Polytestosterone phloretin phosphate (PTPP) is an

androgen An androgen (from Greek ''andr-'', the stem of the word meaning ) is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes ...

and

anabolic steroid Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor (AR). Anabolism, Anaboli ...

as well as

androgen ester An androgen or anabolic steroid ester is an ester of an androgen/anabolic steroid (AAS) such as the natural testosterone or dihydrotestosterone (DHT) or the synthetic nandrolone (19-nortestosterone). Esterification renders AAS into metabolism-res ...

which was never marketed. It is an

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

testosterone Testosterone is the primary male sex hormone and androgen in Male, males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testicles and prostate, as well as promoting se ...

with

phosphoric acid Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, ...

that is in the form of a

polymer A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...

and is coupled with

phloretin Phloretin is a dihydrochalcone, a type of natural phenol. It can be found in apple tree leaves and the Manchurian apricot. Metabolism In rats, ingested phlorizin is converted into phloretin by hydrolytic enzymes in the small intestine. Ph ...

. Like other androgen esters, PTPP acts as a long-lasting

prodrug A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be ...

of testosterone in the body. However, analogously to the polymeric

estrogen ester An estrogen ester is an ester of an estrogen, most typically of estradiol but also of other estrogens such as estrone, estriol, and even nonsteroidal estrogens like diethylstilbestrol. Esterification renders estradiol into a prodrug of estradiol ...

polyestradiol phosphate Polyestradiol phosphate (PEP), sold under the brand name Estradurin, is an estrogen medication which is used primarily in the treatment of prostate cancer in men. It is also used in women to treat breast cancer, as a component of hormone therapy ...

(PEP), polyestriol phosphate (PE3P), and

polydiethylstilbestrol phosphate Polydiethylstilbestrol phosphate (PSP, PDSP) is an estrogen medication which has been used in scientific research and has been studied for use in veterinary medicine as a livestock growth promoter. It is a phosphate ester of diethylstilbestrol ( ...

(PSP), PTPP has a strongly prolonged duration with very uniform testosterone levels in animals compared to non-polymeric

testosterone ester This is a list of androgen esters, including esters (as well as ethers) of natural androgens like testosterone and dihydrotestosterone (DHT) and synthetic anabolic–androgenic steroids (AAS) like nandrolone (19-nortestosterone). Esters ...

s. According to its developers, this is "exactly the effect which should be aimed at in order to approach natural hormone production as closely as possible". PTPP was developed around 1953 at the same time as PEP and its

patent A patent is a type of intellectual property that gives its owner the legal right to exclude others from making, using, or selling an invention for a limited period of time in exchange for publishing an sufficiency of disclosure, enabling discl ...

was published in 1960. The patent was assigned to the

Swedish Swedish or ' may refer to: Anything from or related to Sweden, a country in Northern Europe. Or, specifically: * Swedish language, a North Germanic language spoken primarily in Sweden and Finland ** Swedish alphabet, the official alphabet used by ...

pharmaceutical company The pharmaceutical industry is a Medicine, medical industry that discovers, develops, produces, and markets pharmaceutical goods such as medications and medical devices. Medications are then administered to (or Self-medicate, self-administered b ...

Leo Läkemedel AB, which also developed PEP. PEP is a

linear polymer A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...

of on average 13

repeat unit A repeat unit or repeating unit , or mer, is a part of a polymer whose repetition would produce the complete polymer chain (except for the end groups) by linking the repeat units together successively along the chain, like the beads of a necklace ...

s of

estradiol phosphate Estradiol phosphate, or estradiol 17β-phosphate, also known as estra-1,3,5(10)-triene-3,17β-diol 17β-(dihydrogen phosphate), is an estrogen which was never marketed. It is an estrogen ester, specifically an ester of estradiol with phosphoric ...

. Each individual

estradiol Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible ...

unit in the molecule is connected by its C3 and C17β

hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

s to

linkers that are present between the estradiol moieties. In contrast to estradiol, such a polymer is not possible with testosterone because testosterone has only one hydroxyl group and hence does not have the two hydroxyl groups necessary for linking the testosterone units together. In PTPP, phloretin is used as a coupling agent to solve this problem and create a

testosterone phosphate Testosterone phosphate (brand name Telipex Aquosum) is an androgen and anabolic steroid and a testosterone ester. Its structure A structure is an arrangement and organization of interrelated elements in a material object or system, or the obj ...

polymer. Phloretin has four available hydroxyl groups present in its chemical structure. A linear polymer of phloretin with phosphoric acid linkers is present as the

backbone The spinal column, also known as the vertebral column, spine or backbone, is the core part of the axial skeleton in vertebrates. The vertebral column is the defining and eponymous characteristic of the vertebrate. The spinal column is a segmente ...

of the molecule, and testosterone moieties are connected to the free third and fourth hydroxyl groups of each phloretin unit also with phosphoric acid linkers. As such, two testosterone moieties essentially "hang" or "dangle off" of each phloretin unit in the polymer, and these testosterone moieties are slowly cleaved from the polymer.

References

Abandoned drugs Anabolic–androgenic steroids Androstanes Copolymers Dihydrochalcones Phosphate esters Testosterone esters {{Steroid-stub

See also

References