CAS 50-03-3|β-hc|HYDROCORTISONE ACETATE|2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadec-6-en-14-yl]-2-oxoethyl acetate|2-((8S,9S,10R,11S,13S,...

General Information

Structure

Molecular Formula

C₂₃H₃₂O₆

Molecular Mass

404.49658

Exact Mass

404.21988874

Charge

InChI

InChI=1S/C23H32O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h10,16-18,20,26,28H,4-9,11-12H2,1-3H3/t16-,17-,18-,20+,21-,22-,23-/m0/s1

InChIKey

ALEXXDVDDISNDU-JZYPGELDSA-N

Canonic Smiles

CC(=O)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

Isomeric Smiles

O=C(OCC(=O)[C@@]1(O)CC[C@H]2[C@H]3[C@H]([C@@H](O)C[C@]12C)[C@@]1(C(=CC(=O)CC1)CC3)C)C

Calculated Properties

JChem

LogD (pH = 7.4)

1.72

LogD (pH = 5.5)

1.72

Log P

1.72

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

12.61

Polar Surface Area

100.90

Polarizability

43.71

Molar Refractivity

106.55

LOG S

-3.28

Data Source

Names and Identifiers

IUPAC Traditional name

β-hc 2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2-oxoethyl acetate hydrocortisone acetate

Synonyms

HYDROCORTISONE ACETATE2-((8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate4-孕烯-11β,17α,21-三醇-3,20-二酮 21-乙酸酯17-α-羟基皮质甾酮乙酸酯17-羟基皮质甾酮 21-乙酸酯21-乙酰氧基-4-孕烯-11β,17α-二醇-3,20-二酮Hydrocortisone 21-acetate醋酸氢化可的松氢化可的松乙酸盐醋酸氢化可的松11β,17α,21-三羟基-4-孕烯-3,20-二酮 21-乙酸酯Hydrocortisone acetate salt4-Pregnene-11β,17α,21-triol-3,20-dione 21-acetate17-α-Hydroxycorticosterone acetate21-Acetoxy-4-pregnene-11β,17α-diol-3,20-dione氢化可的松乙酸酯PabracortBambicortHydrocortisone acetateColifoam11β,17α,21-Trihydroxy-4-pregnene-3,20-dione 21-acetate17-Hydroxycorticosterone 21-acetateCortisol AcetateWycortVelopural21-Acetoxy-11β,17-dihydroxypregn-4-ene-3,20-dioneSigmacortHydrocortisoni acetasAbbocortLanacortNSC 741Hydrocortisone 21-AcetateHydrocortisone acetatecortisol 21-acetateCortisol 21-acetatehydrocortisone 21-acetateCortellcortisol acetatecortisol 21-acetate21-O-acetylcortisol

IUPAC name

2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadec-6-en-14-yl]-2-oxoethyl acetate 2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2-oxoethyl acetate 2-[(1R,3aS,3bS,9aR,9bS,10S,11aS)-1,10-dihydroxy-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]-2-oxoethyl acetate

Names and Identifiers

Registration numbers

EC Number

200-004-4

CAS Number

50-03-3

MDL Number

MFCD00037714

PubChem SID

248955472489562016209551824870046248785088144591

Beilstein Number

2066841

PubChem CID

5744

Patent number

EP1757314US2003166601EP0970694

DrugBank ID

BRENDA Database

KEGG DRUG Database

LIPID MAPS Instance

IntEnz Database

MetaboLights Database

MTBLS2825MTBLS2096MTBLS1861MTBLS1918MTBLS4967MTBLS4463

CHEBI ID

CHEBI:14024CHEBI:17609CHEBI:3894CHEBI:58204CHEBI:23394

ACToR Database

BindingDB Database

Rhea Database

CHEMBL

KEGG ID

Drug Central Database

4,213

SureChEMBL Database

SCHEMBL7419

Registration numbers

Properties

Physical Property

Melting Point

223 °C (dec.)(lit.)

216-218°C

Optical Rotation

[α]20/D +165±2°, c = 1% in dioxane

Apperance

White to Off-White Solid

Solubility

DMSO

Dioxane

Pharmacology Properties

Gene Information

human ... SERPINA6(866)

Mechanism of Action

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Sigma Aldrich

H5760

包装
Supplied in amber screw-cap vials

H3035

Application
Hydrocortisone acetate salt is used as a stabilized form of the glucocorticoid in studies on stress and homeostasis.

46329

Biochem/physiol Actions
Hydrocortisone 21-acetate was shown to elevate the number of circulating leukocytes in a rat model of hypertension following adrenalectomy by reducing leukocyte-endothelial cell adhesion. 1
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

54102

Application
Hydrocortisone 21-acetate is used as a stabilized form of the glucocorticoid in studies on stress and homeostasis.

MP Biomedicals

05208521

MP Biomedicals Rare Chemical collection

TRC

H714620

Glucocorticoid.

Molecule Details

References

PubChem Literature

From Data Sources

• Moore, A., et al.: Ann. Clin. Biochem., 22, 435 (1985).

• Middleton, B., et al.: J. Biol. Chem., 256, 4827 (1981)

• Heller, E., Z. Naturforsch., B, 1959, 14, 298, (ir)

• Saucy, G. et al., Helv. Chim. Acta, 1966, 49, 1529; 1967, 50, 1394, (synth, ir, uv, pmr)

• Haskins, N.J. et al., Biomed. Mass Spectrom., 1974, 1, 423, (ms)

• van der Sijde, D. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 721, (synth)

• Bhacca, N.S. et al., J.A.C.S., 1973, 95, 8421, (cmr)

• Fiegel, G., Arzneim.-Forsch., 1975, 25, 560, (use)

• Florey, K., Anal. Profiles Drug Subst., 1983, 12, 277, (rev, synth, pharmacol, anal)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BAV275; HHR000; CNS750; HHQ800; HHQ825; HHQ850; HHQ875

• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)

• U.K. Pat., 1968, 1 111 320; CA, 70, 2447

• Smit, A. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 731, (synth, struct, pmr)

• Castellano, E.E. et al., Acta Cryst. B, 1980, 36, 3063, (cryst. struct)

• Genard, P., Org. Mass Spectrom., 1979, 12, 396, (pmr)

• Minagawa, K. et al., J.C.S. Perkin 1, 1988, 587, (synth)

• Reichstein, T., Helv. Chim. Acta, 1937, 20, 953, (isol)

• v. Euw, J. et al., Helv. Chim. Acta, 1942, 25, 988, (struct)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 584C, (nmr)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 734

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6346; 6986; 7335

• Zaffaroni, A. et al., J.A.C.S., 1951, 73, 1390, (biosynth)

• Wendler, N.L. et al., J.A.C.S., 1951, 73, 3818, (synth)

• Shirasaka, M., Chem. Pharm. Bull., 1961, 9, 152, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

β-hc 2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2-oxoethyl acetate hydrocortisone acetate

Synonyms

IUPAC name

Registration numbers

EC Number

200-004-4

CAS Number

50-03-3

MDL Number

MFCD00037714

PubChem SID

248955472489562016209551824870046248785088144591

Beilstein Number

2066841

PubChem CID

5744

Patent number

EP1757314US2003166601EP0970694

DrugBank ID

BRENDA Database

KEGG DRUG Database

LIPID MAPS Instance

IntEnz Database

MetaboLights Database

MTBLS2825MTBLS2096MTBLS1861MTBLS1918MTBLS4967MTBLS4463

CHEBI ID

CHEBI:14024CHEBI:17609CHEBI:3894CHEBI:58204CHEBI:23394

ACToR Database

BindingDB Database

Rhea Database

CHEMBL

KEGG ID

Drug Central Database

4,213

SureChEMBL Database

SCHEMBL7419

Molecule Details

Sigma Aldrich

H5760

包装
Supplied in amber screw-cap vials

H3035

Application
Hydrocortisone acetate salt is used as a stabilized form of the glucocorticoid in studies on stress and homeostasis.

46329

54102

Application
Hydrocortisone 21-acetate is used as a stabilized form of the glucocorticoid in studies on stress and homeostasis.

MP Biomedicals

05208521

MP Biomedicals Rare Chemical collection

TRC

H714620

Glucocorticoid.

References

PubChem Literature

From Data Sources

• Moore, A., et al.: Ann. Clin. Biochem., 22, 435 (1985).

• Middleton, B., et al.: J. Biol. Chem., 256, 4827 (1981)

• Heller, E., Z. Naturforsch., B, 1959, 14, 298, (ir)

• Saucy, G. et al., Helv. Chim. Acta, 1966, 49, 1529; 1967, 50, 1394, (synth, ir, uv, pmr)

• Haskins, N.J. et al., Biomed. Mass Spectrom., 1974, 1, 423, (ms)

• van der Sijde, D. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 721, (synth)

• Bhacca, N.S. et al., J.A.C.S., 1973, 95, 8421, (cmr)

• Fiegel, G., Arzneim.-Forsch., 1975, 25, 560, (use)

• Florey, K., Anal. Profiles Drug Subst., 1983, 12, 277, (rev, synth, pharmacol, anal)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BAV275; HHR000; CNS750; HHQ800; HHQ825; HHQ850; HHQ875

• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)

• U.K. Pat., 1968, 1 111 320; CA, 70, 2447

• Smit, A. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 731, (synth, struct, pmr)

• Castellano, E.E. et al., Acta Cryst. B, 1980, 36, 3063, (cryst. struct)

• Genard, P., Org. Mass Spectrom., 1979, 12, 396, (pmr)

• Minagawa, K. et al., J.C.S. Perkin 1, 1988, 587, (synth)

• Reichstein, T., Helv. Chim. Acta, 1937, 20, 953, (isol)

• v. Euw, J. et al., Helv. Chim. Acta, 1942, 25, 988, (struct)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 584C, (nmr)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 734

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6346; 6986; 7335

• Zaffaroni, A. et al., J.A.C.S., 1951, 73, 1390, (biosynth)

• Wendler, N.L. et al., J.A.C.S., 1951, 73, 3818, (synth)

• Shirasaka, M., Chem. Pharm. Bull., 1961, 9, 152, (synth)

Bioactivity

PubChem BioAssay

Properties

Physical Property

Melting Point

223 °C (dec.)(lit.)

216-218°C

Optical Rotation

[α]20/D +165±2°, c = 1% in dioxane

Apperance

White to Off-White Solid

Solubility

DMSO

Dioxane

Pharmacology Properties

Gene Information

human ... SERPINA6(866)

Mechanism of Action

Molecule

ID:108727