Flutamide

Modify Date: 2025-08-20 18:07:55

Flutamide Structure
Flutamide structure
 Common Name Flutamide
CAS Number 13311-84-7 Molecular Weight 276.212
Density 1.4±0.1 g/cm3 Boiling Point 400.3±45.0 °C at 760 mmHg
Molecular Formula C11H11F3N2O3 Melting Point 112 °C
MSDS Chinese USA Flash Point 195.9±28.7 °C
Symbol GHS07 GHS08
GHS07, GHS08		 Signal Word Warning

 Use of Flutamide


Flutamide is an antiandrogen drug, with its active metablolite binding at androgen receptor with Ki values of 55 nM, and primarily used to treat prostate cancer.Target: androgen receptor in vitro: Flutamide (Eulexin) is an antiandrogen drug. Flutamide-OH, the active metabolite of flutamide, directly binds at rat anterior pituitary androgen receptor with Ki values of 55 nM [1]. lutamide does not affect the proliferation of an androgen-sensitive clone of the mouse mammary carcinoma Shionogi SC-l 15 cells in culture, shows only antiandrogenic effect, but not androgenic effect [2]. Flutamide provides treatment for prostate cancer when used along with leuprolide [3].in vivo: Flutamide causes a markedly reduction in rat ventral prostate weight from 319 mg to 245 mg. A combination of flutamide and LHRH agonist induces an additive effect with a decrease in prostate weight to 101 mg, and an marked drop in prostatic ODC activity [4].

 Names

Name flutamide
Synonym More Synonyms

 Flutamide Biological Activity

Description Flutamide is an antiandrogen drug, with its active metablolite binding at androgen receptor with Ki values of 55 nM, and primarily used to treat prostate cancer.Target: androgen receptor in vitro: Flutamide (Eulexin) is an antiandrogen drug. Flutamide-OH, the active metabolite of flutamide, directly binds at rat anterior pituitary androgen receptor with Ki values of 55 nM [1]. lutamide does not affect the proliferation of an androgen-sensitive clone of the mouse mammary carcinoma Shionogi SC-l 15 cells in culture, shows only antiandrogenic effect, but not androgenic effect [2]. Flutamide provides treatment for prostate cancer when used along with leuprolide [3].in vivo: Flutamide causes a markedly reduction in rat ventral prostate weight from 319 mg to 245 mg. A combination of flutamide and LHRH agonist induces an additive effect with a decrease in prostate weight to 101 mg, and an marked drop in prostatic ODC activity [4].
Related Catalog
References

[1]. Simard J, et al. Characteristics of interaction of the antiandrogen flutamide with the androgen receptor in various target tissues. Mol Cell Endocrinol. 1986 Mar;44(3):261-70.

[2]. Luthy IA, et al. Androgenic activity of synthetic progestins and spironolactone in androgen-sensitive mouse mammary carcinoma (Shionogi) cells in culture. J Steroid Biochem. 1988 Nov;31(5):845-52.

[3]. Crawford ED, et al. A controlled trial of leuprolide with and without flutamide in prostatic carcinoma. N Engl J Med. 1989 Aug 17;321(7):419-24.

[4]. Marchetti B, et al. Characteristics of flutamide action on prostatic and testicular functions in the rat. J Steroid Biochem. 1988 Jun;29(6):691-8.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 400.3±45.0 °C at 760 mmHg
Melting Point 112 °C
Molecular Formula C11H11F3N2O3
Molecular Weight 276.212
Flash Point 195.9±28.7 °C
Exact Mass 276.072174
PSA 74.92000
LogP 3.72
Vapour Pressure 0.0±0.9 mmHg at 25°C
Index of Refraction 1.521
Storage condition Store at RT

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UG5700000
CHEMICAL NAME :
m-Propionotoluidide, 2-methyl-4'-nitro-alpha,alpha,alpha-triflouro-
CAS REGISTRY NUMBER :
13311-84-7
LAST UPDATED :
199806
DATA ITEMS CITED :
27
MOLECULAR FORMULA :
C11-H11-F3-N2-O3
MOLECULAR WEIGHT :
276.24
WISWESSER LINE NOTATION :
FXFFR BNW EMVY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
310 mg/kg/31D-I
TOXIC EFFECTS :
Behavioral - euphoria
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
787 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - hematuria Kidney, Ureter, Bladder - incontinence Nutritional and Gross Metabolic - body temperature decrease
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
289 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - cyanosis Nutritional and Gross Metabolic - body temperature decrease
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting Gastrointestinal - other changes Liver - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
700 mg/kg/28D-I
TOXIC EFFECTS :
Endocrine - androgenic Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
27300 mg/kg/52W-I
TOXIC EFFECTS :
Blood - pigmented or nucleated red blood cells Biochemical - Metabolism (Intermediary) - other proteins Related to Chronic Data - changes in prostate weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2730 mg/kg/1Y-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Reproductive - Tumorigenic effects - testicular tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1050 mg/kg
SEX/DURATION :
female 14-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
150 mg/kg
SEX/DURATION :
male 30 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 :
Oral
DOSE :
375 mg/kg
SEX/DURATION :
male 15 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 :
Oral
DOSE :
3840 mg/kg
SEX/DURATION :
male 64 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
280 mg/kg
SEX/DURATION :
male 7 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 :
Subcutaneous
DOSE :
525 mg/kg
SEX/DURATION :
female 14-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
275 mg/kg
SEX/DURATION :
female 11-21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
70 mg/kg
SEX/DURATION :
male 7 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - other effects on male
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
400 mg/kg
SEX/DURATION :
female 16-19 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
65 mg/kg
SEX/DURATION :
female 10-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - delayed effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
29040 ug/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 - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
350 mg/kg
SEX/DURATION :
male 7 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Paternal Effects - other effects on male
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
200 mg/kg
SEX/DURATION :
female 16-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Paternal Effects - other effects on male Endocrine - androgenic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
80 mg/kg
SEX/DURATION :
male 10 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
400 mg/kg
SEX/DURATION :
male 10 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 :
Subcutaneous
DOSE :
1 gm/kg
SEX/DURATION :
female 13-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - other postnatal measures or effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
300 mg/kg
SEX/DURATION :
female 14-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1225 mg/kg
SEX/DURATION :
female 6 week(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - other effects to embryo

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - rat Liver
DOSE/DURATION :
50 umol/L
REFERENCE :
CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 13,373,1992

 Safety Information

Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Warning
Hazard Statements H302 + H312 + H332-H361
Precautionary Statements P261-P280-P301 + P312 + P330
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 NONH for all modes of transport
WGK Germany 3
RTECS UG5700000
HS Code 2924299090

 Customs

HS Code 2924299090
Summary 2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

 Articles107

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 Synonyms

2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
4'-Nitro-3'-(trifluoromethyl)isobutyranilide
MFCD00072009
Propanamide, 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-
Eulexin
FXFFR BNW EMVY1&1
Flutamidum
2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propionamide
Drogenil
Niftholide
[14C]-Flutamide
Flutamide
NFBA
4'-nitro-3'-trifluoromethylisobutyranilide
2-Methyl-N-(4-nitro-3-[trifluoromethyl]phenyl)propanamide
Niftolide
niftolid
2-Methyl-N-(4-nitro-3-[trifluoromethyl]phenyl)propanamide,Flutamide
Flutamin
EINECS 236-341-9
Flutamida
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