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50-23-7 molecular structure
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(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 and InChIs

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

Cite this record

CBID:621 http://www.chembase.cn/molecule-621.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[8.7.0.02,7.011,15]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[8.7.0.02,7.011,15]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
Δ4-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
CAS Number
50-23-7
EC Number
200-020-1
MDL Number
MFCD00011654
Beilstein Number
1354819
PubChem SID
24278466
24895560
160964084
24895778
46505089
24895415
24895401
24895394
99444357
PubChem CID
5754
CHEBI ID
17650
ATC CODE
A07EA02
S02BA01
A01AC03
H02AB09
C05AA01
D07AA02
S01BA02
S01CB03
CHEMBL
389621
Chemspider ID
5551
DrugBank ID
DB07886
KEGG ID
D00088
Unique Ingredient Identifier
WI4X0X7BPJ
Wikipedia Title
Cortisol
Medline Plus
a682206

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.584727  H Acceptors
H Donor LogD (pH = 5.5) 1.2751664 
LogD (pH = 7.4) 1.2751637  Log P 1.2751664 
Molar Refractivity 97.4 cm3 Polarizability 38.28427 Å3
Polar Surface Area 94.83 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.79  LOG S -3.26 
Solubility (Water) 1.99e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
320 mg/L expand Show data source
DMSO expand Show data source
H2O: soluble400 mg/mL expand Show data source
Methanol expand Show data source
Apperance
powder expand Show data source
White Solid expand Show data source
Melting Point
211-214 °C(lit.) expand Show data source
211-215°C expand Show data source
212-224 °C expand Show data source
217-220 °C expand Show data source
Optical Rotation
[α]20/D +166±5°, c = 1% in ethanol expand Show data source
[α]25/D +166°, c = 1 in ethanol expand Show data source
Hydrophobicity(logP)
1.61 [HANSCH,C ET AL. (1995)] expand Show data source
1.887 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C), Protect from light expand Show data source
RTECS
GM8925000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
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Download expand Show data source
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German water hazard class
3 expand Show data source
Risk Statements
63 expand Show data source
Safety Statements
36/37 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H361 expand Show data source
GHS Precautionary statements
P281 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
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 expand Show data source
Storage Temperature
-20°C expand Show data source
Admin Routes
Oral tablets, intravenous, topical expand Show data source
Legal Status
Rx-only (U.S.) (excluding 1–2% strength topical) expand Show data source
Pregnancy Category
C expand Show data source
US Licence
Hydrocortisone expand Show data source
Gene Information
human ... ABCB1(5243), CYP3A4(1576), SERPINA6(866)mouse ... Abcb1a(18671), Abcb1b(18669), Ifng(15978), Nos2(18126)rat ... Ar(24208), Nr3c1(24413) expand Show data source
Mechanism of Action
ACTH secretion inhibitor expand Show data source
Calcium mobilizer expand Show data source
Glucocorticoid expand Show data source
Gluconeogenesis promoter expand Show data source
Glycogen deposition inhibitor expand Show data source
Phosphorus mobilizer expand Show data source
Purity
≥97.0% (HPLC) expand Show data source
≥98% expand Show data source
≥98% (HPLC) expand Show data source
95% expand Show data source
98% expand Show data source
Concentration
50 μM expand Show data source
Grade
purum expand Show data source
Sigma Reference Standard expand Show data source
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Potency
0.004-0.005 μg/mL expand Show data source
0.004-5 μg/mL expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Packaging
vial of 250 mg expand Show data source
Suitability
meets USP testing specifications expand Show data source
suitable for cell culture expand Show data source
Impurities
endotoxin, tested expand Show data source
Biological Source
Adrenal cortical hormone expand Show data source
Sterility
sterile-filtered expand Show data source
γ-irradiated expand Show data source
Application(s)
Antiallergic expand Show data source
Immunosuppressive expand Show data source
Topical antiinflammatory agent expand Show data source
Quality Level
GMP expand Show data source
PREMIUM expand Show data source
Pharmacopeia Traceability
traceable to BP 576 expand Show data source
traceable to PhEur H1300000 expand Show data source
traceable to USP 1316004 expand Show data source
Empirical Formula (Hill Notation)
C21H30O5 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02194569 external link
Cell Culture Reagent
Sulfuric acid solutions fluoresce green
MP Biomedicals - 05221729 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02101996 external link
Sulfuric acid solutions fluoresce green
MP Biomedicals - 05209906 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02194568 external link
Cell Culture Reagent
γ-Irradiated
Sulfuric acid solutions fluoresce green.
DrugBank - DB00741 external link
Item Information
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 external link
Drug information: experimental
Selleck Chemicals - S1696 external link
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 external link
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 external link
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 external link
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 external link
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 external link
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 external link
General description
Hydrocortisone for use in epithelial and endothelial adherent cell culture applications.
包装
Package size based on hydrocortisone
Sigma Aldrich - H4001 external link
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 external link
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 external link
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 external link
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 external link
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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