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 Bocci G, Oprea TI, Benet LZ
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 172.87 21.95 43 2378 7519 63479082
Drug ineffective for unapproved indication 95.27 21.95 39 2382 34024 63452577
Angioedema 91.79 21.95 42 2379 47923 63438678
Swollen tongue 84.40 21.95 36 2385 34764 63451837
Dysphonia 79.65 21.95 38 2383 47576 63439025
Swelling face 66.57 21.95 37 2384 63438 63423163
Platelet count decreased 59.49 21.95 43 2378 116079 63370522
Product use in unapproved indication 54.76 21.95 49 2372 179031 63307570
Hypoperfusion 31.77 21.95 8 2413 1459 63485142
Drug ineffective 28.04 21.95 95 2326 1044670 62441931
Hypersensitivity 27.74 21.95 44 2377 292641 63193960
Bone marrow reticulin fibrosis 26.94 21.95 5 2416 216 63486385
Myelofibrosis 22.49 21.95 6 2415 1371 63485230
Drug intolerance 22.12 21.95 41 2380 308620 63177981

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 267.45 28.54 48 2395 924 34953564
Lymphadenitis 232.22 28.54 48 2395 1980 34952508
Haemolysis 193.33 28.54 54 2389 8040 34946448
Migraine 122.55 28.54 46 2397 17432 34937056
Hereditary angioedema 121.05 28.54 25 2418 1022 34953466
Hepatic enzyme increased 110.42 28.54 54 2389 39026 34915462
Infusion related reaction 97.58 28.54 55 2388 53002 34901486
Therapeutic product effect decreased 86.26 28.54 44 2399 34699 34919789
Myelofibrosis 68.46 28.54 17 2426 1594 34952894
Drug ineffective 58.03 28.54 109 2334 456642 34497846
Constipation 54.73 28.54 57 2386 136925 34817563
Myelodysplastic syndrome 49.57 28.54 25 2418 19183 34935305
Rhabdomyolysis 45.90 28.54 38 2405 68125 34886363
Neutropenia 43.47 28.54 54 2389 156724 34797764
Bone marrow reticulin fibrosis 31.30 28.54 6 2437 166 34954322
Platelet count decreased 29.59 28.54 39 2404 119678 34834810

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 272.39 21.66 48 4257 1082 79739001
Lymphadenitis 204.63 21.66 48 4257 4607 79735476
Hereditary angioedema 182.84 21.66 45 4260 5290 79734793
Haemolysis 169.31 21.66 51 4254 12761 79727322
Drug ineffective for unapproved indication 80.70 21.66 44 4261 51194 79688889
Migraine 72.94 21.66 50 4255 87443 79652640
Rhabdomyolysis 65.55 21.66 50 4255 103081 79637002
Swollen tongue 65.48 21.66 36 4269 42534 79697549
Angioedema 64.66 21.66 44 4261 75991 79664092
Drug ineffective 63.04 21.66 162 4143 1080751 78659332
Myelofibrosis 60.57 21.66 16 4289 2484 79737599
Platelet count decreased 58.86 21.66 62 4243 194602 79545481
Hepatic enzyme increased 56.71 21.66 59 4246 182551 79557532
Dysphonia 53.37 21.66 35 4270 56837 79683246
Swelling face 50.75 21.66 37 4268 71175 79668908
Bone marrow reticulin fibrosis 46.52 21.66 9 4296 341 79739742
Myelodysplastic syndrome 44.87 21.66 25 4280 30276 79709807
Product use in unapproved indication 41.71 21.66 59 4246 250300 79489783
Infusion related reaction 40.95 21.66 56 4249 230181 79509902
Therapeutic product effect decreased 37.20 21.66 45 4260 163818 79576265
Constipation 36.21 21.66 59 4246 282991 79457092
Immune thrombocytopenia 32.83 21.66 17 4288 17788 79722295
Neutropenia 31.54 21.66 56 4249 287654 79452429
Cushingoid 26.30 21.66 12 4293 9540 79730543
Mucosal haemorrhage 24.53 21.66 8 4297 2578 79737505
Hypoperfusion 24.37 21.66 8 4297 2631 79737452
Gingival bleeding 22.92 21.66 13 4292 16263 79723820
Splenomegaly 22.50 21.66 14 4291 20740 79719343
Thrombocytopenia 22.12 21.66 46 4259 265213 79474870

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 0527-1368 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 0527-1369 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 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 0555-0633 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 0555-0634 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 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 62135-475 CAPSULE 50 mg ORAL ANDA 11 sections
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 62135-476 CAPSULE 100 mg ORAL ANDA 11 sections
Danazol HUMAN PRESCRIPTION DRUG LABEL 1 62135-477 CAPSULE 200 mg ORAL ANDA 11 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