Identification

Name
Testosterone propionate
Accession Number
DB01420  (DBSALT001032)
Type
Small Molecule
Groups
Approved, Investigational, Vet approved, Withdrawn
Description

Testosterone propionate is a slower releasing anabolic steroid with a short half-life. This characteristic allows the user to run short testosterone propionate cycles of 8-10 weeks as optimal peak blood plasma levels are achieved at 2-4 weeks.[4] It is a synthetic androstane steroid derivative of testosterone in the form of 17β propionate ester of testosterone.[2] Testosterone propionate was developed initially by Watson labs, and FDA approved on February 5, 1974. Currently, this drug has been discontinued in humans, but the vet application is still available as an OTC.[5]

Structure
Thumb
Synonyms
Not Available
External IDs
NRB-03689 / NSC-9166
Active Moieties
NameKindUNIICASInChI Key
Testosteroneprodrug3XMK78S47O58-22-0MUMGGOZAMZWBJJ-DYKIIFRCSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Malogen In Oil Liq 100mg/mlLiquid100 mgIntramuscularGermiphene Corporation1995-12-311999-04-14Canada
Testosterone Propionate Inj 100mg/mlLiquid100 mgIntramuscularTaro Pharmaceuticals, Inc.1972-12-312001-08-21Canada
Testosterone Propionate Injection, USPLiquid100 mgIntramuscularSterimax Inc1992-12-31Not applicableCanada
International/Other Brands
Testex
Categories
UNII
WI93Z9138A
CAS number
57-85-2
Weight
Average: 344.4877
Monoisotopic: 344.23514489
Chemical Formula
C22H32O3
InChI Key
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[C@H](OC(=O)CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Pharmacology

Indication

Testosterone propionate is often used for muscle mass building. The original medical indication is for the treatment of androgen deficiency in male adults either in hypogonadism or andropause.[6] Nowadays testosterone propionate is indicated for its use in heifers in order to stimulate maximal growth.[5]

Pharmacodynamics

The administration of testosterone propionate can induce production of proteins related to male sexual development.[7] On the other hand, testosterone itself present an estrogenic activity due to interaction with aromatase enzyme, thus the continuous aministration of testosterone propionate may cause the elevation of plasma estrogen.[6] Clinical trials showed as well, a decrease in plasma LH after testosterone propionate administration.[1]

Mechanism of action

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.

TargetActionsOrganism
AAndrogen receptor
agonist
Human
Absorption

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.[7] 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.[1]

Volume of distribution

The registered volume of distribution for testosterone propionate is in the range of 75-120 L/kg.[1]

Protein binding

Even 98% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound or bound to albumin and other proteins.[3]

Metabolism

As all testosterone esters, testosterone propionate is rapidly hydrolysed into free testosterone in plasma.[1] Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).[7]

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. From the rest of the dose, approximately 6% of a dose is excreted in the feces, mostly in the unconjugated form.[7]

Half life

Testosterone propionate presents a the shortest half life of all testosterone esters, being of 4.5 days. This characteristic produces a higher administration requirement.[4]

Clearance

Testosterone propionate has a reduced clearance rate compared to testosterone.[7] The reported clearance rate is of approximately 2000 ml/min.[1]

Toxicity

Reports have showed a potential stimulation of cancerous tissue growth. The potential testosterone propionate accumulation in the body produces a high risk of edema secondaryh to water and sodium retention.[7]

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinTestosterone propionate may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinTestosterone propionate may increase the anticoagulant activities of (S)-Warfarin.
2-HydroxyestradiolThe metabolism of 2-Hydroxyestradiol can be decreased when combined with Testosterone propionate.
2,4-thiazolidinedioneTestosterone propionate may increase the hypoglycemic activities of 2,4-thiazolidinedione.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Testosterone propionate.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Testosterone propionate.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Testosterone propionate.
6-Deoxyerythronolide BThe metabolism of Testosterone propionate can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Testosterone propionate.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Testosterone propionate.
Food Interactions
Not Available

References

General References
  1. Fujioka M, Shinohara Y, Baba S, Irie M, Inoue K: Pharmacokinetic properties of testosterone propionate in normal men. J Clin Endocrinol Metab. 1986 Dec;63(6):1361-4. doi: 10.1210/jcem-63-6-1361. [PubMed:3782423]
  2. Elks J. and Ganellin C.R. (1990). The dictionary of drugs. Springer Science.
  3. Woo T.M. and Robinson M. (2016). Pharmacotherapeutics for advanced practice nurse prescribers (4th ed.). Davis Company.
  4. Steroidal [Link]
  5. Dailymed [Link]
  6. Steroidal [Link]
  7. Empowerpharmacy [Link]
  8. Fittness uncovered [Link]
External Links
Human Metabolome Database
HMDB0015489
KEGG Drug
D00959
KEGG Compound
C08158
PubChem Compound
5995
PubChem Substance
46508693
ChemSpider
5774
BindingDB
50215709
ChEBI
9466
ChEMBL
CHEMBL1170
PharmGKB
PA164751373
Drugs.com
Drugs.com Drug Page
Wikipedia
Testosterone_propionate
AHFS Codes
  • 68:08.00 — Androgens
MSDS
Download (50 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2SuspendedTreatmentNeoplasms, Breast / Painful Intercourse / Vaginal Inflammation1
Not AvailableCompletedBasic ScienceFeeling Anxious1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • C.O. Truxton Inc.
  • Cutis Pharma Inc.
  • Dispensing Solutions
  • Lyne Laboratories Inc.
  • Paddock Labs
  • Wa Butler Co.
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)118-123 °CElks. The Dictionary of Drugs. (1990)
water solubility1.48 mg/L (at 25ºC)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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (9.53 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-9800000000-8aff9c2cbe0b5c20d85a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Androgens and derivatives / 3-oxo delta-4-steroids / Delta-4-steroids / Cyclohexenones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Steroid ester / Androgen-skeleton / Androstane-skeleton / 3-oxosteroid / 3-oxo-delta-4-steroid / Oxosteroid / Delta-4-steroid / Cyclohexenone / Ketone / Carboxylic acid ester
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
steroid ester (CHEBI:9466) / C19 steroids (androgens) and derivatives (C08158) / C19 steroids (androgens) and derivatives (LMST02020076)

Targets

Details
1. Androgen receptor
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 ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
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-DOP...
Gene Name
COMT
Uniprot ID
P21964
Uniprot Name
Catechol O-methyltransferase
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...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
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]
Kind
Protein group
Organism
Not Available
Pharmacological action
No
Actions
Substrate
General Function
Electron carrier activity
Specific Function
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and andro...

Components:
References
  1. Empowerpharmacy [Link]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Empowerpharmacy [Link]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Empowerpharmacy [Link]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Empowerpharmacy [Link]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Empowerpharmacy [Link]

Drug created on July 24, 2007 03:23 / Updated on December 10, 2018 06:10