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Identification
NameDanazol
Accession NumberDB01406
TypeSmall Molecule
GroupsApproved
DescriptionA synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders. [PubChem]
Structure
Thumb
Synonyms
Cyclomen
Danazolum
Danocrine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CyclomenCapsule200 mgOralSanofi Aventis Canada Inc1972-12-31Not applicableCanada
CyclomenCapsule100 mgOralSanofi Aventis Canada Inc1976-12-31Not applicableCanada
CyclomenCapsule50 mgOralSanofi Aventis Canada Inc1980-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DanazolCapsule100 mg/1OralTeva Pharmaceuticals Usa, Inc.1998-06-25Not applicableUs
DanazolCapsule100 mg/1OralLannett Company, Inc.2007-04-19Not applicableUs
DanazolCapsule200 mg/1OralAmerican Health Packaging2008-08-272015-12-29Us
DanazolCapsule200 mg/1OralTeva Pharmaceuticals Usa, Inc.1996-08-09Not applicableUs
DanazolCapsule200 mg/1OralLannett Company, Inc.2005-09-28Not applicableUs
DanazolCapsule200 mg/1OralAv Kare, Inc.2016-02-23Not applicableUs
DanazolCapsule50 mg/1OralLannett Company, Inc.2007-04-19Not applicableUs
DanazolCapsule50 mg/1OralTeva Pharmaceuticals Usa, Inc.1998-06-25Not applicableUs
DanazolCapsule200 mg/1OralCarilion Materials Management2005-09-28Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DanocrineSanofi
DanolSanofi
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIN29QWW3BUO
CAS number17230-88-5
WeightAverage: 337.4553
Monoisotopic: 337.204179113
Chemical FormulaC22H27NO2
InChI KeyPOZRVZJJTULAOH-LHZXLZLDSA-N
InChI
InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1
IUPAC Name
(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4(8),5,9-trien-17-ol
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3
Pharmacology
IndicationFor the treatment of endometriosis and fibrocystic breast disease (in patients unresponsive to simple measures). Also used for the prophylactic treatment of all types of hereditary angioedema in males and females.
Structured Indications
PharmacodynamicsDanazol is a derivative of the synthetic steroid ethisterone, a modified testosterone. It was approved by the U.S. Food and Drug Administration (FDA) as the first drug to specifically treat endometriosis, but its role as a treatment for endometriosis has been largely replaced by the gonadotropin-releasing hormone (GnRH) agonists. Danazol has antigonadotropic and anti-estrogenic activities. Danazol acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties.
Mechanism of actionAs a gonadotropin inhibitor, danazol suppresses the pituitary-ovarian axis possibly by inhibiting the output of pituitary gonadotropins. Danazol also depresses the preovulatory surge in output of follicle-stimulating hormone (FSH) and luteinizing hormone (LH), thereby reducing ovarian estrogen production. Danazol may also directly inhibits ovarian steroidogenesis; bind to androgen, progesterone, and glucocorticoid receptors; bind to sex-hormone-binding globulin and corticosteroid-binding globulin; and increases the metabolic clearance rate of progesterone. Another mechanism of action by which danazol may use to facilitate regression of endometriosis is by decreasing IgG, IgM, and IgA concentrations, as well as phospholipid and IgG isotope autoantibodies. In the treatment of endometriosis, as a consequence of suppression of ovarian function, danazol causes both normal and ectopic endometrial tissues to become inactive and atrophic. This leads to anovulation and associated amenorrhea. In fibrocystic breast disease, the exact mechanism of action of danazol is unknown, but may be related to suppressed estrogenic stimulation as a result of decreased ovarian production of estrogen. A direct effect on steroid receptor sites in breast tissue is also possible. This leads to a disappearance of nodularity, relief of pain and tenderness, and possibly changes in the menstrual pattern. In terms of hereditary angioedema, danazol corrects the underlying biochemical deficiency by increasing serum concentrations of the deficient C1 esterase inhibitor, resulting in increased serum concentrations of the C4 component of the complement system. (Source: PharmGKB)
TargetKindPharmacological actionActionsOrganismUniProt ID
Estrogen receptorProteinyes
agonist
HumanP03372 details
Androgen receptorProteinyes
agonist
HumanP10275 details
Progesterone receptorProteinyes
agonist
HumanP06401 details
Gonadotropin-releasing hormone receptorProteinyes
negative modulator
HumanP30968 details
Putative gonadotropin-releasing hormone II receptorProteinyes
negative modulator
HumanQ96P88 details
C-C motif chemokine 2Proteinunknown
inhibitor
HumanP13500 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic, to principal metabolites, ethisterone and 17-hydroxymethylethisterone.

SubstrateEnzymesProduct
Danazol
Not Available
17-hydroxymethylethisteroneDetails
Danazol
Not Available
EthisteroneDetails
Route of eliminationNot Available
Half lifeApproximately 24 hours.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Danazol.Approved, Investigational
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Danazol.Withdrawn
AicarThe therapeutic efficacy of Aicar can be decreased when used in combination with Danazol.Experimental
AlfacalcidolDanazol may increase the hypercalcemic activities of Alfacalcidol.Approved, Nutraceutical
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Danazol.Approved
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Danazol.Approved, Investigational
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Danazol.Approved
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Danazol.Investigational
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Danazol.Withdrawn
CalcidiolDanazol may increase the hypercalcemic activities of Calcidiol.Approved, Nutraceutical
CalcipotriolDanazol may increase the hypercalcemic activities of Calcipotriol.Approved
CalcitriolDanazol may increase the hypercalcemic activities of Calcitriol.Approved, Nutraceutical
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Danazol.Approved
CarbamazepineThe metabolism of Carbamazepine can be decreased when combined with Danazol.Approved, Investigational
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Danazol.Experimental
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Danazol.Withdrawn
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Danazol.Approved
CholecalciferolDanazol may increase the hypercalcemic activities of Cholecalciferol.Approved, Nutraceutical
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Danazol.Experimental
Coenzyme Q10The serum concentration of Coenzyme Q10 can be increased when it is combined with Danazol.Experimental
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Danazol.Investigational
DihydrotachysterolDanazol may increase the hypercalcemic activities of Dihydrotachysterol.Approved
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Danazol.Approved
DoxercalciferolDanazol may increase the hypercalcemic activities of Doxercalciferol.Approved
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Danazol.Approved
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Danazol.Approved
ErgocalciferolDanazol may increase the hypercalcemic activities of Ergocalciferol.Approved, Nutraceutical
ExenatideThe therapeutic efficacy of Exenatide can be decreased when used in combination with Danazol.Approved, Investigational
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Danazol.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Danazol.Approved
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Danazol.Withdrawn
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Danazol.Approved
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Danazol.Approved
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Danazol.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Danazol.Approved
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Danazol.Approved
GusperimusThe therapeutic efficacy of Gusperimus can be decreased when used in combination with Danazol.Investigational
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Danazol.Approved, Illicit
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Danazol.Approved
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Danazol.Approved
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Danazol.Approved
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Danazol.Approved
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Danazol.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Danazol.Approved
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Danazol.Approved
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Danazol.Approved
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Danazol.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Danazol.Approved, Investigational
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Danazol.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Danazol.Experimental
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Danazol.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Danazol.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Danazol.Approved, Investigational
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Danazol.Approved, Investigational
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Danazol.Approved
ParicalcitolDanazol may increase the hypercalcemic activities of Paricalcitol.Approved, Investigational
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Danazol.Approved, Withdrawn
PimozideThe serum concentration of Pimozide can be increased when it is combined with Danazol.Approved
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Danazol.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Danazol.Approved
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Danazol.Approved, Investigational
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Danazol.Approved
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Danazol.Approved, Investigational
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Danazol.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Danazol.Approved
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Danazol.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Danazol.Approved
SitagliptinThe therapeutic efficacy of Sitagliptin can be decreased when used in combination with Danazol.Approved, Investigational
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Danazol.Approved, Investigational
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Danazol.Approved, Investigational
ThiazolidinedioneThe therapeutic efficacy of Thiazolidinedione can be decreased when used in combination with Danazol.Investigational
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Danazol.Approved
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Danazol.Approved
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Danazol.Withdrawn
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Danazol.Approved, Investigational
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Danazol.Approved, Investigational
Food Interactions
  • Take without regard to meals.
References
Synthesis Reference

Clinton, R. and Hanson, A.; US. Patent 3,135,743; June 2, 1964; assigned to Sterling Drug.

General References
  1. Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [PubMed:2404115 ]
  2. Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. [PubMed:2486535 ]
  3. Jenkin G: Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. 1980 May;20(2):113-8. [PubMed:6998453 ]
External Links
ATC CodesG03XA01
AHFS Codes
  • 68:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (75 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9781
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.5938
P-glycoprotein inhibitor INon-inhibitor0.5194
P-glycoprotein inhibitor IINon-inhibitor0.8893
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8487
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.67
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.7407
CYP450 2D6 inhibitorNon-inhibitor0.8731
CYP450 2C19 inhibitorInhibitor0.5962
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7692
Ames testNon AMES toxic0.6885
CarcinogenicityNon-carcinogens0.9083
BiodegradationNot ready biodegradable0.9562
Rat acute toxicity1.3291 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6896
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CapsuleOral100 mg
CapsuleOral200 mg
CapsuleOral50 mg
CapsuleOral100 mg/1
CapsuleOral200 mg/1
CapsuleOral50 mg/1
Prices
Unit descriptionCostUnit
Danazol powder21.42USD g
Danazol 200 mg capsule5.2USD capsule
Danocrine 200 mg capsule4.53USD capsule
Danazol 100 mg capsule2.92USD capsule
Cyclomen 200 mg Capsule2.31USD capsule
Danazol 50 mg capsule1.95USD capsule
Cyclomen 100 mg Capsule1.45USD capsule
Cyclomen 50 mg Capsule0.98USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point224.2-226.8Clinton, R. and Hanson, A.; US. Patent 3,135,743; June 2, 1964; assigned to Sterling Drug.
logP0.51PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
Water Solubility0.0176 mg/mLALOGPS
logP3.62ALOGPS
logP3.46ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)17.59ChemAxon
pKa (Strongest Basic)0.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.26 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity98.54 m3·mol-1ChemAxon
Polarizability38.56 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0009000000-9e745b8feecd354f6618View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01b9-6902000000-854476472755ef5419e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-0d62c0c1b53c1cea5a25View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Estrane-skeleton
  • Ynone
  • Heteroaromatic compound
  • Tertiary alcohol
  • Oxazole
  • Isoxazole
  • Cyclic alcohol
  • Azole
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
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 tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Fujimoto J, Hori M, Itoh T, Ichigo S, Nishigaki M, Tamaya T: Danazol decreases transcription of estrogen receptor gene in human monocytes. Gen Pharmacol. 1995 May;26(3):507-16. [PubMed:7540578 ]
  2. Snyder BW, Beecham GD, Winneker RC: Danazol suppression of luteinizing hormone in the rat: evidence for mediation by both androgen and estrogen receptors. Proc Soc Exp Biol Med. 1990 May;194(1):54-7. [PubMed:2326286 ]
  3. Sanfilippo JS, Barrows GH, Apkarian RP, Wittliff JL: Evaluation of danazol influence upon the uterus using scanning electron microscopic morphometric and biochemical analyses. Surg Gynecol Obstet. 1985 May;160(5):421-8. [PubMed:4039467 ]
  4. 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
yes
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 factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. [PubMed:2486535 ]
  2. Sasagawa S, Shimizu Y, Kami H, Takeuchi T, Mita S, Imada K, Kato S, Mizuguchi K: Dienogest is a selective progesterone receptor agonist in transactivation analysis with potent oral endometrial activity due to its efficient pharmacokinetic profile. Steroids. 2008 Feb;73(2):222-31. Epub 2007 Oct 22. [PubMed:18061638 ]
  3. Gomez F, Ruiz P, Lopez R, Rivera C, Romero S, Bernal JA: Effects of androgen treatment on expression of macrophage Fcgamma receptors. Clin Diagn Lab Immunol. 2000 Jul;7(4):682-6. [PubMed:10882672 ]
  4. Roselli CE: The effect of anabolic-androgenic steroids on aromatase activity and androgen receptor binding in the rat preoptic area. Brain Res. 1998 May 11;792(2):271-6. [PubMed:9593936 ]
  5. Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [PubMed:2404115 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial ...
Gene Name:
PGR
Uniprot ID:
P06401
Molecular Weight:
98979.96 Da
References
  1. Beaumont H, Augood C, Duckitt K, Lethaby A: Danazol for heavy menstrual bleeding. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD001017. [PubMed:17636649 ]
  2. Sasagawa S, Shimizu Y, Kami H, Takeuchi T, Mita S, Imada K, Kato S, Mizuguchi K: Dienogest is a selective progesterone receptor agonist in transactivation analysis with potent oral endometrial activity due to its efficient pharmacokinetic profile. Steroids. 2008 Feb;73(2):222-31. Epub 2007 Oct 22. [PubMed:18061638 ]
  3. Huang HF, Wang M: [Effects of gossypol acetate, danazol, progesterone and GnRH-A on estrogen and progesterone receptors of human endometrial cells]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 1994 Jun;14(6):352-3, 325. [PubMed:8000225 ]
  4. Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [PubMed:2404115 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
negative modulator
General Function:
Peptide binding
Specific Function:
Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle-stimulating hormone (FSH). This receptor mediates its action by association with G-proteins that activate a phosphatidylinositol-calcium second messenger system. Isoform 2 may act as an inhibitor of GnRH-R signaling.
Gene Name:
GNRHR
Uniprot ID:
P30968
Molecular Weight:
37730.355 Da
References
  1. Tian ZZ, Zhao H, Chen BY: [Effect of Chinese herbal medicine for nourishing yin and purging fire on mRNA expressions of gonadotropin-releasing hormone and its receptor in precocious puberty model rats]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 2003 Sep;23(9):695-8. [PubMed:14571621 ]
  2. Menon M, Peegel H, Katta V: Inhibition of gonadotropin-releasing hormone receptors in rat anterior pituitary monolayer cell cultures by danazol. Am J Obstet Gynecol. 1986 Feb;154(2):367-72. [PubMed:3004220 ]
  3. Roth C, Hegemann F, Hildebrandt J, Balzer I, Witt A, Wuttke W, Jarry H: Pituitary and gonadal effects of GnRH (gonadotropin releasing hormone) analogues in two peripubertal female rat models. Pediatr Res. 2004 Jan;55(1):126-33. Epub 2003 Nov 6. [PubMed:14605254 ]
  4. Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [PubMed:2404115 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
negative modulator
General Function:
Gonadotropin-releasing hormone receptor activity
Specific Function:
Putative receptor for gonadotropin releasing hormone II (GnRH II) which is most probably non-functional.
Gene Name:
GNRHR2
Uniprot ID:
Q96P88
Molecular Weight:
32536.935 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [PubMed:2404115 ]
  4. Menon M, Peegel H, Katta V: Inhibition of gonadotropin-releasing hormone receptors in rat anterior pituitary monolayer cell cultures by danazol. Am J Obstet Gynecol. 1986 Feb;154(2):367-72. [PubMed:3004220 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
CCL2
Uniprot ID:
P13500
Molecular Weight:
11024.87 Da
References
  1. Boucher A, Lemay A, Akoum A: Effect of hormonal agents on monocyte chemotactic protein-1 expression by endometrial epithelial cells of women with endometriosis. Fertil Steril. 2000 Nov;74(5):969-75. [PubMed:11056242 ]
  2. Jolicoeur C, Lemay A, Akoum A: Comparative effect of danazol and a GnRH agonist on monocyte chemotactic protein-1 expression by endometriotic cells. Am J Reprod Immunol. 2001 Feb;45(2):86-93. [PubMed:11216879 ]

Enzymes

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
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
inhibitor
General Function:
Vitamin d3 25-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 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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 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 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
yes
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, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration.
Gene Name:
SHBG
Uniprot ID:
P04278
Molecular Weight:
43778.755 Da
References
  1. De Leo V, Morgante G, La Marca A, Musacchio MC, Sorace M, Cavicchioli C, Petraglia F: A benefit-risk assessment of medical treatment for uterine leiomyomas. Drug Saf. 2002;25(11):759-79. [PubMed:12222988 ]
  2. Telimaa S, Apter D, Reinila M, Ronnberg L, Kauppila A: Placebo-controlled comparison of hormonal and biochemical effects of danazol and high-dose medroxyprogesterone acetate. Eur J Obstet Gynecol Reprod Biol. 1990 Jul-Aug;36(1-2):97-105. [PubMed:2142109 ]
  3. Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. [PubMed:2486535 ]
  4. Valimaki M, Nilsson CG, Roine R, Ylikorkala O: Comparison between the effects of nafarelin and danazol on serum lipids and lipoproteins in patients with endometriosis. J Clin Endocrinol Metab. 1989 Dec;69(6):1097-103. [PubMed:2531153 ]
  5. Forbes KL, Dowsett M, Rose GL, Mudge JE, Jeffcoate SL: Dosage-related effects of danazol on sex hormone binding globulin and free and total androgen levels. Clin Endocrinol (Oxf). 1986 Nov;25(5):597-605. [PubMed:3304725 ]
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Drug created on July 13, 2007 14:36 / Updated on August 17, 2016 12:23