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Testosteronpropionat

Testosterone Propionate

HCID 5995
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Grundinformationen

CAS
57-85-2
Standard-SMILES
CCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
PDMMFKSKQVNJMI-BLQWBTBKSA-N
Summenformel
C22H32O3
Durchschnittliche Molmasse
344,5 g/mol
Monoisotopische Masse
344,23514488

Überblick

Testosterone propionate appears as odorless white or yellowish-white crystals or a white or creamy-white crystalline powder. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Testosterone Propionate
IUPAC
[(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] propanoate
Lokaler Name
Testosteronpropionat
Englischer Name
Testosterone propionate
Summenformel
C22H32O3
Molmasse
344.5

Namen und Synonyme

testosterone propionate57-85-2Bio-testiculinaEnarmonAndrotest PAndrolonAndrotestonAquavironHormotestonTestodetTestodrinTestogen
Weitere Namen anzeigen
Androgennsc9166Test PropTestosteron propionate3-Oxoandrost-4-en-17-yl propionateOkasa-masculOrchisteroneoretonpropionate
TestoniqueTestormolTestrexTostrinNeo-HombreolMasenateOrchistinPantestin

Datenbank-Bezeichner

CAS
57-85-2
PubChem CID
5995
DTXSID
DTXSID9036515
ChEMBL
CHEMBL1170
ChEBI
CHEBI:9466
UNII
WI93Z9138A
EC Number
200-351-1
Nikkaji
J4.584E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,4
Polarare Oberfläche (TPSA)
43,4 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
3
Schwere Atome
25
Formalladung
0
Komplexität
621

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202]
SpringerMaterials PropertiesCrystal structure
LogP3.72
Solubility · 2 Einträge

less than 1 mg/mL at 76.1 °F (NTP, 1992)

5.02e-03 g/L

Human Drugs · 3 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Animal DrugsActive Ingredients (Testosterone Propionate) -> FDA Greenbook
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point · 2 Einträge

244 to 252 °F (NTP, 1992)

118-123 °C

Physical Description · 2 Einträge

Testosterone propionate appears as odorless white or yellowish-white crystals or a white or creamy-white crystalline powder. (NTP, 1992)

Solid

Collision Cross Section · 2 Einträge

191.1 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9036515]

188.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
118 · 118-123 °C
Siedepunkt
419.57 °C · 419.57°C (rough estimate)
Dichte
1.0906 · 1.0906 (rough estimate)
Brechungsindex
1.5 · 1.5000 (estimate)
storage temp.
-20 °C · Store at -20°C
Löslichkeit
10 mg/mL · ethanol: 10 mg/mL
Aggregatzustand
solid
Farbe
white
Biologische Quelle
synthetic (organic)
Wasserlöslichkeit
0.1 g/100 · <0.1 g/100 mL at 24.5 ºC
Merck
13 · 13,9255
BRN
3221760 · 3221760
InChI
1S/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1
InChIKey
PDMMFKSKQVNJMI-BLQWBTBKSA-N
SMILES
[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])OC(=O)CC
CAS Datenbank
57 · 57-85-2(CAS DataBase Reference)
NIST chemische Informationen
-17 · Androstene-17(beta)-propionate-3-one,delta8-(57-85-2)
EPA chemische Informationen
Testosterone propionate (57-85-2)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H302 (96.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P263, P264, P270, P273, P280, P301+P317, P318, P319, P330, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 87 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationTestosterone propionate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Androst-4-en-3-one, 17-(1-oxopropoxy)-, (17.beta.)-: Human health tier I assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this compound include increased retention of nitrogen, calcium, sodium, potassium, chloride and phosphate which results in increased skeletal weight; water retention, increased vascularity of the skin, hypercalcemia, increased bone growth and stomatitis. In males, small doses ma cause increased number of spermatozoa produced, while large doses may cause suppressed formation of spermatozoa. In women, this compound may cause suppression of ovarian activity and menstruation, symptoms of virilism, atrophy of the breasts and endometrial tissue, increased libido and suppressed lactation. Other symptoms in women include male-pattern hirsuitism, deepening of the voice, acne and hypertrophy of the clitoris. Other symptoms of exposure to this type of compound through ingestion include menstrual irregularities, excessive body hair, prominent musculature, sustained erections, edema, jaundice, hepatic adenocarcinoma and feminization in males. In children, this chemical may cause serious disturbances of growth and of sexual and osseous development.

Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Reactivity ProfileTESTOSTERONE PROPIONATE is sensitive to light. Incompatible with alkalis and oxidizing agents. (NTP, 1992).
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (96.6%)

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Personal Protective Equipment (PPE) · 1 Eintrag

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Toxikologische Informationen

Toxicity Summary · 1 Eintrag

The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5&alpha;-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5&alpha;-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.

Signs and SymptomsSide effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
2811
hs_code
29372900
RTECS-Nr.
XA3115000
risk_code
45-22-63
Toxizität
LD50 oral in rat: 1gm/kg
hazard_code
T
safety_code
53-36/37-45
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Carc. 2Repr. 1A

Chemie und Industrie

Pharmakologische Informationen

Protein BindingEven 98% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound or bound to albumin and other proteins.
PharmacodynamicsThe administration of testosterone propionate can induce production of proteins related to male sexual development. Clinical trials have shown a decrease in plasma LH after the administration of testosterone propionate.
Mechanism of Action · 1 Eintrag

The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5alpha-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5alpha-reductase. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.

Biological Half-LifeTestosterone propionate possesses a relatively short half-life compared with other testosterone esters at approximately 4.5 days.
Metabolism/Metabolites · 2 Einträge

As all testosterone esters, testosterone propionate is rapidly hydrolysed into free testosterone in plasma. Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).

Testosterone propionate is rapidly hydrolysed into testosterone. Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT). Route of Elimination: About 90% of a dose of testosterone given intramuscularly is excreted in the urine as glucuronic and sulfuric acid conjugates of testosterone and its metabolites; about 6% of a dose is excreted in the feces, mostly in the unconjugated form.

Absorption, Distribution and Excretion · 4 Einträge

Testosterone propionate presents a slow absorption from the intramuscular site of administration. This slow absorption is due to the presence of the less polar ester group. The absorption rate of testosterone propionate generates a frequent injection requirement when compared with testosterone enanthate or testosterone cypionate. It presents absorption parameters of AUC and residence time of 180-210 ng h/ml and 40-60 h, respectively.

About 90% of a dose of testosterone given intramuscularly is excreted in the urine as glucuronic and sulfuric acid conjugates of testosterone and its metabolites. From the rest of the dose, approximately 6% of a dose is excreted in the feces, mostly in the unconjugated form.

The registered volume of distribution for testosterone propionate is in the range of 75-120 L/kg.

Testosterone propionate has a reduced clearance rate compared to testosterone. The reported clearance rate is of approximately 2000 ml/min.

Cellular LocationsCytoplasm

Verwendung und Herstellung

UsesTestosterone propionate is an anabolic steroid and a short ester form of testosterone that becomes active in the body. It is often used for muscle mass building.
Use Classification · 2 Einträge

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Pharmaceuticals

General Manufacturing InformationAndrost-4-en-3-one, 17-(1-oxopropoxy)-, (17.beta.)-: INACTIVE
Anwendungen · 1 Eintrag

VerwendenTestosterone propionate is an is an androgen and anabolic steroid (AAS) medication, which directs the development of the male phenotype during embryogenesis and at puberty. It has been widely used by athletes and bodybuilders for physical performance enhancement. Testosterone propionate has also been used for studying its effects on pregnant ewes.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

TestosteronPropionsureanhydridPropionylchloridPyridin

Nachgelagerte Produkte

Clostebol propionate

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