danazol ๐Ÿถ Veterinary Use | 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 ยตM/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 137.11 21.44 33 1765 5409 50597917
Platelet count decreased 58.08 21.44 39 1759 100687 50502639
Hypoperfusion 33.12 21.44 8 1790 1322 50602004
Bone marrow reticulin fibrosis 29.40 21.44 5 1793 140 50603186
Myelofibrosis 24.00 21.44 6 1792 1141 50602185
Therapeutic response decreased 21.81 21.44 16 1782 47215 50556111

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 180.93 25.38 33 1972 719 29571803
Lymphadenitis 155.92 25.38 33 1972 1574 29570948
Haemolysis 134.04 25.38 39 1966 6917 29565605
Hereditary angioedema 105.35 25.38 21 1984 740 29571782
Migraine 89.14 25.38 33 1972 12397 29560125
Myelofibrosis 70.63 25.38 17 1988 1445 29571077
Hepatic enzyme increased 68.52 25.38 37 1968 33762 29538760
Infusion related reaction 67.26 25.38 40 1965 43846 29528676
Therapeutic product effect decreased 56.23 25.38 31 1974 29420 29543102
Myelodysplastic syndrome 49.11 25.38 24 1981 17770 29554752
Rhabdomyolysis 44.22 25.38 35 1970 60773 29511749
Drug ineffective 37.29 25.38 78 1927 363092 29209430
Constipation 37.07 25.38 42 1963 114118 29458404
Bone marrow reticulin fibrosis 31.55 25.38 6 1999 164 29572358
Therapeutic response decreased 31.35 25.38 20 1985 24691 29547831
Platelet count decreased 29.77 25.38 36 1969 104636 29467886
Cushingoid 27.16 25.38 9 1996 2429 29570093
Neutropenia 26.18 25.38 38 1967 131673 29440849

FDA Adverse Event Reporting System (Geriatric)

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 184.62 21.56 33 3304 845 64494550
Hereditary angioedema 156.46 21.56 37 3300 3839 64491556
Lymphadenitis 136.55 21.56 33 3304 3752 64491643
Haemolysis 113.93 21.56 36 3301 11003 64484392
Rhabdomyolysis 68.10 21.56 48 3289 91678 64403717
Myelofibrosis 63.33 21.56 16 3321 2177 64493218
Platelet count decreased 63.16 21.56 59 3278 167652 64327743
Migraine 56.49 21.56 37 3300 62640 64432755
Bone marrow reticulin fibrosis 48.91 21.56 9 3328 271 64495124
Myelodysplastic syndrome 45.25 21.56 24 3313 27555 64467840
Hepatic enzyme increased 41.86 21.56 42 3295 129901 64365494
Immune thrombocytopenia 36.22 21.56 17 3320 15049 64480346
Infusion related reaction 32.14 21.56 41 3296 164426 64330969
Cushingoid 29.43 21.56 12 3325 7591 64487804
Therapeutic product effect decreased 27.81 21.56 32 3305 115319 64380076
Mucosal haemorrhage 25.86 21.56 8 3329 2273 64493122
Hypoperfusion 25.64 21.56 8 3329 2338 64493057
Gingival bleeding 24.56 21.56 13 3324 14841 64480554
Constipation 24.38 21.56 43 3294 229294 64266101
Therapeutic response decreased 22.79 21.56 20 3317 52168 64443227
Non-cirrhotic portal hypertension 22.52 21.56 5 3332 390 64495005
Splenomegaly 22.25 21.56 13 3324 17948 64477447
Drug ineffective 21.57 21.56 93 3244 840154 63655241

FDA Adverse Event Reporting System (Pediatric)

None

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
CHEBI has role CHEBI:50751 anti-estrogenic drug
CHEBI has role CHEBI:50837 oestrogen antagonist
CHEBI has role CHEBI:176497 geroprotectors
MeSH PA D004965 Estrogen Antagonists
MeSH PA D006727 Hormone Antagonists
FDA EPC N0000175824 Androgen

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
Androgen receptor Nuclear hormone receptor AGONIST UNKNOWN CHEMBL
Progesterone receptor Nuclear hormone receptor AGONIST WOMBAT-PK CHEMBL
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 5.43 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 5.27 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
Steryl-sulfatase Enzyme WOMBAT-PK
Sex hormone-binding globulin Secreted Kd 8.20 CHEMBL
Substance-K receptor GPCR Ki 5.05 DRUG MATRIX
Mu-type opioid receptor GPCR Ki 5.24 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 4.99 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
258343 RXNORM
4018233 VANDF
C0010961 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
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
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 71205-861 CAPSULE 100 mg ORAL ANDA 17 sections
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 71205-862 CAPSULE 200 mg ORAL ANDA 17 sections