CAS 2203-97-6|CAS 83784-20-7|solu-cortef|4-{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-oxoethoxy}-4-oxobutanoic acid|HYDROC...

General Information

Structure

Molecular Formula

C₂₅H₃₄O₈

Molecular Mass

462.53266

Exact Mass

462.22536805

Charge

InChI

InChI=1S/C25H34O8/c1-23-9-7-15(26)11-14(23)3-4-16-17-8-10-25(32,24(17,2)12-18(27)22(16)23)19(28)13-33-21(31)6-5-20(29)30/h11,16-18,22,27,32H,3-10,12-13H2,1-2H3,(H,29,30)/t16-,17-,18-,22+,23-,24-,25-/m0/s1

InChIKey

VWQWXZAWFPZJDA-CGVGKPPMSA-N

Canonic Smiles

OC(=O)CCC(=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(O)CCC(=O)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

Calculated Properties

JChem

LogD (pH = 7.4)

-1.78

LogD (pH = 5.5)

-0.30

Log P

1.54

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.66

Polar Surface Area

138.20

Polarizability

48.46

Molar Refractivity

117.44

LOG S

-2.83

Data Source

Names and Identifiers

IUPAC Traditional name

solu-cortef 4-{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-oxoethoxy}-4-oxobutanoic acid hydrocortisone hemisuccinate

IUPAC name

4-{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-oxoethoxy}-4-oxobutanoic acid 4-{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-oxoethoxy}-4-oxobutanoic acid 4-{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-oxoethoxy}-4-oxobutanoic acid

Synonyms

HYDROCORTISONE HEMISUCCINATEHydrocortisone 21-hemisuccinate氢化可的松琥珀酸酯氢化可的松 21-半琥珀酸酯11β,17α,21-Trihydroxy-4-pregnene-3,20-dione 21-hemisuccinateHydrocortisone hemisuccinate4-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-oxoethoxy}-4-oxobutanoic acid11beta,17alpha,21-trihydroxypregn-4-ene-3,20-dione 21-succinateCortisol succinate11beta,17,21-Trihydroxypregn-4-ene-3,20-dione 21-(hydrogensuccinate)hydrocortisone succinateHydrocortisone succinate

Names and Identifiers

Registration numbers

EC Number

218-612-3

CAS Number

2203-97-683784-20-7

MDL Number

MFCD00046256

PubChem SID

2489553916209477193165424

PubChem CID

16623

Drug Central Database

4,456

LIPID MAPS Instance

LMST02030126

MetaboLights Database

MTBLS673MTBLS2096MTBLS3750MTBLS1693MTBLS1918MTBLS379

BindingDB Database

CHEMBL

KEGG DRUG Database

CompTox Database

LINCS Database

ACToR Database

KEGG ID

CHEBI ID

CHEBI:31677CHEBI:199284

SureChEMBL Database

SCHEMBL7664

Registration numbers

Properties

Product Information

Certificate of Analysis

Download link

Grade

analytical standard, for drug analysis

Application(s)

Immunosuppressive

Antiinflammatory

Antiallergic agent

Purity

95%

Pharmacology Properties

Physical Property

2.002

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

H2882

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H2882.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

ChEBI

CHEBI:31677

A derivative of succinic acid in which one of the carboxy groups is esterified by the C-21 hydroxy group of cortisol (hydrocortisone).

Molecule Details

References

PubChem Literature

From Data Sources

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

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

• 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)

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

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

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

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

• U.S. Pat., 1960, 2 936 313; CA, 54, 19783, (phosphate)

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

• Ger. Pat., 1979, 2 826 257; CA, 93, 26657, (butyrate, propionate)

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

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

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

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

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

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

References

Bioactivity

PubChem BioAssay

Bioactivity

Registration numbers

EC Number

218-612-3

CAS Number

2203-97-683784-20-7

MDL Number

MFCD00046256

PubChem SID

2489553916209477193165424

PubChem CID

16623

Drug Central Database

4,456

LIPID MAPS Instance

LMST02030126

MetaboLights Database

MTBLS673MTBLS2096MTBLS3750MTBLS1693MTBLS1918MTBLS379

BindingDB Database

CHEMBL

KEGG DRUG Database

CompTox Database

LINCS Database

ACToR Database

KEGG ID

CHEBI ID

CHEBI:31677CHEBI:199284

SureChEMBL Database

Molecule Details

H2882

A derivative of succinic acid in which one of the carboxy groups is esterified by the C-21 hydroxy group of cortisol (hydrocortisone).

Bioactivity

PubChem BioAssay

Names and Identifiers

IUPAC Traditional name

solu-cortef 4-{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-oxoethoxy}-4-oxobutanoic acid hydrocortisone hemisuccinate

IUPAC name

Synonyms

Properties

Product Information

Certificate of Analysis

Download link

Grade

analytical standard, for drug analysis

Application(s)

Immunosuppressive

Antiinflammatory

Antiallergic agent

Purity

95%

Pharmacology Properties

Physical Property

2.002

References

PubChem Literature

From Data Sources

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

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

• 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)

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

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

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

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

• U.S. Pat., 1960, 2 936 313; CA, 54, 19783, (phosphate)

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

• Ger. Pat., 1979, 2 826 257; CA, 93, 26657, (butyrate, propionate)

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

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

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

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

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

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

Molecule

ID:109323