Danazol

Names

[ Name ]:
Danazol

[Synonym ]:
(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][1,2]oxazol-1-ol
Danazolum
danazolum [INN_la]
Danol
Danatrol
Ladogal
Winobanin
17a-Pregn-4-en-20-yno[2,3-d]isoxazol-17-ol
MFCD00056838
(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
Chronogyn
Danocrine
(1R,3aS,3bR,10aR,10bS,12aS)-1-éthynyl-10a,12a-diméthyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodécahydro-1H-cyclopenta[7,8]phénanthro[3,2-d]isoxazol-1-ol
Cyclomen
Danzol
EINECS 241-270-1
(1R,3aS,3bR,10aR,10bS,12aS)-1-Ethinyl-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
(17a)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol
17a-Ethynyl-17b-hydroxy-4-androsteno[2,3-d]isoxazole
1H-Cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol, 1-ethynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a,12a-dimethyl-, (1R,3aS,3bR,10aR,10bS,12aS)-

Biological Activity

[Description]:

Danazol is a derivative of the synthetic steroid ethisterone, that suppresses the production of gonadotrophins, and has some weak androgenic effects.

[Related Catalog]:

Signaling Pathways >> Others >> Androgen Receptor

Research Areas >> Endocrinology

[Related Small Molecules]

ARN-509 | Dehydroepiandrosterone | Flutamide | ODM-201 | 3,3'-Diindolylmethane | AZD3514 | RAD140 | BMS-564929 | GLPG0492 | Cyproterone acetate | LGD-4033 | Lupeol | Andarine | MK-0773 | ORM-15341

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
478.2±45.0 °C at 760 mmHg

[ Melting Point ]:
224.4-226.8ºC

[ Molecular Formula ]:
C₂₂H₂₇NO₂

[ Molecular Weight ]:
337.455

[ Flash Point ]:
243.0±28.7 °C

[ Exact Mass ]:
337.204193

[ PSA ]:
46.26000

[ LogP ]:
4.70

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.604

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TU4157070

CHEMICAL NAME :: 17-alpha-Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol

CAS REGISTRY NUMBER :: 17230-88-5

LAST UPDATED :: 199609

DATA ITEMS CITED :: 39

MOLECULAR FORMULA :: C22-H27-N-O2

MOLECULAR WEIGHT :: 337.50

WISWESSER LINE NOTATION :: T G5 E6 B665 HON EU&TTTTJ M1 Q1 RQ R1UU1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 274 mg/kg/32D-I

TOXIC EFFECTS :: Liver - jaundice, cholestatic Liver - other changes Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 120 mg/kg/10D-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, allergic (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 1029 mg/kg/17W-I

TOXIC EFFECTS :: Liver - jaundice, cholestatic

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >17 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4830 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6770 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2500 mg/kg/10D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in bladder weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 91 gm/kg/26W-I

TOXIC EFFECTS :: Liver - fatty liver degeneration Liver - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 2920 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1064 mg/kg

SEX/DURATION :: female 1-19 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Effects on Newborn - germ cell effects (in offspring) Reproductive - Effects on Newborn - physical

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 120 mg/kg

SEX/DURATION :: female 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1028 mg/kg

SEX/DURATION :: male 17 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - impotence

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 16 ug/kg

SEX/DURATION :: female 5 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 90 mg/kg

SEX/DURATION :: female 90 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 430 mg/kg

SEX/DURATION :: male 21 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - other effects on male

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 600 mg/kg

SEX/DURATION :: female 6 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 462 mg/kg

SEX/DURATION :: male 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5600 mg/kg

SEX/DURATION :: female 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1400 mg/kg

SEX/DURATION :: male 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 37500 ug/kg

SEX/DURATION :: female 3 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 56 mg/kg

SEX/DURATION :: male 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 140 mg/kg

SEX/DURATION :: female 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 520 mg/kg

SEX/DURATION :: male 39 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 93 mg/kg

SEX/DURATION :: male 7 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - other effects on male

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 880 mg/kg

SEX/DURATION :: male 22 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 3 gm/kg

SEX/DURATION :: female 15 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 600 mg/kg

SEX/DURATION :: male 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intratesticular

DOSE :: 18 mg/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1800 mg/kg

SEX/DURATION :: female 90 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3600 mg/kg

SEX/DURATION :: female 90 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - menstrual cycle changes or disorders

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 1920 mg/kg

SEX/DURATION :: male 48 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 880 mg/kg

SEX/DURATION :: male 22 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

MUTATION DATA

TEST SYSTEM :: Mammal - dog

DOSE/DURATION :: 13 mg/kg

REFERENCE :: FOBGA8 Folia Biologica (Krakow). (Ars Polona, POB 1001, 00-068 Warsaw 1, Poland) V.1- 1953- Volume(issue)/page/year: 23.305,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5831 No. of Facilities: 9 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 339 (estimated) No. of Female Employees: 170 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H312 + H332-H361

[ Precautionary Statements ]:
P261-P280

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R20/21/22;R63

[ Safety Phrases ]:
S22-S36

[ RIDADR ]:
TU4157070

[ WGK Germany ]:
3

[ RTECS ]:
TU4157070

[ HS Code ]:
2937290014

Customs

[ HS Code ]: 2937290014

[ Summary ]:
HS:2937290014 (3s,8r,9s,10r,13s,14s)-3-hydroxy-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17(2h)-one VAT:17.0% Tax rebate rate:9.0% Supervision conditions:l MFN tariff:4.0% General tariff:30.0%

Articles

Fasted-state simulated intestinal fluid "FaSSIF-C", a cholesterol containing intestinal model medium for in vitro drug delivery development.

J. Pharm. Sci. 104 , 2213-24, (2015)

A set of biorelevant media "fasted-state simulated intestinal fluid with cholesterol (FaSSIF-C)" for the in vitro study of intestinal drug dissolution in the duodenum was developed. These contain chol...

Non-linear increases in danazol exposure with dose in older vs. younger beagle dogs: the potential role of differences in bile salt concentration, thermodynamic activity, and formulation digestion.

Pharm. Res. 31(6) , 1536-52, (2014)

To explore the possibility that age-related changes in physiology may result in differences in drug bioavailability after oral administration of lipid based formulations of danazol.Danazol absorption ...

An in vitro digestion test that reflects rat intestinal conditions to probe the importance of formulation digestion vs first pass metabolism in Danazol bioavailability from lipid based formulations.

Mol. Pharm. 11(11) , 4069-83, (2014)

The impact of gastrointestinal (GI) processing and first pass metabolism on danazol oral bioavailability (BA) was evaluated after administration of self-emulsifying drug delivery systems (SEDDS) in th...