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MedKoo Cat#: 598841 | Name: Prednisolone valerate acetate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Prednisolone valerate acetate is a derivative of Prednisolone, which is a synthetic corticosteroid, metabolically interconvertible with prednisone, and an impurity of Hydrocortisone. Prednisolone 21-Acetate Valerate is used in multifunctional nanoemulsion platform for imaging guided therapy evaluated in experimental cancer.

Chemical Structure

Prednisolone valerate acetate
CAS#72064-79-0 (valerate acetate)

Theoretical Analysis

MedKoo Cat#: 598841

Name: Prednisolone valerate acetate

CAS#: 72064-79-0 (valerate acetate)

Chemical Formula: C28H38O7

Exact Mass: 486.2618

Molecular Weight: 486.61

Elemental Analysis: C, 69.11; H, 7.87; O, 23.02

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Related CAS #
52-21-1 (acetate) 72064-79-0 (valerate acetate) 630-67-1 (sodium metazoate) 125-02-0 (Na+ phosphate) 50-24-8 (free)
Synonym
Prednisolone valerate acetate; Lidomex; Acepreval;
IUPAC/Chemical Name
(8S,9S,10R,11S,13S,14S,17R)-17-(2-acetoxyacetyl)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl pentanoate
InChi Key
DGYSDXLCLKPUBR-SLPNHVECSA-N
InChi Code
InChI=1S/C28H38O7/c1-5-6-7-24(33)35-28(23(32)16-34-17(2)29)13-11-21-20-9-8-18-14-19(30)10-12-26(18,3)25(20)22(31)15-27(21,28)4/h10,12,14,20-22,25,31H,5-9,11,13,15-16H2,1-4H3/t20-,21-,22-,25+,26-,27-,28-/m0/s1
SMILES Code
C[C@@]12[C@](C(COC(C)=O)=O)(OC(CCCC)=O)CC[C@@]1([H])[C@]3([H])CCC4=CC(C=C[C@]4(C)[C@@]3([H])[C@@H](O)C2)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Prednisolone valerate acetate is a derivative of Prednisolone, which is a synthetic corticosteroid, metabolically interconvertible with prednisone, and an impurity of Hydrocortisone.
In vitro activity:
This study reports here a study of Prednisolone treatment using as a model a leukemia cell line with subsequent investigation of resistance-related gene expression. This study analyzed effects of increasing doses of Prednisolone on ALL cell survival and growth, and monitored immediate effects on gene expression through gene expression assays. Upon treatment with escalating Prednisolone concentration, this study observed a gradual decline in cell survival. Prednisolone competitively induces MCL1 expression. Reference: Adv Exp Med Biol. 2021;1339:147-160. https://pubmed.ncbi.nlm.nih.gov/35023102/
In vivo activity:
This study evaluated the effect of in vivo administration of prednisolone on Escherichia coli lipopolysaccharide endotoxin (LPS)-induced increases in plasma RNI and neutrophil mRNA for NOS II and production of RNI in the rat. This study shows that LPS rapidly induces mRNA for NOS II and production of RNI (NO2- and NO3- anion) in rat neutrophils within 2 hr after in vivo administration of a sublethal dose of 0.5 mg/kg, i.v. A pharmacologic dose of prednisolone (50 micrograms/kg, im) given 15 min before LPS-attenuated production of NO2- and NO3- by neutrophils and suppressed LPS-stimulated mRNA for NOS II. 3-Amino, 1,2,4-triazine inhibited NO2- and NO3- production without affecting gene expression for NOS II. Reference: Proc Soc Exp Biol Med. 1994 Mar;205(3):220-9. https://pubmed.ncbi.nlm.nih.gov/7513433/
Solvent mg/mL mM comments
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 486.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. G L, Adamaki M, Hatziagapiou K, Geronikolou SA, Tsartsalis AN, Vlahopoulos S. Early and Very Early GRIM19 and MCL1 Expression Are Correlated to Late Acquired Prednisolone Effects in a T-Cell Acute Leukemia Cell Line. Adv Exp Med Biol. 2021;1339:147-160. doi: 10.1007/978-3-030-78787-5_20. PMID: 35023102. 2. Li C, Yang P, Liu B, Bu J, Liu H, Guo J, Hasegawa T, Si H, Li M. Prednisolone induces osteocytes apoptosis by promoting Notum expression and inhibiting PI3K/AKT/GSK3β/β-catenin pathway. J Mol Histol. 2021 Oct;52(5):1081-1095. doi: 10.1007/s10735-021-10006-0. Epub 2021 Jul 23. PMID: 34297260. 3. Rioja I, Bush KA, Buckton JB, Dickson MC, Life PF. Joint cytokine quantification in two rodent arthritis models: kinetics of expression, correlation of mRNA and protein levels and response to prednisolone treatment. Clin Exp Immunol. 2004 Jul;137(1):65-73. doi: 10.1111/j.1365-2249.2004.02499.x. PMID: 15196245; PMCID: PMC1809073. 4. Kolls J, Xie J, LeBlanc R, Malinski T, Nelson S, Summer W, Greenberg SS. Rapid induction of messenger RNA for nitric oxide synthase II in rat neutrophils in vivo by endotoxin and its suppression by prednisolone. Proc Soc Exp Biol Med. 1994 Mar;205(3):220-9. doi: 10.3181/00379727-205-43700. PMID: 7513433.
In vitro protocol:
1. G L, Adamaki M, Hatziagapiou K, Geronikolou SA, Tsartsalis AN, Vlahopoulos S. Early and Very Early GRIM19 and MCL1 Expression Are Correlated to Late Acquired Prednisolone Effects in a T-Cell Acute Leukemia Cell Line. Adv Exp Med Biol. 2021;1339:147-160. doi: 10.1007/978-3-030-78787-5_20. PMID: 35023102. 2. Li C, Yang P, Liu B, Bu J, Liu H, Guo J, Hasegawa T, Si H, Li M. Prednisolone induces osteocytes apoptosis by promoting Notum expression and inhibiting PI3K/AKT/GSK3β/β-catenin pathway. J Mol Histol. 2021 Oct;52(5):1081-1095. doi: 10.1007/s10735-021-10006-0. Epub 2021 Jul 23. PMID: 34297260.
In vivo protocol:
1. Rioja I, Bush KA, Buckton JB, Dickson MC, Life PF. Joint cytokine quantification in two rodent arthritis models: kinetics of expression, correlation of mRNA and protein levels and response to prednisolone treatment. Clin Exp Immunol. 2004 Jul;137(1):65-73. doi: 10.1111/j.1365-2249.2004.02499.x. PMID: 15196245; PMCID: PMC1809073. 2. Kolls J, Xie J, LeBlanc R, Malinski T, Nelson S, Summer W, Greenberg SS. Rapid induction of messenger RNA for nitric oxide synthase II in rat neutrophils in vivo by endotoxin and its suppression by prednisolone. Proc Soc Exp Biol Med. 1994 Mar;205(3):220-9. doi: 10.3181/00379727-205-43700. PMID: 7513433.
1: Tanabe K, Matsuoka-Uchiyama N, Mifune T, Kawakita C, Sugiyama H, Wada J. Management of corticosteroid-dependent eosinophilic interstitial nephritis: A case report. Medicine (Baltimore). 2021 Dec 17;100(50):e28252. doi: 10.1097/MD.0000000000028252. PMID: 34918693; PMCID: PMC8678027. 2: Miyamoto A, Kitaichi Y, Uchikura K. Degradation of corticosteroids during activated sludge processing. Chem Pharm Bull (Tokyo). 2014;62(1):72-6. doi: 10.1248/cpb.c13-00624. PMID: 24390495. 3: Nomiyama T, Takenaka H, Kishimoto S, Katoh N. Granuloma annulare-like reaction to the bacillus Calmette-Guerin vaccination. Australas J Dermatol. 2013 Feb;54(1):e4-7. doi: 10.1111/j.1440-0960.2011.00814.x. Epub 2011 Sep 20. PMID: 23373894. 4: Gianella A, Jarzyna PA, Mani V, Ramachandran S, Calcagno C, Tang J, Kann B, Dijk WJ, Thijssen VL, Griffioen AW, Storm G, Fayad ZA, Mulder WJ. Multifunctional nanoemulsion platform for imaging guided therapy evaluated in experimental cancer. ACS Nano. 2011 Jun 28;5(6):4422-33. doi: 10.1021/nn103336a. Epub 2011 May 25. PMID: 21557611; PMCID: PMC3296132. 5: Blaschke T, Kankate L, Kramer KD. Structure and dynamics of drug-carrier systems as studied by parelectric spectroscopy. Adv Drug Deliv Rev. 2007 Jul 10;59(6):403-10. doi: 10.1016/j.addr.2007.04.003. Epub 2007 May 3. PMID: 17573146. 6: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2002 May;24(4):217-48. PMID: 12092009. 7: Ko DH, Heiman AS, Hudson CE, Lee HJ. New steroidal antiinflammatory antedrugs: Methyl 3,20-dioxo-9 alpha-fluoro-11 beta,17 alpha,21-trihydroxy-1,4-pregnadiene-16 alpha-carboxylate and its 21-O-acyl derivatives. Steroids. 2002 Mar;67(3-4):211-9. doi: 10.1016/s0039-128x(01)00154-4. PMID: 11856545. 8: Bircher AJ, Levy F, Langauer S, Lepoittevin JP. Contact allergy to topical corticosteroids and systemic contact dermatitis from prednisolone with tolerance of triamcinolone. Acta Derm Venereol. 1995 Nov;75(6):490-3. doi: 10.2340/0001555575490493. PMID: 8651033. 9: Lubach D, Kietzmann M. Investigation of the skin thinning effect of prednicarbate and other corticoids in mouse skin. Skin Pharmacol. 1988;1(3):200-6. doi: 10.1159/000210774. PMID: 3272751. 10: Mizushima Y, Igarashi R, Hoshi K, Muramatsu M, Fujita A. Increase in incorporation into lymphocytes in vitro of esterified anti-inflammatory corticosteroids. Agents Actions. 1986 Oct;19(1-2):123-6. doi: 10.1007/BF01977267. PMID: 3799370. 11: Kimura M, Tarumoto Y, Nakane S, Otomo S. Comparative toxicity study of hydrocortisone 17-butyrate 21-propionate (HBP) ointment and other topical corticosteroids in rats. Drugs Exp Clin Res. 1986;12(8):643-52. PMID: 3757761. 12: Singh PK, Singh G. Relative Potency of Topical Corticosteroid Preparations. Indian J Dermatol Venereol Leprol. 1985 Nov-Dec;51(6):309-312. PMID: 28164900. 13: Luzzani F, Gallico L, Glässer A. In vitro and ex vivo binding to uterine progestin receptors of the rat as a tool to assay progestational activity of glucocorticoids. Methods Find Exp Clin Pharmacol. 1982;4(4):237-42. PMID: 7121132. 14: Nakano M, Takeuchi M, Sugeno K. Effects of dexamethasone 17-esters on adrenal weight and hydrolysis of glucocorticoid 17-esters in rat fetuses. J Pharmacobiodyn. 1981 Mar;4(3):211-6. doi: 10.1248/bpb1978.4.211. PMID: 7252770. 15: Kobayashi F, Hattori Y, Koshi T, Nagoya T. [Effect of prednisolone 17-valerate 21-acetate on immunological responses in mice (author's transl)]. Nihon Yakurigaku Zasshi. 1980 Sep;76(5):363-72. Japanese. PMID: 7203277. 16: Wada Y, Etoh Y, Ohira A, Ikuta J, Kato Y, Sano N. [Anti-inflammatory effects of prednisolone 17-valerate 21-acetate, a new topical corticosteroid (author's transl)]. Nihon Yakurigaku Zasshi. 1980 Sep;76(5):333-45. Japanese. PMID: 7203275. 17: Rampini E, Rastelli A, Cardo P. Comparative study of the vasoconstrictor activity of halopredone acetate in a modified McKenzie test. Eur J Clin Pharmacol. 1978 Dec 18;14(5):325-9. doi: 10.1007/BF00611901. PMID: 729625. 18: Vitali C. Assorbimento percutaneo del prednisolone 17-valerianato-21-acetato un nuovo corticosteroide per uso topico [Percutaneous absorption of prednisolone 17-valerate-21-acetate, a new corticosteroid for topical use]. Clin Ter. 1978 Apr 30;85(2):173-7. Italian. PMID: 657747. 19: Garretts M. Controlled double-blind comparative trial with fluprednylidene acetate cream and its base. Arch Dermatol Forsch. 1975;251(3):165-8. PMID: 1091216. 20: Holzmann H, Morsches B, Gebhardt R. Untersuchungen zur Frage der systemischen Wirkung grossflächig applizierter Stereoidexterna [Studies on the systemic effect of extensively applied topical steroids]. Arztl Forsch. 1972 May 10;26(5):171-7. German. PMID: 5068154.

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