RIMEXOLONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H34O3
Molecular Weight	370.525
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@H](C)[C@](C)(C(=O)CC)[C@@]1(C)C[C@H](O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)C=C[C@]34C

InChI

InChIKey=QTTRZHGPGKRAFB-OOKHYKNYSA-N

InChI=1S/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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020474s021lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/mtm/rimexolone-ophthalmic.html http://www.rxlist.com/vexol-drug.htm http://www.wikidoc.org/index.php/Rimexolone

Rimexolone is a glucocorticoid receptor agonist. Rimexolone ophthalmic (for the eyes) is used to treat eye inflammation caused by infections, injury, surgery, or other conditions. It is FDA approved for the treatment of post-operative inflammation and anterior uveitis. Common adverse reactions include hypotension, erythema, pruritus, taste sense altered, headache, blurred vision, discharge from eye, pain in eye, pharyngitis, and rhinitis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2386110	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anterior uveitis 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020474s021lbl.pdf	Primary		Approved 8429	VEXOL Approved Use VEXOL® 1% (rimexolone ophthalmic suspension) is indicated for the treatment of postoperative inflammation following ocular surgery and in the treatment of anterior uveitis. Launch Date 1994
Postoperative inflammation following ocular surgery 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020474s021lbl.pdf	Primary		Approved 8429	VEXOL Approved Use VEXOL® 1% (rimexolone ophthalmic suspension) is indicated for the treatment of postoperative inflammation following ocular surgery and in the treatment of anterior uveitis. Launch Date 1994

AUC

Value	Dose	Analyte	Population
1091 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2347958	80 mg single, intraarticular dose: 80 mg route of administration: Intraarticular experiment type: SINGLE co-administered:	RIMEXOLONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1331 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2347958	120 mg single, intraarticular dose: 120 mg route of administration: Intraarticular experiment type: SINGLE co-administered:	RIMEXOLONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1786 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2347958	160 mg single, intraarticular dose: 160 mg route of administration: Intraarticular experiment type: SINGLE co-administered:	RIMEXOLONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
564 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2347958	40 mg single, intraarticular dose: 40 mg route of administration: Intraarticular experiment type: SINGLE co-administered:	RIMEXOLONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1 % 4 times / day steady, ophthalmic Recommended Dose: 1 %, 4 times / day Route: ophthalmic Route: steady Dose: 1 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9278798/	unhealthy n = 197 Health Status: unhealthy Condition: intraocular inflammation after cataract extraction Population Size: 197 Sources: https://pubmed.ncbi.nlm.nih.gov/9278798/	Disc. AE: Ocular pain... AEs leading to discontinuation/dose reduction: Ocular pain (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/9278798/

AEs

AE	Significance	Dose	Population
Ocular pain	2% Disc. AE	1 % 4 times / day steady, ophthalmic Recommended Dose: 1 %, 4 times / day Route: ophthalmic Route: steady Dose: 1 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9278798/	unhealthy n = 197 Health Status: unhealthy Condition: intraocular inflammation after cataract extraction Population Size: 197 Sources: https://pubmed.ncbi.nlm.nih.gov/9278798/

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	49697-38-3	https://www.alfa-chemistry.com/rimexolone-cas-49697-38-3-item-72876.htm
Ambinter	Amb17619940	http://www.ambinter.com/reference/17619940
Avantor Inc	101096-096	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-096
Hairui	HR141937	http://www.hairuichem.com/en/product/49697-38-3.html
OChem	18890	http://www.ocheminc.com/index.php?act=psearch&pid=697R383
Smolecule	S541435	http://www.smolecule.com/products/s541435
THE BioTek	bt-280699	https://www.thebiotek.com/product/inhibitors/bt-280699
VladaChem	VL278538-10MG	https://www.vladachem.com/product.php?products=49697-38-3
eNovation Chemicals	D674724	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674724
iChemical	EBD30479	http://www.ichemical.com/products/49697-38-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Intraocular pressure-raising potential of 1.0% rimexolone in patients responding to corticosteroids.	1996 Aug	8694727
Pharmacological validation of a feline model of steroid-induced ocular hypertension.	1999 Mar	10088814
Ocular-hypertensive and anti-inflammatory response to rimexolone therapy in children.	2003 Dec	14662591
Two cases of corneal ulcer due to methicillin-resistant Staphylococcus aureus in high risk groups.	2010 Aug	20714389
Rimexolone inhibits proliferation, cytokine expression and signal transduction of human CD4+ T-cells.	2010 Jun 15	20363256

Patents

Sample Use Guides

In Vivo Use Guide

Post-Operative Inflammation: Apply one - two drops of Rimexolone 1% Ophthalmic Suspension into the conjunctival sac of the affected eye four times daily beginning 24 hours after surgery and continuing throughout the first 2 weeks of the postoperative period. Anterior Uveitis: Apply one - two drops of Rimexolone 1% Ophthalmic Suspension into the conjunctival sac of the affected eye every hour during waking hours for the first week, one drop every two hours during waking hours of the second week, and then taper until uveitis is resolved.

Route of Administration: Topical

In Vitro Use Guide

Isolated CD4+ T-cells were pre-incubated with rimexolone at different concentrations for 10 min (10(-11)/10(-8)/10(-5)M) and stimulated with anti-CD3/anti-CD28 for 96 h. Proliferation was determined by flow cytometry. The percentage of dividing cells was significantly reduced by 10(-5)M rimexolone.

Name

Type

Language

RIMEXOLONE

Official Name

English

11β-Hydroxy-16α,17α-dimethyl-17-propionylandrosta-1,4-dien-3-one

Common Name

English

rimexolone [INN]

Common Name

English

RIMEXOLONE [USAN]

Common Name

English

RIMEXOLON

Common Name

English

RIMEXOLONE [USP MONOGRAPH]

Common Name

English

RIMEXOLONE [MART.]

Common Name

English

VEXOL

Brand Name

English

ANDROSTA-1,4-DIEN-3-ONE, 11-HYDROXY-16,17-DIMETHYL-17-(1-OXOPROPYL)-, (11.BETA.,16,ALPHA.,17.BETA.)-

Common Name

English

RIMEXOLONE [USP IMPURITY]

Common Name

English

RIMEXOLONE [MI]

Common Name

English

Rimexolone [WHO-DD]

Common Name

English

RIMEXOLONE [USP-RS]

Common Name

English

RIMEXOLONE [ORANGE BOOK]

Common Name

English

ORG-6216

Code

English

RIMEXOLONE [VANDF]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175450