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13311-84-7

13311-84-7 structure
13311-84-7 structure
  • Name: Flutamide
  • Chemical Name: flutamide
  • CAS Number: 13311-84-7
  • Molecular Formula: C11H11F3N2O3
  • Molecular Weight: 276.212
  • Catalog: API Antineoplastic agents Hormone antineoplastic agents
  • Create Date: 2018-08-27 09:50:54
  • Modify Date: 2025-08-20 18:07:55
  • 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].
Name flutamide
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
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.
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

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
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
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%
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