(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

• ChemBase ID: 621
• Molecular Formular: C21H30O5
• Molecular Mass: 362.4599
• Monoisotopic Mass: 362.20932406
• SMILES: O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)CC3)C)[C@@H](O)C2)CC1)C)C(=O)CO
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1
• InChIKey: JYGXADMDTFJGBT-VWUMJDOOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one; (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: hydrocortisone; (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Brand Name: Acticort; Aeroseb HC; Aeroseb-HC; Ala-Scalp; Ala-cort; Alacort; Algicirtis; Alphaderm; Amberin; Anflam; Anusol HC; Aquacort; Aquanil HC; Balneol-hc; Barseb HC; Basan-Corti; Beta-hc; CaldeCORT Spray; Cetacort; Clear aid; Cleiton; Cobadex; Colocort; Cortaid; Compound F; Cort-Dome; Cort-Quin; Cortanal; Cortef; Cortef Acetate; Cortenema; Cortesal; Corticreme; Cortifan; Cortifoam; Cortiment; Cortisol; Cortisol alcohol; Cortisolonum; Cortisporin; Cortisporin Otico; Cortispray; Cortolotion; Cortonema; Cortoxide; Cortril; Cremesone; Cremicort-H; Cutisol; Delacort; Derm-Aid; Dermacort; Dermaspray; Dermil; Dermocortal; Dermolate; Dioderm; Dome-cort; Domolene-HC; Dricort; Drotic; EF corlin; Efcorbin; Efcortelan; Efcortelin; Eldecort; Eldercort; Epicort; Epiderm H; Esiderm H; Evacort; Ficortril; Fiocortril; Flexicort; Foille Insetti; Genacort; Glycort; Gyno-Cortisone; H-Cort; Heb Cort; Heb-Cort; Hemsol-HC; Hi-cor; Hidalone; Hidro-Colisona; Hycort; Hycortol; Hycortole; Hydracort; Hydrasson; Hydro-adreson; Hydro-colisona; Hydrocort; Hydrocortal; Hydrocortistab; Hydrocortisyl; Hydrocortone; Hydroskin; Hysone; Hytisone; Hytone; Hytone lotion; Incortin-H; Incortin-hydrogen; Kendall's compound F; Komed HC; Kyypakkaus; Lacticare HC; Lacticare-HC; Lactisona; Locoid; Locoid Lipocream; Lubricort; Maintasone; Medicort; Meusicort; Micort-hc; Mildison; Milliderm; Neosporin-H Ear; Nogenic HC; Nutracort; Nystaform-HC; Optef; Orabase HCA; Otalgine; Otobiotic; Otocort; Otosone-F; Pandel; Pediotic Suspension; Penecort; Permicort; Polcort H; Preparation H Hydrocortisone Cream; Prepcort; Prevex HC; Proctocort; Proctofoam; Protocort; Racet; Rectoid; Reichstein's Substance M; Remederm HC; Sanatison; Scalpicin Capilar; Schericur; Scheroson F; Sigmacort; Signef; Stie-cort; Stiefcorcil; Synacort; Systral Hydrocort; THE; Tarcortin; Tetrahydro E; Tetrahydrocompound E; Texacort; Texacort lotion 25; Thyrotropic-releasing factor; Timocort; Transderma H; Traumaide; Uniderm; Urocortisone; Vioform-Hydrocortisone; VoSol HC; Vytone; Westcort; Zenoxone
• Synonyms: 11beta-Hydroxycortisone; 17alpha-Hydroxycorticosterone; Anti-inflammatory hormone; Dihydrocostisone; Hidrocortisona [INN-Spanish]; Hydrocorticosterone; Hydrocortisone Acetate; Hydrocortisone alcohol; Hydrocortisone Base; Hydrocortisone Butyrate; Hydrocortisone free alcohol; Hydrocortisone Sodium Phosphate; Hydrocortisone Valerate; Hydrocortisonum [INN-Latin]; Hydroxycortisone; Idrocortisone [DCIT]; Hydrocortisone; Δ^4-Pregnen-11β,17α,21-triol-3,20-dione; 17-Hydroxycorticosterone; Kendall's compound F; Reichstein's substance M; Cortisol; CORTISONE (ALCOHOL); (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one; Cortisol; Hydrocortisone(Cortisol); (11alpha,14beta)-11,17,21-trihydroxypregn-4-ene-3,20-dione; 11β,17α,21-Trihydroxypregn-4-ene-3,20-dione; 4-Pregnene-11β,17α,21-triol-3,20-dione; Kendall’s compound F; Reichstein’s substance M; HYDROCORTISONE γ-IRRADIATED; (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one; Hydrocortisone-Water Soluble; Cyclodextrin-encapsulated hydrocortisone; Hydrocortisone solution; Hydrocortisone; Cortisol;11beta,17alpha,21-Trihydroxyprogesterone; Reichstein's Substance M;Cortef; Cortenema; Efcortelan;Ficortril; Hydrocortone; Hydrocortal; Hytone; (11β)-11,17,21-Trihydroxy-pregn-4-ene-3,20-dione; 11β,17,21-Trihydroxypregn-4-ene-3,20-dione; 17α-Hydroxycorticosterone; NSC 10483; 氢化可的松 溶液; 11β,17α,21-三羟基孕甾-4-烯-3,20-二酮; 17-羟基皮质甾酮; 4-孕烯-11β,17α,21-三醇-3,20-二酮; 氢化泼尼松龙; 氢化皮质酮; 皮质醇; 氢化可的松

Database IDs

• CAS Number: 50-23-7
• EC Number: 200-020-1
• MDL Number: MFCD00011654
• Beilstein Number: 1354819
• PubChem SID: 24895778; 46505089; 24895394; 24278466; 24895560; 160964084; 24895415; 99444357; 24895401
• PubChem CID: 5754
• CHEBI ID: 17650
• ATC CODE: C05AA01; S02BA01; D07AA02; S01CB03; H02AB09; A07EA02; S01BA02; A01AC03
• CHEMBL: 389621
• Chemspider ID: 5551
• DrugBank ID: DB07886
• KEGG ID: D00088
• Unique Ingredient Identifier: WI4X0X7BPJ
• Wikipedia Title: Cortisol
• Medline Plus: a682206

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.584727
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.2751664
• LogD (pH = 7.4): 1.2751637
• Log P: 1.2751664
• Molar Refractivity: 97.4 cm^3
• Polarizability: 38.28427 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.79
• LOG S: -3.26
• Solubility (Water): 1.99e-01 g/l

PROPERTIES

Physical Property

• Solubility: 320 mg/L; DMSO; H2O: soluble400 mg/mL; Methanol
• Apperance: powder; White Solid
• Melting Point: 211-214 °C(lit.); 211-215°C; 212-224 °C; 217-220 °C
• Optical Rotation: [α]20/D +166±5°, c = 1% in ethanol; [α]25/D +166°, c = 1 in ethanol
• Hydrophobicity(logP): 1.61 [HANSCH,C ET AL. (1995)]; 1.887

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C), Protect from light
• RTECS: GM8925000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Pharmacology Properties

• Admin Routes: Oral tablets, intravenous, topical
• Legal Status: Rx-only (U.S.) (excluding 1–2% strength topical)
• Pregnancy Category: C
• US Licence: Hydrocortisone
• Gene Information: human ... ABCB1(5243), CYP3A4(1576), SERPINA6(866)mouse ... Abcb1a(18671), Abcb1b(18669), Ifng(15978), Nos2(18126)rat ... Ar(24208), Nr3c1(24413)
• Mechanism of Action: ACTH secretion inhibitor; Calcium mobilizer; Glucocorticoid; Gluconeogenesis promoter; Glycogen deposition inhibitor; Phosphorus mobilizer

Product Information

• Purity: ≥97.0% (HPLC); ≥98%; ≥98% (HPLC); 95%; 98%
• Concentration: 50 μM
• Grade: purum; Sigma Reference Standard; VETRANAL™, analytical standard
• Salt Data: Free Base
• Potency: 0.004-0.005 μg/mL; 0.004-5 μg/mL
• Packaging: vial of 250 mg
• Suitability: meets USP testing specifications; suitable for cell culture
• Impurities: endotoxin, tested
• Biological Source: Adrenal cortical hormone
• Sterility: sterile-filtered; γ-irradiated
• Application(s): Antiallergic; Immunosuppressive; Topical antiinflammatory agent
• Quality Level: GMP; PREMIUM
• Pharmacopeia Traceability: traceable to BP 576; traceable to PhEur H1300000; traceable to USP 1316004
• Empirical Formula (Hill Notation): C21H30O5

DETAILS

MP Biomedicals - 02194569

Cell Culture Reagent
Sulfuric acid solutions fluoresce green

MP Biomedicals - 05221729

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02101996

Sulfuric acid solutions fluoresce green

MP Biomedicals - 05209906

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02194568

Cell Culture Reagent
γ-Irradiated
Sulfuric acid solutions fluoresce green.

DrugBank - DB00741

• Drug Groups: approved
• Description: The main glucocorticoid secreted by the adrenal cortex. Its synthetic counterpart is used, either as an injection or topically, in the treatment of inflammation, allergy, collagen diseases, asthma, adrenocortical deficiency, shock, and some neoplastic conditions. [PubChem]
• Indication: For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also used to treat endocrine (hormonal) disorders (adrenal insufficiency, Addisons disease). It is also used to treat many immune and allergic disorders, such as arthritis, lupus, severe psoriasis, severe asthma, ulcerative colitis, and Crohn's disease.
• Pharmacology: Hydrocortisone is the most important human glucocorticoid. It is essential for life and regulates or supports a variety of important cardiovascular, metabolic, immunologic and homeostatic functions. Topical hydrocortisone is used for its anti-inflammatory or immunosuppressive properties to treat inflammation due to corticosteroid-responsive dermatoses. Glucocorticoids are a class of steroid hormones characterised by an ability to bind with the cortisol receptor and trigger a variety of important cardiovascular, metabolic, immunologic and homeostatic effects. Glucocorticoids are distinguished from mineralocorticoids and sex steroids by having different receptors, target cells, and effects. Technically, the term corticosteroid refers to both glucocorticoids and mineralocorticoids, but is often used as a synonym for glucocorticoid. Glucocorticoids suppress cell-mediated immunity. They act by inhibiting genes that code for the cytokines IL-1, IL-2, IL-3, IL-4, IL-5, IL-6, IL-8 and TNF-alpha, the most important of which is the IL-2. Reduced cytokine production limits T cell proliferation. Glucocorticoids also suppress humoral immunity, causing B cells to express lower amounts of IL-2 and IL-2 receptors. This diminishes both B cell clonal expansion and antibody synthesis. The diminished amounts of IL-2 also leads to fewer T lymphocyte cells being activated.
• Toxicity: Side effects include inhibition of bone formation, suppression of calcium absorption and delayed wound healing
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic via CYP3A4
• Absorption: Topical corticosteroids can be absorbed from normal intact skin. Inflammation and/or other disease processes in the skin increase percutaneous absorption.
• Half Life: 6-8 hours
• Protein Binding: 95%
• Elimination: Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.
• References: de Weerth C, Zijl RH, Buitelaar JK: Development of cortisol circadian rhythm in infancy. Early Hum Dev. 2003 Aug;73(1-2):39-52. [Pubmed] ; Palacios R, Sugawara I: Hydrocortisone abrogates proliferation of T cells in autologous mixed lymphocyte reaction by rendering the interleukin-2 Producer T cells unresponsive to interleukin-1 and unable to synthesize the T-cell growth factor. Scand J Immunol. 1982 Jan;15(1):25-31. [Pubmed] ; KNIGHT RP Jr, KORNFELD DS, GLASER GH, BONDY PK: Effects of intravenous hydrocortisone on electrolytes of serum and urine in man. J Clin Endocrinol Metab. 1955 Feb;15(2):176-81. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

DrugBank - DB07886

Drug information: experimental

Selleck Chemicals - S1696

Research Area: Infection
Biological Activity:
Hydrocortisone is a steroid hormone or glucocorticoid produced by the adrenal gland.It is released in response to stress, and to a low level of blood glucocorticoids. Its primary functions are to increase blood sugar through gluconeogenesis, suppress the immune system, and aid in fat, protein, and carbohydrate metabolism. It also decreases bone formation. Various synthetic forms of cortisol are used to treat a variety of different illnesses. [1]

Sigma Aldrich - H6909

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Hydrocortisone for use in epithelial and endothelial adherent cell culture applications.
Other Notes
Animal-component free
Physical form
frozen in working aliquots, avoid repeated freeze/thaw

Sigma Aldrich - H0135

General description
用于上皮和内皮贴壁细胞培养的氢化可的松。
Reconstitution
要制备 50μg/mL 的储存液，可加入 1mL 无水乙醇，温和搅拌使之溶解，在搅拌下加入 19mL 无菌培养基。
Physical form
室温下为粉末状；分成小份冻存，以避免使用时反复冷冻/解冻
Biochem/physiol Actions
肾上腺皮质分泌的原发性糖皮质激素。消炎效果是皮质酮的三倍，但 Na2+ 保留性能比皮质酮低。

Sigma Aldrich - H3160

Physical form
室温下为粉末状；分成小份冻存，以避免使用时反复冷冻/解冻
Biochem/physiol Actions
肾上腺皮质分泌的原发性糖皮质激素。消炎效果是皮质酮的三倍，但 Na2+ 保留性能比皮质酮低。

Sigma Aldrich - H0888

Reconstitution
To prepare 50 μg/mL stock solution, add 1.0 mL absolute ethanol to 1.0 mg of product, gently swirl to dissolve, add 19 mL sterile medium.
Physical form
powder-RT; stock-frozen in working aliquots, avoid repeated freeze/thaw
Biochem/physiol Actions
肾上腺皮质分泌的原发性糖皮质激素。消炎效果是皮质酮的三倍，但 Na2+ 保留性能比皮质酮低。

Sigma Aldrich - H5885

包装
棕色螺旋盖样品瓶包装
Biochem/physiol Actions
肾上腺皮质分泌的原发性糖皮质激素。消炎效果是皮质酮的三倍，但 Na2+ 保留性能比皮质酮低。

Sigma Aldrich - H0396

General description
Hydrocortisone for use in epithelial and endothelial adherent cell culture applications.
包装
Package size based on hydrocortisone

Sigma Aldrich - H4001

包装
1, 5, 10, 25, 100 g in poly bottle
Biochem/physiol Actions
肾上腺皮质分泌的原发性糖皮质激素。消炎效果是皮质酮的三倍，但 Na2+ 保留性能比皮质酮低。

Sigma Aldrich - 31719

Biochem/physiol Actions
Primary glucocorticoid secreted by the adrenal cortex. It has three times the anti-inflammatory potency of corticosterone but much lower Na2+ retention potency.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 91506

Biochem/physiol Actions
Primary glucocorticoid secreted by the adrenal cortex. It has three times the anti-inflammatory potency of corticosterone but much lower Na2+ retention potency.

Sigma Aldrich - 54090

Biochem/physiol Actions
Primary glucocorticoid secreted by the adrenal cortex. It has three times the anti-inflammatory potency of corticosterone but much lower Na2+ retention potency.

Sigma Aldrich - 286095

Packaging
5 g in glass bottle
Biochem/physiol Actions
Primary glucocorticoid secreted by the adrenal cortex. It has three times the anti-inflammatory potency of corticosterone but much lower Na2+ retention potency.

Toronto Research Chemicals - H714615

Cortisol, or Hydrocortisone, is a steroid hormone, more specifically a glucocorticoid, produced by the zona fasciculata of the adrenal gland. Cortisol is released in response to stress and a low level of blood glucocorticoids. Its primary functions are to

REFERENCES

• de Weerth C, Zijl RH, Buitelaar JK: Development of cortisol circadian rhythm in infancy. Early Hum Dev. 2003 Aug;73(1-2):39-52. Pubmed
• Palacios R, Sugawara I: Hydrocortisone abrogates proliferation of T cells in autologous mixed lymphocyte reaction by rendering the interleukin-2 Producer T cells unresponsive to interleukin-1 and unable to synthesize the T-cell growth factor. Scand J Immunol. 1982 Jan;15(1):25-31. Pubmed
• KNIGHT RP Jr, KORNFELD DS, GLASER GH, BONDY PK: Effects of intravenous hydrocortisone on electrolytes of serum and urine in man. J Clin Endocrinol Metab. 1955 Feb;15(2):176-81. Pubmed
• http://en.wikipedia.org/wiki/Cortisol
• Vigore, L., et al.: Cancer Ther., 6, 699 (2008)
• Puurunen, J., et al.: J. Clin. Endocrinol. Metab., 94, 1973 (2008)
• Lemos, D., et al.: J. Endocrinol., 201, 275 (2008)
• Chen, S., et al.: Am. J. Physiol., 296 (2008)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 584C, (nmr)
• Reichstein, T., Helv. Chim. Acta, 1937, 20, 953, (isol)
• v. Euw, J. et al., Helv. Chim. Acta, 1942, 25, 988, (struct)
• Zaffaroni, A. et al., J.A.C.S., 1951, 73, 1390, (biosynth)
• Shirasaka, M., Chem. Pharm. Bull., 1961, 9, 152, (synth)
• Saucy, G. et al., Helv. Chim. Acta, 1966, 49, 1529; 1967, 50, 1394, (synth, ir, uv, pmr)
• van der Sijde, D. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 721, (synth)
• Smit, A. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 731, (synth, struct, pmr)
• Bhacca, N.S. et al., J.A.C.S., 1973, 95, 8421, (cmr)
• Haskins, N.J. et al., Biomed. Mass Spectrom., 1974, 1, 423, (ms)
• Fiegel, G., Arzneim.-Forsch., 1975, 25, 560, (use)
• Genard, P., Org. Mass Spectrom., 1979, 12, 396, (pmr)
• Castellano, E.E. et al., Acta Cryst. B, 1980, 36, 3063, (cryst. struct)
• Florey, K., Anal. Profiles Drug Subst., 1983, 12, 277, (rev, synth, pharmacol, anal)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6346; 6986; 7335
• Minagawa, K. et al., J.C.S. Perkin 1, 1988, 587, (synth)
• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 734
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BAV275; HHR000; CNS750; HHQ800; HHQ825; HHQ850; HHQ875