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Nilutamide

HCID 4493
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
63612-50-0
표준 SMILES
CC1(C)NC(=O)N(c2ccc([N+](=O)[O-])c(C(F)(F)F)c2)C1=O
InChIKey
XWXYUMMDTVBTOU-UHFFFAOYSA-N
분자식
C12H10F3N3O4
평균 분자량
317.22 g/mol
단동위원소 질량
317.06234046

개요

Nilutamide is a C-nitro compound, an imidazolidinone and a member of (trifluoromethyl)benzenes. It has a role as an androgen antagonist and an antineoplastic agent.

이름 및 식별자

우선 이름
Nilutamide
IUPAC
5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
영어명
Nilutamide
분자식
C12H10F3N3O4
분자량
317.22

이름 및 동의어

nilutamide63612-50-0AnandronNilandron5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)imidazolidine-2,4-dioneNilutamidaNilutamidum5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dioneRU-23908RU 239085,5-Dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoinDTXSID3034165
이름 더 보기
NerumetNilandroneRU 23908-10Nilutamide CRSNilutamide USP/EP/BP
NSC-75868351G6I8B9025,5-Dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)-2,4-imidazolidinedione2,4-IMIDAZOLIDINEDIONE, 5,5-DIMETHYL-3-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)-CHEBI:7573DTXCID10141655,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedioneAnadron

데이터베이스 식별자

CAS
63612-50-0
PubChem CID
4493
DTXSID
DTXSID3034165
ChEMBL
CHEMBL1274
ChEBI
CHEBI:7573
UNII
51G6I8B902
EC Number
624-700-6
Nikkaji
J33.120A

물성

구조 계산 물성보충 중

XLogP
2
극성 표면적
95.2 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
7
회전 가능 결합 수
1
무거운 원자 수
22
형식 전하
0
복잡도
515

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Antineoplastic and immunomodulating agents -> Antineoplastic agents

Pharmaceuticals -> Listed in ZINC15

LogP1.8
Solubility4.19e-03 g/L
Human Drugs · 3건

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Hormones and antihormones

Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid
Collision Cross Section162.8 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID3034165]

물리화학적 성질

녹는점
1490 C · 1490C
밀도
1.463 · 1.463±0.06 g/cm3(Predicted)
저장 조건
Sealed in dry,Room Temperature

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 3 (100%)

독성 정보

Hepatotoxicity · 1건

In large registration clinical trials, ALT elevations occurred in 8% (range 2% to 33%) of patients during nilutamide therapy. The elevations were usually mild, asymptomatic and transient, requiring drug discontinuation in only 1% of treated patients. In rare instances, clinically apparent acute liver injury has occurred during nilutamide therapy, but the number of published cases are few, and the agent appears to be less hepatotoxic than flutamide. Nevertheless, fatal cases have been reported (Case 1). In reported cases, the latency to onset averaged 2 to 4 months and the clinical pattern of enzyme elevations was typically hepatocellular, thus largely resembling flutamide induced liver injury. Signs of hypersensitivity and autoimmunity were not common.

Exposure RoutesRapidly and completely absorbed, yielding high and persistent plasma concentrations.
Toxicity Summary · 1건

Nilutamide competes with androgen for the binding of androgen receptors, consequently blocking the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. This blockade of androgen receptors may result in growth arrest or transient tumor regression through inhibition of androgen-dependent DNA and protein synthesis.

화학 및 산업

약리 정보

ATC Code · 2건

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Pharmacodynamics · 1건

Nilutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Nilutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Nilutamide blocks the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration. The relative binding affinity of nilutamide at the androgen receptor is less than that of bicalutamide, but similar to that of hydroxuflutamide.

Mechanism of Action · 1건

Nilutamide competes with androgen for the binding of androgen receptors, consequently blocking the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. This blockade of androgen receptors may result in growth arrest or transient tumor regression through inhibition of androgen-dependent DNA and protein synthesis.

Biological Half-Life38.0-59.1 hours
Metabolism/Metabolites · 2건

The results of a human metabolism study using 14C-radiolabelled tablets show that nilutamide is extensively metabolized and less than 2% of the drug is excreted unchanged in urine after 5 days.

The results of a human metabolism study using 14C-radiolabelled tablets show that nilutamide is extensively metabolized and less than 2% of the drug is excreted unchanged in urine after 5 days. Route of Elimination: Nilutamide is extensively metabolized andless than 2% of the drug is excreted unchanged in urine after 5 days. Fecal elimination is negligible, ranging from 1.4% to 7% of the dose after 4 to 5 days. Half Life: 38.0-59.1 hours

FDA Pharmacological Classification · 6건

관련 반응

25건
반응 기록 만들기
HRID 35937 반응식
HRID 35937반응물로uspto-grants-1995_05
HRID 35938 반응식
HRID 35938반응물로uspto-grants-1995_05
HRID 35939 반응식
HRID 35939반응물로uspto-grants-1995_05
HRID 112189 반응식
HRID 112189생성물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 355585 반응식
HRID 355585반응물로uspto-grants-1998_11
HRID 355586 반응식
HRID 355586반응물로uspto-grants-1998_11
HRID 355587 반응식
HRID 355587반응물로uspto-grants-1998_11
HRID 374122 반응식
HRID 374122생성물로uspto-grants-1992_11
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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용해도
물에 아주 약간 녹고, 아세톤에 잘 녹고, 무수 에탄올에 녹습니다.
물리적 상태
고체
산도 계수 (pKa)
7.59 · 7.59±0.70(Predicted)
색상
Light yellow to yellow
주요 응용
의약품(소분자)
InChI
InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)
InChIKey
XWXYUMMDTVBTOU-UHFFFAOYSA-N
SMILES
C1(=O)NC(C)(C)C(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1

화학적 성질

Crystalline Solid

Signs and SymptomsSymptoms of overdose include dizziness, general discomfort, headache, nausea, and vomiting.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Nilutamide

vMost-DILI-concern

8

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

안전 데이터

wgk
3
rtecs
NI9453300
ridadr
UN 2811 6.1/PG 3
HS 번호
2933210000
risk_code
60-25
hazard_code
T
safety_code
53-36/37/39-45
위험 등급
6.1
Hazard Classifications
Acute Tox. 3 OralRepr. 1B
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

51G6I8B902

NILUTAMIDE

Mechanisms of Action [MoA] - Androgen Receptor Antagonists

Established Pharmacologic Class [EPC] - Androgen Receptor Inhibitor

Nilutamide is an Androgen Receptor Inhibitor. The mechanism of action of nilutamide is as an Androgen Receptor Antagonist.

NILUTAMIDE

MeSH Pharmacological Classification · 2건

Compounds which inhibit or antagonize the biosynthesis or actions of androgens.

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Absorption, Distribution and Excretion · 2건

Rapidly and completely absorbed, yielding high and persistent plasma concentrations.

Nilutamide is extensively metabolized andless than 2% of the drug is excreted unchanged in urine after 5 days. Fecal elimination is negligible, ranging from 1.4% to 7% of the dose after 4 to 5 days.

Cellular LocationsCytoplasm

용도 및 제조

UsesFor use in combination with surgical castration for the treatment of metastatic prostate cancer involving distant lymph nodes, bone, or visceral organs (Stage D2).
응용 분야 · 4건

개요Nilutamide is a non-steroidal anti-androgen similar in potency to the acyclic urea flutamide (55) and useful in the management of prostatic carcinoma.

역사The second nonsteroidal anti-androgen to be marketed was nilutamide. It was discovered from a series of flutamide analogues at Roussel Uclaf (now Sanofi) in the 1970s using a rat prostate assay determining the inhibition of androgen uptake.The investigational compound code was RU 23908. Its structure is closely related to hydroxyflutamide, particularly under the assumption that the α-hydroxyamide engages in an internal hydrogen bond when bound to the AR LBD. The hydantoin moiety of nilutamide mimics the active conformation of hydroxyflutamide. Like flutamide, nilutamide blocks the action of androgens originating from both testis and adrenal. It also has neither agonist nor any other hormonal activity. Nilutamide has an elimination half-life of approximately 2 days in patients, which is significantly longer than that of flutamide. Thus, a single oral dose of 150 mg daily was feasible.

용도Nonsteroidal antiandrogen. Antineoplastic (hormonal)

일반 설명Nilutamide, 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedione, is usedin combination with surgical castration for the treatment ofmetastatic prostate cancer. Nilutamide, which has an eliminationhalf-life of approximately 40 hours, can also be usedin once-daily dosing, but it has side effects that limit itsuse—visual disturbances, alcohol intolerance, and allergicpneumonitis.

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