Rimexolone (CED0013878)

Record Information

Version

1.0

Creation Date

2016-05-22 05:10:17 UTC

Update Date

2026-05-14 16:52:11 UTC

Accession Number

CHEM018343

Identification

Common Name

Rimexolone

Class

Small Molecule

Description

Rimexolone is an organic compound with the formula C23H32O4 and an average molecular weight of 372.50 g/mol. Rimexolone belongs to the androstane steroids, a subclass of steroids and steroid derivatives within the organic compounds. This compound is found in or released from healthcare, pharmaceuticals, and veterinary products, specifically as an antiinflammatory agent and corticosteroid. Its recorded route of exposure is ophthalmic. Rimexolone acts on two recorded protein targets, serving as an agonist/modulator of the glucocorticoid receptor (NR3C1) and the steroid hormone receptor ERR1 (ESRRA).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂O₄

Average Molecular Mass

372.505 g/mol

Monoisotopic Mass

372.230 g/mol

CAS Registry Number

49697-38-3

IUPAC Name

methyl (1S,2R,10S,11S,13R,14S,15S,17S)-17-hydroxy-2,13,14,15-tetramethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-14-carboxylate

Traditional Name

rimexolone

SMILES

[H][C@@]1(C)C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3([H])[C@@]([H])(O)C[C@]2(C)[C@@]1(C)C(=O)OC

InChI Identifier

InChI=1S/C23H32O4/c1-13-10-17-16-7-6-14-11-15(24)8-9-21(14,2)19(16)18(25)12-22(17,3)23(13,4)20(26)27-5/h8-9,11,13,16-19,25H,6-7,10,12H2,1-5H3/t13-,16+,17+,18+,19-,21+,22+,23-/m1/s1

InChI Key

HJPMTDNGLRNDJA-ZVXCBTRXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxo-delta-1,4-steroid
3-oxosteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-1,4-steroid
Cyclic alcohol
Methyl ester
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	2.95	ALOGPS
logP	3.5	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	18.8	ChemAxon
pKa (Strongest Basic)	-0.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	105.66 m³·mol⁻¹	ChemAxon
Polarizability	41.96 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ab9-0009000000-354a4c512cb19f5f98ca	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0abi-0219000000-089cce23d5836744c053	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0faj-4695000000-9349dd72662a05eb876e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0009000000-46f2be79555e91e21a93	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0009000000-dbb40633c6b0a310a67c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a6r-1019000000-9bce12ac14b874051353	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
855.0	Log mg/kg	[480:1500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
309	Corticosteroids	Healthcare, pharmaceuticals & veterinary products	Not Available
396	Antiinflammatory agents	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

2 pathways

Rimexolone Action Pathway

Rimexolone Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	10.5875
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	5.99439
Click to view 3D structure	Glucocorticoid receptor	P06536	Rattus norvegicus	Predicted (SEA)	2.33548
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	10.5875
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	8.48557
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	29.8941
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	7.62922
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	22.5763
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	16.9711
Click to view 3D structure	Tyrosine aminotransferase	P04694	Rattus norvegicus	Predicted (SEA)	0.700643
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	33.0081
Click to view 3D structure	Glucocorticoid receptor	P06537	Mus musculus	Predicted (SEA)	3.11397
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	17.049
Click to view 3D structure	Interstitial collagenase	P03956	Humans	Predicted (SEA)	156.866
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 2	Q9R1A7	Rattus norvegicus	Predicted (SEA)	0.700643
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	47.4102
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	64.9263
Click to view 3D structure	11-beta-hydroxysteroid dehydrogenase type 2	P80365	Humans	Predicted (SEA)	12.4559
Click to view 3D structure	Pyruvate carboxylase, mitochondrial	P11498	Humans	Predicted (SEA)	1.01204
Click to view 3D structure	Solute carrier family 22 member 3	O88446	Rattus norvegicus	Predicted (SEA)	11.7552
Click to view 3D structure	Solute carrier organic anion transporter family member 1A1	P46720	Rattus norvegicus	Predicted (SEA)	11.8331
Click to view 3D structure	Rho-associated protein kinase 2	O75116	Humans	Predicted (SEA)	2186.63
Click to view 3D structure	Androgen receptor	P19091	Mus musculus	Predicted (SEA)	23.6662
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	3829.25
Click to view 3D structure	Protein kinase C delta type	Q05655	Humans	Predicted (SEA)	1889.63