danazol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
779 17230-88-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • danazol
  • chronogyn
  • danatrol
  • danazolum
  • danocrine
  • danovaol
  • danzol
  • winobanin
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.
  • Molecular weight: 337.46
  • Formula: C22H27NO2
  • CLOGP: 3.75
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 46.26
  • ALOGS: -4.28
  • ROTB: 0

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.60 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.00 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 33.78 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 5.18 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 15.71 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.31 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 21, 1976 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hereditary angioedema 160.33 20.69 38 1731 5478 46678815
Platelet count decreased 60.81 20.69 41 1728 99983 46584310
Hypoperfusion 32.22 20.69 8 1761 1389 46682904
Bone marrow reticulin fibrosis 28.98 20.69 5 1764 143 46684150
Immune thrombocytopenia 28.52 20.69 11 1758 8230 46676063
Therapeutic response decreased 22.19 20.69 16 1753 43129 46641164

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Coombs positive haemolytic anaemia 169.08 27.81 31 1898 734 29949815
Lymphadenitis 144.02 27.81 31 1898 1689 29948860
Haemolysis 125.70 27.81 37 1892 7194 29943355
Hereditary angioedema 111.84 27.81 22 1907 763 29949786
Migraine 82.33 27.81 31 1898 12843 29937706
Hepatic enzyme increased 67.79 27.81 36 1893 33458 29917091
Infusion related reaction 66.68 27.81 38 1891 40526 29910023
Myelofibrosis 65.18 27.81 16 1913 1555 29948994
Therapeutic product effect decreased 52.52 27.81 29 1900 29047 29921502
Myelodysplastic syndrome 46.08 27.81 23 1906 18755 29931794
Rhabdomyolysis 42.30 27.81 34 1895 63546 29887003
Drug ineffective 39.92 27.81 75 1854 340312 29610237
Constipation 35.75 27.81 40 1889 112866 29837683
Therapeutic response decreased 32.57 27.81 20 1909 24329 29926220
Bone marrow reticulin fibrosis 31.62 27.81 6 1923 171 29950378

Pharmacologic Action:

SourceCodeDescription
ATC G03XA01 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
OTHER SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
Antigonadotropins and similar agents
FDA CS M0001109 Androstanes
FDA MoA N0000000146 Androgen Receptor Agonists
FDA EPC N0000175824 Androgen
CHEBI has role CHEBI:50751 anti-estrogenic agent
CHEBI has role CHEBI:50837 oestrogen antagonist
MeSH PA D004965 Estrogen Antagonists
MeSH PA D006727 Hormone Antagonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Fibrocystic breast changes indication 27431007 DOID:10354
Endometriosis indication 129103003
Hereditary Angioedema Prevention indication
Gynecomastia off-label use 4754008 DOID:12698
Menorrhagia off-label use 386692008
Precocious puberty off-label use 400179000
Migraine contraindication 37796009 DOID:6364
Chronic heart failure contraindication 48447003
Intermenstrual bleeding - irregular contraindication 64996003
Epilepsy contraindication 84757009 DOID:1826
Kidney disease contraindication 90708001 DOID:557
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Mixed hyperlipidemia contraindication 267434003
Pregnancy, function contraindication 289908002
Thromboembolic disorder contraindication 371039008
Breastfeeding (mother) contraindication 413712001
Porphyria contraindication 418470004
Carcinoma of female breast contraindication 447782002

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Progesterone receptor Nuclear hormone receptor AGONIST WOMBAT-PK CHEMBL
Androgen receptor Nuclear hormone receptor AGONIST UNKNOWN CHEMBL
D(1A) dopamine receptor GPCR Ki 4.99 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 5.16 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 5.09 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.25 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 5.60 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 4.98 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 5.01 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 5.42 DRUG MATRIX
Glucocorticoid receptor Nuclear hormone receptor Ki 5.71 DRUG MATRIX
Beta-3 adrenergic receptor GPCR Ki 4.89 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 5.46 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.26 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.20 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 5.21 DRUG MATRIX
Estrogen receptor Nuclear hormone receptor Ki 5.29 DRUG MATRIX
Cytochrome P450 2C9 Enzyme IC50 6.52 DRUG MATRIX
Substance-K receptor GPCR Ki 5.05 DRUG MATRIX
Steryl-sulfatase Enzyme WOMBAT-PK
Sex hormone-binding globulin Secreted Kd 8.20 CHEMBL
Mu-type opioid receptor GPCR Ki 5.24 DRUG MATRIX
Androgen receptor Transcription factor Ki 8.10 DRUG MATRIX
Progesterone receptor Transcription factor Ki 7.47 DRUG MATRIX

External reference:

IDSource
4018233 VUID
N0000146564 NUI
D00289 KEGG_DRUG
4018233 VANDF
C0733889 UMLSCUI
CHEBI:4315 CHEBI
QA1 PDB_CHEM_ID
CHEMBL1479 ChEMBL_ID
DB01406 DRUGBANK_ID
D003613 MESH_DESCRIPTOR_UI
28417 PUBCHEM_CID
6942 IUPHAR_LIGAND_ID
2556 INN_ID
N29QWW3BUO UNII
258343 RXNORM
3093 MMSL
4533 MMSL
605 MMSL
d00204 MMSL
002116 NDDF
126124009 SNOMEDCT_US
87881000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 0527-1368 CAPSULE 100 mg ORAL ANDA 17 sections
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 0527-1369 CAPSULE 200 mg ORAL ANDA 17 sections
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 0527-1392 CAPSULE 50 mg ORAL ANDA 17 sections
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 0555-0633 CAPSULE 50 mg ORAL ANDA 17 sections
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 0555-0634 CAPSULE 100 mg ORAL ANDA 17 sections
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 0555-0635 CAPSULE 200 mg ORAL ANDA 17 sections
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 42291-243 CAPSULE 200 mg ORAL ANDA 16 sections
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 68151-2298 CAPSULE 200 mg ORAL ANDA 21 sections