Danazol (CED0004195)

Record Information

Version

1.0

Creation Date

2016-05-22 03:39:30 UTC

Update Date

2026-08-21 22:36:32 UTC

Accession Number

CHEM016653

Identification

Common Name

Danazol

Class

Small Molecule

Description

Danazol is an organic compound with the formula C22H27NO2 and an average molecular weight of 337.46 g/mol. Danazol belongs to the estrane steroids, a subclass of steroids and steroid derivatives within the organic compounds. This substance has been identified in ten recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is associated with sex hormones and modulators of the genital system. It is also found in household cleaning and consumer products, specifically tobacco smoke filters and non-electric simulated smoking devices. Other recorded sources include indoor air, processing meats, and various electrical and electronic equipment, such as television systems, fixed capacitors and their manufacture, electrically stimulated smoking devices, electric switches, and antennas. Exposure to the compound occurs through oral and inhalation routes. Danazol interacts with six recorded protein targets. It acts as an agonist, inhibitor, or negative modulator of the estrogen receptor (ESR1), the gonadotropin-releasing hormone receptor (GNRHR), and the putative gonadotropin-releasing hormone II receptor (GNRHR2). Additionally, it targets C-C motif chemokine 2 (CCL2) and two other proteins.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cyclomen	ChEBI
Danazolum	ChEBI
Danocrine	ChEBI
(17a)-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol	HMDB
1-Ethynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a,12a-dimethyl-1H-cyclopenta[7,8]phenanthro[3,2-D]isoxazol-1-ol	HMDB
17 alpha-Pregna-2,4-dien-20-yno[2,3-D] isoxazol-17 beta-ol	HMDB
17a-Pregna-2,4-dien-20-yne-[2,3-D]isoxazole-17b-ol	HMDB
17a-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol	HMDB
1H-Cyclopenta[7,8]phenanthro[3,2-D]isoxazole- pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol deriv.	HMDB
Bonzol	HMDB
Chronogyn	HMDB
Danol	HMDB
Danovaol	HMDB
Danzol	HMDB
Ladogal	HMDB
Winobanin	HMDB
Alphapharm brand OF danazol	HMDB
Kendrick brand OF danazol	HMDB
Sanofi brand OF danazol	HMDB
Danatrol	HMDB
Danazant	HMDB
Danazol-ratiopharm	HMDB
Danoval	HMDB
Ratiopharm brand OF danazol	HMDB
Antigen brand OF danazol	HMDB
Azol	HMDB
Norciden	HMDB
Panacrine	HMDB
Sanofi synthelabo brand OF danazol	HMDB
Sanofi winthrop brand OF danazol	HMDB
Danazol ratiopharm	HMDB

Chemical Formula

C₂₂H₂₇NO₂

Average Molecular Mass

337.455 g/mol

Monoisotopic Mass

337.204 g/mol

CAS Registry Number

17230-88-5

IUPAC Name

(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

Traditional Name

(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

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3

InChI Identifier

InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1

InChI Key

POZRVZJJTULAOH-LHZXLZLDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

Estrane-skeleton
Hydroxysteroid
17-hydroxysteroid
Ynone
Heteroaromatic compound
Azole
Cyclic alcohol
Tertiary alcohol
Isoxazole
Acetylide
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:4315 )
17beta-hydroxy steroid (CHEBI:4315 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	3.62	ALOGPS
logP	3.46	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	17.59	ChemAxon
pKa (Strongest Basic)	0.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.26 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	98.54 m³·mol⁻¹	ChemAxon
Polarizability	38.44 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0ab9-0669000000-7afc135d5b1e92134191	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-000x-2479000000-d5f94bb7e7215a30f820	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0009000000-9e745b8feecd354f6618	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-6902000000-854476472755ef5419e5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9100000000-0d62c0c1b53c1cea5a25	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0329000000-56adc37fd83dfa3c686f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05ia-3931000000-1490f6c4984a84016076	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-002f-6900000000-529d2d24864b26fdd611	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-002f-6900000000-01f21f6ea357e6649d15	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-1309000000-271d4ce8113e1bf16016	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dj-2910000000-3af637f5ddbf8cfd6b84	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dj-2920000000-ba6bb4b948be2171d864	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05tg-3900000000-29df3c1f08b04956955d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0009000000-5fc69729a45a40e94073	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-002f-4900000000-7ba349192301fd4e5013	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05tg-3900000000-a692616aee182eeb1270	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0119000000-d7acb78e38c02e285d4f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01wr-0289000000-2db311b410937e72f25a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000j-3690000000-5eb98df42b0016f9967a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-d1a89ea3e6c72ff1ab88	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-71fbd4000b06296a8386	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00e9-2089000000-24b6d7f3ec074a6c2b59	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0019000000-2626c30d979a970252f0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-007y-0982000000-4cf29ec44560862d68c7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-1001-1890000000-24565065bfdf6e8edf39	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-8413c28ca2b1374741c7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-3424fea43411af836104	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-0398000000-ab539e7c612667780546	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2126.0	Log mg/kg	[1200:3800]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
19	Indoor air	Air, dust & atmospheric transport	Not Available
325	Sex hormones and modulators of the genital system	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
521	Fixed Capacitors And Their Manufacture	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
602	Molluscicides	Agriculture & land management	Not Available
603	Nematocides	Agriculture & land management	Not Available
605	Pest Repellants	Agriculture & land management	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
655	Slide Fasteners	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Danazol Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	1.24559
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	2.56902
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	0.389246
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	0.311397
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	13.8572
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	3.58106
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	13.7015
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	2.88042
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	28.4928
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	125.337
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	65.549
Click to view 3D structure	Cytochrome P450 2C8	P10632	Humans	Predicted (SEA)	27.7922
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	287.186
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	305.48
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	270.215
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	107.198
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	13.6236
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	30.9061
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	455.496
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	103.929
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	232.847
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	427.081
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	59.4768
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	76.9929
Click to view 3D structure	Cytochrome P450 2J2	P51589	Humans	Predicted (SEA)	4.9045