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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H28O3
Molecular Weight 316.4345
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 17.BETA.-CARBOXYANDROST-4-EN-3-ONE

SMILES

[H][C@@]12CC[C@H](C(O)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=YQACAXHKQZCEOI-UDCWSGSHSA-N
InChI=1S/C20H28O3/c1-19-9-7-13(21)11-12(19)3-4-14-15-5-6-17(18(22)23)20(15,2)10-8-16(14)19/h11,14-17H,3-10H2,1-2H3,(H,22,23)/t14-,15-,16-,17+,19-,20-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/3783591

17β-Carboxyandrost-4-en-3-one is an intermediate in the synthesis of the drugs Dutasteride (D735000) and Finasteride. 17β-Carboxyandrost-4-en-3-one shows weak inhibition of Steroid 5-alpha-reductase and Androgen Receptor antagonism.

Originator

Sources: Helvetica Chimica Acta (1940), 23, 400-4

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
660.0 nM [IC50]
8900.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Development of a progesterone immunosensor based on thionine-graphene oxide composites platforms: Improvement by biotin-streptavidin-amplified system.
2017 Aug 1
Patents

Patents

Sample Use Guides

1.5 mg/rat two times daily
Route of Administration: Other
In Vitro Use Guide
Human benign prostatic hypertrophy tissue that had been obtained by surgery and quickly frozen and stored at -70 "C served as the source of the enzyme. Typically, a 1.8-g portion was thawed, minced, and homogenized in 0.25 M sucrose buffer. The homogenate was centrifuged at 1200 rpm for 10 min, and the supernate was discarded. After the pellet was washed three times in buffer, it was suspended in buffer so that 1.0 mL contained about 300 mg of homogenized tissue. This suspension (0.1 mL) was incubated with 0.01 mL of inhibitor (2g, 17β-Carboxyandrost-4-en-3-one) and 0.1 mL of a mixture containing [3H]testosterone, unlabeled testosterone and dihydrotestosterone, glucose 6-phosphate, glucose-6-phosphate dehydrogenase, and NADP for 30 min at 37 "C. After the incubation, the steroids were extracted with 3.0 mL of ethyl acetate, and the organic phase was separated and evaporated under N2 This extract was spotted onto TLC plates. After the TLC plates were developed in ethyl acetate-cyclohexane (l:l), the [3H]DHT zone was scraped from the plate and counted.
Name Type Language
17.BETA.-CARBOXYANDROST-4-EN-3-ONE
Systematic Name English
3-OXOANDROST-4-ENE-17.BETA.-CARBOXYLIC ACID
Systematic Name English
SKF-106224
Code English
AD-ACID
Common Name English
CC-14837
Code English
AL-3793
Code English
TESTOSTERONE-17.BETA.-CARBOXYLIC ACID
Common Name English
ANDROST-4-ENE-17.BETA.-CARBOXYLIC ACID, 3-OXO-
Common Name English
L-552.803
Code English
NSC-226121
Code English
ANDROST-4-ENE-17-CARBOXYLIC ACID, 3-OXO-, (17.BETA.)-
Common Name English
ETIENIC ACID
Common Name English
Code System Code Type Description
CAS
302-97-6
Created by admin on Fri Dec 15 15:58:44 GMT 2023 , Edited by admin on Fri Dec 15 15:58:44 GMT 2023
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PUBCHEM
99472
Created by admin on Fri Dec 15 15:58:44 GMT 2023 , Edited by admin on Fri Dec 15 15:58:44 GMT 2023
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FDA UNII
6E3DV757KY
Created by admin on Fri Dec 15 15:58:44 GMT 2023 , Edited by admin on Fri Dec 15 15:58:44 GMT 2023
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EPA CompTox
DTXSID0057706
Created by admin on Fri Dec 15 15:58:44 GMT 2023 , Edited by admin on Fri Dec 15 15:58:44 GMT 2023
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NSC
226121
Created by admin on Fri Dec 15 15:58:44 GMT 2023 , Edited by admin on Fri Dec 15 15:58:44 GMT 2023
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