Allylestrenol - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (2)Enzymes (1)

Targets (2)Enzymes (1)Biointeractions (3)

Identification

Name

Allylestrenol

Accession Number

DB01431

Type

Small Molecule

Groups

Approved

Description

A synthetic steroid with progestational activity. It is widely marketed throughout Europe, including Russia and many other European countries, and is also available in Japan, Hong Kong, India, Bangladesh, Indonesia, and much of Southeast Asia, though notably not in the United States or Canada.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

17α-allylestr-4-en-17β-ol

3-deketo-17α-allyl-19-nortestosterone

Allyl estrenol

Allyloestrenol

External IDs

NSC-37723

Product Ingredients

Not Available

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Gestanin	Not Available
Gestanol	Not Available
Gestanon	Not Available
Gestin	Not Available
Gestrenol	Not Available
Maintaine	Not Available
Orageston	Not Available
Perselin	Not Available
Profar	Not Available
Turinal	Not Available

Brand mixtures

Not Available

Categories

UNII

I47VB5DZ8O

CAS number

432-60-0

Weight

Average: 300.4782
Monoisotopic: 300.245315646

Chemical Formula

C₂₁H₃₂O

InChI Key

ATXHVCQZZJYMCF-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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-ol

SMILES

[H][[email protected]@]12CC[[email protected]@](O)(CC=C)[[email protected]@]1(C)CC[[email protected]]1([H])[[email protected]@]3([H])CCCC=C3CC[[email protected]@]21[H]

Pharmacology

Indication

Allylestrenol 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.

Structured Indications

Not Available

Pharmacodynamics

Allylestrenol 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 action

Allylestrenol 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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Progesterone receptor	Protein	yes	agonist	Human	P06401	details
Estrogen receptor alpha	Protein	unknown	agonist	Human	P03372	details

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

The 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 life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
Abciximab	The therapeutic efficacy of Abciximab can be decreased when used in combination with Allylestrenol.	Approved
Acenocoumarol	The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Allylestrenol.	Approved
Amiodarone	The metabolism of Allylestrenol can be decreased when combined with Amiodarone.	Approved, Investigational
Ancrod	The therapeutic efficacy of Ancrod can be decreased when used in combination with Allylestrenol.	Investigational
Antithrombin III human	The therapeutic efficacy of Antithrombin III human can be decreased when used in combination with Allylestrenol.	Approved
Apixaban	The therapeutic efficacy of Apixaban can be decreased when used in combination with Allylestrenol.	Approved
Aprepitant	The serum concentration of Allylestrenol can be increased when it is combined with Aprepitant.	Approved, Investigational
Ardeparin	The therapeutic efficacy of Ardeparin can be decreased when used in combination with Allylestrenol.	Approved, Withdrawn
Argatroban	The therapeutic efficacy of Argatroban can be decreased when used in combination with Allylestrenol.	Approved, Investigational
Atazanavir	The metabolism of Allylestrenol can be decreased when combined with Atazanavir.	Approved, Investigational
Atomoxetine	The metabolism of Allylestrenol can be decreased when combined with Atomoxetine.	Approved
Becaplermin	The therapeutic efficacy of Becaplermin can be decreased when used in combination with Allylestrenol.	Approved, Investigational
Bexarotene	The serum concentration of Allylestrenol can be decreased when it is combined with Bexarotene.	Approved, Investigational
Bivalirudin	The therapeutic efficacy of Bivalirudin can be decreased when used in combination with Allylestrenol.	Approved, Investigational
Boceprevir	The metabolism of Allylestrenol can be decreased when combined with Boceprevir.	Withdrawn
Bortezomib	The metabolism of Allylestrenol can be decreased when combined with Bortezomib.	Approved, Investigational
Bosentan	The serum concentration of Allylestrenol can be decreased when it is combined with Bosentan.	Approved, Investigational
Carbamazepine	The metabolism of Allylestrenol can be increased when combined with Carbamazepine.	Approved, Investigational
Ceritinib	The serum concentration of Allylestrenol can be increased when it is combined with Ceritinib.	Approved
Certoparin	The therapeutic efficacy of Certoparin can be decreased when used in combination with Allylestrenol.	Approved
Citric Acid	The therapeutic efficacy of Citric Acid can be decreased when used in combination with Allylestrenol.	Nutraceutical, Vet Approved
Clarithromycin	The metabolism of Allylestrenol can be decreased when combined with Clarithromycin.	Approved
Clemastine	The metabolism of Allylestrenol can be decreased when combined with Clemastine.	Approved
Clotrimazole	The metabolism of Allylestrenol can be decreased when combined with Clotrimazole.	Approved, Vet Approved
Cobicistat	The metabolism of Allylestrenol can be decreased when combined with Cobicistat.	Approved
Conestat alfa	Allylestrenol may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).	Approved
Conivaptan	The serum concentration of Allylestrenol can be increased when it is combined with Conivaptan.	Approved, Investigational
Crizotinib	The metabolism of Allylestrenol can be decreased when combined with Crizotinib.	Approved
Cyclosporine	The metabolism of Allylestrenol can be decreased when combined with Cyclosporine.	Approved, Investigational, Vet Approved
Dabigatran etexilate	The therapeutic efficacy of Dabigatran etexilate can be decreased when used in combination with Allylestrenol.	Approved
Dabrafenib	The serum concentration of Allylestrenol can be decreased when it is combined with Dabrafenib.	Approved
Dalteparin	The therapeutic efficacy of Dalteparin can be decreased when used in combination with Allylestrenol.	Approved
Danaparoid	The therapeutic efficacy of Danaparoid can be decreased when used in combination with Allylestrenol.	Approved, Withdrawn
Darexaban	The therapeutic efficacy of Ym150 can be decreased when used in combination with Allylestrenol.	Investigational
Darunavir	The metabolism of Allylestrenol can be decreased when combined with Darunavir.	Approved
Dasatinib	The serum concentration of Allylestrenol can be increased when it is combined with Dasatinib.	Approved, Investigational
Deferasirox	The serum concentration of Allylestrenol can be decreased when it is combined with Deferasirox.	Approved, Investigational
Delavirdine	The metabolism of Allylestrenol can be decreased when combined with Delavirdine.	Approved
Desirudin	The therapeutic efficacy of Desirudin can be decreased when used in combination with Allylestrenol.	Approved
Dexamethasone	The serum concentration of Allylestrenol can be decreased when it is combined with Dexamethasone.	Approved, Investigational, Vet Approved
Dextran	The therapeutic efficacy of Dextran can be decreased when used in combination with Allylestrenol.	Approved, Vet Approved
Dextran 40	The therapeutic efficacy of Dextran 40 can be decreased when used in combination with Allylestrenol.	Approved
Dextran 70	The therapeutic efficacy of Dextran 70 can be decreased when used in combination with Allylestrenol.	Approved
Dextran 75	The therapeutic efficacy of Dextran 75 can be decreased when used in combination with Allylestrenol.	Approved
Dicoumarol	The therapeutic efficacy of Dicoumarol can be decreased when used in combination with Allylestrenol.	Approved
Dihydroergotamine	The metabolism of Allylestrenol can be decreased when combined with Dihydroergotamine.	Approved
Diltiazem	The metabolism of Allylestrenol can be decreased when combined with Diltiazem.	Approved
Doxycycline	The metabolism of Allylestrenol can be decreased when combined with Doxycycline.	Approved, Investigational, Vet Approved
Dronedarone	The metabolism of Allylestrenol can be decreased when combined with Dronedarone.	Approved
Edetic Acid	The therapeutic efficacy of Edetic Acid can be decreased when used in combination with Allylestrenol.	Approved, Vet Approved
Edoxaban	The therapeutic efficacy of Edoxaban can be decreased when used in combination with Allylestrenol.	Approved
Efavirenz	The serum concentration of Allylestrenol can be decreased when it is combined with Efavirenz.	Approved, Investigational
Enoxaparin	The therapeutic efficacy of Enoxaparin can be decreased when used in combination with Allylestrenol.	Approved
Enzalutamide	The serum concentration of Allylestrenol can be decreased when it is combined with Enzalutamide.	Approved
Erythromycin	The metabolism of Allylestrenol can be decreased when combined with Erythromycin.	Approved, Vet Approved
Eslicarbazepine acetate	The serum concentration of Allylestrenol can be decreased when it is combined with Eslicarbazepine acetate.	Approved
Ethyl biscoumacetate	The therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Allylestrenol.	Withdrawn
Etravirine	The serum concentration of Allylestrenol can be decreased when it is combined with Etravirine.	Approved
Fluconazole	The metabolism of Allylestrenol can be decreased when combined with Fluconazole.	Approved
Fluindione	The therapeutic efficacy of Fluindione can be decreased when used in combination with Allylestrenol.	Investigational
Fluvoxamine	The metabolism of Allylestrenol can be decreased when combined with Fluvoxamine.	Approved, Investigational
Fondaparinux	The therapeutic efficacy of Fondaparinux can be decreased when used in combination with Allylestrenol.	Investigational
Fondaparinux sodium	The therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Allylestrenol.	Approved, Investigational
Fosamprenavir	The metabolism of Allylestrenol can be decreased when combined with Fosamprenavir.	Approved
Fosaprepitant	The serum concentration of Allylestrenol can be increased when it is combined with Fosaprepitant.	Approved
Fosphenytoin	The metabolism of Allylestrenol can be increased when combined with Fosphenytoin.	Approved
Fusidic Acid	The serum concentration of Allylestrenol can be increased when it is combined with Fusidic Acid.	Approved
Gabexate	The therapeutic efficacy of Gabexate can be decreased when used in combination with Allylestrenol.	Investigational
Heparin	The therapeutic efficacy of Heparin can be decreased when used in combination with Allylestrenol.	Approved, Investigational
Human C1-esterase inhibitor	Allylestrenol may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).	Approved
Idelalisib	The serum concentration of Allylestrenol can be increased when it is combined with Idelalisib.	Approved
Idraparinux	The therapeutic efficacy of idraparinux can be decreased when used in combination with Allylestrenol.	Investigational
Imatinib	The metabolism of Allylestrenol can be decreased when combined with Imatinib.	Approved
Indinavir	The metabolism of Allylestrenol can be decreased when combined with Indinavir.	Approved
Isavuconazonium	The metabolism of Allylestrenol can be decreased when combined with Isavuconazonium.	Approved, Investigational
Isradipine	The metabolism of Allylestrenol can be decreased when combined with Isradipine.	Approved
Itraconazole	The metabolism of Allylestrenol can be decreased when combined with Itraconazole.	Approved, Investigational
Ivacaftor	The serum concentration of Allylestrenol can be increased when it is combined with Ivacaftor.	Approved
Ketoconazole	The metabolism of Allylestrenol can be decreased when combined with Ketoconazole.	Approved, Investigational
Lepirudin	The therapeutic efficacy of Lepirudin can be decreased when used in combination with Allylestrenol.	Approved
Lopinavir	The metabolism of Allylestrenol can be decreased when combined with Lopinavir.	Approved
Lovastatin	The metabolism of Allylestrenol can be decreased when combined with Lovastatin.	Approved, Investigational
Luliconazole	The serum concentration of Allylestrenol can be increased when it is combined with Luliconazole.	Approved
Lumacaftor	The metabolism of Allylestrenol can be increased when combined with Lumacaftor.	Approved
Mifepristone	The serum concentration of Allylestrenol can be increased when it is combined with Mifepristone.	Approved, Investigational
Mitotane	The serum concentration of Allylestrenol can be decreased when it is combined with Mitotane.	Approved
Modafinil	The serum concentration of Allylestrenol can be decreased when it is combined with Modafinil.	Approved, Investigational
Nadroparin	The therapeutic efficacy of Nadroparin can be decreased when used in combination with Allylestrenol.	Approved
Nafamostat	The therapeutic efficacy of Nafamostat can be decreased when used in combination with Allylestrenol.	Approved, Investigational
Nafcillin	The serum concentration of Allylestrenol can be decreased when it is combined with Nafcillin.	Approved
Nefazodone	The metabolism of Allylestrenol can be decreased when combined with Nefazodone.	Approved, Withdrawn
Nelfinavir	The metabolism of Allylestrenol can be decreased when combined with Nelfinavir.	Approved
Netupitant	The serum concentration of Allylestrenol can be increased when it is combined with Netupitant.	Approved
Nevirapine	The metabolism of Allylestrenol can be increased when combined with Nevirapine.	Approved
Nilotinib	The metabolism of Allylestrenol can be decreased when combined with Nilotinib.	Approved, Investigational
Olaparib	The metabolism of Allylestrenol can be decreased when combined with Olaparib.	Approved
Osimertinib	The serum concentration of Allylestrenol can be increased when it is combined with Osimertinib.	Approved
Otamixaban	The therapeutic efficacy of Otamixaban can be decreased when used in combination with Allylestrenol.	Investigational
Palbociclib	The serum concentration of Allylestrenol can be increased when it is combined with Palbociclib.	Approved
Pentobarbital	The metabolism of Allylestrenol can be increased when combined with Pentobarbital.	Approved, Vet Approved
Pentosan Polysulfate	The therapeutic efficacy of Pentosan Polysulfate can be decreased when used in combination with Allylestrenol.	Approved
Phenindione	The therapeutic efficacy of Phenindione can be decreased when used in combination with Allylestrenol.	Approved
Phenobarbital	The metabolism of Allylestrenol can be increased when combined with Phenobarbital.	Approved
Phenprocoumon	The therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Allylestrenol.	Approved
Phenytoin	The metabolism of Allylestrenol can be increased when combined with Phenytoin.	Approved, Vet Approved
Posaconazole	The metabolism of Allylestrenol can be decreased when combined with Posaconazole.	Approved, Investigational, Vet Approved
Primidone	The metabolism of Allylestrenol can be increased when combined with Primidone.	Approved, Vet Approved
Protein C	The therapeutic efficacy of Protein C can be decreased when used in combination with Allylestrenol.	Approved
Protein S human	The therapeutic efficacy of Protein S human can be decreased when used in combination with Allylestrenol.	Approved
Protocatechualdehyde	The therapeutic efficacy of Protocatechualdehyde can be decreased when used in combination with Allylestrenol.	Approved
Ranolazine	The metabolism of Allylestrenol can be decreased when combined with Ranolazine.	Approved, Investigational
Reviparin	The therapeutic efficacy of Reviparin can be decreased when used in combination with Allylestrenol.	Approved
Rifabutin	The metabolism of Allylestrenol can be increased when combined with Rifabutin.	Approved
Rifampicin	The metabolism of Allylestrenol can be increased when combined with Rifampicin.	Approved
Rifapentine	The metabolism of Allylestrenol can be increased when combined with Rifapentine.	Approved
Ritonavir	The metabolism of Allylestrenol can be decreased when combined with Ritonavir.	Approved, Investigational
Rivaroxaban	The therapeutic efficacy of Rivaroxaban can be decreased when used in combination with Allylestrenol.	Approved
Saquinavir	The metabolism of Allylestrenol can be decreased when combined with Saquinavir.	Approved, Investigational
Sildenafil	The metabolism of Allylestrenol can be decreased when combined with Sildenafil.	Approved, Investigational
Siltuximab	The serum concentration of Allylestrenol can be decreased when it is combined with Siltuximab.	Approved
Simeprevir	The serum concentration of Allylestrenol can be increased when it is combined with Simeprevir.	Approved
St. John's Wort	The serum concentration of Allylestrenol can be decreased when it is combined with St. John's Wort.	Nutraceutical
Stiripentol	The serum concentration of Allylestrenol can be increased when it is combined with Stiripentol.	Approved
Sulfisoxazole	The metabolism of Allylestrenol can be decreased when combined with Sulfisoxazole.	Approved, Vet Approved
Sulodexide	The therapeutic efficacy of Sulodexide can be decreased when used in combination with Allylestrenol.	Approved, Investigational
Telaprevir	The metabolism of Allylestrenol can be decreased when combined with Telaprevir.	Withdrawn
Telithromycin	The metabolism of Allylestrenol can be decreased when combined with Telithromycin.	Approved
Ticlopidine	The metabolism of Allylestrenol can be decreased when combined with Ticlopidine.	Approved
Tocilizumab	The serum concentration of Allylestrenol can be decreased when it is combined with Tocilizumab.	Approved
Ulipristal	The therapeutic efficacy of Allylestrenol can be decreased when used in combination with Ulipristal.	Approved
Venlafaxine	The metabolism of Allylestrenol can be decreased when combined with Venlafaxine.	Approved
Verapamil	The metabolism of Allylestrenol can be decreased when combined with Verapamil.	Approved
Voriconazole	The metabolism of Allylestrenol can be decreased when combined with Voriconazole.	Approved, Investigational
Warfarin	The therapeutic efficacy of Warfarin can be decreased when used in combination with Allylestrenol.	Approved
Ximelagatran	The therapeutic efficacy of Ximelagatran can be decreased when used in combination with Allylestrenol.	Approved, Investigational, Withdrawn
Ziprasidone	The metabolism of Allylestrenol can be decreased when combined with Ziprasidone.	Approved

Food Interactions

Not Available

References

Synthesis Reference

Not Available

General References

Not Available

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB15500
KEGG Drug	D01374
KEGG Compound	C12811
PubChem Compound	235905
PubChem Substance	46506946
ChemSpider	205855
ChEBI	31189
ChEMBL	CHEMBL3185133
Therapeutic Targets Database	DPR000085
PharmGKB	PA164745307

ATC Codes

G03DC01 — Allylestrenol

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Clinical Trials

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	80 °C	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.000558 mg/mL	ALOGPS
logP	5.14	ALOGPS
logP	4.83	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-0.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.14 m³·mol^-1	ChemAxon
Polarizability	37.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

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 inhibitor	Non-inhibitor	0.8006
CYP450 2D6 inhibitor	Non-inhibitor	0.9427
CYP450 2C19 inhibitor	Inhibitor	0.5498
CYP450 3A4 inhibitor	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

17-hydroxysteroids / Delta-4-steroids / Tertiary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives

Substituents

17-hydroxysteroid / Hydroxysteroid / Estrane-skeleton / Delta-4-steroid / Tertiary alcohol / Cyclic alcohol / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Alcohol

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid (CHEBI:31189 ) / Estrane and derivatives, C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C12811 ) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030125 )

Targets

Details

1. Progesterone receptor

Kind: Protein
Organism: Human
Pharmacological action: yes
Actions: agonist

General Function:: Zinc ion binding
Specific Function:: The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial ...
Gene Name:: PGR
Uniprot ID:: P06401
Uniprot Name:: Progesterone receptor
Molecular Weight:: 98979.96 Da

References

Madauss KP, Stewart EL, Williams SP: The evolution of progesterone receptor ligands. Med Res Rev. 2007 May;27(3):374-400. [PubMed:17013809 ]
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:17015480 ]
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:17109827 ]
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:17138644 ]
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:17169175 ]
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:3928974 ]

Details

2. Estrogen receptor alpha

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: agonist

General Function:: Zinc ion binding
Specific Function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:: ESR1
Uniprot ID:: P03372
Uniprot Name:: Estrogen receptor
Molecular Weight:: 66215.45 Da

References

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:17103262 ]
Lessey BA, Palomino WA, Apparao KB, Young SL, Lininger RA: Estrogen receptor-alpha (ER-alpha) and defects in uterine receptivity in women. Reprod Biol Endocrinol. 2006;4 Suppl 1:S9. [PubMed:17118173 ]
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:17203775 ]
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:17341305 ]
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:17415709 ]
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:8820988 ]

Enzymes

Details

1. Cytochrome P450 3A4

Kind: Protein
Organism: Human
Pharmacological action: unknown
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:: CYP3A4
Uniprot ID:: P08684
Uniprot Name:: Cytochrome P450 3A4
Molecular Weight:: 57342.67 Da

References

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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Drug created on July 24, 2007 10:58 / Updated on September 01, 2017 10:39

Structure for DB01431 (Allylestrenol)

Targets

References

References

Enzymes

References