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Identification
NameTestosterone Propionate
Accession NumberDB01420
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

An ester of testosterone with a propionate substitution at the 17-beta position. [PubChem]

Structure
Thumb
Synonyms
Testex
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Malogen In Oil Liq 100mg/mlliquid100 mgintramuscularGermiphene Corporation1995-12-311999-04-14Canada
Testosterone Propionate Inj 100mg/mlliquid100 mgintramuscularTaro Pharmaceuticals Inc1972-12-312001-08-21Canada
Testosterone Propionate Injection, USPliquid100 mgintramuscularSterimax Inc1992-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIIWI93Z9138A
CAS number57-85-2
WeightAverage: 344.4877
Monoisotopic: 344.23514489
Chemical FormulaC22H32O3
InChI KeyInChIKey=PDMMFKSKQVNJMI-BLQWBTBKSA-N
InChI
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
IUPAC Name
(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl propanoate
SMILES
[H][C@@]12CC[[email protected]](OC(=O)CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androgen-skeleton
  • Androstane-skeleton
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C19 steroids (androgens) and derivatives (C08158 )
  • C19 steroids (androgens) and derivatives (LMST02020076 )
Pharmacology
IndicationTestosterone 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.
PharmacodynamicsTestosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted from the testes of males. In females, it is produced in the ovaries, adrenal glands and by conversion of adrostenedione in the periphery. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. Examples include enhanced libido, energy, immune function, and protection against osteoporosis. On average, the adult male body produces about twenty times the amount of testosterone than an adult female's body does. In the body, this ester form of testosterone is hydrolyzed rapidly and become actively available as testosterone.
Mechanism of actionThe 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 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding40% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound and the rest is bound to albumin and other proteins.
Metabolism

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 eliminationAbout 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.
Half lifeNot Available
ClearanceNot Available
ToxicitySide effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.974
Caco-2 permeable+0.6304
P-glycoprotein substrateSubstrate0.6262
P-glycoprotein inhibitor IInhibitor0.8746
P-glycoprotein inhibitor IIInhibitor0.7623
Renal organic cation transporterNon-inhibitor0.776
CYP450 2C9 substrateNon-substrate0.8672
CYP450 2D6 substrateNon-substrate0.9159
CYP450 3A4 substrateSubstrate0.7429
CYP450 1A2 substrateNon-inhibitor0.9445
CYP450 2C9 inhibitorNon-inhibitor0.8459
CYP450 2D6 inhibitorNon-inhibitor0.9301
CYP450 2C19 inhibitorInhibitor0.6089
CYP450 3A4 inhibitorNon-inhibitor0.7576
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5939
Ames testNon AMES toxic0.9474
CarcinogenicityNon-carcinogens0.9046
BiodegradationNot ready biodegradable0.9777
Rat acute toxicity2.0463 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8475
hERG inhibition (predictor II)Non-inhibitor0.7643
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Liquidintramuscular100 mg
Prices
Unit descriptionCostUnit
Testosterone propionate powder6.25USD g
First-testosterone mc 2% cr0.91USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point120 °CPhysProp
water solubility1.48 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logS-5.37ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.00502 mg/mLALOGPS
logP3.65ALOGPS
logP4.51ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.21 m3·mol-1ChemAxon
Polarizability40.43 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.53 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-8aff9c2cbe0b5c20d85aView in MoNA
1D NMR13C NMR SpectrumNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 68:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Small EJ, Ryan CJ: The case for secondary hormonal therapies in the chemotherapy age. J Urol. 2006 Dec;176(6 Pt 2):S66-71. [PubMed:17084172 ]
  2. Omwancha J, Brown TR: Selective androgen receptor modulators: in pursuit of tissue-selective androgens. Curr Opin Investig Drugs. 2006 Oct;7(10):873-81. [PubMed:17086931 ]
  3. Petraki CD, Sfikas CP: Histopathological changes induced by therapies in the benign prostate and prostate adenocarcinoma. Histol Histopathol. 2007 Jan;22(1):107-18. [PubMed:17128417 ]
  4. Maudsley S, Davidson L, Pawson AJ, Freestone SH, Lopez de Maturana R, Thomson AA, Millar RP: Gonadotropin-releasing hormone functionally antagonizes testosterone activation of the human androgen receptor in prostate cells through focal adhesion complexes involving Hic-5. Neuroendocrinology. 2006;84(5):285-300. Epub 2007 Jan 4. [PubMed:17202804 ]
  5. Lapauw B, Goemaere S, Crabbe P, Kaufman JM, Ruige JB: Is the effect of testosterone on body composition modulated by the androgen receptor gene CAG repeat polymorphism in elderly men? Eur J Endocrinol. 2007 Mar;156(3):395-401. [PubMed:17322500 ]
  6. Yin D, Gao W, Kearbey JD, Xu H, Chung K, He Y, Marhefka CA, Veverka KA, Miller DD, Dalton JT: Pharmacodynamics of selective androgen receptor modulators. J Pharmacol Exp Ther. 2003 Mar;304(3):1334-40. [PubMed:12604714 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
O-methyltransferase activity
Specific Function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular Weight:
30036.77 Da
References
  1. Ladosky W, Schneider HT: Changes in hypothalamic catechol-O-methyl-transferase during sexual differentiation of the brain. Braz J Med Biol Res. 1981 Dec;14(6):409-13. [PubMed:6153046 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Steroid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naph...
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular Weight:
59590.91 Da
References
  1. Stern ST, Tallman MN, Miles KK, Ritter JK, Smith PC: Androgen regulation of renal uridine diphosphoglucuronosyltransferase 1A1 in rats. Drug Metab Dispos. 2008 Sep;36(9):1737-9. doi: 10.1124/dmd.108.020610. Epub 2008 May 30. [PubMed:18515331 ]
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Drug created on July 24, 2007 03:23 / Updated on September 16, 2013 17:14