CAS 13311-84-7|Flutamide

Introduction：Basic information about CAS 13311-84-7|Flutamide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Flutamide BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles107
8. Synonyms

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	ChineseUSA	Flash Point	195.9±28.7 °C
Symbol	GHS07, GHS08	Signal Word	Warning

Names

Name	flutamide
Synonym	More Synonyms

Flutamide BiologicalActivity

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	Signaling Pathways >>Others >>Androgen ReceptorResearch Areas >>Cancer
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.

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

Signaling Pathways >>Others >>Androgen ReceptorResearch Areas >>Cancer

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
InChIKey	MKXKFYHWDHIYRV-UHFFFAOYSA-N
SMILES	CC(C)C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1
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
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

Evolutionary history and functional characterization of androgen receptor genes in jawed vertebrates.

Endocrinology 150 , 5415-27, (2009)

Vertebrates show diverse sexual characters in sexually attractive and reproductive organs, which are regulated by steroid hormones, particularly androgens. However, the evolutionary history of androge...

Extending an in vitro panel for estrogenicity testing: the added value of bioassays for measuring antiandrogenic activities and effects on steroidogenesis.

Toxicol. Sci. 141(1) , 78-89, (2014)

In the present study, a previously established integrated testing strategy (ITS) for in vitro estrogenicity testing was extended with additional in vitro assays in order to broaden its sensitivity to ...

Inhibition of SGK1 enhances mAR-induced apoptosis in MCF-7 breast cancer cells.

Cancer Biol. Ther. 16(1) , 52-9, (2015)

Functional membrane androgen receptors (mAR) have previously been described in MCF-7 breast cancer cells. Their stimulation by specific testosterone albumin conjugates (TAC) activate rapidly non-genom...

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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