danazol 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 µM/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
BA (Bioavailability) 14 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 4.084 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.883 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 32.584 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 20.464 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 0.650 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 0.790 % High 1
herg hERG pIC50 4.996 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 17.418 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 35.400 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 0.610 % High 1
kinase-safety-class ACVR2B,EIF2AK3,ERBB2,GRK2,ITK,MAPK10,PDK1,PDK2,PDK4,PRKDC 10
kinase-selectivity-class EIF2AK3,PDK1 2
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.561 High 1
mh-clint Mouse hepatocyte intrinsic clearance 66.069 High 1
mppb Mouse plasma protein binding (% unbound) 0.800 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.521 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 0.880 % High 1
rh-clint Rat hepatocyte intrinsic clearance 81.658 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 6.710 % High 1
rppb Rat plasma protein binding (% unbound) 0.820 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 8.414 uM High 1

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
Swollen tongue 554.05 26.11 161 3704 45795 90578787
Angioedema 524.06 26.11 167 3698 64709 90559873
Dysphonia 507.89 26.11 162 3703 62922 90561660
Swelling face 467.44 26.11 162 3703 81190 90543392
Drug ineffective for unapproved indication 458.62 26.11 152 3713 66492 90558090
Hypersensitivity 219.24 26.11 169 3696 454508 90170074
Drug intolerance 208.40 26.11 163 3702 447428 90177154
Hereditary angioedema 173.01 26.11 46 3819 9319 90615263
Headache 160.15 26.11 189 3676 862557 89762025
Off label use 142.71 26.11 202 3663 1102050 89522532
Product use in unapproved indication 77.69 26.11 83 3782 336153 90288429
Platelet count decreased 59.17 26.11 48 3817 136921 90487661
Drug ineffective 57.88 26.11 158 3707 1384140 89240442
Hypoperfusion 29.33 26.11 8 3857 1776 90622806
Bone marrow reticulin fibrosis 26.57 26.11 5 3860 208 90624374

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 340.89 28.89 61 2871 1174 42617229
Lymphadenitis 297.69 28.89 61 2871 2450 42615953
Haemolysis 244.01 28.89 67 2865 9522 42608881
Migraine 143.88 28.89 57 2875 25357 42593046
Hepatic enzyme increased 141.70 28.89 67 2865 45717 42572686
Infusion related reaction 126.50 28.89 68 2864 60738 42557665
Hereditary angioedema 123.88 28.89 27 2905 1454 42616949
Therapeutic product effect decreased 117.12 28.89 56 2876 39094 42579309
Migraine with aura 106.89 28.89 22 2910 897 42617506
Drug ineffective 72.76 28.89 143 2789 630054 41988349
Constipation 70.27 28.89 70 2862 162221 42456182
Myelofibrosis 66.41 28.89 17 2915 1830 42616573
Neutropenia 55.08 28.89 68 2864 199363 42419040
Myelodysplastic syndrome 51.58 28.89 27 2905 22718 42595685
Cushingoid 43.47 28.89 14 2918 3408 42614995
Rhabdomyolysis 41.93 28.89 38 2894 77981 42540422
Thrombocytopenia 37.35 28.89 55 2877 190224 42428179

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
Swollen tongue 471.93 23.57 163 6118 60199 110522819
Dysphonia 428.09 23.57 161 6120 75768 110507250
Angioedema 421.60 23.57 171 6110 98329 110484689
Swelling face 407.90 23.57 164 6117 92157 110490861
Drug ineffective for unapproved indication 394.16 23.57 165 6116 102673 110480345
Coombs positive haemolytic anaemia 337.33 23.57 61 6220 1516 110581502
Lymphadenitis 261.42 23.57 61 6220 5432 110577586
Haemolysis 210.96 23.57 64 6217 15575 110567443
Hereditary angioedema 201.21 23.57 52 6229 7062 110575956
Hypersensitivity 195.14 23.57 170 6111 403828 110179190
Drug intolerance 184.20 23.57 165 6116 406347 110176671
Headache 125.93 23.57 198 6083 882179 109700839
Drug ineffective 115.38 23.57 260 6021 1520280 109062738
Off label use 107.62 23.57 251 6030 1499934 109083084
Migraine with aura 81.83 23.57 22 6259 3470 110579548
Migraine 60.82 23.57 61 6220 171591 110411427
Product use in unapproved indication 58.76 23.57 97 6184 447280 110135738
Myelofibrosis 56.60 23.57 16 6265 3035 110579983
Rhabdomyolysis 56.46 23.57 50 6231 120351 110462667
Platelet count decreased 52.48 23.57 65 6216 230378 110352640
Bone marrow reticulin fibrosis 46.17 23.57 9 6272 337 110582681
Hepatic enzyme increased 45.37 23.57 72 6209 320820 110262198
Constipation 44.82 23.57 76 6205 357710 110225308
Myelodysplastic syndrome 43.76 23.57 27 6254 37457 110545561
Cushingoid 38.78 23.57 17 6264 11695 110571323
Therapeutic product effect decreased 37.56 23.57 57 6224 244259 110338759
Neutropenia 36.03 23.57 71 6210 374549 110208469
Immune thrombocytopenia 33.59 23.57 19 6262 22475 110560543
Infusion related reaction 32.81 23.57 69 6212 381093 110201925
Thrombocytopenia 32.20 23.57 65 6216 348820 110234198
Splenomegaly 24.49 23.57 16 6265 24482 110558536
Blood stem cell transplant failure 23.99 23.57 6 6275 712 110582306

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
MeSH PA D004965 Estrogen Antagonists
MeSH PA D006727 Hormone Antagonists
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:50751 anti-estrogen
CHEBI has role CHEBI:50837 estrogen antagonist
CHEBI has role CHEBI:75835 anti-anaemic agent
CHEBI has role CHEBI:176497 geroprotector
FDA EPC N0000175824 Androgen

Related Drugs by ATC class:

G03XA Antigonadotropins and similar agents 1 drug
gestrinone

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




🐶 Veterinary Drug Use

None

🐶 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
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
4018233 VANDF
N29QWW3BUO INXIGHT DRUGS

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 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