Dihydrotestosterone
Grundinformationen
- CAS
361432-57-7- Standard-SMILES
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12- InChIKey
NVKAWKQGWWIWPM-ABEVXSGRSA-N- Summenformel
- C19H30O2
- Durchschnittliche Molmasse
- 290,4 g/mol
Überblick
17beta-hydroxy-5alpha-androstan-3-one is a 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5. It has a role as an androgen, a mouse metabolite, a human metabolite and a Daphnia magna metabolite. It is a 3-oxo-5alpha-steroid, a 17beta-hydroxy steroid and a 17beta-hydroxyandrostan-3-one. It derives from a hydride of a 5alpha-androstane.
Namen und Bezeichner
- Bevorzugter Name
- Dihydrotestosterone
- IUPAC
- (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
- Englischer Name
- d3-5α-Dihydrotestosterone
- Summenformel
- C19H30O2
- Molmasse
- 290.45
Namen und Synonyme
STANOLONEAndrostanolonedihydrotestosterone521-18-6AnabolexAndractimAndroloneNeodrol4-DihydrotestosteroneAnaboleenProteinaStanaprol
Weitere Namen anzeigen
d3-5α-Dihydrotestosterone
Protona5alpha-DihydrotestosteroneCristerona MB17beta-Hydroxy-5alpha-androstan-3-oneAndrostanolona5alpha-Androstan-17beta-ol-3-one5-alpha-DihydrotestosteroneTestosterone, dihydro-
Datenbank-Bezeichner
- CAS
361432-57-7- ChEMBL
CHEMBL27769- ChEBI
CHEBI:16330- UNII
- 08J2K08A3Y
- EC Number
- 208-307-3
- Nikkaji
- J39.503J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,7
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 21
- Formalladung
- 0
- Komplexität
- 458
Experimentelle und physikochemische Eigenschaften
Chemical ClassesHormone
Drugs
DEA NFLIS-Drug Category -> Steroids
DEA Schedule III Controlled Substance -> Anabolic steroids
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202]
SpringerMaterials PropertiesChemical shift
LogP3.55
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point181 °C
Physical DescriptionSolid
Collision Cross Section177.31 Ų [M+H]+
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
Danger
H351 (98.3%): Suspected of causing cancer [Warning Carcinogenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 60 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
DEA schedule III controlled substance
Status: Cease Manufacture Update: 31-10-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/12136
Hazard Classes and CategoriesCarc. 2 (98.3%)
Toxikologische Informationen
Exposure RoutesBioavailability is very low (0-2%) following oral administration.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
ANDROSTANOLONE
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
USGS Health-Based Screening Levels for Evaluating Water-Quality
Dihydrotestosterone
Hormone
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
Chemie und Industrie
Pharmakologische Informationen
ATC Code
A - Alimentary tract and metabolism
G - Genito urinary system and sex hormones
QA - Alimentary tract and metabolism
QG - Genito urinary system and sex hormones
MeSH Pharmacological Classification
Compounds that interact with ANDROGEN RECEPTORS in target tissues to bring about the effects similar to those of TESTOSTERONE. Depending on the target tissues, androgenic effects can be on SEX DIFFERENTIATION; male reproductive organs, SPERMATOGENESIS; secondary male SEX CHARACTERISTICS; LIBIDO; development of muscle mass, strength, and power.
Absorption, Distribution and ExcretionBioavailability is very low (0-2%) following oral administration.
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite PathwaysAndrogen and Estrogen Metabolism
Verwendung und Herstellung
UsesDihydrotestosterone is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Use ClassificationPharmaceuticals
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