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HCID 5755Erstellt: 27. Oktober 2026

Prednisolon

Prednisolon · (+)-Melezitose · Hydroprednisone · 11BETA,17ALPHA,21-TRIHYDROXYPREGNA-1,4-DIENE-3,20-DIONE · cortalone · delta-cortef · Prednisolone CRS · Hydrocortisone EP Impurity A

https://huagongshe.com/de/chemical/5755

Molekülstruktur von Prednisolon

Identifikatoren & physikalische Daten

CAS No.50-24-8
SummenformelC21H28O5
Durchschnittliche Molmasse360,4 g/mol
Monoisotopische Masse360,193674 g/mol
SMILESC[C@]12C=CC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
InChIKeyOIGNJSKKLXVSLS-VWUMJDOOSA-N
PubChem CID5755
ChEMBLCHEMBL131
ChEBICHEBI:8378
EC No.200-021-7
DTXSIDDTXSID9021184
Lokaler NamePrednisolon

Chemische & physikalische Eigenschaften

XLogP1,6
Polarare Oberfläche (TPSA)94,8
H-Brücken-Donoren3
H-Brücken-Akzeptoren5
Frei drehbare Bindungen2
Schwere Atome26
Formalladung0
Komplexität724
StoffklassenPharmaceutical
ArzneimittelPharmaceuticals -> SteroidsPharmaceuticals -> Metabolite of PrednisonePharmaceuticals -> Listed in ZINC15
LipideLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
SpringerMaterials PropertiesCrystal structure
LogP (Verteilungskoeffizient)log Kow = 1.62
GeruchOdorless
Color/FormCrystalsWhite to practically white crystalline powder
LöslichkeitSPECIFIC OPTICAL ROTATION: +102.5 DEG @ 25 °C/DPH OF 1% SOLN 7.5 TO 8.5SOL IN WATER, METHANOL, ETHANOL. /PHOSPHATE SODIUM/1 g dissolves in about 30 mL of alc, in about 180 mL of chloroform, in about 50 mL of acetonesol in methanol, dioxane.In water, 2.23X10+2 mg/L at 25 °C2.39e-01 g/LVery slightly soluble in water, soluble in ethanol (96 per cent) and in methanol, sparingly soluble in acetone, slightly soluble in methylene chloride. It shows polymorphism (5.9).2.225g/L(25 ºC)
Human DrugsBreast FeedingLactationMilk, HumanCorticosteroids, SystemicCorticosteroids, OphthalmicGlucocorticoidsAnti-Inflammatory AgentsFDA approved drugs -> Active ingredientAnti-inflammatory medicines
Animal DrugsEMA approved medicines: Veterinary medicineActive Ingredients (Prednisolone) -> FDA GreenbookPharmaceuticals -> Animal Drugs -> Approved in TaiwanPharmaceuticals -> UK Veterinary Medicines Directorate List
Endocrine DisruptorsPotential endocrine disrupting compound
Schmelzpunkt235 °C with some decompositionCRYSTALS FROM ETHANOLMP: 266-273 °C /TEBUTATE/240 °C (dec.) (lit.)
Siedepunkt412.46°C (rough estimate)
Dichte1.0963 (rough estimate)
Brechungsindex100 ° (C=1, Dioxane)
Flammpunkt2℃
Lagerbedingungen2-8°C
Aggregatzustandpowder
pKa (Säurekonstante)12.46±0.70(Predicted)
FarbeWhite to Off-White
Merck14,7721
BRN1354103
Henry-Konstante3.7×102 mol/(m3Pa) at 25℃, HSDB (2015)
BCS Class1
Hauptanwendungenclinical testing
InChIKeyOIGNJSKKLXVSLS-VWUMJDOOSA-N
SMILESO[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)C=C4)CC3)C)[C@H](C2)O)CC1)C)C(=O)CO
CAS Datenbank50-24-8(CAS DataBase Reference)
EPA chemische InformationenPrednisolone (50-24-8)

Sicherheit & Vorschriften

GHS-EinstufungThis chemical does not meet GHS hazard criteria for 0.5% (1 of 207) of reports.DangerH302 (31.9%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P261, P264, P270, P271, P273, P280, P301+P317, P304+P340, P317, P318, P319, P330, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 207 reports by companies from 29 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische InformationenStatus: Active Update: 04-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14158Prednisolone: Does not have an individual approval but may be used under an appropriate group standard
Weitere SicherheitsinformationenIMAP assessments - Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-, (11.beta.)-: Environment tier I assessment
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl prednisolone approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl prednisolone sodium phosphate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Prednisolone sodium phosphate/The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl prednisolone acetate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Prednisolone acetate/The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies discontinued drug products, incl prednisolone tebutate. /Prednisolone tebutate/For more FDA Requirements (Complete) data for PREDNISOLONE (15 total), please visit the HSDB record page.
Special ReportsAli SLPrednisoloneAnal Profiles Drug Subst Excipients 21: 415-500 (1992). A review with 153 references on the synthesis, properties, pharmacology, and analysis of prednisolone.

Anwendungen & Verwendung

Beschreibung

Prednisolone is the active metabolite of the synthetic corticosteroid prednisone , which is used in the suppression of inflammation and autoimmunity, as well as in other conditions. It alters gene expression through both the glucocorticoid and mineralocorticoid receptors.

Verwenden

Prednisolone is used for the same indications as all corticosteroids: rheumatism, polyarthritis, bronchial asthma, neurodermatitis, and eczema.

Wald JA et al
Evaluation of Dose-Related Pharmacokinetics and Pharmacodynamics of Prednisolone in Man
J Pharmacokinet Biopharm 20 (Dec): 567-89 (1992). To investigate the pharmacokinetics and pharmacodynamics of prednisolone and to develop predictive models, 7 healthy volunteers, ages 21-37 yr, received between 16.4 and 49.2 mg of iv prednisolone sodium phosphate (Hydeltrasol) on 2 occasions in increasing doses
blood and urine samples were taken frequently and analyzed for pharmacokinetic parameters, suppression of plasma cortisol, and alterations in blood basophil and helper-T cells trafficking. Results indicated that the pharmacokinetics of total drug were comparable to previous findings. Pharmacodynamic models characterized the suppression/trafficking phenomenon with the use of total or free drug concn. It was concluded that the models provided realistic values of parameters relating to steroid sensitivity.
Hazard Classes and CategoriesAcute Tox. 4 (31.9%)
LagerbedingungenStore between 20 and 25 °C (68 and 77 °F), unless otherwise specified by manufacturer. Store in a tight container.
EntsorgungsverfahrenSRP: 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.
Allowable TolerancesA tolerance of zero is established for residues of prednisolone in milk from dairy animals.
WechselwirkungenSeizures have been observed in patients receiving cyclosporine and high doses of methylprednisolone. /MethylprednisoloneIn one study, women taking oral contraceptives or postmenopausal estrogen therapy were given prednisolone concurrently. Alterations in metabolism of prednisolone, including incr half-life, were consistent with a potential for enhanced pharmacologic effect or toxicity when prednisolone was added to an estrogen regimen.Ketoconazole inhibits the deposition of ... prednisolone by inhibiting 6beta-hydroxylase, thereby prolonging the adrenal suppressive effect of ... /prednisolone/.Drugs reported to increase blood levels of cyclosporine include ... prednisolone.For more Interactions (Complete) data for PREDNISOLONE (26 total), please visit the HSDB record page.
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 180(SRC), determined from a log Kow of 1.62(2) and a regression-derived equation(3), indicates that prednisolone is expected to have moderate mobility in soil(SRC). Volatilization of prednisolone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.7X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Prednisolone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-13 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data for prednisolone were not available (SRC, 2007).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 180(SRC), determined from a log Kow of 1.62(2) and a regression-derived equation(3), indicates that prednisolone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.7X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(6), an estimated BCF of 3.5(SRC), from an estimated log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data for prednisolone were not available (SRC, 2007).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), prednisolone, which has an estimated vapor pressure of 1.2X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase prednisolone may be removed from the air by wet or dry deposition(SRC). Prednisolone contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight.
Milk ConcentrationsCorticosteroids may be distributed into milk ... . /Corticosteroids/The transfer of prednisolone to breast milk was studied in 3 nursing women (ages 28-37 yr) who received an intravenous injection of 50 mg prednisolone sodium phosphate (Hydeltrasol). Concn of prednisolone in milk declined more rapidly than in serum, but were similar to expected unbound serum levels. Milk levels ranged from about 15% to 40% of serum levels. The exchange between unbound drug in serum and breast milk appeared to be relatively rapid and bidirectional. An average of 0.025% (0.01-0.49%) of the prednisolone dose was recovered in milk.
Ökotoxizitätsauszüge/AQUATIC SPECIES/ Light exposure of aqueous suspensions of prednisolone and dexamethasone causes their partial phototransformation. The photoproducts, isolated by chromatographic techniques, have been identified by spectroscopic means. Prednisolone, dexamethasone and their photoproducts have been tested to evaluate their acute and chronic toxic effects on some freshwater chain organisms. The rotifer Brachionus calyciflorus and the crustaceans Thamnocephalus platyurus and Daphnia magna were chosen to perform acute toxicity tests, while the alga Pseudokircheneriella subcapitata (formerly known as Selenastrum capricornutum) and the crustacean Ceriodaphnia dubia to perform chronic tests. The photochemical derivatives are more toxic than the parent compounds. Generally low acute toxicity was found. Chronic exposure to this class of pharmaceuticals caused inhibition of growth population on the freshwater crustacean C. dubia while the alga P. subcapitata seems to be less affected by the presence of these drugs.
Soil Adsorption/MobilityThe Koc of prednisolone is estimated as 180(SRC), using a log Kow of 1.62(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that prednisolone is expected to have moderate mobility in soil.
Human Toxicity Excerpts/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//CASE REPORTS/ Acute generalized exanthematous pustulosis (AGEP) is a rare cutaneous eruption which is often provoked by drugs. CASE Two cases of AGEP which showed rapidly spreading pustular eruptions accompanied by malaise, fever and neutrophilia after the administration of systemic prednisolone (corticosteroid of group A, hydrocortisone type) /are described/. The histological examination showing neutrophilic subcorneal spongiform pustules was consistent with the diagnosis of AGEP. In both cases the rash cleared within a week upon treatment with topical steroids (corticosteroid of group D1, betamethasonedipropionate type and corticosteroid of group D2, hydrocortisone-17-butyrate type). Three months after recovery, the sensitization to corticosteroids of group A was confirmed by epicutaneous testing and positive lymphocyte transformation tests./CASE REPORTS/ The case of a 27-year-old female who had an allergic contact dermatitis to topical corticosteroids belonging to the corticosteroid groups A and D /was reported/. Upon oral treatment with prednisolone a disseminated exanthema began within 24 hr. Patch tests revealed sensitization to corticosteroids of group A, C and D, including prednisolone-21-acetate and betamethasone valerate, but not of group B corticosteroids such as triamcinolone. After intradermal testing of corticosteroids the exanthema flared again and the patient was treated with oral triamcinolone, with rapid improvement of her symptoms. A literature review revealed that exanthematous reactions after systemic treatment with corticosteroids have been rarely reported. Since corticosteroids are essential emergency drugs, a safe corticosteroid should be identified for such patients./CASE REPORTS/ Although positive reactions to topical corticosteroids can occur in over 1% of a patch-test population, systemic reactions to oral corticosteroids are uncommon. A 45-year-old woman who gave a clear history of the generalization of a cutaneous eruption following oral prednisolone was positive on patch testing using prednisolone eye drops.For more Human Toxicity Excerpts (Complete) data for PREDNISOLONE (7 total), please visit the HSDB record page.
Artificial Pollution SourcesPrednisolone's production and use as a glucocorticoid(1) may result in its release to the environment through various waste streams(SRC).
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)PrednisolonevLess-DILI-concern3Adverse reactionsDOI:10.1016/j.drudis.2016.02.015
Environmental BioconcentrationAn estimated BCF of 3.5 was calculated for prednisolone(SRC), using a log Kow of 1.62(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC), provided the compound is not metabolized by the organism(SRC).
Volatilization from Water/SoilThe Henry's Law constant for prednisolone is estimated as 2.7X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that prednisolone is expected to be essentially nonvolatile from water surfaces(2). Prednisolone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-13 mm Hg(SRC), determined from a fragment constant method(3).
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ Various tests for irritation, phototoxicity, contact sensitivity and photocontact sensitivity of prednisolone farnesylate gel were conducted. The results were as follows. 1) In the primary dermal irritation test and trypan blue test, slight erythema was noted in the rabbits treated with 0.8 and 1.6% prednisolone farnesylate gel, although similar reaction occurred in those treated with the base. 2) In the test for the primary irritation to the ocular mucosa, severe irritant reactions were caused by 0.8 and 1.6% prednisolone farnesylate gel and its base. However these reactions disappeared 7 days after irritation. 3) In the phototoxicity test and contact sensitivity test, no positive reactions were detected by 0.8 and 1.6% prednisolone farnesylate gel. On the other hand, in the photocontact sensitivity test, positive reaction were noted in the guinea pig treated with 0.8 and 1.6% prednisolone farnesylate gel and its base. /Prednisolone farnesylate//LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The toxicity of prednisolone farnesylate (PNF) gel, a synthetic glucocorticoid, was investigated in the Sprague-Dawley rat. PNF gel was administered dermally to the rats at doses of 0.25, 1, 4 and 16 mg/kg/day for 13 weeks, then the drug was withdrawn for 5 weeks to evaluate the reversibility. In addition, 10 mg/kg/day prednisolone gel, which is approximate to 16 mg/kg/day prednisolone farnesylate gel in prednisolone molarity, was also administered to the rats for comparison. The results are summarized as follows: 1. In the prednisolone farnesylate gel 16 mg/kg/day group, temporary erythema at the application site, retarded body weight gains, a decrease in the white blood cell count and lymphocyte ratio with an increase in the segmented neutrophil ratio, an elevation of serum ALP activity were observed. The pathological examinations revealed atrophy of the adrenal glands, lymphatic organs and skin. In addition, histopathological lesions were also found in the liver, pancreatic islets, bone, bone marrow and mammary glands. 2. In the prednisolone farnesylate gel 4 mg/kg/day group, retarded body weight gains were observed, and histopathological lesions were noted in the adrenal glands, lymphatic organs, skin at the application site, liver and bone marrows. 3. In the groups that received less than 1 mg/kg/day of prednisolone farnesylate gel, there were no toxic signs induced by the drug. 4. In the prednisolone gel 10 mg/kg/day group, drug-related changes were almost similar to those of the prednisolone farnesylate gel group, but the severity of the lesions was stronger than in the prednisolone farnesylate gel group. 5. After the 5-week recovery period, the above changes almost completely disappeared and so it was demonstrated that the changes were reversible. 6. Based on these results, it was concluded that the overt toxic dose of prednisolone farnesylate gel was 4 mg/kg/day and the non-toxic dose was 1 mg/kg/day in the present study./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Repeated dose toxicity studies were also carried out in rabbits (intramuscular doses of 0.5 to 2.5 mg prednisolone acetate/kg body weight, for up to 22 doses) and guinea pigs (intramuscular dose of 2.2 mg prednisolone/kg body weight for up to 8 doses and oral doses of 0, 1, or 10 mg prednisolone/kg body weight administered in the drinking water or 0, 10, or 100 mg/kg body weight administered in the feed for 24 weeks). ... Hepatotoxicity was observed at the lowest dose tested in rabbits and ws dose-related in severityrabbits appeared to be the species most susceptible to this effect. In guinea pigs the main effects were reduced body-weight gain (apparent at the lowest dose of 1 mg/kg body weight), increase in hematocrit and hemoglobin values and decreased bone mineral concentrations./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of Mongrel dogs (2 animals per sex and dose) were given daily oral doses of 0, 2.5 or 5 mg/kg body weight per day for 6 weeks. Bodyweight gain was reduced at 5 mg/kg body weight. There was no significant effects on hematology or clinical chemistry values. There were dose-related increase in urine volume and mean urine sodium and potassium concentrations and a corresponding reduction in urinary specific gravity. At necropsy, glycogen deposition in the liver and adrenal cortical atrophy were found in treated dogs.For more Non-Human Toxicity Excerpts (Complete) data for PREDNISOLONE (14 total), please visit the HSDB record page.
Populations at Special RiskGlucocorticoids 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/
Wassergefährdungsklasse (WGK)WGK 2
TSCA-Inventar-StatusTSCA listed
RTECS-Nr.TU4152000
ToxizitätLD50 oral in mouse: 1680mg/kg
Lagerklasse3 - Flammable liquids
Gefahrstoffdaten50-24-8(Hazardous Substances Data)
GefahrenklasseAcute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2