StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
Huagongshe Open Project:[email protected]KI-Anbindung: llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.7.8
  1. Startseite
  2. /Verbindung

Fluprednisolon

Fluprednisolone

HCID 5876
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
53-34-9
Standard-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
Summenformel
C21H27FO5
Durchschnittliche Molmasse
378,4 g/mol
Monoisotopische Masse
378,18425212

Überblick

6alpha-Fluoroprednisolone is a fluorinated steroid.

Namen und Bezeichner

Bevorzugter Name
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
Lokaler Name
Fluprednisolon
Englischer Name
Fluprednisolone
Summenformel
C21H27FO5
Molmasse
378.43

Namen und Synonyme

fluprednisolone53-34-9AlphadrolEtadrolVladicort6alpha-FluoroprednisoloneFluprednisolonumDTXSID5046067fluprednisolonaNSC-47439U-78006alpha-Fluoro-1-dehydrohydrocortisone
Weitere Namen anzeigen
6α-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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,4
Polarare Oberfläche (TPSA)
94,8 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
2
Schwere Atome
27
Formalladung
0
Komplexität
760

Experimentelle und physikochemische Eigenschaften

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

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 · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point · 2 Einträge

208-213 °C

Crystals. MP: 235-238 °C /21-Acetate/

Optical RotationSpecific optical rotation: +92 deg

Physikochemische Eigenschaften

Schmelzpunkt
208 · 208-213°

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

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

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

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.

Toxikologische Informationen

Interactions · 5 Einträge

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.

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

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 · 2 Einträge

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 · 2 Einträge

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/.

Verwendung und Herstellung

Uses · 3 Einträge

THERAP CAT: Glucocortioid; anti-inflammatory

THERAP CAT (VET): Anti-inflammatory

MEDICATION

Zugehörige Reaktionen

0
Reaktionsaufzeichnung erstellen

Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
CHEBI:34474
UNII
9H05937G3X
EC Number
200-170-8
Nikkaji
J4.143B
Dichte
1.1023 · 1.1023 (rough estimate)
Brechungsindex
1.598 · 1.5980 (estimate)
storage temp.
Refrigerator
Löslichkeit
Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
Farbe
White
Wasserlöslichkeit
174.2 mg/L · 174.2mg/L(20 ºC)
EPA chemische Informationen
Fluprednisolone (53-34-9)

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/

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 · 1 Eintrag

/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 · 5 Einträge

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 · 1 Eintrag

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 · 3 Einträge

/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/

Regulatorische Informationen

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

Sicherheitsdaten

wgk
3
Giftige Stoffe Daten
53-34-9(Hazardous Substances Data)
Methods of Manufacturing · 2 Einträge

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.
Anwendungen · 2 Einträge

BeschreibungFluprednisolone (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).

Verwenden6α-Fluprednisolone is an anti-inflammatory corticosteroid metabolite.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

SchwefelsureEssigsureNatriumhydrogencarbonatPregn-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)

Anbieter38 Anbieter

武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
杭州扬德医药科技有限公司0571-81953185 +86-15381198709 · [email protected]
NANJING YINGWEN BIOTECHNOLOGY CO LTD+8613382787392 · [email protected]
Nanjing Shizhou Biotechnology Co., Ltd+86-15850508050 · [email protected]
Xunteng International Trading Co.,Limited—
南京世洲生物科技有限公司025-0258556344 17301488900 · [email protected]
Chongqing jooe co., ltd+86-15223382610 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +86-15355479329 · [email protected]
上海超岚化工科技中心(原宁波市超明生物科技有限公司)13301662590 · [email protected]
深圳卓越生物医药科技有限公司26050679 18318671572 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
BOC Sciences16314854226 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
上海泰坦科技股份有限公司13023226327 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
南京克罗托鲁宁医药科技有限公司13382066392
上海杰瑞兴生物医药科技有限公司17521512546 17721492509 · [email protected]
Aladdin Scientific[email protected]
陕西缔都医药化工有限公司029-029-029-81148696 18161915376 · [email protected]
长沙福臻生物科技有限公司15111215862 18229892877 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]
重庆卡兰医药有限公司[email protected]
上海相辉医药科技有限公司13611835272 13611835272 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
陕西缔都医药化工有限公司+86-29-87569266 +86-17392581500 · [email protected]
Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418671 +86-189 4982 3763 · [email protected]
上海阿摩尔生物科技有限公司13370042665 18916960931 · [email protected]