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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyAllylestrenol
Identification
- Name
- Allylestrenol
- Accession Number
- DB01431
- Type
- Small Molecule
- Groups
- Experimental
- 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
Structure for Allylestrenol (DB01431)
- Synonyms
- 17α-allylestr-4-en-17β-ol
- 3-deketo-17α-allyl-19-nortestosterone
- Alilestrenol
- Allilestrenolo
- Allyl estrenol
- Allylestrenol
- Allylestrenolum
- Allyloestrenol
- External IDs
- NSC-37723
- International/Other Brands
- Gestanin / Gestanol / Gestanon / Gestin / Gestrenol / Maintaine / Orageston / Perselin / Profar / Turinal
- Categories
- Adrenal Cortex Hormones
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates (strength unknown)
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Estranes
- Estren Derivatives
- Estrenes
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Progestins
- Sex Hormones and Modulators of the Genital System
- Steroids
- 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][C@@]12CC[C@@](O)(CC=C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]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.
- 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 Actions Organism AProgesterone receptor agonistHumans UEstrogen receptor alpha agonistHumans - 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
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional Data(R)-warfarin Allylestrenol may decrease the anticoagulant activities of (R)-warfarin. (S)-Warfarin Allylestrenol may decrease the anticoagulant activities of (S)-Warfarin. 4-hydroxycoumarin The metabolism of 4-hydroxycoumarin can be decreased when combined with Allylestrenol. 6-Deoxyerythronolide B The metabolism of Allylestrenol can be decreased when combined with 6-Deoxyerythronolide B. 7-ethyl-10-hydroxycamptothecin The metabolism of Allylestrenol can be decreased when combined with 7-ethyl-10-hydroxycamptothecin. 9-aminocamptothecin The metabolism of 9-aminocamptothecin can be decreased when combined with Allylestrenol. Abacavir Abacavir may decrease the excretion rate of Allylestrenol which could result in a higher serum level. Abatacept The metabolism of Allylestrenol can be increased when combined with Abatacept. Abciximab Allylestrenol may decrease the anticoagulant activities of Abciximab. Abiraterone The metabolism of Abiraterone can be decreased when combined with Allylestrenol. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015500
- KEGG Drug
- D01374
- KEGG Compound
- C12811
- PubChem Compound
- 235905
- PubChem Substance
- 46506946
- ChemSpider
- 205855
- RxNav
- 525
- ChEBI
- 31189
- ChEMBL
- CHEMBL3185133
- ZINC
- ZINC000004214767
- Therapeutic Targets Database
- DPR000085
- PharmGKB
- PA164745307
- Wikipedia
- Allylestrenol
- ATC Codes
- G03DC01 — Allylestrenol
Clinical Trials
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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS 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
- Kind
- Protein
- Organism
- Humans
- 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 ...
- 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]
- Kind
- Protein
- Organism
- Humans
- 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 tissu...
- 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]
Drug created on July 24, 2007 10:58 / Updated on May 02, 2020 03:29
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