Identification

Name
Danazol
Accession Number
DB01406
Type
Small Molecule
Groups
Approved
Description

A 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
External IDs
WIN 17,757 / WIN-17757
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CyclomenCapsule200 mgOralSanofi Aventis1972-12-31Not applicableCanada
CyclomenCapsule50 mgOralSanofi Aventis1980-12-31Not applicableCanada
CyclomenCapsule100 mgOralSanofi Aventis1976-12-31Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DanazolCapsule200 mg/1OralCarilion Materials Management2005-09-28Not applicableUs
DanazolCapsule200 mg/1OralTeva1996-08-09Not applicableUs00555 0635 09 nlmimage10 92304922
DanazolCapsule50 mg/1OralLannett Company, Inc.2007-04-19Not applicableUs
DanazolCapsule200 mg/1OralAv Kare, Inc.2016-02-23Not applicableUs
DanazolCapsule100 mg/1OralTeva1998-06-25Not applicableUs00555 0634 02 nlmimage10 670533f9
DanazolCapsule200 mg/1OralLannett Company, Inc.2005-09-28Not applicableUs
DanazolCapsule200 mg/1OralAmerincan Health Packaging2008-08-272015-12-29Us
DanazolCapsule50 mg/1OralTeva1998-06-25Not applicableUs00555 0633 02 nlmimage10 72303931
DanazolCapsule100 mg/1OralLannett Company, Inc.2007-04-19Not applicableUs
International/Other Brands
Danocrine (Sanofi) / Danol (Sanofi)
Categories
UNII
N29QWW3BUO
CAS number
17230-88-5
Weight
Average: 337.4553
Monoisotopic: 337.204179113
Chemical Formula
C22H27NO2
InChI Key
POZRVZJJTULAOH-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

Pharmacology

Indication

For 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
Pharmacodynamics

Danazol 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 action

As 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)

TargetActionsOrganism
AEstrogen receptor alpha
agonist
Human
AAndrogen receptor
agonist
Human
AProgesterone receptor
agonist
Human
AGonadotropin-releasing hormone receptor
negative modulator
Human
APutative gonadotropin-releasing hormone II receptor
negative modulator
Human
UC-C motif chemokine 2
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

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

Route of elimination
Not Available
Half life

Approximately 24 hours.

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

Interactions

Drug Interactions
DrugInteractionDrug group
16-Bromoepiandrosterone16-Bromoepiandrosterone may increase the fluid retaining activities of Danazol.Investigational
19-norandrostenedione19-norandrostenedione may increase the fluid retaining activities of Danazol.Experimental, Illicit
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Danazol.Investigational
5-androstenedione5-androstenedione may increase the fluid retaining activities of Danazol.Experimental, Illicit
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Danazol.Approved, Investigational
AcenocoumarolDanazol may increase the anticoagulant activities of Acenocoumarol.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Danazol.Investigational, Withdrawn
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be decreased when used in combination with Danazol.Experimental, Investigational
AlclometasoneAlclometasone may increase the fluid retaining activities of Danazol.Approved
AldosteroneAldosterone may increase the fluid retaining activities of Danazol.Experimental, Investigational
AllicinThe therapeutic efficacy of Allicin can be decreased when used in combination with Danazol.Investigational
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Danazol.Approved
AmcinonideAmcinonide may increase the fluid retaining activities of Danazol.Approved
AndrostenedioneAndrostenedione may increase the fluid retaining activities of Danazol.Experimental, Illicit
AnecortaveAnecortave may increase the fluid retaining activities of Danazol.Investigational
anecortave acetateanecortave acetate may increase the fluid retaining activities of Danazol.Investigational
AtamestaneAtamestane may increase the fluid retaining activities of Danazol.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
Beclomethasone dipropionateBeclomethasone dipropionate may increase the fluid retaining activities of Danazol.Approved, Investigational
Bempedoic acidThe therapeutic efficacy of Bempedoic acid can be decreased when used in combination with Danazol.Investigational
BetamethasoneBetamethasone may increase the fluid retaining activities of Danazol.Approved, Vet Approved
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Danazol.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Danazol.Approved, Investigational
BudesonideBudesonide may increase the fluid retaining activities of Danazol.Approved
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Danazol.Investigational, Withdrawn
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Danazol.Approved
CalcidiolDanazol may increase the hypercalcemic activities of Calcidiol.Approved, Nutraceutical
CalcipotriolDanazol may increase the hypercalcemic activities of Calcipotriol.Approved
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Danazol.Approved
Capromab pendetideDanazol may decrease effectiveness of Capromab pendetide as a diagnostic agent.Approved
CarbamazepineThe metabolism of Carbamazepine can be decreased when combined with Danazol.Approved, Investigational
CarbutamideThe therapeutic efficacy of Carbutamide can be decreased when used in combination with Danazol.Experimental
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
CiclesonideCiclesonide may increase the fluid retaining activities of Danazol.Approved, Investigational
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Danazol.Experimental
ClobetasolClobetasol may increase the fluid retaining activities of Danazol.Investigational
Clobetasol propionateClobetasol propionate may increase the fluid retaining activities of Danazol.Approved
ClobetasoneClobetasone may increase the fluid retaining activities of Danazol.Approved
ClocortoloneClocortolone may increase the fluid retaining activities of Danazol.Approved
ClorindioneDanazol may increase the anticoagulant activities of Clorindione.Experimental
Conestat alfaDanazol may increase the thrombogenic activities of Conestat alfa.Approved
Cortexolone 17α-propionateCortexolone 17α-propionate may increase the fluid retaining activities of Danazol.Investigational
CorticosteroneCorticosterone may increase the fluid retaining activities of Danazol.Experimental
Cortisone acetateCortisone acetate may increase the fluid retaining activities of Danazol.Approved
CyclosporineDanazol may increase the hepatotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
DeflazacortDeflazacort may increase the fluid retaining activities of Danazol.Approved
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Danazol.Investigational
DesonideDesonide may increase the fluid retaining activities of Danazol.Approved, Investigational
DesoximetasoneDesoximetasone may increase the fluid retaining activities of Danazol.Approved
Desoxycorticosterone acetateDesoxycorticosterone acetate may increase the fluid retaining activities of Danazol.Approved
Desoxycorticosterone PivalateDesoxycorticosterone Pivalate may increase the fluid retaining activities of Danazol.Experimental, Vet Approved
DexamethasoneDexamethasone may increase the fluid retaining activities of Danazol.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateDexamethasone isonicotinate may increase the fluid retaining activities of Danazol.Vet Approved
DicoumarolDanazol may increase the anticoagulant activities of Dicoumarol.Approved
DiflorasoneDiflorasone may increase the fluid retaining activities of Danazol.Approved
DifluocortoloneDifluocortolone may increase the fluid retaining activities of Danazol.Approved, Investigational
DifluprednateDifluprednate may increase the fluid retaining activities of Danazol.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Danazol.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Danazol.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Danazol.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Danazol.Approved
DihydrotachysterolDanazol may increase the hypercalcemic activities of Dihydrotachysterol.Approved
DiphenadioneDanazol may increase the anticoagulant activities of Diphenadione.Experimental
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
EquileninEquilenin may increase the fluid retaining activities of Danazol.Experimental
EquilinEquilin may increase the fluid retaining activities of Danazol.Approved
ErgocalciferolDanazol may increase the hypercalcemic activities of Ergocalciferol.Approved, Nutraceutical
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Danazol.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Danazol.Approved
EstroneEstrone may increase the fluid retaining activities of Danazol.Approved
Estrone sulfateEstrone sulfate may increase the fluid retaining activities of Danazol.Approved
Ethyl biscoumacetateDanazol may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
ExenatideThe therapeutic efficacy of Exenatide can be decreased when used in combination with Danazol.Approved, Investigational
fluasteronefluasterone may increase the fluid retaining activities of Danazol.Investigational
FludrocortisoneFludrocortisone may increase the fluid retaining activities of Danazol.Approved
FluindioneDanazol may increase the anticoagulant activities of Fluindione.Investigational
FlumethasoneFlumethasone may increase the fluid retaining activities of Danazol.Approved, Vet Approved
FlunisolideFlunisolide may increase the fluid retaining activities of Danazol.Approved, Investigational
Fluocinolone AcetonideFluocinolone Acetonide may increase the fluid retaining activities of Danazol.Approved, Investigational, Vet Approved
FluocinonideFluocinonide may increase the fluid retaining activities of Danazol.Approved, Investigational
FluocortoloneFluocortolone may increase the fluid retaining activities of Danazol.Approved, Withdrawn
FluorometholoneFluorometholone may increase the fluid retaining activities of Danazol.Approved
FluprednideneFluprednidene may increase the fluid retaining activities of Danazol.Approved, Withdrawn
FluprednisoloneFluprednisolone may increase the fluid retaining activities of Danazol.Approved
FlurandrenolideFlurandrenolide may increase the fluid retaining activities of Danazol.Approved
Fluticasone furoateFluticasone furoate may increase the fluid retaining activities of Danazol.Approved
Fluticasone propionateFluticasone propionate may increase the fluid retaining activities of Danazol.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Danazol.Approved
FormestaneFormestane may increase the fluid retaining activities of Danazol.Approved, Investigational, Withdrawn
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Danazol.Investigational, 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, Investigational
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
HalcinonideHalcinonide may increase the fluid retaining activities of Danazol.Approved, Investigational, Withdrawn
HE3286HE3286 may increase the fluid retaining activities of Danazol.Investigational
Human C1-esterase inhibitorDanazol may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
HydrocortisoneHydrocortisone may increase the fluid retaining activities of Danazol.Approved, Vet Approved
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 HumanThe therapeutic efficacy of Insulin Human can be decreased when used in combination with Danazol.Approved, Investigational
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
IstaroximeIstaroxime may increase the fluid retaining activities of Danazol.Investigational
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
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Danazol.Approved, Investigational
LoteprednolLoteprednol may increase the fluid retaining activities of Danazol.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Danazol.Approved, Investigational
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Danazol.Illicit, Investigational, Withdrawn
ME-609ME-609 may increase the fluid retaining activities of Danazol.Investigational
MedrysoneMedrysone may increase the fluid retaining activities of Danazol.Approved
MelengestrolMelengestrol may increase the fluid retaining activities of Danazol.Vet Approved
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Danazol.Experimental
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Danazol.Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Danazol.Approved
MethylprednisoloneMethylprednisolone may increase the fluid retaining activities of Danazol.Approved, Vet Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined 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
MometasoneMometasone may increase the fluid retaining activities of Danazol.Approved, Vet Approved
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Danazol.Approved, Investigational
NCX 1022NCX 1022 may increase the fluid retaining activities of Danazol.Investigational
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Danazol.Approved, Investigational
Oleoyl-estroneOleoyl-estrone may increase the fluid retaining activities of Danazol.Investigational
ParamethasoneParamethasone may increase the fluid retaining activities of Danazol.Approved
ParicalcitolDanazol may increase the hypercalcemic activities of Paricalcitol.Approved, Investigational
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Danazol.Approved, Investigational, Vet Approved, Withdrawn
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Danazol.Approved, Investigational, Withdrawn
PhenindioneDanazol may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonDanazol may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
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
PrasteronePrasterone may increase the fluid retaining activities of Danazol.Approved, Nutraceutical
Prasterone sulfatePrasterone sulfate may increase the fluid retaining activities of Danazol.Investigational
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Danazol.Approved
PrednicarbatePrednicarbate may increase the fluid retaining activities of Danazol.Approved
PrednisolonePrednisolone may increase the fluid retaining activities of Danazol.Approved, Vet Approved
PrednisonePrednisone may increase the fluid retaining activities of Danazol.Approved, Vet Approved
PregnenolonePregnenolone may increase the fluid retaining activities of Danazol.Experimental, Investigational
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Danazol.Approved, Investigational
RimexoloneRimexolone may increase the fluid retaining activities of Danazol.Approved
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
SotagliflozinThe therapeutic efficacy of Sotagliflozin can be decreased when used in combination with Danazol.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
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Danazol.Experimental
TioclomarolDanazol may increase the anticoagulant activities of Tioclomarol.Experimental
TixocortolTixocortol may increase the fluid retaining activities of Danazol.Approved
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
TriamcinoloneTriamcinolone may increase the fluid retaining activities of Danazol.Approved, Vet Approved
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Danazol.Investigational, Withdrawn
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Danazol.Approved, Investigational, Nutraceutical
UlobetasolUlobetasol may increase the fluid retaining activities of Danazol.Approved
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
WarfarinDanazol may increase the anticoagulant activities of Warfarin.Approved
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
Human Metabolome Database
HMDB02835
KEGG Drug
D00289
PubChem Compound
28417
PubChem Substance
46506475
ChemSpider
26436
BindingDB
50423541
ChEBI
4315
ChEMBL
CHEMBL1479
Therapeutic Targets Database
DAP001017
PharmGKB
PA164749056
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Danazol
ATC Codes
G03XA01 — Danazol
AHFS Codes
  • 68:08.00 — Androgens
MSDS
Download (75 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2CompletedTreatmentAplastic Anaemia (AA)1
1, 2TerminatedTreatmentCongenital Hypoplastic Anemia / Dyskeratosis Congenita1
2CompletedSupportive CareAnemias / Primary Myelofibrosis / Secondary Myelofibrosis1
2CompletedTreatmentAutoimmune Thrombocytopenia1
2CompletedTreatmentDiabetic Macular Edema (DME)1
2CompletedTreatmentEndometrial Cancers1
2CompletedTreatmentFibrocystic Disease of Breast1
2CompletedTreatmentModerate to Severe Cyclic Mastalgia1
2RecruitingTreatmentTelomere Disease1
2RecruitingTreatmentThrombotic Thrombocytopenic Purpura (TTP)1
3CompletedTreatmentDiabetic Macular Edema (DME)1
4CompletedTreatmentEndometriosis / Infertilities / Ovarian Cysts1

Pharmacoeconomics

Manufacturers
Not 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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)224.2-226.8Clinton, 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0009000000-9e745b8feecd354f6618
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-01b9-6902000000-854476472755ef5419e5
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0006-9100000000-0d62c0c1b53c1cea5a25
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
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0329000000-56adc37fd83dfa3c686f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-05ia-3931000000-1490f6c4984a84016076
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrane steroids
Alternative Parents
17-hydroxysteroids / Ynones / Tertiary alcohols / Isoxazoles / Heteroaromatic compounds / Cyclic alcohols and derivatives / Oxacyclic compounds / Azacyclic compounds / Acetylides / Organopnictogen compounds
show 2 more
Substituents
Estrane-skeleton / Hydroxysteroid / 17-hydroxysteroid / Ynone / Heteroaromatic compound / Azole / Cyclic alcohol / Tertiary alcohol / Isoxazole / Acetylide
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
terminal acetylenic compound, 17beta-hydroxy steroid (CHEBI:4315)

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 tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
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 ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
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 ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
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...
Gene Name
GNRHR
Uniprot ID
P30968
Uniprot Name
Gonadotropin-releasing hormone receptor
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
Uniprot Name
Putative gonadotropin-releasing hormone II receptor
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
Uniprot Name
C-C motif chemokine 2
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
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
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
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]

Drug created on July 13, 2007 14:36 / Updated on December 10, 2017 17:18