| Version |
2.5 |
| Creation Date |
2007-07-06 20:34:53 |
| Update Date |
2009-02-19 16:04:37 |
| Primary Accession Number |
DB01384 |
| Secondary Accession Number |
Not Available |
| Name |
Paramethasone |
| Drug Type |
|
| Description |
A glucocorticoid with the general properties of corticosteroids. It has been used by mouth in the treatment of all conditions in which corticosteroid therapy is indicated except adrenal-deficiency states for which its lack of sodium-retaining properties makes it less suitable than hydrocortisone with supplementary fludrocortisone. (From Martindale, The Extra Pharmacopoeia, 30th ed, p737) |
| Synonyms |
Not Available |
| Brand Names |
- Haldrone
|
| Brand Mixtures |
Not Available |
| Chemical IUPAC Name |
(6S,8S,9S,10R,11S,13S,14S,16R,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one |
| Chemical Formula |
C22H29FO5 |
| Chemical Structure |
 |
| CAS Registry Number |
53-33-8 |
| InChI Identifier |
InChI=1/C22H29FO5/c1-11-6-14-13-8-16(23)15-7-12(25)4-5-20(15,2)19(13)17(26)9-21(14,3)22(11,28)18(27)10-24/h4-5,7,11,13-14,16-17,19,24,26,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19-,20+,21+,22+/m1/s1 |
| InChI Key |
MKPDWECBUAZOHP-AFYJWTTEBS |
| KEGG Drug |
Not Available |
| KEGG Compound |
C07413  |
| PubChem Compound |
5875  |
| PubChem Substance |
9617  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
Not Available |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
Not Available |
| RxList Link |
Not Available |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Paramethasone  |
| FDA Label |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| Synthesis Reference |
Not Available |
| Average Molecular Weight |
392.4611 |
| Monoisotopic Molecular Weight |
392.1999 |
| State |
Solid |
| Melting Point |
Not Available |
| Experimental Water Solubility |
Not Available
Source: PhysProp
|
| Predicted Water Solubility |
1.45e-01 mg/mL
Calculated using ALOGPS
|
| Experimental LogP/Hydrophobicity |
Not Available
Source: PhysProp
|
| Predicted LogP |
1.51
Calculated using ALOGPS
|
| Experimental LogS |
Not Available |
| Predicted LogS |
-3.43
Calculated using ALOGPS
|
| Experimental Caco2 Permeability |
Not Available |
| pKa/Isoelectric Point |
Not Available |
| Mass Spectrum |
Not Available
|
| MOL File |
Show | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
Not Available |
| Isomeric SMILES |
C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO |
| Canonical SMILES |
CC1CC2C3CC(F)C4=CC(=O)C=CC4(C)C3C(O)CC2(C)C1(O)C(=O)CO |
| Drug Category |
- Anti-inflammatory Agents
- Glucocorticoids
|
| ATC Codes |
|
| AHFS Codes |
Not Available |
| Indication |
For the treatment of all conditions in which corticosteroid therapy is indicated except adrenal-deficiency states for which its lack of sodium-retaining properties makes it less suitable than hydrocortisone with supplementary fludrocortisone. |
| Pharmacology |
Paramethasone is a glucocorticoid with the general properties of corticosteroids. |
| Mechanism of Action |
Glucocorticoids such as paramethasone can inhibit leukocyte infiltration at the site of inflammation, interfere with mediators of inflammatory response, and suppress humoral immune responses. The antiinflammatory actions of glucocorticoids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. Paramethasone reduces inflammatory reaction by limiting the capillary dilatation and permeability of the vascular structures. These compounds restrict the accumulation of polymorphonuclear leukocytes and macrophages and reduce the release of vasoactive kinins. Recent research suggests that corticosteroids may inhibit the release of arachidonic acid from phospholipids, thereby reducing the formation of prostaglandins. Prednisolone is a glucocorticoid receptor agonist. On binding, the corticoreceptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing an increase or decrease in expression of specific target genes, including suppression of IL2 (interleukin 2) expression. |
| Absorption |
Not Available |
| Toxicity |
Not Available |
| Protein Binding |
80% |
| Biotransformation |
Hepatic. |
| Half Life |
Not Available |
| Dosage Forms |
|
| Patient Information |
Not Available |
| Contraindications |
Not Available |
| Interactions |
Not Available |
| Drug Interactions |
Not Available
|
| Food Interactions |
Not Available
|
| Pathways |
Not Available
|
| General References |
- Wikipedia

|
| Organisms Affected |
|
| Targets |
- Corticosteroid-binding globulin
|
|
Drug Target 1
[top]
|
| Target 1 ID |
232 |
| Target 1 Name |
Corticosteroid-binding globulin |
| Target 1 Synonyms |
- CBG
- Corticosteroid-binding globulin precursor
- Serpin A6
- Transcortin
|
| Target 1 Gene Name |
SERPINA6 |
| Target 1 Protein Sequence |
>Corticosteroid-binding globulin precursor
MPLLLYTCLLWLPTSGLWTVQAMDPNAAYVNMSNHHRGLASANVDFAFSLYKHLVALSPK
KNIFISPVSISMALAMLSLGTCGHTRAQLLQGLGFNLTERSETEIHQGFQHLHQLFAKSD
TSLEMTMGNALFLDGSLELLESFSADIKHYYESEVLAMNFQDWATASRQINSYVKNKTQG
KIVDLFSGLDSPAILVLVNYIFFKGTWTQPFDLASTREENFYVDETTVVKVPMMLQSSTI
SYLHDSELPCQLVQMNYVGNGTVFFILPDKGKMNTVIAALSRDTINRWSAGLTSSQVDLY
IPKVTISGVYDLGDVLEEMGIADLFTNQANFSRITQDAQLKSSKVVHKAVLQLNEEGVDT
AGSTGVTLNLTSKPIILRFNQPFIIMIFDHFTWSSLFLARVMNPV
|
| Target 1 Number of Residues |
411 |
| Target 1 Molecular Weight |
45141 |
| Target 1 Theoretical pI |
5.94 |
| Target 1 GO Classification |
|
Function
|
enzyme regulator activity
enzyme inhibitor activity
protease inhibitor activity
endopeptidase inhibitor activity
serine-type endopeptidase inhibitor activity |
|
Process
|
| Not Available |
|
Component
|
| Not Available |
|
| Target 1 General Function |
Involved in serine-type endopeptidase inhibitor activity |
| Target 1 Specific Function |
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species |
| Target 1 Pathways |
Not Available
|
| Target 1 Reactions |
Not Available |
| Target 1 Pfam Domain Function |
|
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
|
| Target 1 Essentiality |
Non-Essential |
| Target 1 GenBank ID Protein |
179971  |
| Target 1 UniProtKB/Swiss-Prot ID |
P08185  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
CBG_HUMAN  |
| Target 1 PDB ID |
Not Available |
| Target 1 Cellular Location |
|
| Target 1 Gene Sequence |
>1218 bp
ATGCCACTCCTCCTGTACACCTGTCTTCTCTGGCTGCCCACCAGCGGCCTCTGGACCGTC
CAGGCCATGGATCCTAACGCTGCTTATGTGAACATGAGTAACCATCACCGGGGCCTGGCT
TCAGCCAACGTTGACTTTGCCTTCAGCCTGTATAAGCACCTAGTGGCCTTGAGTCCCAAA
AAGAACATTTTCATCTCCCCTGTGAGCATCTCCATGGCCTTAGCTATGCTGTCCCTGGGC
ACCTGTGGCCACACACGGGCCCAGCTTCTCCAGGGCCTGGGTTTCAACCTCACTGAGAGG
TCTGAGACTGAGATCCACCAGGGTTTCCAGCACCTGCACCAACTCTTTGCAAAGTCAGAC
ACCAGCTTAGAAATGACTATGGGCAATGCCTTGTTTCTTGATGGCAGCCTGGAGTTGCTG
GAGTCATTCTCAGCAGACATCAAGCACTACTATGAGTCAGAGGTCTTGGCTATGAATTTC
CAGGACTGGGCAACAGCCAGCAGACAGATCAACAGCTATGTCAAGAATAAGACACAGGGG
AAAATTGTCGACTTGTTTTCAGGGCTGGATAGCCCAGCCATCCTCGTCCTGGTCAACTAT
ATCTTCTTCAAAGGCACATGGACACAGCCCTTTGACCTGGCAAGCACCAGGGAGGAGAAC
TTCTATGTGGACGAGACAACTGTGGTGAAGGTGCCCATGATGTTGCAGTCGAGCACCATC
AGTTACCTTCATGACTCAGAGCTCCCCTGCCAGCTGGTGCAGATGAACTACGTGGGCAAT
GGGACTGTCTTCTTCATCCTTCCGGACAAGGGGAAGATGAACACAGTCATCGCTGCACTG
AGCCGGGACACGATTAACAGGTGGTCCGCAGGCCTGACCAGCAGCCAGGTGGACCTGTAC
ATTCCAAAGGTCACCATCTCTGGAGTCTATGACCTTGGAGATGTGCTGGAGGAAATGGGC
ATTGCAGACTTGTTCACCAACCAGGCAAATTTCTCACGCATCACCCAGGACGCCCAGCTG
AAGTCATCAAAGGTGGTCCATAAAGCTGTGCTGCAACTCAATGAGGAGGGTGTGGACACA
GCTGGCTCCACTGGGGTCACCCTAAACCTGACGTCCAAGCCTATCATCTTGCGTTTCAAC
CAGCCCTTCATCATCATGATCTTCGACCACTTCACCTGGAGCAGCCTTTTCCTGGCGAGG
GTTATGAACCCAGTGTAA
|
| Target 1 GenBank Gene ID |
|
| Target 1 GeneCard ID |
SERPINA6  |
| Target 1 GenAtlas ID |
SERPINA6  |
| Target 1 HGNC ID |
HGNC:1540  |
| Target 1 Chromosome Location |
14 |
| Target 1 Locus |
14q32.1 |
| Target 1 SNPs |
SNPJam Report  |
| Target 1 General References |
- Emptoz-Bonneton A, Cousin P, Seguchi K, Avvakumov GV, Bully C, Hammond GL, Pugeat M: Novel human corticosteroid-binding globulin variant with low cortisol-binding affinity. J Clin Endocrinol Metab. 2000 Jan;85(1):361-7. [PubMed
]
- Smith CL, Power SG, Hammond GL: A Leu----His substitution at residue 93 in human corticosteroid binding globulin results in reduced affinity for cortisol. J Steroid Biochem Mol Biol. 1992 Aug;42(7):671-6. [PubMed
]
- Hammond GL, Smith CL, Goping IS, Underhill DA, Harley MJ, Reventos J, Musto NA, Gunsalus GL, Bardin CW: Primary structure of human corticosteroid binding globulin, deduced from hepatic and pulmonary cDNAs, exhibits homology with serine protease inhibitors. Proc Natl Acad Sci U S A. 1987 Aug;84(15):5153-7. [PubMed
]
- Kato EA, Hsu BR, Kuhn RW: Comparative structural analyses of corticosteroid binding globulin. J Steroid Biochem. 1988 Feb;29(2):213-20. [PubMed
]
- Bardin CW, Gunsalus GL, Musto NA, Cheng CY, Reventos J, Smith C, Underhill DA, Hammond G: Corticosteroid binding globulin, testosterone-estradiol binding globulin, and androgen binding protein belong to protein families distinct from steroid receptors. J Steroid Biochem. 1988;30(1-6):131-9. [PubMed
]
- Van Baelen H, Power SG, Hammond GL: Decreased cortisol-binding affinity of transcortin Leuven is associated with an amino acid substitution at residue-93. Steroids. 1993 Jun;58(6):275-7. [PubMed
]
|
| Target 1 Drug References |
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed
]
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed
]
|