Home > Compound List > Compound details
595-33-5 molecular structure
click picture or here to close

(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 and InChIs

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

Cite this record

CBID:72619 http://www.chembase.cn/molecule-72619.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[8.7.0.02,7.011,15]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
CAS Number
595-33-5
3562-63-8
EC Number
209-864-5
MDL Number
MFCD00056470
Beilstein Number
1917291
PubChem SID
162037544
24896559
24870151
PubChem CID
11683
ATC CODE
G03AC05
Chemspider ID
11192
DrugBank ID
DB00351
Wikipedia Title
Megestrol_acetate

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 17.826162  H Acceptors
H Donor LogD (pH = 5.5) 3.7237444 
LogD (pH = 7.4) 3.7237444  Log P 3.7237444 
Molar Refractivity 108.6554 cm3 Polarizability 42.444622 Å3
Polar Surface Area 60.44 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
210-212°C expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
RTECS
TU4075000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
40-48 expand Show data source
Safety Statements
22-24/25 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H351-H373 expand Show data source
GHS Precautionary statements
P281 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Target
Androgen receptor expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
100% (oral) expand Show data source
Half Life
13 to 105 hours (mean 34 hours) expand Show data source
Protein Bound
Yes (to albumin, but not to sex hormone-binding globulin or transcortin) expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
X (US) expand Show data source
Purity
≥99% (HPLC) expand Show data source
Grade
analytical standard, for drug analysis expand Show data source
VETRANAL™, analytical standard expand Show data source
Salt Data
Acetate expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C24H32O4 expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S1304 external link
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 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - M208050 external link
Orally active progestogen; formerly used in combinations as oral contraceptive.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Megestrol
  • • Chang, K., et al.: Steroids 12, 689 (1968)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle