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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H32O
Molecular Weight 300.4782
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALLYLESTRENOL

SMILES

[H][C@@]12CC[C@@](O)(CC=C)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCCC=C4CC[C@@]23[H]

InChI

InChIKey=ATXHVCQZZJYMCF-XUDSTZEESA-N
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

HIDE SMILES / InChI

Molecular Formula C21H32O
Molecular Weight 300.4782
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Allylestrenol (INN) (brand names Gestanon, Gestanin, Orageston, Turinal, Gestin, others), or allyloestrenol (BAN), also known as 17α-allylestr-4-en-17β-ol or as 3-deketo-17α-allyl-19-nortestosterone, is a synthetic steroid with progestational activity, that is used to prevent threatened miscarriage, recurrent pregnancy loss, and premature labor. Allylestrenol has also been studied as a treatment for benign prostatic hyperplasia in men, with encouraging results. Although it is less potent as a progestogen relative to many other 19-nortestosterone derivatives, allylestrenol is said to be virtually devoid of androgenic, estrogenic, or glucocorticoid activity, and hence, unlike virtually all other 19-nortestosterone derivatives, appears to be a pure progestogen with similar effects to those of progesterone. Allylestrenol 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.

Originator

Sources: Chem. and Ind. (London), Pages 905, Journal, 1959

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Allynol

Approved Use

Unknown
Preventing
Allynol

Approved Use

Unknown
Preventing
Allynol

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of tamoxifen treatment at adolescent age on the sexual behaviour and steroid hormone receptor binding of adult female rats.
2001
Similarities and dissimilarities of newborn and adolescent rats in the binding capacity of thymic glucocorticoid receptors.
2001 Mar
[Clinical effects of allylestrenol on patients with benign prostatic hyperplasia (BPH) evaluated with criteria for treatment efficacy in BPH].
2002 May
Effect of anti-estrogens on the androgen receptor activity and cell proliferation in prostate cancer cells.
2004 Dec
Recovery of serum prostate specific antigen value after interruption of antiandrogen therapy with allylestrenol for benign prostatic hyperplasia.
2006 Jul
Effects of steroidal and non-steroidal antiandrogens on wild-type and mutant androgen receptors.
2007 Jun 1
Application of a sensitive liquid chromatographic/tandem mass spectrometric method to a pharmacokinetic study of allylestrenol in healthy Chinese female volunteers.
2008 Aug 1
Patents

Patents

Sample Use Guides

Adult: PO- The recommended dose is 10 to 40 mg per day 1 week.
Route of Administration: Oral
PC-3 cells were transfected with a DNA mixture containing pMMTV-luc reporter (1 lg), pSG5AR (960 ng), and pRL-TK (40 ng), and grown for 24 h. Then, 5 nM of DHT with/ without allylestrenol was added. The cells were incubated for another 24 h and luciferase activities were measured.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:12:38 UTC 2023
Edited
by admin
on Fri Dec 15 15:12:38 UTC 2023
Record UNII
I47VB5DZ8O
Record Status Validated (UNII)
Record Version
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Name Type Language
ALLYLESTRENOL
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
Allylestrenol [WHO-DD]
Common Name English
ALLYLESTRENOL [MI]
Common Name English
ALLYLESTRENOL [MART.]
Common Name English
ALLYLESTRENOL [JAN]
Common Name English
17.ALPHA.-ALLYLESTR-4-EN-17.BETA.-OL
Common Name English
NSC-37723
Code English
ALLYLOESTRENOL
Common Name English
allylestrenol [INN]
Common Name English
PERSELIN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C776
Created by admin on Fri Dec 15 15:12:38 UTC 2023 , Edited by admin on Fri Dec 15 15:12:38 UTC 2023
WHO-ATC G03DC01
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WHO-VATC QG03DC01
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Code System Code Type Description
NSC
37723
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EVMPD
SUB05339MIG
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EPA CompTox
DTXSID9022574
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CAS
432-60-0
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ChEMBL
CHEMBL2105618
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SMS_ID
100000087457
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PUBCHEM
235905
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MESH
D000500
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DRUG CENTRAL
125
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PRIMARY
RXCUI
525
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PRIMARY RxNorm
INN
953
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NCI_THESAURUS
C80270
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PRIMARY
DRUG BANK
DB01431
Created by admin on Fri Dec 15 15:12:38 UTC 2023 , Edited by admin on Fri Dec 15 15:12:38 UTC 2023
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FDA UNII
I47VB5DZ8O
Created by admin on Fri Dec 15 15:12:38 UTC 2023 , Edited by admin on Fri Dec 15 15:12:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-082-9
Created by admin on Fri Dec 15 15:12:38 UTC 2023 , Edited by admin on Fri Dec 15 15:12:38 UTC 2023
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WIKIPEDIA
ALLYLESTRENOL
Created by admin on Fri Dec 15 15:12:38 UTC 2023 , Edited by admin on Fri Dec 15 15:12:38 UTC 2023
PRIMARY
MERCK INDEX
m1552
Created by admin on Fri Dec 15 15:12:38 UTC 2023 , Edited by admin on Fri Dec 15 15:12:38 UTC 2023
PRIMARY Merck Index
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY