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Pregna-1,4-diene-3,20-dione,11,17,21-trihydroxy-6-methyl-, (6a,11b)-(CAS No. 83-43-2)

Pregna-1,4-diene-3,20-dione,11,17,21-trihydroxy-6-methyl-, (6a,11b)- C22H30O5 (cas 83-43-2) Molecular Structure

83-43-2 Structure

Identification and Related Records

【Name】
Pregna-1,4-diene-3,20-dione,11,17,21-trihydroxy-6-methyl-, (6a,11b)-
【CAS Registry number】
83-43-2
【Synonyms】
Pregna-1,4-diene-3,20-dione,11b,17,21-trihydroxy-6a-methyl- (7CI,8CI)
11b,17,21-Trihydroxy-6a-methylpregna-1,4-diene-3,20-dione
6a-Methyl-11b,17a,21b-trihydroxy-1,4-pregnadiene-3,20-dione
6a-Methylprednisolone
Besonia
Duralone
M-Prednisol
Medorol
Medralone
Medrol
Metastab
Methylprednisolone
Metilbetasone
Metrisone
NSC 19987
Prednol
Promacortine
Suprametil
Urbason
Urbasone
Wyacort
Methylphenisolone
【EINECS(EC#)】
201-476-4
【Molecular Formula】
C22H30O5 (Products with the same molecular formula)
【Molecular Weight】
374.48
【Inchi】
InChI=1/C22H30O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1
【InChIKey】
VHRSUDSXCMQTMA-UHFFFAOYSA-N
【Canonical SMILES】
CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O
【Isomers smiles】
C[C@H]1C[C@H]2[C@@H]3CC[C@@]([C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)C=C4)
C)O)C)(C(=O)CO)O
【MOL File】
83-43-2.mol

Chemical and Physical Properties

【Appearance】
white to off-white crystalline powder
【Density】
1.28
【Melting Point】
228-237℃ (dec.)
【Boiling Point】
571.8 °C at 760 mmHg
【Refractive Index】
82 ° (C=1, Dioxane)
【Flash Point】
571.8 °C at 760 mmHg
【Solubilities】
Sparingly sol in alc, dioxane, methanol; slightly sol in acetone, chloroform; very slightly sol in ether.
In water, 1.20X10+2 mg/L at 25 deg C
【Color/Form】
Crystals
White to practically white crystalline powder
【Storage temp】
0-6°C
【Spectral properties】
Specific optical rotation: +83 deg at 20 deg C/D (dioxane); max absorption (95% ethanol): 243 nm (alpha(m)= 14,875)
【Computed Properties】
Molecular Weight:374.4706 [g/mol]
Molecular Formula:C22H30O5
XLogP3:1.9
H-Bond Donor:3
H-Bond Acceptor:5
Rotatable Bond Count:2
Tautomer Count:9
Exact Mass:374.209324
MonoIsotopic Mass:374.209324
Topological Polar Surface Area:94.8
Heavy Atom Count:27
Formal Charge:0
Complexity:754
Isotope Atom Count:0
Defined Atom Stereocenter Count:8
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:3
Feature 3D Ring Count:4
Effective Rotor Count:3.4
Conformer Sampling RMSD:0.8
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xi
【Risk Statements】
R36/37/38
【Safety Statements 】
S22;S36
【Safety】
Moderately toxic by intraperitoneal route. A steroid hormone. Human systemic effects include arrhythmias, blood pressure lowering, heart rate changes, increased body temperature, pulse rate increase, respiratory depression. When heated to decomposition it emits acrid smoke and irritating fumes.
【Formulations/Preparations】
Oral: Tablets: 2 mg Medrol (scored), (Pfizer), 4 mg Medrol (scored), (Pfizer), Medrol Dosepak, (Pfizer), Meprolone Unipak, (Major), Methylprednisolone, (Barr), Methylprednisolone, (Par), Methylprednisolone, (Trigen); 8 mg Medrol (scored), (Pfizer), Methylprednisolone, (Par); 16 mg Medrol (scored), (Pfizer); 32 mg Medrol (scored), (Pfizer).
Parenteral: Injectable suspension: 20 mg/mL Depo-Medrol, (Pfizer); 40 mg/mL Depo-Medrol, (Pfizer), Methylprednisolone Acetate Injection, (Sicor), Methylprednisolone Acetate Injection, (Teva); 80 mg/mL Depo-Medrol, (Pfizer) Methylprednisolone Acetate Injection, (Sicor), Methylprednisolone Acetate Injection, (Teva). /Methylprednisolone acetate/
Parenteral: For injection: 40 mg (of methylprednisolone) A-methaPred ( with benzyl alcohol in Univial), (Hospira), Methylprednisolone Sodium Succinate Injection (with benzyl alcohol), (Abraxis) Solu-Medrol (with benzyl alcohol 8.8 mg in Act-O-Vial), (Pfizer); 125 mg (of methylprednisolone) A-methaPred (with benzyl alcohol in Univial), (Hospira), Methylprednisolone Sodium Succinate Injection (with benzyl alcohol), Abraxis Solu-Medrol (with benzyl alcohol 17.6 mg in Act-O-Vial), (Pfizer); 500 mg (of methylprednisolone) A-methaPred (with benzyl alcohol in Univial), (Hospira), A-methaPred ADD-Vantage, (Hospira) Solu-Medrol (with and without diluent containing benzyl alcohol 70.2 mg), (Pfizer); 1 g (of methylprednisolone) A-methaPred (with benzyl alcohol in Univial), (Hospira), A-methaPred ADD-Vantage, (Hospira), Methylprednisolone Sodium Succinate Injection (with benzyl alcohol), (Abraxis), Solu-Medrol (with benzyl alcohol 141 mg and with benzyl alcohol 66.8 mg in Act-O-Vial), (Pfizer); 2 g (of methylprednisolone) Solu-Medrol (with and without diluent containing benzyl alcohol 273 mg), (Pfizer). /Methylprednisolone sodium succinate/
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methylprednisolone 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 methylprednisolone acetate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Methylprednisolone acetate/
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methylprednisolone sodium succinate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Methylprednisolone sodium succinate/
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Methylprednisolone is included on this list.
Oral dosage form new animal drugs. Methylprednisolone tablets. ... For use in dogs and cats as an anti-inflammatory agent. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian.
Implantation or injectable dosage form new animal drugs. Sterile methylprednisolone acetate suspension. ... Indications for use: Treatment of inflammation and related disorders in dogs, cats, and horses;1 treatment of allergic and dermatologic disorders in dogs and cats; and as supportive therapy to antibacterial treatment of severe infections in dogs and cats. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian. /Methylprednisolone acetate/
A tolerance is established for negligible residues of methylprednisolone in milk at 10 parts per billion.
【Specification】

The Methylprednisolone?with cas registry number of 83-43-2 has?other registry numbers which are 121673-01-6 and 570-35-4. Its EINECS?registry number is 201-476-4. It belongs to the classes of Miscellaneous Biochemicals; Biochemistry; Hydroxyketosteroids; Steroids; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical is also known as Promacortine, Reactenol, Sieropresol, Solomet, Solu-medrol, Summicort; Suprametil.Its systematic name is called (6alpha,11beta)-11,17,21-trihydroxy-6-methylpregna-1,4-diene-3,20-dione. And its IUPAC name is also called(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one. It is white to off-white crystalline powder.

Physical properties about this chemical are:?(1)ACD/LogP: 1.99; (2) # of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.99; (4)ACD/LogD (pH 7.4): 1.99; (5)ACD/BCF (pH 5.5): 19.06; (6)ACD/BCF (pH 7.4): 19.06; (7)ACD/KOC (pH 5.5): 287.01; (8)ACD/KOC (pH 7.4): 287.01; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 61.83??2; (13)Index of Refraction: 1.602; (14)Molar Refractivity: 100.08 cm3; (15)Molar Volume: 291.4 cm3; (16)Surface Tension: 58.1 dyne/cm; (17)Density: 1.28 g/cm3; (18)Flash Point: 313.7 °C; (19)Enthalpy of Vaporization: 98.47 kJ/mol; (20)Boiling Point: 571.8 °C at 760 mmHg; (21)Vapour Pressure: 1.86E-15 mmHg at 25°C; (22)Refractive index: 82 ° (C=1, Dioxane); (23)Melting Point: 228-237°C.

Uses of?Methylprednisolone : this chemical can be used as a glucocorticoid. And it is used for rheumatoid arthritis, collagen diseases, allergic disease, ophthalmic disease, lymphatic leukemia, soft tissue inflammation and hemolytic anemia.

When you are using this chemical, please be cautious about it as the following:
Moderately toxic by intraperitoneal route. A steroid hormone. Human systemic effects include arrhythmias, blood pressure lowering, heart rate changes, increased body temperature, pulse rate increase, respiratory depression. When heated to decomposition it emits acrid smoke and irritating fumes.?Wear suitable protective clothing, gloves and eye/face protection when you are using it. Do not breathe dust.?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?Store it at?temperature of 0-6°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C\1\C=C/[C@]4(/C(=C/1)[C@@H](C)C[C@@H]2[C@@H]4[C@@H](O)C[C@@]3([C@@](O)(C(=O)CO)CC[C@@H]23)C)C;
(2)InChI: InChI=1/C22H30O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1;
(3)InChIKey: VHRSUDSXCMQTMA-PJHHCJLFBP

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 2292mg/kg (2292mg/kg) ? Drugs in Japan Vol. 6, Pg. 832, 1982.
rat LD50 oral > 4gm/kg (4000mg/kg) ? Drugs in Japan Vol. 6, Pg. 832, 1982.
women TDLo intravenous 20mg/kg/45M-C (20mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Journal of Rheumatology. Vol. 13, Pg. 477, 1986.
women TDLo intravenous 60mg/kg/3D-I (60mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Annals of Internal Medicine. Vol. 99, Pg. 282, 1983.
women TDLo parenteral 2400ug/kg (2.4mg/kg) CARDIAC: CHANGE IN RATE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
British Journal of Anesthesia. Vol. 69, Pg. 422, 1992.

【Octanol/Water Partition Coefficient】
log Kow = 1.82 (est)
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation: Sebek, Spero, US 2897218 (1959 to Upjohn); Gould, US 3053832 (1962 to Schering)
Cortisone is first converted to the 6-keto derivative via suitable intermediates. Subsequent Grignard reaction with methylmagnesium bromide and further reaction steps then yield 6a-methylprednisolone.
【Usage】

A glucocorticoid

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that reduce or suppress INFLAMMATION.
- Drugs used to prevent NAUSEA or VOMITING.
- 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.
- Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
【Therapeutic Uses】
Anti-Inflammatory Agents, Steroidal; Antiemetics; Glucocorticoids, Synthetic; Glucocorticoids, Topical; Neuroprotective Agents
MEDICATION (VET): Treatment with methylprednisolone may be helpful if instituted within the first few hours of /spinal cord/ injury.
MEDICATION (VET): Glucocorticoids are usually contraindicated in animals with meningitis or meningoencephalitis with an infectious etiology; however, a high-dose, short-term course of ... methylprednisolone may control life-threatening complications such as acute cerebral edema and impending brain herniation.
MEDICATION (VET): In cats with mild to moderate inflammatory bowel disease (IBD) or relapse of clinical signs, and in those in which administration of oral medication is difficult, methylprednisolone ... may be effective as the sole treatment or as an adjunct to prednisone and metronidazole.
Methylprednisolone and its derivatives are used principally as anti-inflammatory or immunosuppressant agents. Because methylprednisolone has only minimal mineralocorticoid properties, the drug is inadequate alone for the management of adrenocortical insufficiency. If methylprednisolone is used in the treatment of this condition, concomitant therapy with a mineralocorticoid is also required.
In adults and adolescents older than 13 years of age with acquired immunodeficiency syndrome (AIDS) who require parenteral glucocorticoid therapy as an adjunct to anti-infective treatment of moderate to severe Pneumocystis carinii pneumonia, an iv methylprednisolone regimen ... currently is recommended. Such adjunctive glucocorticoid therapy preferably should be initiated within 24-72 hr of initial antipneumocystis therapy. However, it should be recognized that this recommendation is based on limited data and may not represent the optimum dosage and schedule. Therefore, clinicians should consult published protocols and the most current clinical guidelines. Shorter courses of glucocorticoid therapy would be desirable, but rebound deterioration in pulmonary function has occurred in some patients following discontinuance of glucocorticoid therapy, and some clinicians discourage the use of shorter treatment courses.
In life-threatening shock, massive iv doses of methylprednisolone as the sodium succinate ... have been recommended. ... High dose therapy should be continued only until the patient's condition has stabilized and usually should not be continued beyond 48-72 hr. /Methylprednisolone sodium succinate/
When used to treat motor and/or sensory deficits and potentially minimize disability in patients with acute spinal cord injury, an initial dose ... given by rapid iv injection over 15 minutes, followed in 45 min by iv infusion ... for 23 hr (total dose administered over 24 hr), has been recommended. Other glucocorticoids and other methylprednisolone dosage regimens have not been shown to be effective in humans to date, and glucocorticoid therapy should be initiated as early as possible after spinal cord injury since appreciable benefit has been observed only when methylprednisolone therapy was initiated within 8 hr of injury. /Methylprednisolone sodium succinate/
In the successful management of severe lupus nephritis, methylprednisolone as the sodium succinate has been administered by so-called "pulse" therapy. ... "Pulse" therapy with methylprednisolone sodium succinate has been followed by long-term oral prednisone or prednisolone therapy ... /Methylprednisolone sodium succinate/
Fifty six cases of De Quervain's tenosynovitis (in 55 patients) were treated with a long acting corticosteroid, methylprednisolone acetate, and followed prospectively over a 4 yr period. Approximately 90% of these patients were effectively managed either with a single injection (58%) or with multiple injections (33%) of this compound. Seventeen patients experienced recurrence a mean of 11.9 months after the initial injection. Three had minor flares and were not reinjected; the others responded to reinjections. Ten percent of the cases could not be controlled with local injection, and these patients were referred for surgery. Adverse reactions were self-limited and relatively minor; no tendon ruptures or local infections occurred. A discussion of review of the literature regarding medical therapy and surgical release for this condition is presented. Treatment of De Quervain's tenosynovitis with methylprednisolone acetate injection rapidly controls the signs and symptoms, does not lead to serious adverse reactions, and should be the preferred initial treatment. /Methylprednisolone acetate/ [Anderson BC et al; Arthritis Rheum 34 (7): 793-8 (1991)]
【Biomedical Effects and Toxicity】
ORAL ABSORPTION IN SINGLE-DOSE STUDY OF 12 NORMAL MALE VOLUNTEERS. MEAN BIOAVAIL AFTER ORAL ADMIN 89.9%, INDICATING BETTER SYSTEMIC AVAIL OF ESTER THAN ALC. AVG ELIMINATION RATE CONSTANT AFTER ORAL ADMIN OF ESTER & ALC 0.290 H-1, HALF-LIFE OF 2.39 HR. [GARG DC ET AL; CLIN PHARMACOL THER 26 (2): 232-9 (1979)] PubMed Abstract
The pharmacokinetics of methylprednisolone (MP) were studied in five normal subjects following intravenous doses of 20, 40 and 80 mg methylprednisolone sodium succinate (MPSS) and an oral dose of 20 mg methylprednisolone as 4 x 5 mg tablets. Plasma concentrations of MP and MPSS were measured by both high performance thin layer (h.p.t.l.c.) and high pressure liquid chromatography (h.p.l.c.). 2. The mean values (+/- s.d.) of half-life, mean residence time (MRT), systemic clearance (CL) and volume of distribution at steady state (Vss) of MP following intravenous administration were 1.93 +/- 0.35 h, 3.50 +/- 1.01 h, 0.45 +/- 0.12 lh-1 kg-1 and 1.5 +/- 0.63 1 kg-1, respectively. There was no evidence of dose-related changes in these values. The plasma MP concentration-time curves were superimposable when normalized for dose. 3. The bioavailability of methylprednisolone from the 20 mg tablet was 0.82 +/- 0.11 (s.d.). 4. In vivo hydrolysis of MPSS was rapid with a half-life of 4.14 +/- 1.62 (s.d.) min, and was independent of dose. In contrast, in vitro hydrolysis in plasma, whole blood and red blood cells was slow; the process continuing for more than 7 days. Sodium fluoride did not prevent the hydrolysis of MPSS. [Al-Habet SM, Rogers HJ; Br J Clin Pharmacol 27 (3): 285-90 (1989)] PubMed Abstract
High-dose methylprednisolone is used to treat acute spinal cord injury (ASCI). The objective of the present study was to determine the pharmacokinetics of the pro-drug methylprednisolone hemisuccinate and methylprednisolone in accident victims with ASCI. The patients (n = 26) were treated with a bolus intravenous loading dose of 30 mg/kg MPHS within 2 hr after injury and this was followed by a maintenance infusion of 5.4 mg/kg/h up to 24 hr. Blood, CSF and saliva samples were collected up to 48 hr after the initial dose and the samples were analyzed by HPLC. Concentration-time data of MPHS and methylprednisolone were analyzed using population pharmacokinetic analysis with NONMEM software. RESULTS: Methylprednisolone hemisuccinate and methylprednisolone could be monitored in plasma and CSF. Methylprednisolone but not methylprednisolone hemisuccinate was present in saliva. High variability was seen in the methylprednisolone hemisuccinate levels in CSF. The pharmacokinetics of the pro-drug and the metabolite were adequately described by a 2-compartment model with exponential distribution models assigned to the interindividual and the residual variability. At steady state, the average measured methylprednisolone concentration in plasma was 12.3+/-7.0 microg/ml and 1.74+/-0.85 microg/ml in CSF. The CSF levels of methylprednisolone could be modeled as a part of the peripheral compartment. This study demonstrated that CSF concentrations of methylprednisolone were sufficiently high after IV. administration and reflected the concentrations of unbound drug in plasma. Salivary levels of methylprednisolone were about 32% of the plasma level and may serve as an easily accessible body fluid for drug level monitoring. [Barth J et al; Int J Clin Pharmacol Ther 42 (9): 504-11 (2004)] PubMed Abstract
Sodium fluoride (6--8 mg/ml) inhibits hydrolysis of methylprednisolone acetate to methylprednisolone. An HPLC method for simultaneous determination of hydrocortisone, methylprednisolone and methylprednisolone acetate in plasma is presented. Analysis of plasma samples (containing NaF) for methylprednisolone acetate shows no significant change in concentration over extended periods of storage at -20 degrees C. In vitro hydrolysis of methylprednisolone acetate at 37 degrees C in human whole blood is rapid (average t1/2 = 19 min). In one cat, the bioavailabilities of methylprednisolone acetate rectally was 13% and of methylprednisolone (alcohol) rectally was 26%, relative to intravenous administration of methylprednisolone. In the same cat, the bioavailabilities of methylprednisolone acetate orally was 93% and of methylprednisolone was 82%, relative to intravenous administration of methylprednisolone. All samples collected after oral administration of methylprednisolone acetate to a human subject were found to contain only methylprednisolone (alcohol) indicating hydrolysis of the drug during absorption through the gastrointestinal membrane and/or in the liver. If the ester had the same half-life in blood in vivo as measured in vitro, it would have been measurable in plasma. [Garg DC et al; Res Commun Chem Pathol Pharmacol 22 (1): 37-48 (1978)] PubMed Abstract
Rectal absorption of methylprednisolone acetate and oral absorption of methylprednisolone and methylprednisolone acetate were investigated in a single-dose 3-way crossover study of 12 normal male volunteers. The median value of bioavailability (relative to oral dose) of methylprednisolone acetate based on unchanged methylprednisolone plasma levels was 14.2% after rectal administration, suggesting that the drug exerts its therapeutic effect topically rather than systemically. In contrast, the median of total radioactivity in urine (as a percentage of rectal dose) was 34.3% (range, 4.52% to 58.8%), suggesting partial bacterial metabolism in the rectum prior to absorption. Mean bioavailability (relative to oral administration of methylprednisolone acetate) of methylprednisolone after oral administration was 89.9%, indicating somewhat better systemic availability of the ester than the alcohol. The average apparent elimination rate constant for methylprednisolone after oral administration of both ester and alcohol was 0.290 hr-1, corresponding to a half-life of 2.39 hr. [Garg DC et al; Clin Pharmacol Ther 26 (2): 232-9 (1979)] PubMed Abstract
Methylprednisolone pharmacokinetics was examined in adrenalectomized (ADX) and normal rats to assess the feasibility of intramuscular (IM) dosing for use in pharmacodynamic studies. Several study phases were pursued. Parallel group studies were performed in normal and adrenalectomized rats given 50 mg/kg methylprednisolone (IV or IM) and blood samples were collected up to 6 hr. Data from studies where normal rats were dosed with 50 mg/kg methylprednisolone i.m. and killed over either 6 or 96 hr were combined to determine muscle site and plasma methylprednisolone concentrations. Lastly, adrenalectomized rats were dosed with 50 mg/kg methylprednisolone IM and killed over 18 hr to assess hepatic tyrosine aminotransferase dynamics. Methylprednisolone exhibited bi-exponential kinetics after IV dosing with a terminal slope of 2.1 hr(-1). The IM drug was absorbed slowly with two first-order absorption rate constants, 1.26 and 0.219 hr(-1) indicating flip-flop kinetics with overall 50% bioavailability. The kinetics of methylprednisolone at the injection site exhibited slow, dual absorption rates. Although IM methylprednisolone showed lower bioavailability compared with other corticosteroids in rats, tyrosine aminotransferase dynamics revealed similar IM and IV response profiles. The more convenient intramuscular dosing can replace the IV route without causing marked differences in pharmacodynamics. [Hazra A et al; Biopharm Drug Dispos 28 (6): 263-73 (2007)] PubMed Abstract
Oral: Rapidly and almost completely absorbed. Parenteral: Intramuscular: Freely soluble esters (sodium phosphate, sodium succinate) - Rapidly absorbed. Poorly soluble derivatives (acetate, acetonide, diacetate, hexacetonide, tebutate) - Slowly but completely absorbed. Local: Freely soluble esters - Less rapidly absorbed than with intramuscular injection. Poorly soluble derivatives - Slowiy but completely absorbed. /Corticosteroids (glucocorticoid effects - systemic)/

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 310(SRC), determined from a water solubility of 1.2X10+2 mg/L(2) and a regression-derived equation(3), indicates that methylprednisolone is expected to have moderate mobility in soil(SRC). Volatilization of methylprednisolone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.6X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Methylprednisolone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.9X10-14 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data for methylprednisolone were not available(SRC, 2007).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 310(SRC), determined from a water solubility of 1.20X10+2 mg/L(2) and a regression-derived equation(3), indicates that methylprednisolone is 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 3.6X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 41(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data for methylprednisolone were not available(SRC, 2007).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methylprednisolone, which has an estimated vapor pressure of 3.9X10-14 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase methylprednisolone may be removed from the air by wet or dry deposition(SRC). Methylprednisolone absorbs UV light at a maximum of 243 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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