General Information of Drug (ID: DML8KTN)

Drug Name
Danazol Drug Info
Synonyms
Anatrol; Chronogyn; Cyclomen; Danatrol; Danazant; Danazole; Danazolum; Danocrine; Danogen; Danokrin; Danol; Danoval; Danzol; Ladogal; Norciden; Panacrine; Winobanin; Alphapharm Brand of Danazol; Antigen Brand of Danazol; Kendrick Brand of Danazol; Ratiopharm Brand of Danazol; Sanofi Brand of Danazol; Sanofi Synthelabo Brand ofDanazol; Sanofi Winthrop Brand of Danazol; WIN 17757; Danazol-ratiopharm; Danazolum [INN-Latin]; Danocrine (TN); WIN 17,757; WIN-17757; Win 17, 757; Danazol (JAN/USP/INN); Danazol [USAN:BAN:INN:JAN];[1,2]oxazolo[4',5':2,3]-17alpha-pregn-4-en-20-yn-17-ol; (1R,3aS,3bR,10aR,10bS,12aS)-1-ethynyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1H-cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol; (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol; 1-Ethynyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1H-cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol; 17-alpha-2,4-Pregnadien-20-yno(2,3-d)isoxazol-17-ol; 17-alpha-Pregn-4-en-20-yno(2,3-d)isoxazol-17-ol; 17-alpha-Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol; 17.Alpha.-Pregna-2, {4-dien-20-yno[2,3-d]isoxazol-17-ol}; 17alpha-Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol
Indication
Disease Entry ICD 11 Status REF
Menorrhagia GA20.50 Approved [1]
Breast cancer 2C60-2C65 Phase 2 [1]
Breast fibrocystic disease Investigative [2]
Endometriosis GA10 Investigative [2]
Therapeutic Class
Fertility Agents
Cross-matching ID
PubChem CID
28417
ChEBI ID
CHEMBL1479
CAS Number
CAS 17230-88-5
TTD Drug ID
DML8KTN
INTEDE Drug ID
DR2401
ACDINA Drug ID
D00165

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Drug(s) Targeting Estrogen receptor (ESR)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [7]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [8]
Estrone DM5T6US Acne vulgaris ED80 Approved [8]
Estradiol Valerate DM8MC6O Hormone replacement therapy 8E01 Approved [9]
Estradiol Acetate DM07U2A Hormone replacement therapy 8E01 Approved [9]
Estradiol Cypionate DM27Z5T Hormone replacement therapy 8E01 Approved [9]
Ethinyl Estradiol DMODJ40 Acne vulgaris ED80 Approved [10]
Raloxifene DMDKF3M Osteoporosis FB83.0 Approved [11]
Ospemifene DMC4GEI Dyspareunia GA12 Approved [12]
Toremifene DMQYUWG Breast cancer 2C60-2C65 Approved [13]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Bile salt export pump (ABCB11)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Glimepiride DM5FSJA Diabetic complication 5A2Y Approved [14]
Ezetimibe DM7A8TW Atherosclerosis BD40 Approved [15]
Glipizide DMZA5PQ Diabetic complication 5A2Y Approved [15]
Bosentan DMIOGBU Pulmonary arterial hypertension BB01.0 Approved [16]
Indinavir DM0T3YH Human immunodeficiency virus infection 1C62 Approved [14]
Ofloxacin DM0VQN3 Acute gonococcal cervicitis Approved [15]
Primidone DM0WX6I Epilepsy 8A60-8A68 Approved [17]
Gefitinib DM15F0X Colon adenocarcinoma Approved [14]
Drospirenone DM1A9W3 Acne vulgaris ED80 Approved [4]
Nitrendipine DM21C09 Hypertension BA00-BA04 Approved [14]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [18]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [19]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [20]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [21]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [22]
Cupric Sulfate DMP0NFQ Fungal infection 1F29-1F2F Approved [23]
Olanzapine DMPFN6Y Bipolar depression Approved [24]
Arsenic DMTL2Y1 N. A. N. A. Approved [25]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [26]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [27]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [28]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [29]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [30]
Gefitinib DM15F0X Colon adenocarcinoma Approved [31]
Talazoparib DM1KS78 Breast cancer 2C60-2C65 Approved [32]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [33]
Etretinate DM2CZFA Keratosis ED56 Approved [34]
Prednisone DM2HG4X Acute asthma CA23 Approved [35]
Ciprofloxacin XR DM2NLS9 Acute gonococcal cervicitis Approved [36]
Colchicine DM2POTE Acute gout flare FA25.0 Approved [37]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Antagonist [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [4]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [5]
Plasma protease C1 inhibitor (SERPING1) OT6CVN45 IC1_HUMAN Gene/Protein Processing [6]

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6942).
2 Danazol FDA Label
3 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.
4 A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov;136(1):216-41.
5 High-content imaging-based BAC-GFP toxicity pathway reporters to assess chemical adversity liabilities. Arch Toxicol. 2017 Mar;91(3):1367-1383. doi: 10.1007/s00204-016-1781-0. Epub 2016 Jun 29.
6 Guillain-Barr syndrome following danazol and corticosteroid therapy for hereditary angioedema. Am J Med. 1985 Jul;79(1):111-4. doi: 10.1016/0002-9343(85)90553-4.
7 Modulators of vascular sex hormone receptors and their effects in estrogen-deficiency states associated with menopause. Recent Pat Cardiovasc Drug Discov. 2008 Nov;3(3):165-86.
8 Reprint of Are all estrogens the same Maturitas. 2008 Sep-Oct;61(1-2):195-201.
9 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
10 17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8.
11 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 620).
12 Clinical pipeline report, company report or official report of Shionogi (2011).
13 Effect of selective estrogen receptor modulators on cell proliferation and estrogen receptor activities in normal human prostate stromal and epithe... Prostate Cancer Prostatic Dis. 2009;12(4):375-81.
14 Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. Toxicol Sci. 2010 Dec; 118(2):485-500.
15 Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43.
16 Omics-based responses induced by bosentan in human hepatoma HepaRG cell cultures. Arch Toxicol. 2018 Jun;92(6):1939-1952.
17 Evaluating the Role of Multidrug Resistance Protein 3 (MDR3) Inhibition in Predicting Drug-Induced Liver Injury Using 125 Pharmaceuticals. Chem Res Toxicol. 2017 May 15;30(5):1219-1229. doi: 10.1021/acs.chemrestox.7b00048. Epub 2017 May 4.
18 Development of a neural teratogenicity test based on human embryonic stem cells: response to retinoic acid exposure. Toxicol Sci. 2011 Dec;124(2):370-7.
19 Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action. Dermatoendocrinol. 2009 May;1(3):177-87.
20 THC exposure of human iPSC neurons impacts genes associated with neuropsychiatric disorders. Transl Psychiatry. 2018 Apr 25;8(1):89. doi: 10.1038/s41398-018-0137-3.
21 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
22 Human embryonic stem cell-derived test systems for developmental neurotoxicity: a transcriptomics approach. Arch Toxicol. 2013 Jan;87(1):123-43.
23 Physiological and toxicological transcriptome changes in HepG2 cells exposed to copper. Physiol Genomics. 2009 Aug 7;38(3):386-401.
24 Effects of olanzapine on serum protein phosphorylation patterns in patients with schizophrenia. Proteomics Clin Appl. 2015 Oct;9(9-10):907-16. doi: 10.1002/prca.201400148. Epub 2015 May 15.
25 Fetal-sex dependent genomic responses in the circulating lymphocytes of arsenic-exposed pregnant women in New Hampshire. Reprod Toxicol. 2017 Oct;73:184-195. doi: 10.1016/j.reprotox.2017.07.023. Epub 2017 Aug 6.
26 Gene expression data from acetaminophen-induced toxicity in human hepatic in vitro systems and clinical liver samples. Data Brief. 2016 Mar 26;7:1052-1057. doi: 10.1016/j.dib.2016.03.069. eCollection 2016 Jun.
27 Endometrial receptivity is affected in women with high circulating progesterone levels at the end of the follicular phase: a functional genomics analysis. Hum Reprod. 2011 Jul;26(7):1813-25.
28 Zidovudine induces S-phase arrest and cell cycle gene expression changes in human cells. Mutagenesis. 2005 Mar;20(2):139-46. doi: 10.1093/mutage/gei019. Epub 2005 Mar 22.
29 Cannabidiol Activates Neuronal Precursor Genes in Human Gingival Mesenchymal Stromal Cells. J Cell Biochem. 2017 Jun;118(6):1531-1546. doi: 10.1002/jcb.25815. Epub 2016 Dec 29.
30 Gene expression profiles with activation of the estrogen receptor alpha-selective estrogen receptor modulator complex in breast cancer cells expressing wild-type estrogen receptor. Cancer Res. 2002 Aug 1;62(15):4419-26.
31 Leptomycin B reduces primary and acquired resistance of gefitinib in lung cancer cells. Toxicol Appl Pharmacol. 2017 Nov 15;335:16-27. doi: 10.1016/j.taap.2017.09.017. Epub 2017 Sep 21.
32 BMN 673 (talazoparib): A potent PARP inhibitor for triple negative breast cancer with different genetic profile. J Biochem Mol Toxicol. 2019 May;33(5):e22286. doi: 10.1002/jbt.22286. Epub 2019 Jan 23.
33 Gene expression after treatment with hydrogen peroxide, menadione, or t-butyl hydroperoxide in breast cancer cells. Cancer Res. 2002 Nov 1;62(21):6246-54.
34 Bexarotene activates the p53/p73 pathway in human cutaneous T-cell lymphoma. Br J Dermatol. 2009 Mar;160(3):519-26. doi: 10.1111/j.1365-2133.2008.08931.x. Epub 2008 Nov 25.
35 Glucocorticoids induce G1 arrest of lymphoblastic cells through retinoblastoma protein Rb1 dephosphorylation in childhood acute lymphoblastic leukemia in vivo. Cancer Biol Ther. 2004 May;3(5):470-6. doi: 10.4161/cbt.3.5.838. Epub 2004 May 9.
36 Ciprofloxacin mediated cell growth inhibition, S/G2-M cell cycle arrest, and apoptosis in a human transitional cell carcinoma of the bladder cell line. Clin Cancer Res. 2000 Mar;6(3):891-900.
37 Utilization of CDKN1A/p21 gene for class discrimination of DNA damage-induced clastogenicity. Toxicology. 2014 Jan 6;315:8-16. doi: 10.1016/j.tox.2013.10.009. Epub 2013 Nov 6.