(1S,2R,8S,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 138
• Molecular Formular: C22H32O3
• Molecular Mass: 344.48768
• Monoisotopic Mass: 344.23514488
• SMILES: O[C@@H]1[C@H]2[C@H]([C@H]3[C@](C1)([C@H](CC3)C(=O)C)C)C[C@@H](C1=CC(=O)CC[C@]21C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
• InChI: InChI=1S/C22H32O3/c1-12-9-15-17-6-5-16(13(2)23)22(17,4)11-19(25)20(15)21(3)8-7-14(24)10-18(12)21/h10,12,15-17,19-20,25H,5-9,11H2,1-4H3/t12-,15-,16+,17-,19-,20+,21-,22+/m0/s1
• InChIKey: GZENKSODFLBBHQ-ILSZZQPISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one; (1S,2R,8S,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• IUPAC Traditional name: medrysone
• Brand Name: HMS Liquifilm; Medrifar; Medritonic; Medrocort; Visudrisone; HMS
• Synonyms: 11β-Hydroxy-6α-methyl-4-pregnene-3,20-dione; 6α-Methyl-11β-hydroxyprogesterone; 11β-Hydroxy-6α-methyl-4-pregnene-3,20-dione; Medrysone; 6α-METHYL-11β-HYDROXYPROGESTERONE; Hydroxymesterone; Medrysone

Database IDs

• CAS Number: 2668-66-8
• EC Number: 220-208-7
• MDL Number: MFCD00056477
• PubChem SID: 24896551; 46506584; 160963601
• PubChem CID: 247839

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.136774
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.1268592
• LogD (pH = 7.4): 3.1268587
• Log P: 3.1268587
• Molar Refractivity: 98.8464 cm^3
• Polarizability: 38.85521 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.06
• LOG S: -4.01
• Solubility (Water): 3.37e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.2

Safety Information

• Storage Condition: 2-8°C
• RTECS: TU5250000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

MP Biomedicals - 02155577

(11β-Hydroxy-6α-methyl-4-pregnene-3,20-dione; Medrysone)

DrugBank - DB00253

• Drug Groups: approved
• Description: Medrysone is a corticosteroid used in ophthalmology. [Wikipedia]
• Indication: For the treatment of allergic conjunctivitis, vernal conjunctivitis, episcleritis, and epinephrine sensitivity.
• Pharmacology: Medrysone is a topical anti-inflammatory corticoidsteroids for ophthalmic use. In patients with increased intraocular pressure and in those susceptible to a rise in intraocular pressure, there is less effect on pressure with medrysone than with dexamethasone or betamethasone. Corticoidsteroids inhibit the edema, fibrin deposition, capillary dilation, and phagocytic migration of the acute inflammatory response, as well as capillary proliferation, deposition of collagen, and scar formation.
• Affected Organisms: Humans and other mammals
• Absorption: Rapidly absorbed following oral administration.
• External Links: Wikipedia; RxList; Drugs.com