Melengestrol

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Melengestrol
Accession Number
DB11529
Type
Small Molecule
Groups
Vet approved
Description

Melengestrol is a steroidal progestin and antineoplastic agent which was never marketed. An acylated derivative, melengestrol acetate, is used as a growth promoter in animals.

Structure
Thumb
Synonyms
  • Melengesterol
  • Melengestrel
  • Melengestrolo
  • Melengestrolum
External IDs
BDH-1921
Categories
UNII
BX98J4T6JU
CAS number
5633-18-1
Weight
Average: 354.49
Monoisotopic: 354.219494826
Chemical Formula
C23H30O3
InChI Key
OKHAOBQKCCIRLO-IBVJIVQJSA-N
InChI
InChI=1S/C23H30O3/c1-13-10-17-18(21(4)8-6-16(25)12-19(13)21)7-9-22(5)20(17)11-14(2)23(22,26)15(3)24/h10,12,17-18,20,26H,2,6-9,11H2,1,3-5H3/t17-,18+,20+,21-,22+,23+/m1/s1
IUPAC Name
(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyl-13-methylidenetetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one
SMILES
[H][C@@]12CC(=C)[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=C(C)C2=CC(=O)CC[C@]12C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Melengestrol.
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Melengestrol is combined with 1,10-Phenanthroline.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Melengestrol.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Melengestrol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Melengestrol.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Melengestrol.
AlclofenacThe risk or severity of adverse effects can be increased when Alclofenac is combined with Melengestrol.
AlclometasoneThe risk or severity of adverse effects can be increased when Melengestrol is combined with Alclometasone.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Melengestrol.
AlemtuzumabThe risk or severity of adverse effects can be increased when Alemtuzumab is combined with Melengestrol.
Food Interactions
Not Available

References

General References
  1. Kountz SL, Wechter WJ: Immunosuppression with melengestrol. Transplant Proc. 1977 Jun;9(2):1447-53. [PubMed:327640]
  2. Cooper JM, Elce JS, Kellie AE: The metabolism of melengestrol acetate. Biochem J. 1967 Sep;104(3):57P-58P. [PubMed:6049897]
  3. DUNCAN GW, LYSTER SC, HENDRIX JW, CLARK JJ, WEBSTER HD: BIOLOGIC EFFECTS OF MELENGESTROL ACETATE. Fertil Steril. 1964 Jul-Aug;15:416-32. [PubMed:14192473]
  4. Pritchard DE, Wettemann RP, Hafs HD: Fertility of rabbits after melengestrol acetate administration. J Anim Sci. 1970 Oct;31(4):729-32. [PubMed:5465999]
  5. Herrick JB: Answers to questions about MGA (melengestrol acetate). Vet Med Small Anim Clin. 1974 Aug;69(8):1040-2. [PubMed:4495779]
  6. Krzeminski LF, Cox BL: Electron capture determination of melengestrol acetate in bovine tissue. J Assoc Off Anal Chem. 1973 Jan;56(1):74-6. [PubMed:4781045]
  7. Krzeminski LF, Geng S, Cox BL: Determination of melengestrol acetate in bovine tissue: collaborative study. J Assoc Off Anal Chem. 1976 May;59(3):507-15. [PubMed:1270378]
  8. Nugent CA, Bressler R, Kayan S, Worrall P: Suppression of cortisol by a progestational steroid, melengestrol. Clin Pharmacol Ther. 1975 Sep;18(3):338-44. [PubMed:1100303]
  9. Sud SC: Synchronization of estrus in cows with melengestrol acetate. Indian J Exp Biol. 1971 Oct;9(4):498-9. [PubMed:5169599]
  10. Sokolowski JH, VanRavenswaay F: Effects of melengestrol acetate on reproduction in the Beagle bitch. Am J Vet Res. 1976 Aug;37(8):943-5. [PubMed:949121]
External Links
ChemSpider
8082266
Wikipedia
Melengestrol

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00748 mg/mLALOGPS
logP3.02ALOGPS
logP3.38ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity103.68 m3·mol-1ChemAxon
Polarizability40.91 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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
20-oxosteroids / 3-oxosteroids / 17-hydroxysteroids / Cyclohexenones / Tertiary alcohols / Alpha-hydroxy ketones / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Progestogin-skeleton / 20-oxosteroid / 3-oxosteroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Cyclohexenone / Alpha-hydroxy ketone / Cyclic alcohol / Tertiary alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Melegestrol acetate, Australia [File]

Drug created on February 26, 2016 10:36 / Updated on September 07, 2018 03:27