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3562-63-8 molecular structure
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(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-5-one

ChemBase ID: 235
Molecular Formular: C22H30O3
Molecular Mass: 342.4718
Monoisotopic Mass: 342.21949482
SMILES and InChIs

SMILES:
O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)C(=C3)C)C)CC2)CC1)C)C(=O)C
Canonical SMILES:
O=C1CC[C@]2(C(=C1)C(=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C)C
InChI:
InChI=1S/C22H30O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h11-12,16-18,25H,5-10H2,1-4H3/t16-,17+,18+,20-,21+,22+/m1/s1
InChIKey:
VXIMPSPISRVBPZ-NWUMPJBXSA-N

Cite this record

CBID:235 http://www.chembase.cn/molecule-235.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-5-one
(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-5-one
IUPAC Traditional name
megestrol
Brand Name
Magestin
Maygace
Megace
Megeron
Megestat
Megestil
Megestin
Nia
Niagestin
Ovaban
Ovarid
Volidan
Synonyms
17-Hydroxy-6-methylpregna-4,6-diene-3,20-dione
Megestrol Acetate
Megestrolo [DCIT]
Megestrolum [INN-Latin]
Megestryl acetate
MGA
Megestrol
CAS Number
3562-63-8
PubChem SID
160963698
PubChem CID
1909019090
19090
Chemspider ID
18023
Wikipedia Title
Megestrol

DATA SOURCES

DATA SOURCES

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Data Source Data ID Price
TRC
M208040 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.6991005  H Acceptors
H Donor LogD (pH = 5.5) 3.2826188 
LogD (pH = 7.4) 3.2826166  Log P 3.282619 
Molar Refractivity 99.5039 cm3 Polarizability 38.614105 Å3
Polar Surface Area 54.37 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.7  LOG S -4.52 
Solubility (Water) 1.04e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
2 µg/mL (at 37°C for the acetate salt) expand Show data source
Hydrophobicity(logP)
3.2 expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB00351 external link
Item Information
Drug Groups approved
Description 17-Hydroxy-6-methylpregna-3,6-diene-3,20-dione. A progestational hormone used most commonly as the acetate ester. As the acetate, it is more potent than progesterone both as a progestagen and as an ovulation inhibitor. It has also been used in the palliative treatment of breast cancer. [PubChem]
Indication For the treatment of anorexia, cachexia, or an unexplained, significant weight loss in patients with a diagnosis of acquired immunodeficiency syndrome (AIDS). Also used for the palliative management of recurrent, inoperable, or metastatic breast cancer, endometrial cancer, and prostate cancer in Canada and some other countries.
Pharmacology Megestrol is a synthetic progestin and has the same physiologic effects as natural progesterone. These effects include induction of secretory changes in the endometrium, increase in basal body temperature, pituitary inhibition, and production of withdrawal bleeding in the presence of estrogen. Mestrogel has slight glucocorticoid activity and very slight mineralocorticoid activity. This drug has no estrogenic, androgenic, or anabolic activity. The precise mechanism of megestrol’s antianorexic and anticachetic effects is unknown. Initially developed as a contraceptive, it was first evaluated in breast cancer treatment in 1967.
Toxicity No serious unexpected side effects have resulted from studies involving megestrol acetate oral suspension administered in dosages as high as 1200 mg/day. Treatment with megestrol acetate, an orexigenic agent, has also resulted in iatrogenic adrenal suppression. The mechanism is presumably related to the glucocorticoid properties of megestrol acetate [PMID: 12872362].
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic. Megestrol metabolites which were identified in urine constituted 5% to 8% of the dose administered. Respiratory excretion as labeled carbon dioxide and fat storage may have accounted for at least part of the radioactivity not found in urine and feces. No active metabolites have been identified.
Absorption Variable, but well absorbed orally.
Half Life 34 hours
Elimination The major route of drug elimination in humans is urine.
Respiratory excretion as labeled carbon dioxide and fat storage may have accounted for at least part of the radioactivity not found in urine and feces.
References
Berenstein EG, Ortiz Z: Megestrol acetate for the treatment of anorexia-cachexia syndrome. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD004310. [Pubmed]
Pascual Lopez A, Roque i Figuls M, Urrutia Cuchi G, Berenstein EG, Almenar Pasies B, Balcells Alegre M, Herdman M: Systematic review of megestrol acetate in the treatment of anorexia-cachexia syndrome. J Pain Symptom Manage. 2004 Apr;27(4):360-9. [Pubmed]
Rao GG, Miller DS: Hormonal therapy in epithelial ovarian cancer. Expert Rev Anticancer Ther. 2006 Jan;6(1):43-7. [Pubmed]
Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH: Classification and pharmacology of progestins. Maturitas. 2008 Sep-Oct;61(1-2):171-80. [Pubmed]
Orme LM, Bond JD, Humphrey MS, Zacharin MR, Downie PA, Jamsen KM, Mitchell SL, Robinson JM, Grapsas NA, Ashley DM: Megestrol acetate in pediatric oncology patients may lead to severe, symptomatic adrenal suppression. Cancer. 2003 Jul 15;98(2):397-405. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - M208040 external link
Megestrol is an orally active progestogen. Megestrol is used in combinations as oral contraceptive and as antineoplastic agent.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Berenstein EG, Ortiz Z: Megestrol acetate for the treatment of anorexia-cachexia syndrome. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD004310. Pubmed
  • • Pascual Lopez A, Roque i Figuls M, Urrutia Cuchi G, Berenstein EG, Almenar Pasies B, Balcells Alegre M, Herdman M: Systematic review of megestrol acetate in the treatment of anorexia-cachexia syndrome. J Pain Symptom Manage. 2004 Apr;27(4):360-9. Pubmed
  • • Rao GG, Miller DS: Hormonal therapy in epithelial ovarian cancer. Expert Rev Anticancer Ther. 2006 Jan;6(1):43-7. Pubmed
  • • Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH: Classification and pharmacology of progestins. Maturitas. 2008 Sep-Oct;61(1-2):171-80. Pubmed
  • • Orme LM, Bond JD, Humphrey MS, Zacharin MR, Downie PA, Jamsen KM, Mitchell SL, Robinson JM, Grapsas NA, Ashley DM: Megestrol acetate in pediatric oncology patients may lead to severe, symptomatic adrenal suppression. Cancer. 2003 Jul 15;98(2):397-405. Pubmed
  • • Dea-Ayuela, M., et al.: Bioorg. Med. Chem., 16, 7770 (2008)
  • • Santana, L., et al.: J. Med. Chem., 51, 6740 (2008)
  • • Gonzalez-Diaz, H., et al.: Curr. Pharm. Des., 16, 2737 (2008)
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PATENTS

PATENTS

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