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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H28O
Molecular Weight 272.425
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 5.ALPHA.-ANDROST-16-EN-3-ONE

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(=O)CC[C@]34C)[C@@H]1CC=C2

InChI

InChIKey=HFVMLYAGWXSTQI-QYXZOKGRSA-N
InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13,15-17H,4-8,10-12H2,1-2H3/t13-,15-,16-,17-,18-,19-/m0/s1

HIDE SMILES / InChI

Description

The compound believed to be principally responsible for the unpleasant odor sometimes produced during cooking of pork or bacon from boars has been isolated and identified as 5a-androst-16-en-3-one. It is the first mammalian pheromone to be identified. Androstenone is the active ingredient in a commercial products which were developed for farmers and breeders who need help determining the best fertilization time for sows and gilts. In humans, androstenone also has been suggested to be a pheromone. Excessive exposures may affect human health, as follows: Upper respiratory tract: Irritation, Dizziness, Drowsiness, Headache, Nausea; Skin: Redness.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
30.0 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Boarmate

Funbound

ValueDoseCo-administeredAnalytePopulation
85.1%
FLUTAZOLAM plasma
Homo sapiens

Doses

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Spray product at the gilt or sows snout for two seconds from a distance of approximately 60 centimetres, then apply pressure to the back of the sow (the „backpressure“ test).
Route of Administration: Irrigation
In Vitro Use Guide
Analysis of receptor binding of 5alpha-androst-16-en-3-one gave a value for the affinity constant (Ka) of approx. 8.3-10(8) M-1 and the value for the molar concentration of binding sites (n[M]) was approx. 3.3 pmol/mg protein.