| Version |
2.5 |
| Creation Date |
2005-06-13 13:24:05 |
| Update Date |
2009-05-07 19:52:54 |
| Primary Accession Number |
DB00896 |
| Secondary Accession Number |
|
| Name |
Rimexolone |
| Drug Type |
|
| Description |
Rimexolone is a glucocorticoid steroid used to treat inflammation in the eye. It is marketed as a 1% eye drop solution under the trade name Vexol |
| Synonyms |
Not Available |
| Brand Names |
- Vexol
|
| Brand Mixtures |
Not Available |
| Chemical IUPAC Name |
(10R,11S,13S,16R,17S)-11-hydroxy-10,13,16,17-tetramethyl-17-propanoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one |
| Chemical Formula |
C24H34O3 |
| Chemical Structure |
 |
| CAS Registry Number |
49697-38-3 |
| InChI Identifier |
InChI=1/C24H34O3/c1-6-20(27)24(5)14(2)11-18-17-8-7-15-12-16(25)9-10-22(15,3)21(17)19(26)13-23(18,24)4/h9-10,12,14,17-19,21,26H,6-8,11,13H2,1-5H3/t14-,17?,18?,19+,21?,22+,23+,24-/m1/s1 |
| InChI Key |
QTTRZHGPGKRAFB-PAIWTFDUBR |
| KEGG Drug |
D05729  |
| KEGG Compound |
Not Available |
| PubChem Compound |
39507  |
| PubChem Substance |
180512  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA451254  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
02163691  |
| RxList Link |
http://www.rxlist.com/cgi/generic3/rimexol.htm  |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Rimexolone  |
| FDA Label |
|
| Material Safety Data Sheet (MSDS) |
|
| Synthesis Reference |
Not Available |
| Average Molecular Weight |
370.5250 |
| Monoisotopic Molecular Weight |
370.2508 |
| State |
Solid |
| Melting Point |
Not Available |
| Experimental Water Solubility |
Insoluble
Source: PhysProp
|
| Predicted Water Solubility |
1.21e-02 mg/mL
Calculated using ALOGPS
|
| Experimental LogP/Hydrophobicity |
4.2
Source: PhysProp
|
| Predicted LogP |
3.64
Calculated using ALOGPS
|
| Experimental LogS |
Not Available |
| Predicted LogS |
-4.48
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 |
CCC(=O)[C@@]1(C)[C@H](C)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@]12C |
| Canonical SMILES |
CCC(=O)C1(C)C(C)CC2C3CCC4=CC(=O)C=CC4(C)C3C(O)CC12C |
| Drug Category |
- Anti-inflammatory Agents
- Corticosteroids
|
| ATC Codes |
|
| AHFS Codes |
|
| Indication |
For the treatment of postoperative inflammation following ocular surgery and in the treatment of anterior uveitis. |
| Pharmacology |
Rimexolone is a glucocorticoid corticosteroid for systemic use. Corticosteroids suppress the inflammatory response to a variety of inciting agents of a mechanical, chemical, or immunological nature. They inhibit edema, cellular infiltration, capillary dilatation, fibroblastic proliferation, deposition of collagen and scar formation associated with inflammation. |
| Mechanism of Action |
Betamethasone is a glucocorticoid receptor agonist. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition of arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. |
| Absorption |
Systemically absorbed. |
| Toxicity |
Symptoms of overdose include retinal toxicity, glaucoma, and subcapsular cataract. |
| Protein Binding |
Not Available |
| Biotransformation |
Undergoes extensive metabolism. Following intravenous administration of radiolabeled rimexolone in rats, more than 80% of the dose was excreted in the feces as rimexolone and metabolites. Metabolites have been shown to be either less active than rimexolone or inactive in human glucocorticoid receptor binding assays. |
| Half Life |
The serum half-life of rimexolone could not be reliably estimated due to the large number of samples below the quantitation limit of the assay (80 pg/mL). However, based on the time required to reach steady-state, the half-life appears to be short (1-2 hours). |
| Dosage Forms |
| Form |
Route |
| Suspension |
Ophthalmic |
|
| Patient Information |
Show  |
| Contraindications |
Show  |
| Interactions |
Not Available |
| Drug Interactions |
Not Available
|
| Food Interactions |
Not Available
|
| Pathways |
Not Available
|
| General References |
- Wikipedia

- RxList

|
| Organisms Affected |
|
| Targets |
- Corticosteroid-binding globulin
- Annexin A1
|
|
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
]
|
|
Drug Target 2
[top]
|
| Target 2 ID |
469 |
| Target 2 Name |
Annexin A1 |
| Target 2 Synonyms |
- Annexin I
- Calpactin II
- Chromobindin-9
- Lipocortin I
- Phospholipase A2 inhibitory protein
- p35
|
| Target 2 Gene Name |
ANXA1 |
| Target 2 Protein Sequence |
>Annexin A1
AMVSEFLKQAWFIENEEQEYVQTVKSSKGGPGSAVSPYPTFNPSSDVAALHKAIMVKGVD
EATIIDILTKRNNAQRQQIKAAYLQETGKPLDETLKKALTGHLEEVVLALLKTPAQFDAD
ELRAAMKGLGTDEDTLIEILASRTNKEIRDINRVYREELKRDLAKDITSDTSGDFRNALL
SLAKGDRSEDFGVNEDLADSDARALYEAGERRKGTDVNVFNTILTTRSYPQLRRVFQKYT
KYSKHDMNKVLDLELKGDIEKCLTAIVKCATSKPAFFAEKLHQAMKGVGTRHKALIRIMV
SRSEIDMNDIKAFYQKMYGISLCQAILDETKGDYEKILVALCGGN
|
| Target 2 Number of Residues |
350 |
| Target 2 Molecular Weight |
38583 |
| Target 2 Theoretical pI |
7.04 |
| Target 2 GO Classification |
|
Function
|
enzyme regulator activity
enzyme inhibitor activity
phospholipase inhibitor activity
lipid binding
phospholipid binding
calcium-dependent phospholipid binding
binding
ion binding
cation binding
calcium ion binding |
|
Process
|
| Not Available |
|
Component
|
| Not Available |
|
| Target 2 General Function |
Involved in calcium ion binding |
| Target 2 Specific Function |
Calcium/phospholipid-binding protein which promotes membrane fusion and is involved in exocytosis. This protein regulates phospholipase A2 activity. It seems to bind from two to four calcium ions with high affinity |
| Target 2 Pathways |
Not Available
|
| Target 2 Reactions |
Not Available |
| Target 2 Pfam Domain Function |
|
| Target 2 Signals |
|
| Target 2 Transmembrane Regions |
|
| Target 2 Essentiality |
Non-Essential |
| Target 2 GenBank ID Protein |
12654863  |
| Target 2 UniProtKB/Swiss-Prot ID |
P04083  |
| Target 2 UniProtKB/Swiss-Prot Entry Name |
ANXA1_HUMAN  |
| Target 2 PDB ID |
Not Available |
| Target 2 Cellular Location |
Not Available |
| Target 2 Gene Sequence |
>1041 bp
ATGGCAATGGTATCAGAATTCCTCAAGCAGGCCTGGTTTATTGAAAATGAAGAGCAGGAA
TATGTTCAAACTGTGAAGTCATCCAAAGGTGGTCCCGGATCAGCGGTGAGCCCCTATCCT
ACCTTCAATCCATCCTCGGATGTCGCTGCCTTGCATAAGGCCATAATGGTTAAAGGTGTG
GATGAAGCAACCATCATTGACATTCTAACTAAGCGAAACAATGCACAGCGTCAACAGATC
AAAGCAGCATATCTCCAGGAAACAGGAAAGCCCCTGGATGAAACACTTAAGAAAGCCCTT
ACAGGTCACCTTGAGGAGGTTGTTTTAGCTCTGCTAAAAACTCCAGCGCAATTTGATGCT
GATGAACTTCGTGCTGCCATGAAGGGCCTTGGAACTGATGAAGATACTCTAATTGAGATT
TTGGCATCAAGAACTAACAAAGAAATCAGAGACATTAACAGGGTCTACAGAGAGGAACTG
AAGAGAGATCTGGCCAAAGACATAACCTCAGACACATCTGGAGATTTTCGGAACGCTTTG
CTTTCTCTTGCTAAGGGTGACCGATCTGAGGACTTTGGTGTGAATGAAGACTTGGCTGAT
TCAGATGCCAGGGCCTTGTATGAAGCAGGAGAAAGGAGAAAGGGGACAGACGTAAACGTG
TTCAATACCATCCTTACCACCAGAAGCTATCCACAACTTCGCAGAGTGTTTCAGAAATAC
ACCAAGTACAGTAAGCATGACATGAACAAAGTTCTGGACCTGGAGTTGAAAGGTGACATT
GAGAAATGCCTCACAGCTATCGTGAAGTGCGCCACAAGCAAACCAGCTTTCTTTGCAGAG
AAGCTTCATCAAGCCATGAAAGGTGTTGGAACTCGCCATAAGGCATTGATCAGGATTATG
GTTTCCCGTTCTGAAATTGACATGAATGATATCAAAGCATTCTATCAGAAGATGTATGGT
ATCTCCCTTTGCCAAGCCATCCTGGATGAAACCAAAGGAGATTATGAGAAAATCCTGGTG
GCTCTTTGTGGAGGAAACTAA
|
| Target 2 GenBank Gene ID |
|
| Target 2 GeneCard ID |
ANXA1  |
| Target 2 GenAtlas ID |
ANXA1  |
| Target 2 HGNC ID |
HGNC:533  |
| Target 2 Chromosome Location |
9 |
| Target 2 Locus |
9q12-q21.2|9q12-q21.2 |
| Target 2 SNPs |
SNPJam Report  |
| Target 2 General References |
- Kovacic RT, Tizard R, Cate RL, Frey AZ, Wallner BP: Correlation of gene and protein structure of rat and human lipocortin I. Biochemistry. 1991 Sep 17;30(37):9015-21. [PubMed
]
- Varticovski L, Chahwala SB, Whitman M, Cantley L, Schindler D, Chow EP, Sinclair LK, Pepinsky RB: Location of sites in human lipocortin I that are phosphorylated by protein tyrosine kinases and protein kinases A and C. Biochemistry. 1988 May 17;27(10):3682-90. [PubMed
]
- Pepinsky RB, Sinclair LK, Chow EP, O'Brine-Greco B: A dimeric form of lipocortin-1 in human placenta. Biochem J. 1989 Oct 1;263(1):97-103. [PubMed
]
- Wallner BP, Mattaliano RJ, Hession C, Cate RL, Tizard R, Sinclair LK, Foeller C, Chow EP, Browing JL, Ramachandran KL, et al.: Cloning and expression of human lipocortin, a phospholipase A2 inhibitor with potential anti-inflammatory activity. Nature. 1986 Mar 6-12;320(6057):77-81. [PubMed
]
- Biemann K, Scoble HA: Characterization by tandem mass spectrometry of structural modifications in proteins. Science. 1987 Aug 28;237(4818):992-8. [PubMed
]
- Arcone R, Arpaia G, Ruoppolo M, Malorni A, Pucci P, Marino G, Ialenti A, Di Rosa M, Ciliberto G: Structural characterization of a biologically active human lipocortin 1 expressed in Escherichia coli. Eur J Biochem. 1993 Jan 15;211(1-2):347-55. [PubMed
]
- Weng X, Luecke H, Song IS, Kang DS, Kim SH, Huber R: Crystal structure of human annexin I at 2.5 A resolution. Protein Sci. 1993 Mar;2(3):448-58. [PubMed
]
- Gao J, Li Y, Yan H: NMR solution structure of domain 1 of human annexin I shows an autonomous folding unit. J Biol Chem. 1999 Jan 29;274(5):2971-7. [PubMed
]
|
| Target 2 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
]
|