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Identification
NameAllylestrenol
Accession NumberDB01431
Typesmall molecule
Groupsapproved
Description

A synthetic steroid with progestational activity. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
Allyl estrenolNot AvailableNot Available
AllyloestrenolNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
GestaninNot Available
GestanolNot Available
GestanonNot Available
GestinNot Available
GestrenolNot Available
MaintaineNot Available
OragestonNot Available
ProfarNot Available
TurinalNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number432-60-0
WeightAverage: 300.4782
Monoisotopic: 300.245315646
Chemical FormulaC21H32O
InChI KeyATXHVCQZZJYMCF-XUDSTZEESA-N
InChI
InChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1
IUPAC Name
(1S,2R,10R,11S,14R,15S)-15-methyl-14-(prop-2-en-1-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
SMILES
[H][C@@]12CC[C@@](O)(CC=C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassHydroxysteroids
Direct parentHydroxysteroids
Alternative parentsEstrogens and Derivatives; Tertiary Alcohols; Cyclic Alcohols and Derivatives; Polyamines
Substituentscyclic alcohol; tertiary alcohol; polyamine; alcohol
Classification descriptionThis compound belongs to the hydroxysteroids. These are compounds containing an steroid backbone, with at least one hydrogen substituted by an hydroxyl group.
Pharmacology
IndicationAllylestrenol was designed to be used for miscarriage prevention, prevention of premature labour and has been investigated for possible use in men for treatment for benign prostatic hyperplasia.
PharmacodynamicsAllylestrenol is a progestogen structurally related to progesterone that has been given in threatened and recurrent miscarriage, and to prevent premature labour. However, with the exception of proven progesterone deficiency, such use is no longer recommended. In threatened miscarriage in progesterone-deficient women a suggested dose is 5 mg three times daily by mouth for 5 to 7 days.
Mechanism of actionAllylestrenol is similar in structure and function to progesterone. Progesterone shares the pharmacological actions of the progestins. Progesterone binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Progesterone will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. In women who have adequate endogenous estrogen, progesterone transforms a proliferative endometrium into a secretory one. Progesterone is essential for the development of decidual tissue and is necessary to increase endometrial receptivity for implantation of an embryo. Once an embryo has been implanted, progesterone acts to maintain the pregnancy. Progesterone also stimulates the growth of mammary alveolar tissue and relaxes uterine smooth muscle. It has little estrogenic and androgenic activity.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationThe glucuronide and sulfate conjugates of pregnanediol and pregnanolone are excreted in the urine and bile. Progesterone metabolites which are excreted in the bile may undergo enterohepatic recycling or may be excreted in the feces. Progesterone metabolites are excreted mainly by the kidneys.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9966
Blood Brain Barrier + 0.9817
Caco-2 permeable + 0.8469
P-glycoprotein substrate Substrate 0.6615
P-glycoprotein inhibitor I Inhibitor 0.5781
P-glycoprotein inhibitor II Non-inhibitor 0.795
Renal organic cation transporter Non-inhibitor 0.6625
CYP450 2C9 substrate Non-substrate 0.807
CYP450 2D6 substrate Non-substrate 0.9046
CYP450 3A4 substrate Substrate 0.6941
CYP450 1A2 substrate Non-inhibitor 0.8345
CYP450 2C9 substrate Non-inhibitor 0.8006
CYP450 2D6 substrate Non-inhibitor 0.9427
CYP450 2C19 substrate Inhibitor 0.5498
CYP450 3A4 substrate Non-inhibitor 0.8408
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6449
Ames test Non AMES toxic 0.936
Carcinogenicity Non-carcinogens 0.9458
Biodegradation Not ready biodegradable 0.9828
Rat acute toxicity 2.4200 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.6669
hERG inhibition (predictor II) Non-inhibitor 0.7541
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point80 °CPhysProp
Predicted Properties
PropertyValueSource
water solubility5.58e-04 g/lALOGPS
logP5.14ALOGPS
logP4.83ChemAxon
logS-5.7ALOGPS
pKa (strongest basic)-0.17ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count2ChemAxon
refractivity93.14ChemAxon
polarizability37.17ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD01374
KEGG CompoundC12811
PubChem Compound235905
PubChem Substance46506946
ChemSpider205855
Therapeutic Targets DatabaseDPR000085
PharmGKBPA164745307
ATC CodesG03DC01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Progesterone receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Progesterone receptor P06401 Details

References:

  1. Madauss KP, Stewart EL, Williams SP: The evolution of progesterone receptor ligands. Med Res Rev. 2007 May;27(3):374-400. Pubmed
  2. Gizard F, Robillard R, Gross B, Barbier O, Revillion F, Peyrat JP, Torpier G, Hum DW, Staels B: TReP-132 is a novel progesterone receptor coactivator required for the inhibition of breast cancer cell growth and enhancement of differentiation by progesterone. Mol Cell Biol. 2006 Oct;26(20):7632-44. Pubmed
  3. Wu HB, Fabian S, Jenab S, Quinones-Jenab V: Progesterone receptors activation after acute cocaine administration. Brain Res. 2006 Dec 18;1126(1):188-92. Epub 2006 Nov 15. Pubmed
  4. Boonyaratanakornkit V, McGowan E, Sherman L, Mancini MA, Cheskis BJ, Edwards DP: The role of extranuclear signaling actions of progesterone receptor in mediating progesterone regulation of gene expression and the cell cycle. Mol Endocrinol. 2007 Feb;21(2):359-75. Epub 2006 Nov 30. Pubmed
  5. Tranguch S, Smith DF, Dey SK: Progesterone receptor requires a co-chaperone for signalling in uterine biology and implantation. Reprod Biomed Online. 2006 Nov;13(5):651-60. Pubmed
  6. Bergink EW, Loonen PB, Kloosterboer HJ: Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties. J Steroid Biochem. 1985 Aug;23(2):165-8. Pubmed

2. Estrogen receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Estrogen receptor P03372 Details

References:

  1. Kumar AS, Cureton E, Shim V, Sakata T, Moore DH, Benz CC, Esserman LJ, Hwang ES: Type and duration of exogenous hormone use affects breast cancer histology. Ann Surg Oncol. 2007 Feb;14(2):695-703. Epub 2006 Nov 14. Pubmed
  2. Lessey BA, Palomino WA, Apparao K, Young SL, Lininger RA: Estrogen receptor-alpha (ER-alpha) and defects in uterine receptivity in women. Reprod Biol Endocrinol. 2006 Oct 9;4 Suppl 1:S9. Pubmed
  3. Yuri T, Tsukamoto R, Uehara N, Matsuoka Y, Tsubura A: Effects of different durations of estrogen and progesterone treatment on development of N-methyl-N-nitrosourea-induced mammary carcinomas in female Lewis rats. In Vivo. 2006 Nov-Dec;20(6B):829-36. Pubmed
  4. Montero Girard G, Vanzulli SI, Cerliani JP, Bottino MC, Bolado J, Vela J, Becu-Villalobos D, Benavides F, Gutkind S, Patel V, Molinolo A, Lanari C: Association of estrogen receptor-alpha and progesterone receptor A expression with hormonal mammary carcinogenesis: role of the host microenvironment. Breast Cancer Res. 2007;9(2):R22. Pubmed
  5. Ghebeh H, Tulbah A, Mohammed S, Elkum N, Bin Amer SM, Al-Tweigeri T, Dermime S: Expression of B7-H1 in breast cancer patients is strongly associated with high proliferative Ki-67-expressing tumor cells. Int J Cancer. 2007 Aug 15;121(4):751-8. Pubmed
  6. Csaba G, Gonda AI, Karabelyos C: Contraceptive treatment increases the affinity of uterine estrogen receptor in adult rat: perinatal gestagen treatment changes the reaction. Horm Metab Res. 1996 Jan;28(1):16-9. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on July 24, 2007 10:58 / Updated on September 16, 2013 17:14