Allylestrenol
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Allylestrenol
structure -
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CAS No:
432-60-0
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Formula:
C21H32O
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Chemical Name:
Allylestrenol
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Synonyms:
Estr-4-en-17-ol,17-(2-propen-1-yl)-,(17β)-;Estr-4-en-17β-ol,17-allyl-;Estr-4-en-17-ol,17-(2-propenyl)-,(17β)-;(17β)-17-(2-Propen-1-yl)estr-4-en-17-ol;Allylestrenol;17α-Allylestr-4-en-17β-ol;17α-Allyl-17β-hydroxy-Δ4-estren;Gestanin;Gestanon;17α-Allylestrenol;Gestanol;Orageston;Turinal;17α-Allyl-4-oestren-17β-ol;NSC 37723;26624-23-7
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Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System
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CAS No:
Description
Allylestrenol, a synthetic sexualsteroid, is used worldwide in case of endangered pregnancies.
Solid
Allylestrenol is a steroid. It derives from a hydride of an estrane.|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.|A synthetic steroid with progestational activity.
Allylestrenol Basic Attributes
300.48
300.48
207-082-9
I47VB5DZ8O
37723
DTXSID9022574
G - Genito urinary system and sex hormones
Characteristics
20.2
6.64
Solid
1.0±0.1 g/cm3
80 °C
405.4±44.0 °C at 760 mmHg
170.6±20.7 °C
1.553
5.58e-04 g/L
2.92E-08mmHg at 25°C
Oral-Mouse LD50: >640 mg/kg
Flammable; burning produces irritating fumes
Safety Information
KG7960000
Treasury is ventilated, low temperature and dry; stored separately from food materials
P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P405, P501
H302
Drug Information
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.
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.
Compounds that interact with PROGESTERONE RECEPTORS in target tissues to bring about the effects similar to those of PROGESTERONE. Primary actions of progestins, including natural and synthetic steroids, are on the UTERUS and the MAMMARY GLAND in preparation for and in maintenance of PREGNANCY. (See all compounds classified as Progestins.)
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.
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.
Allylestrenol
Allylestrenol Use and Manufacturing
A synthetic steroid with progestational activity.
Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
Computed Properties
Molecular Weight:300.5
XLogP3:5.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:300.245315640
Monoisotopic Mass:300.245315640
Topological Polar Surface Area:20.2
Heavy Atom Count:22
Complexity:492
Defined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Extract from the above information
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