Identification

Name
Clomifene
Accession Number
DB00882  (APRD00880)
Type
Small Molecule
Groups
Approved, Investigational
Description

A triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue.

Structure
Thumb
Synonyms
  • 2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine
  • 2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)triethylamine
  • 2-(p-(β-chloro-α-phenylstyryl)phenoxy)triethylamine
  • Clomifeno
  • Clomifenum
  • Clomiphene
Product Ingredients
IngredientUNIICASInChI Key
Clomifene citrate1B8447E7YI50-41-9PYTMYKVIJXPNBD-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ClomidTablet50 mgOralSanofi Aventis1995-12-31Not applicableCanada
ClomidTablet50 mg/1OralSanofi Aventis1967-02-012014-08-21Us
Clomid 50mgTablet50 mgOralMerrell Pharms Inc., Division Of Merrell Dow (Can)1967-12-311996-09-09Canada
SeropheneTablet50 mg/1OralPhysicians Total Care, Inc.1982-03-222013-06-30Us
SeropheneTablet50 mg/1OralEmd Serono1982-03-222014-11-30Us
Serophene Tab 50mgTablet50 mgOralEmd Serono, A Division Of Emd Inc., Canada1991-12-312017-07-07Canada
Serophene Tab 50mgTablet50 mgOralPharmascience Inc1985-12-312014-09-08Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Clomiphene CitrateTablet50 mg/1OralA-S Medication Solutions1999-08-30Not applicableUs50090 067820180907 15195 tu5hdi
Clomiphene CitrateTablet50 mg/1OralRebel Distributors1999-08-30Not applicableUs49884 0701 55 nlmimage10 1b398dec
Clomiphene CitrateTablet50 mg/1OralA-S Medication Solutions1990-10-01Not applicableUs
Clomiphene CitrateTablet50 mg/1OralActavis Pharma Company1990-10-012018-06-30Us
Clomiphene CitrateTablet50 mg/1OralPhysicians Total Care, Inc.1996-08-22Not applicableUs54868 305920180907 15195 1wvd4ws
Clomiphene CitrateTablet50 mg/1Oralbryant ranch prepack1999-08-30Not applicableUs
Clomiphene CitrateTablet50 mg/1OralPar Pharmaceutical1999-08-30Not applicableUs
ClomiPHENE CitrateTablet50 mg/1OralTeva1992-11-01Not applicableUs00093 0041 65 nlmimage10 f7297bbb
Clomiphene CitrateTablet50 mg/1OralNucare Pharmaceuticals, Inc.1999-08-30Not applicableUs
Clomiphene CitrateTablet50 mg/1OralPd Rx Pharmaceuticals, Inc.1990-10-012018-06-30Us
International/Other Brands
Androxal / Clomifert / Clostilbegyt (Egis) / Omifin (Sanofi)
Categories
UNII
1HRS458QU2
CAS number
911-45-5
Weight
Average: 405.96
Monoisotopic: 405.18594223
Chemical Formula
C26H28ClNO
InChI Key
GKIRPKYJQBWNGO-UHFFFAOYSA-N
InChI
InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3
IUPAC Name
{2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]ethyl}diethylamine
SMILES
CCN(CC)CCOC1=CC=C(C=C1)C(=C(Cl)C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication

Used mainly in female infertility due to anovulation (e.g. due to polycystic ovary syndrome) to induce ovulation.

Associated Conditions
Pharmacodynamics

Clomifene (previously clomiphene) is an orally administered, non steroidal, ovulatory stimulant that acts as a selective estrogen receptor modulator (SERM). Clomifene can lead to multiple ovulation, and hence increase the risk of conceiving twins. In comparison to purified FSH, the rate of ovarian hyperstimulation syndrome is low. There may be an increased risk of ovarian cancer and weight gain. Clomifene is capable of interacting with estrogen-receptor-containing tissues, including the hypothalamus, pituitary, ovary, endometrium, vagina, and cervix. It may compete with estrogen for estrogen-receptor-binding sites and may delay replenishment of intracellular estrogen receptors. Clomifene initiates a series of endocrine events culminating in a preovulatory gonadotropin surge and subsequent follicular rupture. The first endocrine event, in response to a course of clomifene therapy, is an increase in the release of pituitary gonadotropins. This initiates steroidogenesis and folliculogenesis resulting in growth of the ovarian follicle and an increase in the circulating level of estradiol. Following ovulation, plasma progesterone and estradiol rise and fall as they would in a normal ovulatory cycle.

Mechanism of action

Clomifene has both estrogenic and anti-estrogenic properties, but its precise mechanism of action has not been determined. Clomifene appears to stumulate the release of gonadotropins, follicle-stimulating hormone (FSH), and leuteinizing hormone (LH), which leads to the development and maturation of ovarian follicle, ovulation, and subsequent development and function of the coprus luteum, thus resulting in pregnancy. Gonadotropin release may result from direct stimulation of the hypothalamic-pituitary axis or from a decreased inhibitory influence of estrogens on the hypothalamic-pituitary axis by competing with the endogenous estrogens of the uterus, pituitary, or hypothalamus. Clomifene has no apparent progestational, androgenic, or antrandrogenic effects and does not appear to interfere with pituitary-adrenal or pituitary-thyroid function.

TargetActionsOrganism
AEstrogen receptor alpha
antagonist
agonist
Human
USex hormone-binding globulinNot AvailableHuman
Absorption

Based on early studies with 14 C-labeled clomifene, the drug was shown to be readily absorbed orally in humans.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic

Route of elimination

Based on early studies with 14C-labeled clomiphene citrate, the drug was shown to be readily absorbed orally in humans and excreted principally in the feces. Mean urinary excretion was approximately 8% with fecal excretion of about 42%.

Half life

5-7 days

Clearance
Not Available
Toxicity

The acute oral LD50 of clomifene is 1700 mg/kg in mice and 5750 mg/kg in rats. The toxic dose in humans is not known. Toxic effects accompanying acute overdosage of clomifene have not been reported. Signs and symptoms of overdosage as a result of the use of more than the recommended dose during clomifene therapy include nausea, vomiting, vasomotor flushes, visual blurring, spots or flashes, scotomata, ovarian enlargement with pelvic or abdominal pain.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Clomifene.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Clomifene.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Clomifene.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Clomifene.
9-DeazaguanineThe metabolism of 9-Deazaguanine can be decreased when combined with Clomifene.
9-MethylguanineThe metabolism of 9-Methylguanine can be decreased when combined with Clomifene.
AbemaciclibThe serum concentration of Clomifene can be increased when it is combined with Abemaciclib.
AcefyllineThe metabolism of Acefylline can be decreased when combined with Clomifene.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Clomifene.
AcetaminophenThe serum concentration of Clomifene can be increased when it is combined with Acetaminophen.
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

Allen, R.E., Palopoli, F.P., Schumann, E.L. and Van Carnpen, M.G. Jr.; US. Patent 2,914,563; November 24, 1959; assigned to The Wrn. S. Merrell Company.

General References
  1. Purvin VA: Visual disturbance secondary to clomiphene citrate. Arch Ophthalmol. 1995 Apr;113(4):482-4. [PubMed:7710399]
  2. Hayon T, Atlas L, Levy E, Dvilansky A, Shpilberg O, Nathan I: Multifactorial activities of nonsteroidal antiestrogens against leukemia. Cancer Detect Prev. 2003;27(5):389-96. [PubMed:14585326]
  3. Fritz MA, Holmes RT, Keenan EJ: Effect of clomiphene citrate treatment on endometrial estrogen and progesterone receptor induction in women. Am J Obstet Gynecol. 1991 Jul;165(1):177-85. [PubMed:1906682]
  4. Hughes E, Brown J, Collins JJ, Vanderkerchove P: Clomiphene citrate for unexplained subfertility in women. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD000057. doi: 10.1002/14651858.CD000057.pub2. [PubMed:20091498]
  5. Brown J, Farquhar C, Beck J, Boothroyd C, Hughes E: Clomiphene and anti-oestrogens for ovulation induction in PCOS. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD002249. doi: 10.1002/14651858.CD002249.pub4. [PubMed:19821295]
  6. Authors unspecified: Use of clomiphene citrate in women. Fertil Steril. 2006 Nov;86(5 Suppl 1):S187-93. [PubMed:17055820]
  7. Homburg R: Oral agents for ovulation induction--clomiphene citrate versus aromatase inhibitors. Hum Fertil (Camb). 2008 Mar;11(1):17-22. doi: 10.1080/14647270701689670. [PubMed:18320435]
  8. Homburg R: Clomiphene citrate--end of an era? A mini-review. Hum Reprod. 2005 Aug;20(8):2043-51. Epub 2005 May 5. [PubMed:15878925]
External Links
Human Metabolome Database
HMDB0015020
KEGG Drug
D07726
KEGG Compound
C06917
PubChem Compound
2800
PubChem Substance
46504463
ChemSpider
2698
ChEBI
3752
ChEMBL
CHEMBL2355051
Therapeutic Targets Database
DAP001013
PharmGKB
PA449046
RxList
RxList Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Clomifene
ATC Codes
G03GB02 — Clomifene
AHFS Codes
  • 68:16.12 — Estrogen Agonist-antagonists

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentPioglitazone1
0RecruitingTreatmentInfertilities1
1Active Not RecruitingBasic ScienceAbuse of Steroids or Hormones / Sports Drug Abuse1
1CompletedBasic ScienceAnovulatory cycle / Cytochrome P450 CYP3A Enzyme Deficiency / Disorder Due Cytochrome P450 CYP2D6 Variant1
1CompletedTreatmentBioequivalence1
1Unknown StatusTreatmentPolycystic Ovarian Syndrome1
1, 2CompletedTreatmentInfertilities1
2CompletedTreatmentAcquired Hypogonadotropic Hypogonadism / BMI >30 kg/m21
2CompletedTreatmentAcromegaly1
2CompletedTreatmentAndrogen Deficiency / BMI >30 kg/m21
2CompletedTreatmentAnovulatory cycle2
2CompletedTreatmentHypogonadism / Male Infertility / Opioid-Related Disorders1
2CompletedTreatmentIdiopathic Hypogonadotropic Hypogonadism / Prolactinoma1
2CompletedTreatmentInfertilities1
2CompletedTreatmentSecondary Hypogonadotrophic hypogonadism1
2Enrolling by InvitationTreatmentHyperandrogenism / Polycystic Ovaries Syndrome1
2Not Yet RecruitingTreatmentAnovulatory cycle / Polycystic Ovaries Syndrome1
2Not Yet RecruitingTreatmentHypogonadism, Hypogonadotropic1
2RecruitingTreatmentClomiphene Citrate Resistant Polycystic Ovary Syndrome1
2RecruitingTreatmentFemale Reproductive Problem1
2RecruitingTreatmentTesticular Hypogonadism1
2TerminatedTreatmentIdiopathic Hypogonadotropic Hypogonadism / Type 2 Diabetes Mellitus1
2, 3CompletedTreatmentInfertilities2
2, 3Not Yet RecruitingTreatmentInfertilities1
2, 3RecruitingTreatmentClomiphene Citrate Resistant Polycystic Ovary Syndrome1
2, 3Unknown StatusTreatmentInfertility, Female1
3CompletedTreatmentAnovulatory cycle / Hyperandrogenism / Infertilities / Oligoovulation / Polycystic Ovaries Syndrome1
3CompletedTreatmentAnovulatory cycle / Ovulation induction therapy / Ovulatory Dysfunction1
3CompletedTreatmentInfertilities1
3CompletedTreatmentInfertilities / Polycystic Ovaries Syndrome / Pregnancy1
3CompletedTreatmentPolycystic Ovaries Syndrome1
3CompletedTreatmentPolycystic Ovaries Syndrome / Pregnancy1
3CompletedTreatmentPregnancy / Unexplained Infertility1
3Not Yet RecruitingTreatmentAzoospermia, Nonobstructive1
3Not Yet RecruitingTreatmentPolycystic Ovaries Syndrome1
3Not Yet RecruitingTreatmentPolycystic Ovaries Syndrome / Reproductive Medicine1
3RecruitingTreatmentOvulation induction therapy1
3WithdrawnTreatmentInsulin Resistance / Polycystic Ovaries Syndrome1
4Active Not RecruitingTreatmentInfertilities / Polycystic Ovaries Syndrome1
4CompletedNot AvailableInfertility, Female1
4CompletedSupportive CarePolycystic Ovarian Syndrome1
4CompletedTreatmentAnovulatory cycle / Infertilities / Polycystic Ovaries Syndrome1
4CompletedTreatmentAnovulatory cycle / Polycystic Ovaries Syndrome1
4CompletedTreatmentInfertilities2
4CompletedTreatmentInfertilities / Polycystic Ovarian Syndrome1
4CompletedTreatmentOvarian Stimulation1
4CompletedTreatmentPolycystic Ovaries Syndrome3
4CompletedTreatmentPregnancy2
4Not Yet RecruitingTreatmentInfertilities2
4RecruitingTreatmentAnovulatory cycle / Infertilities1
4RecruitingTreatmentIn Vitro Fertilisation / Infertility, Female / Ovarian Stimulation1
4RecruitingTreatmentInfertilities2
4RecruitingTreatmentInfertilities / Polycystic Ovarian Syndrome2
4Unknown StatusTreatmentClomiphene Citrate / GnRH Antagonist / Gonadotropin-releasing Hormone Agonist / IVF / Poor Responders1
4WithdrawnTreatmentInfertilities / Polycystic Ovaries Syndrome1
Not AvailableCompletedNot AvailableAnovulatory cycle1
Not AvailableCompletedNot AvailableInfertilities1
Not AvailableCompletedNot AvailableMood1
Not AvailableCompletedOtherInfertilities1
Not AvailableCompletedTreatmentAnovulatory cycle1
Not AvailableCompletedTreatmentFemale Infertility Associated With Anovulation1
Not AvailableCompletedTreatmentHyperinsulinism / Polycystic Ovaries Syndrome2
Not AvailableCompletedTreatmentInfertilities1
Not AvailableCompletedTreatmentPolycystic Ovaries Syndrome4
Not AvailableNot Yet RecruitingScreeningPolycystic Ovaries Syndrome1
Not AvailableNot Yet RecruitingTreatmentInfertilities1
Not AvailableNot Yet RecruitingTreatmentUnexplained Infertility1
Not AvailableRecruitingTreatmentAsymptomatic Diseases1
Not AvailableRecruitingTreatmentFemale Infertility Due to Nonimplantation of Ovum1
Not AvailableRecruitingTreatmentHypogonadism / Non Obstructive Azoospermia1
Not AvailableRecruitingTreatmentPolycystic Ovarian Syndrome / Subfertility1
Not AvailableRecruitingTreatmentPolycystic Ovaries Syndrome1
Not AvailableTerminatedTreatmentInfertilities / Polycystic Ovaries Syndrome1
Not AvailableTerminatedTreatmentPolycystic Ovarian Syndrome1
Not AvailableUnknown StatusTreatmentInfertilities1
Not AvailableWithdrawnTreatmentEndometriosis / Infertilities1

Pharmacoeconomics

Manufacturers
  • Sanofi aventis us llc
  • Par pharmaceutical inc
  • Milex products inc
  • Emd serono inc
Packagers
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • EMD Canada Inc.
  • Medisca Inc.
  • Merrell Pharmaceuticals Inc.
  • Nucare Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • Patheon Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Sanofi-Aventis Inc.
  • Teva Pharmaceutical Industries Ltd.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral50 mg
TabletOral50 mg/1
Prices
Unit descriptionCostUnit
ClomiPHENE Citrate 30 50 mg tablet Box215.9USD box
Clomiphene citrate powder47.74USD g
Clomid 50 mg tablet17.1USD tablet
Serophene 50 mg tablet11.08USD tablet
Clomiphene citrate 50 mg tab6.86USD tablet
Clomid 50 mg Tablet6.09USD tablet
Serophene 50 mg Tablet5.52USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)116.5-118Allen, R.E., Palopoli, F.P., Schumann, E.L. and Van Carnpen, M.G. Jr.; US. Patent 2,914,563; November 24, 1959; assigned to The Wrn. S. Merrell Company.
water solubilitySlightly solubleNot Available
logP7.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000414 mg/mLALOGPS
logP6.08ALOGPS
logP6.47ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity133.76 m3·mol-1ChemAxon
Polarizability46.72 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8723
Caco-2 permeable+0.7235
P-glycoprotein substrateSubstrate0.7536
P-glycoprotein inhibitor IInhibitor0.7799
P-glycoprotein inhibitor IINon-inhibitor0.6476
Renal organic cation transporterInhibitor0.7021
CYP450 2C9 substrateNon-substrate0.7972
CYP450 2D6 substrateNon-substrate0.6847
CYP450 3A4 substrateSubstrate0.7021
CYP450 1A2 substrateInhibitor0.9332
CYP450 2C9 inhibitorNon-inhibitor0.6036
CYP450 2D6 inhibitorInhibitor0.8315
CYP450 2C19 inhibitorInhibitor0.7004
CYP450 3A4 inhibitorNon-inhibitor0.8089
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9254
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.621
BiodegradationNot ready biodegradable0.9895
Rat acute toxicity1.8805 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8038
hERG inhibition (predictor II)Inhibitor0.8672
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0000900000-6e563271338e3449b9f0

Taxonomy

Description
This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Diphenylmethanes / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Trialkylamines / Vinyl chlorides / Chloroalkenes / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
Stilbene / Diphenylmethane / Phenoxy compound / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / Benzenoid / Tertiary amine / Tertiary aliphatic amine / Ether
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary amine (CHEBI:3752)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
Agonist
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
  1. Sasson S: Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor. Pathol Biol (Paris). 1991 Jan;39(1):59-69. [PubMed:2011412]
  2. Kurosawa T, Hiroi H, Momoeda M, Inoue S, Taketani Y: Clomiphene citrate elicits estrogen agonistic/antagonistic effects differentially via estrogen receptors alpha and beta. Endocr J. 2010;57(6):517-21. Epub 2010 Apr 6. [PubMed:20379036]
  3. Hughes E, Brown J, Collins JJ, Vanderkerchove P: Clomiphene citrate for unexplained subfertility in women. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD000057. doi: 10.1002/14651858.CD000057.pub2. [PubMed:20091498]
  4. Brown J, Farquhar C, Beck J, Boothroyd C, Hughes E: Clomiphene and anti-oestrogens for ovulation induction in PCOS. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD002249. doi: 10.1002/14651858.CD002249.pub4. [PubMed:19821295]
  5. Authors unspecified: Use of clomiphene citrate in women. Fertil Steril. 2006 Nov;86(5 Suppl 1):S187-93. [PubMed:17055820]
  6. Overbeek A, Lambalk N: Pharmacogenomics of ovulation induction: facilitating decisions on who, when and how to treat. Pharmacogenomics. 2009 Sep;10(9):1377-9. doi: 10.2217/pgs.09.110. [PubMed:19761360]
  7. Homburg R: Oral agents for ovulation induction--clomiphene citrate versus aromatase inhibitors. Hum Fertil (Camb). 2008 Mar;11(1):17-22. doi: 10.1080/14647270701689670. [PubMed:18320435]
  8. Homburg R: Clomiphene citrate--end of an era? A mini-review. Hum Reprod. 2005 Aug;20(8):2043-51. Epub 2005 May 5. [PubMed:15878925]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [PubMed:25349334]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name
CYP11A1
Uniprot ID
P05108
Uniprot Name
Cholesterol side-chain cleavage enzyme, mitochondrial
Molecular Weight
60101.87 Da
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d 24-hydroxylase 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 un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
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. Styles JA, Davies A, Davies R, White IN, Smith LL: Clastogenic and aneugenic effects of tamoxifen and some of its analogues in hepatocytes from dosed rats and in human lymphoblastoid cells transfected with human P450 cDNAs (MCL-5 cells). Carcinogenesis. 1997 Feb;18(2):303-13. [PubMed:9054622]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Rao US, Fine RL, Scarborough GA: Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. [PubMed:7914405]

Drug created on June 13, 2005 07:24 / Updated on November 18, 2018 13:32