3e6c2265c3889fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-8900000000-0b0167121b798e7e7534View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9400000000-881510cbcecd9cb61f4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-024l-6923000000-639c7405f69825de7f90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0229-2941000000-1e075d8489b79cf4e34aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0950000000-ca28d8dfdf780c201716View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-1900000000-857f6720dd17fb2547d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-3930000000-fda87095285a83b85ad5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-7955000000-a22f06eac940cd4f753dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0139000000-6b47f75a44df3e20fa3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0aba-0950000000-b26d04d179294aa67cc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0aba-0920000000-d0a3365efe1f8a589564View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05aj-0910000000-61d7a07e6be85600e1f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0009000000-67c6f0147801f0ece957View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05mk-8956000000-aa5fe992c41261b62fbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052b-6910000000-5e26497eb2d0150a30acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4j-8900000000-7ca6fd15f0ccc18bfa31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052b-9700000000-523fe1ad11bfcbb46f85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-054k-9400000000-e3d581bd8685e1d3f35dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0269000000-9aa25f8d44bc44ee4d4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06dj-0491000000-c312ac322a549be24facView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbc-2290000000-859101eb546be9ddc938View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-e021f799bd2d232a0592View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0049000000-55066424591bf87a4a49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1090000000-e9387b8ab692f5ef9083View in MoNA
MSMass Spectrum (Electron Ionization)splash10-006x-7931000000-f6ad83adccd7e016fa29View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Adipose Tissue
  • Fibroblasts
  • Gonads
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000320 - 0.0795 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0 - 0.000320 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00267-0.0432 uMNewborn (0-30 days old)Female
Normal
details
BloodDetected and Quantified0.0019 (0.0-0.0038) uMAdult (>18 years old)MaleNormal
    • The Merck Manual,...
details
BloodDetected and Quantified0.0020 (0.00-0.0045) uMAdult (>18 years old)FemaleNormal
    • The Merck Manual,...
details
BloodDetected and Quantified0.049 (0.008-0.089) uMAdult (>18 years old)FemaleNormal
    • The Merck Manual,...
details
BloodDetected and Quantified0.001 (0.00- 0.0022) uMAdult (>18 years old)FemaleNormal
    • The Merck Manual,...
details
BloodDetected and Quantified0.32 - 79.5 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00-0.32 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0042 uMInfant (4 days - <1 year old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified0.0011 uMChildren (1 - <10 years old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified0.00041-0.0027 uMAdolescent (10 - <15 years old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified0.00064-0.033 uMAdolescent (15 - <19 years old)Female
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified0.00051-0.0018 uMAdolescent (15 - <19 years old)Male
Normal
    • CALIPER Paediatri...
details
BloodDetected but not Quantified Adult (>18 years old)Male
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.000300-0.00240 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified0.0025 +/- 0.0005 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.035 +/-0.0184 uMAdult (>18 years old)FemaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.001 (0.00002-0.002) uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.000318 uMNewborn (0-30 days old)Female
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
details
BloodDetected and Quantified0.00191-0.115 uMNewborn (0-30 days old)MaleAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.0006 (0.0003-0.001) uMAdult (>18 years old)BothPregnene hydroxylation deficiency details
BloodDetected and Quantified0.089 (0.029-0.150) uMAdult (>18 years old)Female
Pregnancy
    • The Merck Manual,...
details
BloodDetected and Quantified0.259 (0.054-0.464) uMAdult (>18 years old)Female
Pregnancy
    • The Merck Manual,...
details
BloodDetected and Quantified0.493 (0.175-0.811) uMAdult (>18 years old)Female
Pregnancy
    • The Merck Manual,...
details
BloodDetected and Quantified0.00223 uMAdult (>18 years old)Female
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected but not Quantified Adult (>18 years old)Male
Schizophrenia
details
BloodDetected but not Quantified Adult (>18 years old)Female
Schizophrenia
details
BloodDetected and Quantified0.0108-0.119 uMInfant (0-1 year old)Both
Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis
details
BloodDetected and Quantified0.0025 +/- 0.0017 uMAdult (>18 years old)Both
Psychiatric disorder
details
Associated Disorders and Diseases
Disease References
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
  1. Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ]
  2. Guven A, Polat S: Testicular Adrenal Rest Tumor in Two Brothers with a Novel Mutation in the 3-Beta-Hydroxysteroid Dehydrogenase-2 Gene. J Clin Res Pediatr Endocrinol. 2017 Mar 1;9(1):85-90. doi: 10.4274/jcrpe.3306. Epub 2016 Jul 29. [PubMed:27476613 ]
Alcoholism
  1. Nieminen LR, Makino KK, Mehta N, Virkkunen M, Kim HY, Hibbeln JR: Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Prostaglandins Leukot Essent Fatty Acids. 2006 Oct-Nov;75(4-5):309-14. Epub 2006 Sep 7. [PubMed:16959481 ]
Pregnancy
  1. (). The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.. .
Major depressive disorder
  1. Nieminen LR, Makino KK, Mehta N, Virkkunen M, Kim HY, Hibbeln JR: Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Prostaglandins Leukot Essent Fatty Acids. 2006 Oct-Nov;75(4-5):309-14. Epub 2006 Sep 7. [PubMed:16959481 ]
Schizophrenia
  1. Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
Pregnene hydroxylation deficiency
  1. Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. [PubMed:14625002 ]
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
  1. Kim CJ, Lin L, Huang N, Quigley CA, AvRuskin TW, Achermann JC, Miller WL: Severe combined adrenal and gonadal deficiency caused by novel mutations in the cholesterol side chain cleavage enzyme, P450scc. J Clin Endocrinol Metab. 2008 Mar;93(3):696-702. doi: 10.1210/jc.2007-2330. Epub 2008 Jan 8. [PubMed:18182448 ]
Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis
  1. Fukami M, Hasegawa T, Horikawa R, Ohashi T, Nishimura G, Homma K, Ogata T: Cytochrome P450 oxidoreductase deficiency in three patients initially regarded as having 21-hydroxylase deficiency and/or aromatase deficiency: diagnostic value of urine steroid hormone analysis. Pediatr Res. 2006 Feb;59(2):276-80. doi: 10.1203/01.pdr.0000195825.31504.28. [PubMed:16439592 ]
Associated OMIM IDs
  • 608516 (Major depressive disorder)
  • 181500 (Schizophrenia)
  • 201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
  • 201750 (Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis)
  • 613743 (Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete)
DrugBank IDDB00396
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001871
KNApSAcK IDC00034649
Chemspider ID5773
KEGG Compound IDC00410
BioCyc IDPROGESTERONE
BiGG ID34898
Wikipedia LinkProgesterone
METLIN ID402
PubChem Compound5994
PDB IDSTR
ChEBI ID17026
References
Synthesis ReferenceVasquez, L.; Alarcon, J.; Zunza, H.; Becerra, J.; Silva, M. Chemical-microbiological synthesis of progesterone. Boletin de la Sociedad Chilena de Quimica (2001), 46(1), 29-31.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pierson-Mullany LK, Lange CA: Phosphorylation of progesterone receptor serine 400 mediates ligand-independent transcriptional activity in response to activation of cyclin-dependent protein kinase 2. Mol Cell Biol. 2004 Dec;24(24):10542-57. [PubMed:15572662 ]
  2. Callaghan MJ, Russell AJ, Woollatt E, Sutherland GR, Sutherland RL, Watts CK: Identification of a human HECT family protein with homology to the Drosophila tumor suppressor gene hyperplastic discs. Oncogene. 1998 Dec 31;17(26):3479-91. [PubMed:10030672 ]
  3. Schwarz S, Pohl P: Steroid hormones and steroid hormone binding globulins in cerebrospinal fluid studied in individuals with intact and with disturbed blood-cerebrospinal fluid barrier. Neuroendocrinology. 1992 Feb;55(2):174-82. [PubMed:1620285 ]
  4. Afsar NA, Barakzai Q, Adil SN: Effect of a 'progestin only' contraceptive on platelet aggregation in a Pakistani set of population. J Ayub Med Coll Abbottabad. 2005 Jul-Sep;17(3):21-5. [PubMed:16320790 ]
  5. Moguilewsky M, Tournemine C: The antiandrogen anandron potentiates the castrating effect of the LH-RH agonist buserelin in the rat. Am J Clin Oncol. 1988;11 Suppl 2:S148-51. [PubMed:3149454 ]
  6. Wang C, Swerdloff RS: Male hormonal contraception. Am J Obstet Gynecol. 2004 Apr;190(4 Suppl):S60-8. [PubMed:15105800 ]
  7. Landi N, Manfredini D, Lombardi I, Casarosa E, Bosco M: 17-beta-estradiol and progesterone serum levels in temporomandibular disorder patients. Minerva Stomatol. 2004 Nov-Dec;53(11-12):651-60. [PubMed:15894940 ]
  8. Classen-Linke I, Alfer J, Krusche CA, Chwalisz K, Rath W, Beier HM: Progestins, progesterone receptor modulators, and progesterone antagonists change VEGF release of endometrial cells in culture. Steroids. 2000 Oct-Nov;65(10-11):763-71. [PubMed:11108887 ]
  9. Casey ML, MacDonald PC, Andersson S: 17 beta-Hydroxysteroid dehydrogenase type 2: chromosomal assignment and progestin regulation of gene expression in human endometrium. J Clin Invest. 1994 Nov;94(5):2135-41. [PubMed:7962560 ]
  10. Lueprasitsakul P, Longcope C: Aromatase activity of human adipose tissue stromal cells: effects of thyroid hormones and progestogens. Proc Soc Exp Biol Med. 1990 Sep;194(4):337-41. [PubMed:2167478 ]
  11. Kaaks R, Berrino F, Key T, Rinaldi S, Dossus L, Biessy C, Secreto G, Amiano P, Bingham S, Boeing H, Bueno de Mesquita HB, Chang-Claude J, Clavel-Chapelon F, Fournier A, van Gils CH, Gonzalez CA, Gurrea AB, Critselis E, Khaw KT, Krogh V, Lahmann PH, Nagel G, Olsen A, Onland-Moret NC, Overvad K, Palli D, Panico S, Peeters P, Quiros JR, Roddam A, Thiebaut A, Tjonneland A, Chirlaque MD, Trichopoulou A, Trichopoulos D, Tumino R, Vineis P, Norat T, Ferrari P, Slimani N, Riboli E: Serum sex steroids in premenopausal women and breast cancer risk within the European Prospective Investigation into Cancer and Nutrition (EPIC). J Natl Cancer Inst. 2005 May 18;97(10):755-65. [PubMed:15900045 ]
  12. Oliveira RL, Aldrighi JM, Gebara OE, Rocha TR, D'Amico E, Rosano GM, Ramires JA: Postmenopausal hormone replacement therapy increases plasmatic thromboxane beta 2. Int J Cardiol. 2005 Mar 30;99(3):449-54. [PubMed:15771927 ]
  13. Magee JA, Chang LW, Stormo GD, Milbrandt J: Direct, androgen receptor-mediated regulation of the FKBP5 gene via a distal enhancer element. Endocrinology. 2006 Jan;147(1):590-8. Epub 2005 Oct 6. [PubMed:16210365 ]
  14. Baum LW: Sex, hormones, and Alzheimer's disease. J Gerontol A Biol Sci Med Sci. 2005 Jun;60(6):736-43. [PubMed:15983176 ]
  15. Seibert B, Gunzel P: Animal toxicity studies performed for risk assessment of the once-a-month injectable contraceptive Mesigyna. Contraception. 1994 Apr;49(4):303-33. [PubMed:8013217 ]
  16. Payer AF, Meyer WJ 3rd, Walker PA: The ultrastructural response of human Leydig cells to exogenous estrogens. Andrologia. 1979;11(6):423-36. [PubMed:532984 ]
  17. Hould FS, Fried GM, Fazekas AG, Tremblay S, Mersereau WA: Progesterone receptors regulate gallbladder motility. J Surg Res. 1988 Dec;45(6):505-12. [PubMed:3184927 ]
  18. Allen WM: Progesterone: how did the name originate? South Med J. 1970 Oct;63(10):1151-5. [PubMed:4922128 ]
  19. Schumacher M, Guennoun R, Robert F, Carelli C, Gago N, Ghoumari A, Gonzalez Deniselle MC, Gonzalez SL, Ibanez C, Labombarda F, Coirini H, Baulieu EE, De Nicola AF: Local synthesis and dual actions of progesterone in the nervous system: neuroprotection and myelination. Growth Horm IGF Res. 2004 Jun;14 Suppl A:S18-33. [PubMed:15135772 ]
  20. Allen WM: THE ISOLATION OF CRYSTALLINE PROGESTIN. Science. 1935 Aug 2;82(2118):89-93. [PubMed:17747122 ]

Only showing the first 10 proteins. There are 37 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular weight:
57572.44
Reactions
Progesterone + Reduced ferredoxin + Oxygen → 11b-Hydroxyprogesterone + Oxidized ferredoxin + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
5a-Pregnane-3,20-dione + Acceptor → Progesterone + Reduced acceptordetails
Progesterone + NADPH + Hydrogen Ion → 5a-Pregnane-3,20-dione + NADPdetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular weight:
60101.87
General function:
Involved in monooxygenase activity
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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Lin Y, Lu P, Tang C, Mei Q, Sandig G, Rodrigues AD, Rushmore TH, Shou M: Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):368-74. [PubMed:11259318 ]
General function:
Involved in 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 and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:
CYP17A1
Uniprot ID:
P05093
Molecular weight:
57369.995
Reactions
Progesterone + Reduced acceptor + Oxygen → 17-Hydroxyprogesterone + Acceptor + Waterdetails
References
  1. Haidar S, Hartmann RW: C16 and C17 substituted derivatives of pregnenolone and progesterone as inhibitors of 17alpha-hydroxylase-C17, 20-lyase: synthesis and biological evaluation. Arch Pharm (Weinheim). 2002;335(11-12):526-34. [PubMed:12596217 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

General function:
Involved in ATP binding
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, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular weight:
171589.5
References
  1. Payen L, Delugin L, Courtois A, Trinquart Y, Guillouzo A, Fardel O: Reversal of MRP-mediated multidrug resistance in human lung cancer cells by the antiprogestatin drug RU486. Biochem Biophys Res Commun. 1999 May 19;258(3):513-8. [PubMed:10329417 ]
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular weight:
146405.8
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]
General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. [PubMed:12387747 ]
  2. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
  3. Leonessa F, Kim JH, Ghiorghis A, Kulawiec RJ, Hammer C, Talebian A, Clarke R: C-7 analogues of progesterone as potent inhibitors of the P-glycoprotein efflux pump. J Med Chem. 2002 Jan 17;45(2):390-8. [PubMed:11784143 ]
  4. Ueda K, Okamura N, Hirai M, Tanigawara Y, Saeki T, Kioka N, Komano T, Hori R: Human P-glycoprotein transports cortisol, aldosterone, and dexamethasone, but not progesterone. J Biol Chem. 1992 Dec 5;267(34):24248-52. [PubMed:1360010 ]
  5. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
  6. Yamazaki M, Neway WE, Ohe T, Chen I, Rowe JF, Hochman JH, Chiba M, Lin JH: In vitro substrate identification studies for p-glycoprotein-mediated transport: species difference and predictability of in vivo results. J Pharmacol Exp Ther. 2001 Mar;296(3):723-35. [PubMed:11181899 ]
  7. Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [PubMed:11785684 ]
  8. Borgnia MJ, Eytan GD, Assaraf YG: Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 1996 Feb 9;271(6):3163-71. [PubMed:8621716 ]
  9. Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [PubMed:15290871 ]
General function:
Involved in bile acid:sodium symporter activity
Specific function:
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:
SLC10A1
Uniprot ID:
Q14973
Molecular weight:
38118.64
References
  1. Schroeder A, Eckhardt U, Stieger B, Tynes R, Schteingart CD, Hofmann AF, Meier PJ, Hagenbuch B: Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells. Am J Physiol. 1998 Feb;274(2 Pt 1):G370-5. [PubMed:9486191 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular weight:
61187.4
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]
  2. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular weight:
62564.0
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]
  2. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]
General function:
Involved in transmembrane transport
Specific function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular weight:
61279.5
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]
  2. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]

Only showing the first 10 proteins. There are 37 proteins in total.