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플루프레드니솔론

Fluprednisolone

HCID 5876
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
53-34-9
표준 SMILES
C[C@]12C=CC(=O)C=C1[C@@H](F)C[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
InChIKey
MYYIMZRZXIQBGI-HVIRSNARSA-N
분자식
C21H27FO5
평균 분자량
378.4 g/mol
단동위원소 질량
378.18425212

개요

6alpha-Fluoroprednisolone is a fluorinated steroid.

이름 및 식별자

우선 이름
Fluprednisolone
IUPAC
(6S,8S,9S,10R,11S,13S,14S,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
현지명
플루프레드니솔론
영어명
Fluprednisolone
분자식
C21H27FO5
분자량
378.43

이름 및 동의어

fluprednisolone53-34-9AlphadrolEtadrolVladicort6alpha-FluoroprednisoloneFluprednisolonumDTXSID5046067fluprednisolonaNSC-47439U-78006alpha-Fluoro-1-dehydrohydrocortisone
이름 더 보기
플루프레드니솔론6α-Fluprednisolone6-a-Fluorprednisolone6a-fluoroprednisolone6-α-fluoroprednisolone6alpha-Fluprednisolone
FI 6150Pregna-1,4-diene-3,20-dione, 6-fluoro-11,17,21-trihydroxy-, (6alpha,11beta)-9H05937G3XDTXCID30260676alpha-Fluoro-1,4-pregnadiene-11beta,17alpha,21-triol-3,20-dioneNSC47439Pregna-1,4-diene-3,20-dione, 6alpha-fluoro-11beta,17,21-trihydroxy-6alpha-Fluoro-11beta,17alpha,21-trihydroxypregna-1,4-diene-3,20-dione

데이터베이스 식별자

CAS
53-34-9
PubChem CID
5876
DTXSID
DTXSID5046067
ChEMBL
CHEMBL1200774
ChEBI
CHEBI:34474

물성

구조 계산 물성

XLogP
1.4
극성 표면적
94.8 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
6
회전 가능 결합 수
2
무거운 원자 수
27
형식 전하
0
복잡도
760

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
OdorODORLESS
Color/Form · 2건

WHITE TO OFF-WHITE POWDER

Crystals

SolubilitySPARINGLY SOL IN ALC, METHANOL, ETHYL ACETATE. SLIGHTLY SOL IN CHLOROFORM, ETHER, ETHYLENE DICHLORIDE. VERY SLIGHTLY SOL IN BENZENE.
Human Drugs · 2건

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point · 2건

208-213 °C

Crystals. MP: 235-238 °C /21-Acetate/

Optical RotationSpecific optical rotation: +92 deg

물리화학적 성질

녹는점
208 · 208-213°
밀도
1.1023 · 1.1023 (rough estimate)
굴절률
1.598 · 1.5980 (estimate)
저장 조건
Refrigerator
용해도
디옥산(약간 용해됨), DMSO(약간 용해됨), 메탄올(약간 용해됨)

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P263, P264, P270, P280, P301+P317, P302+P352, P317, P318, P319, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

유해성 정보

FDA RequirementsThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies discontinued drug products, incl fluprednisolone.
Hazard Classes and CategoriesAcute Tox. 4 (100%)

안전 및 보호

Disposal Methods · 1건

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

독성 정보

Interactions · 5건

SYSTEMIC EFFECTS OF ADMIN CORTICOSTEROIDS SUCH AS...DEXAMETHASONE...MAY BE DIMINISHED BY LARGE DOSES OF BARBITURATES... FLUPREDNISOLONE...ALSO MAY BE EXPECTED TO INTERACT WITH PHENOBARBITAL, ALTHOUGH THERE HAVE BEEN NO REPORTS DOCUMENTING SUCH INTERATIONS.

PHENYTOIN IS...KNOWN TO INCR METAB OF HYDROCORTISONE...IN HUMANS. IT IS LIKELY THAT...FLUPREDNISOLONE...WOULD INTERACT SIMILARLY.

The effect of glucocorticoids on oral anticoagulant therapy is variable, and the efficacy of oral anticoagulants has been reported to be enhanced or diminished with concomitant glucocorticoid administration. Patients receiving glucocorticoids and oral anticoagulants concomitantly should be monitored (e.g., using coagulation indices) in order to maintain desired anticoagulant effect. /Corticosteroids/

화학 및 산업

약리 정보

Mechanism of Action · 1건

Glucocorticoids are capable of suppressing the inflammatory process through numerous pathways. They interact with specific intracellular receptor proteins in target tissues to alter the expression of corticosteroid-responsive genes. Glucocorticoid-specific receptors in the cell cytoplasm bind with steroid ligands to form hormone-receptor complexes that eventually translocate to the cell nucleus. There these complexes bind to specific DNA sequences and alter their expression. The complexes may induce the transcription of mRNA leading to synthesis of new proteins. Such proteins include lipocortin, a protein known to inhibit PLA2a and thereby block the synthesis of prostaglandins, leukotrienes, and PAF. Glucocorticoids also inhibit the production of other mediators including AA metabolites such as COX, cytokines, the interleukins, adhesion molecules, and enzymes such as collagenase. /Glucocorticoids/

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 · 2건

EXCELLENT CORRELATIONS WERE OBTAINED BETWEEN DISSOLUTION RATES OF SOLVATED & NON-SOLVATED PHASES OF FLUPREDNISOLONE & IN VIVO DISSOLUTION RATES OF PELLET IMPLANTS IN RATS.

CONJUGATED MOSTLY IN LIVER BUT ALSO IN KIDNEY /HUMAN, ORAL/.

용도 및 제조

Uses · 3건

THERAP CAT: Glucocortioid; anti-inflammatory

THERAP CAT (VET): Anti-inflammatory

MEDICATION

Methods of Manufacturing

관련 반응

0건
반응 기록 만들기

현재 필터 조건에 해당하는 반응 기록이 없습니다.

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
UNII
9H05937G3X
EC Number
200-170-8
Nikkaji
J4.143B
물리적 상태
Solid
색상
하얀색
수용성
174.2 mg/L · 174.2mg/L(20 ºC)
EPA
Fluprednisolone (53-34-9)

Because corticosteroids inhibit antibody response, the drugs may cause a diminished response to toxoids and live or inactivated vaccines. In addition, corticosteroids may potentiate replication of some organisms contained in live, attenuated vaccines and supraphysiologic dosages of the drugs can aggravate neurologic reactions to some vaccines. Routine administration of vaccines or toxoids should generally be deferred until corticosteroid therapy is discontinued. Administration of live virus or live, attenuated vaccines, including smallpox vaccine, is contraindicated in patients receiving immunosuppressive dosages of glucocorticoids. In addition, if inactivated vaccines are administered to such patients, expected serum antibody response may not be obtained. The Public Health Service Advisory Committee on Immunization Practices (ACIP) and American Academy of Family Physicians (AAFP) state that administration of live virus vaccines usually is not contraindicated in patients receiving corticosteroid therapy as short-term (less than 2 weeks) treatment, in low to moderate dosages, as long-term alternate-day treatment with short-acting preparations, in maintenance physiologic dosages (replacement therapy), or if corticosteroids are administered topically, ophthalmically, intra-articularly, bursally, or into a tendon. If immunization is necessary in a patient receiving corticosteroid therapy, serologic testing may be needed to ensure adequate antibody response and additional doses of the vaccine or toxoid may be necessary. Immunization procedures may be undertaken in patients receiving nonimmunosuppressive doses of glucocorticoids or in patients receiving glucocorticoids as replacement therapy (e.g., Addison's disease). /Corticosteroids/

For more Interactions (Complete) data for FLUPREDNISOLONE (6 total), please visit the HSDB record page.

Milk ConcentrationsCorticosteroids may be distributed into milk ... . /Corticosteroids/
Human Toxicity Excerpts · 1건

/SIGNS AND SYMPTOMS/ Glucocorticoids may cause fetal damage when administered to pregnant women. One retrospective study of 260 women who received pharmacologic dosages of glucocorticoids during pregnancy revealed 2 instances of cleft palate, 8 stillbirths, 1 spontaneous abortion, and 15 premature births. Another study reported 2 cases of cleft palate in 86 births. Occurrence of cleft palate in these studies is higher than in the general population but could have resulted from the underlying diseases as well as from the steroids. Other fetal abnormalities that have been reported following glucocorticoid administration in pregnant women include hydrocephalus and gastroschisis. Women should be instructed to inform their physicians if they become or wish to become pregnant while receiving glucocorticoids. If glucocorticoids must be used during pregnancy or if the patient becomes pregnant while taking one of these drugs, the potential risks should be carefully considered. /Corticosteroids/

Populations at Special Risk · 5건

Glucocorticoids should be used with caution in patients with hypothyroidism or cirrhosis, because such patients often show exaggerated response to the drugs. Glucocorticoids should be used with caution in psychotic patients or patients with hypertension or congestive heart failure. /Corticosteroids/

Because an apparent association has been suggested between use of corticosteroids and left ventricular free-wall rupture after a recent myocardial infarction, corticosteroids should be used with extreme caution in these patients. /Corticosteroids/

Because glucocorticoids increase susceptibility to and mask symptoms of infection, the drugs should not be used, except in life-threatening situations, in patients with viral infections or bacterial infections not controlled by anti-infectives. Manufacturers state that glucocorticoid oral inhalation therapy should be used with caution, if at all, in patients with untreated systemic fungal, bacterial, viral, or parasitic infections. Patients whose susceptibility to infection is high, such as those receiving glucocorticoids as immunosuppressive therapy, are especially likely to develop secondary infections. Patients receiving glucocorticoids who are potentially immunosuppressed should be warned of the risk of exposure to certain infections (e.g., chickenpox, measles) and of the importance of obtaining medical advice if such exposure occurs. Since glucocorticoid therapy can reactivate tuberculosis, treatment of latent tuberculosis infection should be included in the regimen of patients with a history of active tuberculosis undergoing prolonged glucocorticoid therapy. If glucocorticoids are indicated in patients with latent tuberculosis or tuberculin reactivity, close observation is necessary. Use of glucocorticoids in patients with active tuberculosis should be restricted to those with fulminating or disseminated tuberculosis in which glucocorticoids are used in conjunction with appropriate antimycobacterial chemotherapy. Manufacturers state that glucocorticoid oral inhalation therapy should be used with caution, if at all, in patients with clinical or asymptomatic Mycobacterium tuberculosis infections of the respiratory tract. Since glucocorticoids can reactivate latent amebiasis, any patient who has been in the tropics or who has unexplained diarrhea should be evaluated for amebiasis to exclude these patients prior to initiating therapy. In the treatment of acute or disseminated tuberculosis, glucocorticoids should only be used as part of a total antituberculosis regimen. ... /Corticosteroids/

Corticosteroids should be used with caution in patients with active or latent peptic ulcer, diverticulitis, nonspecific ulcerative colitis (if there is a probability of impending perforation, abscess, or other pyogenic infection), and in those with recent intestinal anastomoses. Manifestations of peritoneal irritation following GI perforation may be minimal or absent in patients receiving glucocorticoids. /Corticosteroids/

Glucocorticoids may cause fetal damage when administered to pregnant women. One retrospective study of 260 women who received pharmacologic dosages of glucocorticoids during pregnancy revealed 2 instances of cleft palate, 8 stillbirths, 1 spontaneous abortion, and 15 premature births. Another study reported 2 cases of cleft palate in 86 births. Occurrence of cleft palate in these studies is higher than in the general population but could have resulted from the underlying diseases as well as from the steroids. Other fetal abnormalities that have been reported following glucocorticoid administration in pregnant women include hydrocephalus and gastroschisis. Women should be instructed to inform their physicians if they become or wish to become pregnant while receiving glucocorticoids. If glucocorticoids must be used during pregnancy or if the patient becomes pregnant while taking one of these drugs, the potential risks should be carefully considered. /Corticosteroids/

Environmental Water Concentrations · 1건

While data specific to fluprednisolone were not located(SRC, 2007), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2). Studies have indicated that several polar pharmaceutically active compounds can leach through soil(1).

Antidote and Emergency Treatment · 3건

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

규제 정보

FDA RequirementsThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies discontinued drug products, incl fluprednisolone.

안전 데이터

wgk
3
유해 물질 데이터
53-34-9(Hazardous Substances Data)
· 2건

Preparation: Hogg, Spero, US 2841600 (1958 to Upjohn); Batres et al, DE 1079042 (1960 to Syntex); Lettre, Hotz, DE 1088953 (1960 to Bayer).

Synthesized with methods developed by Upjohn, Syntex, and Bayer.

Formulations/PreparationsALPHADROL (UPJOHN). ORAL: TABLETS 1.5 MG.
General Manufacturing InformationPATENTS: US PATENT 2,841,600.
응용 분야 · 2건

개요Fluprednisolone (6α-fluoro-11β,17,21-trihydroxy-pregna-1,4-diene-3,20-dione) is the 16-desmethyl analogue of paramethasone. Its activity is similar to that of paramethasone, and it has approximately 2.5 times the antirheumatic potency of prednisolone. With doses of 2 to 7 mg, evidence of salt and water retention has not been noted. The therapeutic index, however, probably is the same or only a little greater than that for prednisolone. Because no new adverse reactions have been noted during the administration of this drug on a short-term basis, it seems that a 6α-fluoro group does not deleteriously affect the activity of prednisolone (49,75).

용도6α-Fluprednisolone is an anti-inflammatory corticosteroid metabolite.

상·하류 제품 정보

상류 원료

황산아세트산(빙초산)중탄산나트륨(중조)Pregn-4-ene-3,20-dione,21-(acetyloxy)-6-fluoro-11,17-dihydroxy-, (6a,11b)- (9CI)Pregn-4-ene-3,20-dione, 6β-fluoro-11β,17,21-trihydroxy-, 21-acetate (7CI,8CI)

공급사38 곳

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