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플루오시놀론아세토나이드

Fluocinolone Acetonide

HCID 6215
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
67-73-2
표준 SMILES
CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1
InChIKey
FEBLZLNTKCEFIT-VSXGLTOVSA-N
분자식
C24H30F2O6
평균 분자량
452.5 g/mol
단동위원소 질량
452.201045

개요

Fluocinolone acetonide is a fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders. It has a role as an anti-inflammatory drug and an antipruritic drug. It is a primary alpha-hydroxy ketone, a glucocorticoid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, an organic heteropentacyclic compound, a fluorinated steroid, a cyclic ketal and a 3-oxo-Delta(1),Delta(4)-steroid.

이름 및 식별자

우선 이름
Fluocinolone Acetonide
IUPAC
(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
현지명
플루오시놀론아세토나이드
영어명
Fluocinolone Acetonide
분자식
C24H30F2O6
분자량
452.49

이름 및 동의어

FLUOCINOLONE ACETONIDE67-73-2SynalarFluonidFlucinarFlupollonSynamolSynandoneJellinCoriphateDermalarFluovitif
이름 더 보기
플루오시놀론아세토나이드Fluocinolone acetonide for system suitability6-alpha,9-alpha-difluoro-16-alpha-hydroxyprednisolone16,17-acetonidesynsacFluzon
PercutinaRadiocinRetisertSynandroneTefunoteLocalynSinalarSynotic

데이터베이스 식별자

CAS
67-73-2
PubChem CID
6215
DTXSID
DTXSID0040674
ChEMBL
CHEMBL989
ChEBI
CHEBI:31623
UNII
0CD5FD6S2M
EC Number
200-668-5
Nikkaji
J1.414A

물성

구조 계산 물성

XLogP
2.5
극성 표면적
93.1 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
8
회전 가능 결합 수
2
무거운 원자 수
32
형식 전하
0
복잡도
960

실험 및 물리화학적 성질

Drugs · 4건

Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Analgesics and anti-inflammatories

LogP2.48
OdorODORLESS
Color/Form · 2건

CRYSTALS FROM ACETONE & HEXANE

WHITE, CRYSTALLINE POWDER

Solubility · 2건

Insoluble

SOL IN ALC, ACETONE, & METHANOL; INSOL IN WATER; SLIGHTLY SOL IN CHLOROFORM

Human Drugs · 4건

Breast Feeding; Lactation; Milk, Human; Corticosteroids, Topical; Glucocorticoids; Anti-Inflammatory Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Animal DrugsFDA approved animal drugs -> Active ingredient
Melting Point · 2건

266-268

266 °C

Optical RotationSPECIFIC OPTICAL ROTATION: +95 DEG @ 25 °C/D (CHLOROFORM); MAX ABSORPTION: 238 NM (LOG E= 4.21)

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Warning

H315 (40.8%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 98 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Other Safety InformationIMAP assessments - Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (6.alpha.,11.beta.,16.alpha.)-: Environment tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (40.8%)

독성 정보

InteractionsREVERSAL OF CORTICOSTEROID-INDUCED IMPAIRMENT OF WOUND HEALING HAS BEEN REPORTED AFTER TOPICAL APPLICATION OF VITAMIN /VITAMIN A/. /CORTICOSTEROIDS/
Human Toxicity Excerpts · 5건

...FOLLICULITIS OR STRIAE IS FREQUENT COMPLICATION, ESP IF OCCLUSIVE DRESSINGS ARE USED.

PHARMACOLOGICAL DOSES OF GLUCOCORTICOIDS RETARD OR INTERRUPT GROWTH OF CHILDREN, INDICATING ADVERSE EFFECT ON EPIPHYSEAL CARTILAGE. INHIBITION OF GROWTH IS RATHER WIDESPREAD EFFECT... /GLUCOCORTICOIDS/

PROLONGED THERAPY WITH CORTICOSTEROIDS MAY RESULT IN SUPPRESSION OF PITUITARY-ADRENAL FUNCTION THAT CAN BE SLOW IN RETURNING TO NORMAL. /CORTICOSTEROIDS/

...PRINCIPAL COMPLICATIONS RESULTING FROM PROLONGED THERAPY...ARE FLUID & ELECTROLYTE DISTURBANCES; HYPERGLYCEMIA & GLYCOSURIA; INCR SUSCEPTIBILITY TO INFECTIONS, INCL TUBERCULOSIS; PEPTIC ULCERS, WHICH MAY BLEED OR PERFORATE; OSTEOPOROSIS; CHARACTERISTIC MYOPATHY; BEHAVIORAL DISTURBANCES... /CORTICOSTEROIDS/

화학 및 산업

약리 정보

ATC Code · 6건

C - Cardiovascular system

S - Sensory organs

S - Sensory organs

D - Dermatologicals

QS - Sensory organs

QC - Cardiovascular system

Protein BindingThis pharmacokinetic parameter is not relevant as the systemic absorption of fluocinolone acetonide is very minimal.
Pharmacodynamics · 1건

Fluocinolone acetonide is a synthetic anti-inflammatory corticosteroid and thus, the effect of its interaction with the body produces vasoconstriction and suppression of membrane permeability, mitotic activity, immune response and release of inflammatory mediators. For its ophthalmic indications, fluocinolone acetonide is administered as intravitreal micro-insert. This preparation was observed in clinical trials to reduce the recurrence of uveitis flares by 2 fold when compared with the non treated patients even after six months after initial administration. As well the intraocular pressure seemed to increase slightly with the presence of the fluocinolone implant but it is important to monitor intraocular pressure.

Mechanism of Action · 3건

Fluocinolone acetonide is a corticosteroid and thus, it can be inferred that it acts by inhibiting the edema, fibrin deposition, capillary dilation, leukocyte migration, capillary proliferation, fibroblast proliferation, collagen deposition, and scar formation. Some reports have indicated that fluocinolone acetonide presents a high binding affinity for the glucocorticoid receptor. After binding the receptor, the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements in the promoter region of the target genes. This effect promotes the induction of phospholipase A2 inhibitory proteins (lipocortins). Through this mechanism of action, it is thought that fluocinolone induces mainly one of the lipocortins, annexin 1, which will later mediate the synthesis of inflammatory mediators such as prostaglandins and leukotrienes by inhibiting the release of arachidonic acid which is the precursor of all these inflammatory mediators. Hence, the induction of these proteins will prevent the release of arachidonic acid by phospholipase A2.

CORTICOSTEROIDS...ARE THOUGHT TO ACT BY CONTROLLING RATE OF SYNTH OF PROTEINS. ...CORTICOSTEROIDS REACT WITH RECEPTOR PROTEINS IN CYTOPLASM OF SENSITIVE CELLS TO FORM STEROID-RECEPTOR COMPLEX. ... STEROID HORMONES APPEAR TO STIMULATE TRANSCRIPTION & ULTIMATELY SYNTH OF SPECIFIC PROTEINS. /CORTICOSTEROIDS/

관련 반응

0건
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
Stability/Shelf LifeSTABLE IN LIGHT
Dissociation Constants13.9
Collision Cross Section · 2건

226.8 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0040674]

199.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
267 · 267-269 °C(lit.)
끓는 점
578.5 · 578.5±50.0 °C(Predicted)
밀도
1.1826 · 1.1826 (estimate)
굴절률
103 ° · 103 ° (C=1, MeOH)
저장 조건
Refrigerator
용해도
물에는 거의 녹지 않으며, 아세톤과 에탄올에는 녹는다.
물리적 상태
Solid
산도 계수 (pKa)
12.78 · 12.78±0.70(Predicted)
색상
흰색에서 황백색까지
수용성
물(부분적으로 용해됨), DMSO, 알코올, 클로로포름 및 메탄올에 용해됩니다.
Merck
14 · 14,4150
주요 응용
법의학 및 독성학수의사
InChIKey
FEBLZLNTKCEFIT-VSXGLTOVSA-N
SMILES
CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]2(O1)C(=O)CO
EPA
Fluocinolone acetonide (67-73-2)

화학적 성질

Crystalline Solid

...PRINCIPAL COMPLICATIONS...POSTERIOR SUBCAPSULAR CATARACTS; & CUSHING'S HABITUS, CONSISTING OF "MOON FACE," "BUFFALO HUMP," SUPRACLAVICULAR FAT PADS, "CENTRAL OBESITY," STRIAE, ECCHYMOSES, ACNE, & HIRSUTISM. /CORTICOSTEROIDS/

Non-Human Toxicity Excerpts · 4건

IN YOUNG GROWING ANIMALS THERE IS...ADVERSE EFFECT UPON GROWTH APPARATUS, RESULTING IN SLOWING OF GROWTH. RETARDATION OF HEALING OF EXPTL FRACTURES IN ANIMALS FROM ADMIN OF GLUCOCORTICOIDS IS ATTRIBUTED TO DEPRESSION OF OSTEOBLASTIC ACTIVITY. /ADRENOCORTICOSTEROIDS/

SINGLE DOSES OF GLUCOCORTICOIDS (0.5-8.0 G/KG) CAN SUPPRESS IMMUNE RESPONSE IN MICE TO EXTENT THAT HIGH MORTALITY OCCURS AS RESULT OF INTERCURRENT INFECTIONS OVER 1-3 WK. RATS ARE 10-20 TIMES MORE SENSITIVE THAN MICE TO THIS EFFECT. /CORTICOSTEROIDS/

LARGE SINGLE DOSES OF SOME STEROIDS GIVEN PARENTERALLY TO ANIMALS PRODUCE SEDATION, WHEREAS OTHERS INDUCE SIGNS OF CENTRAL STIMULATION. TO SOME EXTENT THESE PHENOMENA MAY BE DOSE-RELATED. /CORTICOSTEROIDS/

Fifteen pregnant New Zealand rabbits were given 125 ug/kg fluocinolone acetonide subcutaneously on days 6-18 of gestation. The same number of controls were given the vehicle. Fluocinolone acetonide decreased the body weight of dams compared with controls and caused 100% abortions before day 29 of gestation.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
3
rtecs
TU3830000
독성
LD50 oral in rat: > 4gm/kg
HS 번호
2937220000
risk_code
36/37/38-40-20/21/22
hazard_code
Xi,Xn
safety_code
26-36-22
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
67-73-2(Hazardous Substances Data)

...CORTICOSTEROIDS...INFLUENCE CARBOHYDRATE, PROTEIN, FAT, & PURINE METABOLISM; ELECTROLYTE & WATER BALANCE; & FUNCTIONS OF CVS, KIDNEY, SKELETAL MUSCLE, NERVOUS SYSTEM, & OTHER ORGANS & TISSUES. ...CORTICOSTEROIDS ENDOW ORGANISM WITH CAPACITY TO RESIST MANY TYPES OF NOXIOUS STIMULI & ENVIRONMENTAL CHANGE. /CORTICOSTEROIDS/

Biological Half-LifeThe reported half-life of fluocinolone acetonide ranges between 1.3-1.7 hours.
Metabolism/Metabolites · 2건

Following absorption, fluocinolone acetonide metabolism is primarily hepatic. It is important to mention that the systemically absorbed dose is very minimal.

...IT IS GENERALLY ASSUMED THAT METAB OF /CORTISOL &/ ITS CONGENERS & SYNTH DERIV IS QUALITATIVELY SIMILAR. ...METABOLIZED PRINCIPALLY BY REDN OF RING A, REDN OF KETONE AT C 20, & CLEAVAGE OF SIDE CHAIN. METABOLITES ARE EXCRETED...AS GLUCURONIDES, SULFATES, & UNCONJUGATED COMPOUNDS. /CORTICOSTEROIDS/

FDA Pharmacological Classification · 6건

0CD5FD6S2M

FLUOCINOLONE ACETONIDE

Established Pharmacologic Class [EPC] - Corticosteroid

Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists

Fluocinolone acetonide is a Corticosteroid. The mechanism of action of fluocinolone acetonide is as a Corticosteroid Hormone Receptor Agonist.

FLUOCINOLONE ACETONIDE

MeSH Pharmacological Classification · 2건

Substances that reduce or suppress INFLAMMATION.

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.

Absorption, Distribution and Excretion · 6건

When administered as an eye implant, fluocinolone acetonide presents a sustained delivery for even 12 months in which there can be observed a sustained release. The concentration of fluocinolone acetonide are generally higher in the vitreous and retina with a little dispersion to the aqueous humor. There are reports indicating that topical administration of fluocinolone acetonide produces a percutaneous absorption which is determined by the vehicle, integrity of the epidermal barrier and the use of occlusive dressing. Independently of the route of administration, the systemic absorption of fluocinolone acetonide is below 0.1 ng/ml which indicates that the systemic distribution is very minimal and the effect of fluocinolone is mainly local.

Fluocinolone acetonide is mainly excreted by the kidneys. It is important to mention that the systemically absorbed dose is very minimal.

This pharmacokinetic parameter is not relevant as the systemic absorption of fluocinolone acetonide is very minimal.

This pharmacokinetic parameter is not relevant as the systemic absorption of fluocinolone acetonide is very minimal and the concentration in urine is lower than the minimum quantitation limit.

METABOLISM OF CORTICOSTEROIDS IS GREATLY SLOWED BY INTRODUCTION OF THE 1,2 DOUBLE BOND OR A FLUORINE ATOM INTO MOLECULE, & HALF-LIFE IS CORRESPONDINGLY PROLONGED. /CORTICOSTEROIDS/

(14)C WAS RAPIDLY & MAINLY EXCRETED IN 48-HR FECES (90%), VIA BILE (70% IN 24 HR), & IN URINE (8%). AFTER DERMAL APPLICATION OF CREAM CONTAINING [(14)C]FLUOCINOLONE ACETONIDE TO MICE, GREATER THAN 7% OF (14)C WAS ABSORBED.

용도 및 제조

Uses · 2건

MEDICATION (VET)

MEDICATION

Methods of ManufacturingMILLS ET AL, J AM CHEM SOC 82, 3399 (1960); MILLS, BOWERS, US PATENT 3,014,938 (1961 TO SYNTEX).
Formulations/Preparations · 2건

FLUOCINOLONE ACETONIDE, USP (FLUONID, SYNALAR); TOPICAL FORMS: 0.01, 0.025, 0.2% CREAM; 0.025% OINTMENT; 0.01% TOPICAL SOLN. /FROM TABLE/

NEOMYCIN IS OFTEN INCL IN TOPICAL PREPN OF FLUOCINOLONE ACETONIDE TO SUPPRESS INFECTIONS SECONDARY TO INFLAMMATORY PROCESS OR WHICH RESULT FROM USE OF THE GLUCOCORTICOID.

Use ClassificationPharmaceuticals
응용 분야 · 2건

용도Fluocinolone acetonide (Derma-Smoothe/FS, Flurosyn, Capex, Synalar) is a synthetic fluorinated corticosteroid.

일반 설명Fluocinolone acetonide,6α,9-difluoro-11β,21-dihydroxy-16α,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione, also known as6α-fluorotriamcinolone acetonide, is the 21-acetate derivativeof fluocinolone acetonide and is about 5 times morepotent than fluocinolone acetonide in at least one topicalactivity assay.

상·하류 제품 정보

상류 원료

hydrogen fluoride이산화셀레늄N-Bromoacetamide메탄설포닐 클로라이드수산화칼륨무수초산불산

공급사100 곳

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추가 설명 · 1건

정의ChEBI: Fluocinolone acetonide is a fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders. It has a role as an anti-inflammatory drug and an antipruritic drug. It is an 11beta-hydroxy steroid, a 21-hydroxy steroid, a 20-oxo steroid, a cyclic ketal, a glucocorticoid, a fluorinated steroid, a 3-oxo-Delta(1),Delta(4)-steroid, an organic heteropentacyclic compound and a primary alpha-hydroxy ketone.