ContaminantDB: Megestrol acetate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:28:23 UTC

Update Date

2016-11-09 01:15:37 UTC

Accession Number

CHEM017577

Identification

Common Name

Megestrol acetate

Class

Small Molecule

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.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Megace	Kegg
Megestrol acetic acid	Generator
Mestrel	MeSH
Nu megestrol	MeSH
NuMegestrol	MeSH
apo Megestrol	MeSH
Lin megestrol	MeSH
Nu-megestrol	MeSH
Nu-pharm brand OF megestrol acetate	MeSH
LinMegestrol	MeSH
Prasfarma brand OF megestrol acetate	MeSH
apo-Megestrol	MeSH
ApoMegestrol	MeSH
Bristol-myers squibb brand OF megestrol acetate	MeSH
Maygace	MeSH
Borea	MeSH
Linson pharma brand OF megestrol acetate	MeSH
Megestat	MeSH
Megostat	MeSH
Apotex brand OF megestrol acetate	MeSH
Bristol-myers brand OF megestrol acetate	MeSH
Lin-megestrol	MeSH
Acetate, megestrol	MeSH
Bristol myers brand OF megestrol acetate	MeSH
Lemery brand OF megestrol acetate	MeSH
Nu pharm brand OF megestrol acetate	MeSH
Bristol myers squibb brand OF megestrol acetate	MeSH
Madaus brand OF megestrol acetate	MeSH
Megefren	MeSH
Squibb brand OF megestrol acetate	MeSH

Chemical Formula

C₂₄H₃₂O₄

Average Molecular Mass

384.516 g/mol

Monoisotopic Mass

384.230 g/mol

CAS Registry Number

595-33-5

IUPAC Name

(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

Traditional Name

DMAP

SMILES

[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=C(C)C2=CC(=O)CC[C@]12C

InChI Identifier

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

InChI Key

RQZAXGRLVPAYTJ-GQFGMJRRSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
Steroid ester
3-oxosteroid
Oxosteroid
Cyclohexenone
Alpha-acyloxy ketone
Ketone
Carboxylic acid ester
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C08151 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030118 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	0.0034 g/L	ALOGPS
logP	3.71	ALOGPS
logP	3.72	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	17.83	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.66 m³·mol⁻¹	ChemAxon
Polarizability	43.51 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	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	View
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-002r-0379000000-6d73cd082b939b89d5ce	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-060r-2890000000-fa2ec02a8c51a731cc7b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00n0-0497000000-046272fbcad7d1d41298	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0009000000-59a0980387ea4612f8f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00mo-0059000000-5a746fc4d3061ff006bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v4i-1981000000-0886e38a4167a0cb7c1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001l-1009000000-3ddafe06b118017c8af5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000x-2029000000-ae6024f2a71c21be2d49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6v-9067000000-723980bd7c6c229868b9	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00351

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Megestrol acetate

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

11683

Kegg Compound ID

C08151

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Megestrol acetate (CHEM017577)

Structure for CHEM017577: Megestrol acetate