(1S,2R,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-14-yl acetate

• ChemBase ID: 72619
• Molecular Formular: C24H32O4
• Molecular Mass: 384.50848
• Monoisotopic Mass: 384.2300595
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](C=C2C)[C@H]2[C@](CC1)([C@](CC2)(C(=O)C)OC(=O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C(=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(OC(=O)C)C(=O)C)C)C)C
• InChI: InChI=1S/C24H32O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h12-13,18-20H,6-11H2,1-5H3/t18-,19+,20+,22-,23+,24+/m1/s1
• InChIKey: RQZAXGRLVPAYTJ-GQFGMJRRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-14-yl acetate; (1S,2R,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• IUPAC Traditional name: DMAP
• Synonyms: Megestrol acetate; 17-(Acetyloxy)-6-methypregna-4,6-diene-3,20-dione; BDH 1298; DMAP; MGA; Magestin; Maygace; Megeron; Megestat; Magestryl Acetate; Ovarid; Megace; Megace ES; Megestrol Acetate; BDH-1298, NSC-71423; 17α-Acetoxy-6-methyl-4,6-pregnadiene-3,20-dione; 17α-Hydroxy-6-methyl-4,6-pregnadiene-3,20-dione 17-acetate; 17α-Hydroxy-6-methyl-6-dehydroprogesterone 17-acetate; Megestrol 17-acetate; 17α-乙酰氧基-6-甲基孕甾-4,6-二烯-3,20-二酮; 17α-羟基-6-甲基-6-去氢孕酮 17-乙酸酯; 17α-羟基-6-甲基孕甾-4,6-二烯-3,20-二酮 17-乙酸酯; 甲地孕酮 17-乙酸酯; 甲地孕酮乙酸酯

Database IDs

• CAS Number: 595-33-5; 3562-63-8
• EC Number: 209-864-5
• MDL Number: MFCD00056470
• Beilstein Number: 1917291
• PubChem SID: 162037544; 24870151; 24896559
• PubChem CID: 11683
• ATC CODE: G03AC05
• Chemspider ID: 11192
• DrugBank ID: DB00351
• Wikipedia Title: Megestrol_acetate

CALCULATED PROPERTIES

• Acid pKa: 17.826162
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.7237444
• LogD (pH = 7.4): 3.7237444
• Log P: 3.7237444
• Molar Refractivity: 108.6554 cm^3
• Polarizability: 42.444622 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 210-212°C

Safety Information

• Storage Condition: -20°C; Refrigerator
• RTECS: TU4075000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40-48
• Safety Statements: 22-24/25
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351-H373
• GHS Precautionary statements: P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: Androgen receptor
• Admin Routes: Oral
• Bioavailability: 100% (oral)
• Half Life: 13 to 105 hours (mean 34 hours)
• Protein Bound: Yes (to albumin, but not to sex hormone-binding globulin or transcortin)
• Legal Status: Rx-only
• Pregnancy Category: X (US)

Product Information

• Purity: ≥99% (HPLC)
• Grade: analytical standard, for drug analysis; VETRANAL™, analytical standard
• Salt Data: Acetate
• Empirical Formula (Hill Notation): C24H32O4

DETAILS

Selleck Chemicals - S1304

Research Area: Cancer
Biological Activity:
Megestrol Acetate is a synthetic progesteronal agent with an IC50 of 260 μM for the inhibition of HegG2. It inhibits the growth of HepG2 cells in vitro in dose- and time-dependent manners. Megestrol is a progesterone derivative with antineoplastic properties used in the treatment of advanced carcinoma of the breast and endometrium. When given in relatively high doses, Megestrol can substantially increase appetite in most individuals, even those with advanced cancer. It is also used to boost appetite in individuals with other cancers or HIV/AIDS. [1][2][3]References on Megestrol Acetate[] Clin Cancer Res, 2004, 10:5226-5232

Sigma Aldrich - 46420

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M208050

Orally active progestogen; formerly used in combinations as oral contraceptive.

REFERENCES

• http://en.wikipedia.org/wiki/Megestrol
• Chang, K., et al.: Steroids 12, 689 (1968)