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Identification
NameEthinyl Estradiol
Accession NumberDB00977  (APRD00691)
TypeSmall Molecule
GroupsApproved
Description

A semisynthetic alkylated estradiol with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally and is often used as the estrogenic component in oral contraceptives [PubChem]. Ethinyl estradiol is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Tri-Cyclen, Triphasil, and Yasmin. The FDA label includes a black box warning that states that combination oral contraceptives should not be used in women over 35 years old who smoke due to the increased risk of serious cardiovascular side effects.

Structure
Thumb
Synonyms
SynonymLanguageCode
17 alpha-EthinylestradiolNot AvailableNot Available
17 alpha-EthynylestradiolNot AvailableNot Available
17 alpha-EthynyloestradiolNot AvailableNot Available
17-ethinyl-3,17-estradiolNot AvailableNot Available
17-ethinyl-3,17-oestradiolNot AvailableNot Available
17-ethinylestradiolNot AvailableNot Available
17alpha-Ethinyl estradiolNot AvailableNot Available
17α-ethynylestradiolNot AvailableNot Available
Ethinyl-OestranolNot AvailableNot Available
EthinylestradiolNot AvailableNot Available
EthinylestradiolumLatinINN
EthinylestriolNot AvailableNot Available
EthinyloestradiolNot AvailableNot Available
Ethynyl estradiolNot AvailableNot Available
EthynylestradiolNot AvailableNot Available
EthynyloestradiolNot AvailableNot Available
EtinilestradiolSpanishINN
SaltsNot Available
Brand names
NameCompany
EstinylSchering
Brand mixtures
Brand NameIngredients
AlesseEthinyl Estradiol + Levonorgestrel
AmethystLevonorgestrel + Ethinyl Estradiol
ApriEthinyl Estradiol + desogestrel
AvianeEthinyl Estradiol + Levonorgestrel
BreviconEthinyl Estradiol + Norethindrone
CyclenEthinyl Estradiol + Norgestimate
DemulenEthinyl Estradiol + Ethynodiol Diacetate
DesogenEthinyl Estradiol + desogestrel
Diane-35Cyproterone Acetate + Ethinyl Estradiol
EvraEthinyl Estradiol + Norelgestromin
femhrtNorethindrone + Ethinyl Estradiol
Femhrt 1/5Ethinyl Estradiol + Norethindrone Acetate
FemodeneEthinyl Estradiol + gestodene
FemodetteEthinyl Estradiol + gestodene
JinteliNorethindrone + Ethinyl Estradiol
JINTELINorethindrone + Ethinyl Estradiol
JolessaEthinyl Estradiol + Levonorgestrel
Junelnorethindrone acetate+ Ethinyl Estradiol
KarivaEthinyl Estradiol + desogestrel
LessinaEthinyl Estradiol + Levonorgestrel
Lo MinastrinNorethindrone acetate, ethinyl estradiol, ferrous fumarate
Lo-FemenalEthinyl Estradiol + Norgestrel
LoestrinEthinyl Estradiol + Norethindrone Acetate
LuteraEthinyl Estradiol + Levonorgestrel
LybrelEthinyl Estradiol + Levonorgestrel
MarvelonDesogestrel + Ethinyl Estradiol
MercilonEthinyl Estradiol + desogestrel
Microgestinnorethindrone acetate+ Ethinyl Estradiol
Min-OvralEthinyl Estradiol + Levonorgestrel
Minestrin 1/20Ethinyl Estradiol + Norethindrone Acetate
MinuletEthinyl Estradiol + gestodene
MircetteEthinyl Estradiol + desogestrel
Neo Mens TabEthinyl Estradiol + Ethisterone
NuvaringEthinyl Estradiol + Etonogestrel
OcellaDrospirenone + Ethinyl Estradiol
OrthoEthinyl Estradiol + Norethindrone
Ortho-CeptDesogestrel + Ethinyl Estradiol
OvconEthinyl Estradiol + Norethindrone
OvralEthinyl Estradiol + Norgestrel
PrevenEthinyl Estradiol + Levonorgestrel
QuartetteLevonorgestrel/Ethinyl Estradiol + Ethinyl Estradiol
QuasenseEthinyl Estradiol + Levonorgestrel
SeasonaleEthinyl Estradiol + Levonorgestrel
SeasoniqueEthinyl Estradiol + Levonorgestrel
Select 1/35Ethinyl Estradiol + Norethindrone
SronyxEthinyl Estradiol + Levonorgestrel
SynphasicEthinyl Estradiol + Norethindrone
Tri-CyclenEthinyl Estradiol + Norgestimate
Tri-Cyclen LoEthinyl Estradiol + Norgestimate
TriphasilEthinyl Estradiol + Levonorgestrel
TriquilarEthinyl Estradiol + Levonorgestrel
YasminDrospirenone + Ethinyl Estradiol
YasminelleDrospirenone + Ethinyl Estradiol
YazDrospirenone + Ethinyl Estradiol
ZarahDrospirenone + Ethinyl Estradiol
Categories
CAS number57-63-6
WeightAverage: 296.4034
Monoisotopic: 296.177630012
Chemical FormulaC20H24O2
InChI KeyBFPYWIDHMRZLRN-RHKZOZTBNA-N
InChI
InChI=1/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/s2
IUPAC Name
(1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,14-diol
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
Mass Specshow(9.42 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassHydroxysteroids
Direct parentHydroxysteroids
Alternative parentsPhenanthrenes and Derivatives; Tetralins; Phenols and Derivatives; Ynones; Tertiary Alcohols; Cyclic Alcohols and Derivatives; Enols; Polyamines
Substituentsphenanthrene; tetralin; phenol derivative; ynone; benzene; cyclic alcohol; tertiary alcohol; polyamine; enol; alcohol
Classification descriptionThis compound belongs to the hydroxysteroids. These are compounds containing an steroid backbone, with at least one hydrogen substituted by an hydroxyl group.
Pharmacology
IndicationFor treatment of moderate to severe vasomotor symptoms associated with the menopause, female hypogonadism, prostatic carcinoma-palliative therapy of advanced disease, breast cancer, as an oral contraceptive, and as emergency contraceptive.
PharmacodynamicsEthinyl estradiol is a synthetic derivative of the natural estrogen estradiol. It is one of two estrogens currently used in oral contraceptive pills. The other, mestranol, is converted to ethinyl estradiol before it is biologically active. Ethinyl estradiol and norethindrone are used together as an oral contraceptive agent.
Mechanism of actionEstrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. This cascade is initiated by initially binding to the estrogen receptors. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
AbsorptionRapid and complete absorption follows oral intake of ethinyl estradiol (bioavailability 43%).
Volume of distributionNot Available
Protein binding97%
Metabolism

Hepatic. Quantitatively, the major metabolic pathway for ethinyl estradiol, both in rats and in humans, is aromatic hydroxylation, as it is for the natural estrogens.

SubstrateEnzymesProduct
Ethinyl Estradiol
2β-OH-17β-ethinylestradiolDetails
Route of eliminationNot Available
Half life36 +/- 13 hours
ClearanceNot Available
ToxicityOral, mouse LD50: 1737 mg/kg. Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females. The FDA label includes a black box warning that states that combination oral contraceptives with ethinyl estradiol should not be used in women over 35 years old who smoke due to the increased risk of serious cardiovascular side effects.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9965
Blood Brain Barrier + 0.8546
Caco-2 permeable + 0.8638
P-glycoprotein substrate Substrate 0.6892
P-glycoprotein inhibitor I Non-inhibitor 0.9006
P-glycoprotein inhibitor II Non-inhibitor 0.9449
Renal organic cation transporter Non-inhibitor 0.84
CYP450 2C9 substrate Non-substrate 0.7178
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Substrate 0.715
CYP450 1A2 substrate Inhibitor 0.8941
CYP450 2C9 substrate Non-inhibitor 0.9186
CYP450 2D6 substrate Non-inhibitor 0.9506
CYP450 2C19 substrate Non-inhibitor 0.6641
CYP450 3A4 substrate Inhibitor 0.5224
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6776
Ames test Non AMES toxic 0.9155
Carcinogenicity Non-carcinogens 0.8519
Biodegradation Not ready biodegradable 0.9879
Rat acute toxicity 2.4584 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8805
hERG inhibition (predictor II) Inhibitor 0.5788
Pharmacoeconomics
Manufacturers
  • Schering corp sub schering plough corp
  • Pharmacia and upjohn co
  • Organon usa inc
Packagers
Dosage forms
FormRouteStrength
CreamIntravaginal
Insert, extended releaseTransdermal
TabletOral
Prices
Unit descriptionCostUnit
Ethinyl estradiol powder140.0USDg
Ortho-Cyclen (28) 28 0.25-35 mg-mcg tablet Disp Pack38.99USDdisp
Ortho tri-cyclen lo tablet2.68USDtablet
Ortho-cyclen 28 tablet1.13USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point142-144Inhoffen, H.H. and Hohlweg, W.; U.S. Patent 2,265,976; December 9, 1941; assigned to Schering Corp.
water solubility11.3 mg/L (at 27 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.67HANSCH,C ET AL. (1995)
logS-4.3ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.00677ALOGPS
logP3.63ALOGPS
logP3.9ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity87.37 m3·mol-1ChemAxon
Polarizability34.53 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Andreas Sachse, “Method of female hormonal contraception using a fixed extended cycle hormonal preparation containing dienogest and ethinyl estradiol.” U.S. Patent US20060079491, issued April 13, 2006.

US20060079491
General Reference
  1. FDA label.
External Links
ResourceLink
KEGG DrugD00554
KEGG CompoundC07534
ChEBI4903
ChEMBLCHEMBL691
Therapeutic Targets DatabaseDAP001018
PharmGKBPA449527
Drug Product Database28231
RxListhttp://www.rxlist.com/cgi/generic/estinyl.htm
WikipediaEthinylestradiol
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelshow(470 KB)
MSDSshow(73.9 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolIncreased thrombotic risk due to estrogen
AminophyllineThe contraceptive increases the effect and toxicity of theophylline
AmobarbitalThis product may cause a slight decrease of contraceptive effect
AmoxicillinThis anti-infectious agent could decrease the effect of the oral contraceptive
AmpicillinThis anti-infectious agent could decrease the effect of the oral contraceptive
AmprenavirRitonavir could decrease the contraceptive efficacy
AnisindioneIncreased thrombotic risk due to estrogen
AprepitantAprepitant could decrease the effect of the oral contraceptive
AprobarbitalThis product may cause a slight decrease of contraceptive effect
ArtemetherArtemether may decrease the effectiveness of ethinyl estradiol by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
AzlocillinThis anti-infectious agent could decrease the effect of the oral contraceptive
AztreonamThis anti-infectious agent could decrease the effect of the oral contraceptive
BacampicillinThis anti-infectious agent could decrease the effect of the oral contraceptive
BendamustineIncreases levels of bendamustine by decreasing metabolism. Ethinyl Estradiol is a CYP1A2 inhibitor and concurrent administration may result in elevated plasma concentrations of bendamustine.
BosentanBosentan may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be relied on alone during concomitant therapy with bosentan.
ButabarbitalThis product may cause a slight decrease of contraceptive effect
ButalbitalThis product may cause a slight decrease of contraceptive effect
ButethalThis product may cause a slight decrease of contraceptive effect
CarbamazepineCarbamazepine may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be relied on alone during concomitant therapy with carbamazepine.
ClavulanateThis anti-infectious agent could decrease the effect of the oral contraceptive
CloxacillinThis anti-infectious agent could decrease the effect of the oral contraceptive
ColesevelamBile Acid Sequestrants may decrease the serum concentration of Contraceptives (Estrogens). Administer estrogen-based oral contraceptives at least 1-4 hours prior to or 4-6 hours after administration of a bile acid sequestrant. Consider alternatives in order to avoid this combination when possible, due to the risk for impaired contraceptive effectiveness. Ethinyl estradiol patches and vaginal rings may also be somewhat impacted by this interaction, though the extent and significance of such an interaction is uncertain.
CyclacillinThis anti-infectious agent could decrease the effect of the oral contraceptive
CyclosporineThe contraceptive increases the effect and toxicity of cyclosporine
DemeclocyclineThis anti-infectious agent could decrease the effect of the oral contraceptive
DicloxacillinThis anti-infectious agent could decrease the effect of the oral contraceptive
DicoumarolIncreased thrombotic risk due to estrogen
DoxycyclineDoxycycline may decrease the contraceptive effect of ethinyl estradiol.
DyphyllineThe contraceptive increases the effect and toxicity of theophylline
EltrombopagAffects hepatic CYP1A2 metabolism, increases Eltrombopag level or affect.
EthotoinThis product may cause a slight decrease of contraceptive effect
EtoricoxibEtoricoxib may increase the levels of ethinyl estradiol.
FlucloxacillinThis anti-infectious agent could decrease the effect of the oral contraceptive
FosphenytoinThis product may cause a slight decrease of contraceptive effect
GriseofulvinThis product may cause a slight decrease of contraceptive effect
HeptabarbitalThis product may cause a slight decrease of contraceptive effect
HetacillinThis anti-infectious agent could decrease the effect of the oral contraceptive
HexobarbitalThis product may cause a slight decrease of contraceptive effect
KetoconazoleThis anti-infectious agent could decrease the effect of the oral contraceptive
LamotrigineThe oral contraceptive decreases the effect of lamotrigine
MephenytoinThis product may cause a slight decrease of contraceptive effect
MethacyclineThis anti-infectious agent could decrease the effect of the oral contraceptive
MethohexitalThis product may cause a slight decrease of contraceptive effect
MethylphenobarbitalThis product may cause a slight decrease of contraceptive effect
MeticillinThis anti-infectious agent could decrease the effect of the oral contraceptive
MezlocillinThis anti-infectious agent could decrease the effect of the oral contraceptive
MinocyclineThis anti-infectious agent could decrease the effect of the oral contraceptive
ModafinilModafinil may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be solely relied on during concomitant therapy with modafinil.
NafcillinThis anti-infectious agent could decrease the effect of the oral contraceptive
NelfinavirRitonavir could decrease the contraceptive efficacy
OxacillinThis anti-infectious agent could decrease the effect of the oral contraceptive
OxcarbazepineOxcarbazepine may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be solely relied upon during concomitant therapy with oxcarbazepine.
OxtriphyllineThe contraceptive increases the effect and toxicity of theophylline
OxytetracyclineThis anti-infectious agent could decrease the effect of the oral contraceptive
PentobarbitalThis product may cause a slight decrease of contraceptive effect
PhenobarbitalThis product may cause a slight decrease of contraceptive effect
PhenytoinThis product may cause a slight decrease of contraceptive effect
PiperacillinThis anti-infectious agent could decrease the effect of the oral contraceptive
PivampicillinThis anti-infectious agent could decrease the effect of the oral contraceptive
PrednisoloneThe estrogenic agent, ethinyl estradiol, may increase the effect of the corticosteroid, prednisolone.
PrednisoneThe estrogenic agent, ethinyl estradiol, may increase the effect of corticosteroid, prednisone.
PrimidoneThis product may cause a slight decrease of contraceptive effect
RaloxifeneAssociation not recommended
RifabutinRifabutin may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be solely relied on alone during concomitant therapy with rifabutin.
RifampicinThis product may cause a slight decrease of contraceptive effect
RifapentineThis product may cause a slight decrease of contraceptive effect
RitonavirRitonavir could decrease the contraceptive efficacy
RolitetracyclineThis anti-infectious agent could decrease the effect of the oral contraceptive
RufinamideRufinamide decreases plasma concentrations of ethinyl estradiol, thus consider therapy modification
SecobarbitalThis product may cause a slight decrease of contraceptive effect
St. John's WortSt. John's Wort could reduce the contraceptive effect
TacrolimusEthinyl estradiol may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Ethinyl estradiol therapy is initiated, discontinued or altered.
TalbutalThis product may cause a slight decrease of contraceptive effect
TazobactamThis anti-infectious agent could decrease the effect of the oral contraceptive
TetracyclineThis anti-infectious agent could decrease the effect of the oral contraceptive
TheophyllineThe contraceptive increases the effect and toxicity of theophylline
ThiopentalThiopental may decrease the effect of Ethinyl estradiol. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
TicarcillinThis anti-infectious agent could decrease the effect of the oral contraceptive
TipranavirTipranavir, co-administered with Ritonavir, decreases Ethinyl estradiol concentrations. Ethinyl estradiol may increase the adverse dermatological effects (i.e. skin rash) of Tipranavir. Use an alternate form of contraception or monitor for estrogen deficiency if Ethinyl estradiol is used for hormone replacement therapy.
TizanidineEthinyl estradiol may increase the serum concentration of tizanidine. Monitor for changes in the therapeutic and adverse effects of tizanidine if ethinyl estradiol is initiated, discontinued or dose changed.
TopiramateTopiramate may decrease the effect of the oral contraceptive, Ethinyl estradiol. An alternate form of contraception should be used during concomitant therapy.
TretinoinOral Tretinoin may decrease the effect of the oral contraceptive, Ethinyl Estradiol. An alternate form of contraception should be used during concomitant therapy.
TroglitazonePossible loss of contracepitve effect
Ursodeoxycholic acidEstrogens decreases the effect of ursodiol
WarfarinEthinyl estradiol may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if ethinyl estradiol is initiated, discontinued or dose changed.
Food InteractionsNot Available

Targets

1. Estrogen receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Estrogen receptor P03372 Details

References:

  1. Micevych PE, Chaban V, Ogi J, Dewing P, Lu JK, Sinchak K: Estradiol stimulates progesterone synthesis in hypothalamic astrocyte cultures. Endocrinology. 2007 Feb;148(2):782-9. Epub 2006 Nov 9. Pubmed
  2. Garcia-Segura LM, Sanz A, Mendez P: Cross-talk between IGF-I and estradiol in the brain: focus on neuroprotection. Neuroendocrinology. 2006;84(4):275-9. Epub 2006 Nov 23. Pubmed
  3. Brama M, Gnessi L, Basciani S, Cerulli N, Politi L, Spera G, Mariani S, Cherubini S, d’Abusco AS, Scandurra R, Migliaccio S: Cadmium induces mitogenic signaling in breast cancer cell by an ERalpha-dependent mechanism. Mol Cell Endocrinol. 2007 Jan 29;264(1-2):102-8. Epub 2006 Nov 27. Pubmed
  4. Lehnes K, Winder AD, Alfonso C, Kasid N, Simoneaux M, Summe H, Morgan E, Iann MC, Duncan J, Eagan M, Tavaluc R, Evans CH Jr, Russell R, Wang A, Hu F, Stoica A: The effect of estradiol on in vivo tumorigenesis is modulated by the human epidermal growth factor receptor 2/phosphatidylinositol 3-kinase/Akt1 pathway. Endocrinology. 2007 Mar;148(3):1171-80. Epub 2006 Nov 30. Pubmed
  5. Mukai H, Tsurugizawa T, Ogiue-Ikeda M, Murakami G, Hojo Y, Ishii H, Kimoto T, Kawato S: Local neurosteroid production in the hippocampus: influence on synaptic plasticity of memory. Neuroendocrinology. 2006;84(4):255-63. Epub 2006 Dec 1. Pubmed
  6. Notch EG, Mayer GD: 17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8. Epub 2009 Jan 23. Pubmed
  7. Bennink HJ: Reprint of Are all estrogens the same? Maturitas. 2008 Sep-Oct;61(1-2):195-201. Pubmed
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Nuclear receptor subfamily 1 group I member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Nuclear receptor subfamily 1 group I member 2 O75469 Details

References:

  1. Xue Y, Moore LB, Orans J, Peng L, Bencharit S, Kliewer SA, Redinbo MR: Crystal structure of the pregnane X receptor-estradiol complex provides insights into endobiotic recognition. Mol Endocrinol. 2007 May;21(5):1028-38. Epub 2007 Feb 27. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Wang B, Sanchez RI, Franklin RB, Evans DC, Huskey SE: The involvement of CYP3A4 and CYP2C9 in the metabolism of 17 alpha-ethinylestradiol. Drug Metab Dispos. 2004 Nov;32(11):1209-12. Epub 2004 Aug 10. Pubmed

2. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. Pubmed

Transporters

1. Bile salt export pump

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor inducer

Components

Name UniProt ID Details
Bile salt export pump O95342 Details

References:

  1. Lee JM, Trauner M, Soroka CJ, Stieger B, Meier PJ, Boyer JL: Expression of the bile salt export pump is maintained after chronic cholestasis in the rat. Gastroenterology. 2000 Jan;118(1):163-72. Pubmed
  2. Huang L, Smit JW, Meijer DK, Vore M: Mrp2 is essential for estradiol-17beta(beta-D-glucuronide)-induced cholestasis in rats. Hepatology. 2000 Jul;32(1):66-72. Pubmed

2. Sodium/bile acid cotransporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Sodium/bile acid cotransporter Q14973 Details

References:

  1. Lee JM, Trauner M, Soroka CJ, Stieger B, Meier PJ, Boyer JL: Expression of the bile salt export pump is maintained after chronic cholestasis in the rat. Gastroenterology. 2000 Jan;118(1):163-72. Pubmed

3. Canalicular multispecific organic anion transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Canalicular multispecific organic anion transporter 1 Q92887 Details

References:

  1. Kauffmann HM, Schrenk D: Sequence analysis and functional characterization of the 5’-flanking region of the rat multidrug resistance protein 2 (mrp2) gene. Biochem Biophys Res Commun. 1998 Apr 17;245(2):325-31. Pubmed
  2. Trauner M, Arrese M, Soroka CJ, Ananthanarayanan M, Koeppel TA, Schlosser SF, Suchy FJ, Keppler D, Boyer JL: The rat canalicular conjugate export pump (Mrp2) is down-regulated in intrahepatic and obstructive cholestasis. Gastroenterology. 1997 Jul;113(1):255-64. Pubmed

4. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. 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

Comments
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Drug created on June 13, 2005 07:24 / Updated on October 29, 2013 15:35