NAV

Testosterone propionate

Identification

Summary

Testosterone propionate is a slow-release anabolic steroid no longer used commonly for the treatment of androgen deficiency or promotion of anabolic effects on muscles.

Generic Name
Testosterone propionate
DrugBank Accession Number
DB01420
Background

Testosterone propionate is a slower-releasing anabolic steroid with a short half-life. 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.4

Type
Small Molecule
Groups
Approved, Investigational, Vet approved, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 344.4877
Monoisotopic: 344.23514489
Chemical Formula
C22H32O3
Synonyms
  • Testosterone propionate
External IDs
  • NRB-03689
  • NSC-9166
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Pharmacology

Indication

Testosterone propionate is used in veterinary practice in heifers in order to stimulate maximal growth.4

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofBreast cancer•••••••••••••••••••••• ••••••••
Symptomatic treatment ofBreast cancer•••••••••••••••••••••
Treatment ofPuberty, delayed•••••••••••••••••••••• ••••••••
Treatment ofPuberty, delayed•••••••••••••••••••••
Treatment ofTestosterone deficiency•••••••••••••••••••••• ••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

The administration of testosterone propionate can induce production of proteins related to male sexual development.5 Clinical trials have shown a decrease in plasma LH after the administration of testosterone propionate.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
Humans
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.5 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).5

Hover over products below to view reaction partners

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.5

Half-life

Testosterone propionate possesses a relatively short half-life compared with other testosterone esters at approximately 4.5 days.

Clearance

Testosterone propionate has a reduced clearance rate compared to testosterone.5 The reported clearance rate is of approximately 2000 ml/min.1

Adverse Effects
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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.5

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbacavirThe metabolism of Abacavir can be increased when combined with Testosterone propionate.
AbametapirThe serum concentration of Testosterone propionate can be increased when it is combined with Abametapir.
AbciximabTestosterone propionate may increase the anticoagulant activities of Abciximab.
AcarboseTestosterone propionate may increase the hypoglycemic activities of Acarbose.
AceclofenacAceclofenac may decrease the excretion rate of Testosterone propionate which could result in a higher serum level.
Food Interactions
No interactions found.

Products

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Active Moieties
NameKindUNIICASInChI Key
Testosteroneprodrug3XMK78S47O58-22-0MUMGGOZAMZWBJJ-DYKIIFRCSA-N
International/Other Brands
Testex
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
SUSTANON 250 INJECTIONTestosterone propionate (30 mg/ml) + Testosterone decanoate (100 mg/ml) + Testosterone isocaproate (60 mg/ml) + Testosterone phenylpropionate (60 mg/ml)InjectionIntramuscularDCH AURIGA SINGAPORE1990-05-31Not applicableSingapore flag
TEST - COMP 250Testosterone propionate (30 mg/mL) + Testosterone decanoate (100 mg/mL) + Testosterone isocaproate (60 mg/mL) + Testosterone phenylpropionate (60 mg/mL)Injection, solutionบริษัท กรุงเทพ ฟาร์มา ดิสทริบิวชั่น จำกัด2018-06-06Not applicableThailand flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
3-oxo-delta-4-steroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Androgen-skeleton / Androstane-skeleton / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Cyclohexenone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
steroid ester (CHEBI:9466) / C19 steroids (androgens) and derivatives (C08158) / C19 steroids (androgens) and derivatives (LMST02020076)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
WI93Z9138A
CAS number
57-85-2
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,3aS,3bR,9aR,9bS,11aS)-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-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

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. [Article]
  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. Dailymed [Link]
  5. Empowerpharmacy [Link]
  6. Fittness uncovered [Link]
Human Metabolome Database
HMDB0015489
KEGG Drug
D00959
KEGG Compound
C08158
PubChem Compound
5995
PubChem Substance
46508693
ChemSpider
5774
BindingDB
50215709
RxNav
10382
ChEBI
9466
ChEMBL
CHEMBL1170
ZINC
ZINC000000490791
PharmGKB
PA164751373
Drugs.com
Drugs.com Drug Page
Wikipedia
Testosterone_propionate
MSDS
Download (50 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceDyssocial Behavior1
1CompletedOtherHealthy Subjects (HS)2
1, 2SuspendedTreatmentBreast Neoplasms / Painful Intercourse / Vaginal Inflammation1
Not AvailableCompletedBasic ScienceAnxiety1

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 / mL
InjectionIntramuscular100 mg/ml
Injection, solution
Solution50 mg/1ml
PowderNot applicable1 g/1g
Injection, solutionIntramuscular100 mg
Injection, solutionIntramuscular50 mg
Solution25 mg/1ml
Suspension50 mg/1ml
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)18.52Chemaxon
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
Polarizability40.45 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-MSsplash10-00or-4395000000-e888bc1b6c2a4c99d301
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-9800000000-8aff9c2cbe0b5c20d85a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0069000000-23e8258356498877fc59
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-3009000000-a0f78f73e4177f83b36e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05g0-0292000000-533867218cac3efeab1d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-9044000000-ede187917a81fcb43829
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9001000000-a258c68e357f2a72fd1b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052p-2941000000-33a6d31811949b2fe20d
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-198.0835187
predicted
DarkChem Lite v0.1.0
[M-H]-196.4586187
predicted
DarkChem Lite v0.1.0
[M-H]-198.7317187
predicted
DarkChem Lite v0.1.0
[M-H]-185.98064
predicted
DeepCCS 1.0 (2019)
[M+H]+198.8095187
predicted
DarkChem Lite v0.1.0
[M+H]+196.8297187
predicted
DarkChem Lite v0.1.0
[M+H]+199.8690187
predicted
DarkChem Lite v0.1.0
[M+H]+188.09769
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.1602187
predicted
DarkChem Lite v0.1.0
[M+Na]+196.4684187
predicted
DarkChem Lite v0.1.0
[M+Na]+195.40611
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
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Details1. Androgen receptor
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Details1. Catechol O-methyltransferase
Kind
Protein
Organism
Humans
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. [Article]
Details2. UDP-glucuronosyltransferase 1-1
Kind
Protein
Organism
Humans
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. [Article]
Details3. 3-oxo-5-alpha-steroid 4-dehydrogenase (Protein Group)
Kind
Protein group
Organism
Humans
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:
NameUniProt ID
3-oxo-5-alpha-steroid 4-dehydrogenase 1P18405
3-oxo-5-alpha-steroid 4-dehydrogenase 2P31213
Polyprenol reductaseQ9H8P0
References
  1. Empowerpharmacy [Link]
Details4. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
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

Details1. Sex hormone-binding globulin
Kind
Protein
Organism
Humans
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]
Details2. Serum albumin
Kind
Protein
Organism
Humans
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

Details1. P-glycoprotein 1
Kind
Protein
Organism
Humans
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 at July 24, 2007 09:23 / Updated at February 20, 2024 23:55