Identification

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Name
Testosterone
Accession Number
DB00624  (APRD00433, DB05720, DB05275)
Type
Small Molecule
Groups
Approved, Investigational
Description

Testosterone is a steroid sex hormone indicated to treat primary hypogonadism and hypogonadotropic hypogonadism.14,15,16,17,18,19,20 Testosterone antagonizes the androgen receptor to induce gene expression that causes the growth and development of masculine sex organs and secondary sexual characteristics.5,14,15,16,17,18,19,20

Testosterone was isolated from samples and also synthesized in 1935.1

Structure
Thumb
Synonyms
  • 17beta-hydroxy-4-androsten-3-one
  • 4-androsten-17β-ol-3-one
  • Testosteron
  • Testosterona
  • Testosterone
  • Testostérone
  • Testosteronum
  • Virosterone
External IDs
4-08-00-00979 / BRN 3170544 / CCRIS 7082 / EINECS 206-253-5 / EINECS 227-712-6 / NSC-17591 / NSC-9700
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AndrodermPatch4 mg/1dTransdermalAllergan, Inc.1995-09-29Not applicableUs
AndrodermPatch24.3 mg/1TransdermalWatson Pharma, Inc.2006-09-192006-09-19Us
AndrodermPatch5 mg/1dTransdermalPhysicians Total Care, Inc.2009-05-072013-02-28Us
AndrodermPatch2 mg/1dTransdermalAllergan, Inc.1995-09-29Not applicableUs
AndrodermPatch12.2 mg/1TransdermalWatson Pharma, Inc.2006-09-192006-09-19Us
AndrodermPatch2.5 mg/1dTransdermalPhysicians Total Care, Inc.2007-11-132011-06-30Us
AndrodermPatch4 mg/1dTransdermalActavis Pharma, Inc.1995-09-292020-01-31Us
AndrodermPatch2 mg/1dTransdermalActavis Pharma, Inc.1995-09-292020-01-31Us
AndrogelGel10 mg/1gTransdermalAbbVie Inc.2011-03-14Not applicableUs
AndrogelGel10 mg/1gTransdermalRebel Distributors2003-06-05Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TestopelPellet75 mg/1SubcutaneousEndo Pharmaceuticals, Inc.2014-10-31Not applicableUs
TestopelPellet75 mg/1SubcutaneousSlate Pharma2009-07-21Not applicableUs
TestosteroneGel50 mg/5gTransdermalPar Pharmaceutical, Inc.2015-09-022021-06-30Us
TestosteroneSolution30 mg/1.5mLTopicalPrasco, Laboratories2017-01-232018-12-31Us
TestosteroneGel20.25 mg/1.25gTopicalPerrigo New York Inc2019-06-27Not applicableUs
TestosteroneGel50 mg/5gTransdermalPar Pharmaceutical, Inc.2017-02-28Not applicableUs
TestosteroneGel, metered10 mg/0.5gTopicalActavis Pharma, Inc.2015-06-01Not applicableUs
TestosteroneSolution30 mg/1.5mLTopicalActavis Pharma, Inc.2017-08-18Not applicableUs
TestosteroneGel50 mg/5gTransdermalPrasco, Laboratories2014-06-092019-02-12Us
TestosteroneGel16.2 mg/1gTopicalPerrigo New York Inc2018-10-12Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
TestosteroneTestosterone (25 mg/1)PelletOralQualgen Llc2015-09-012018-02-13Us
TestosteroneTestosterone (200 mg/1)PelletOralQualgen Llc2015-09-012018-02-13Us
TestosteroneTestosterone (87.5 mg/1)PelletOralQualgen Llc2015-09-012018-02-13Us
TestosteroneTestosterone (37.5 mg/1)PelletOralQualgen Llc2015-09-012018-02-13Us
TestosteroneTestosterone (50 mg/1)PelletOralQualgen Llc2015-09-012018-02-13Us
TestosteroneTestosterone (100 mg/1)PelletOralQualgen Llc2015-09-012018-02-13Us
Testosterone / AnastrozoleTestosterone (200 mg/1) + Anastrozole (20 mg/1)PelletOralQualgen Llc2017-11-142018-05-21Us
International/Other Brands
Andronate 100 / Andronate 200 / Andropatch (GlaxoSmithKline) / Andropository 200 / Andryl 200 / Bio-T-Gel (BioSante Pharmaceuticals, Inc. and Teva Pharmaceuticals USA, Inc.) / Nebido (Bayer) / Sustanon (Organon) / Synandrol F / Testamone 100 / Testaqua IM / Testoderm / Testoderm TTS / Testogel (Bayer) / Testolin / Testopatch (Pierre Fabre) / Testopel Pellets / Testrin-P.A / Testro AQ / Virormone (Nordic Pharma)
Categories
UNII
3XMK78S47O
CAS number
58-22-0
Weight
Average: 288.4244
Monoisotopic: 288.20893014
Chemical Formula
C19H28O2
InChI Key
MUMGGOZAMZWBJJ-DYKIIFRCSA-N
InChI
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
IUPAC Name
(1S,3aS,3bR,9aR,9bS,11aS)-1-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Pharmacology

Indication

Testosterone is indicated to treat primary hypogonadism and hypogonadotropic hypogonadism.14,15,16,17,18,19,20

Associated Conditions
Pharmacodynamics

Testosterone antagonizes the androgen receptor to induce gene expression that causes the growth and development of masculine sex organs and secondary sexual characteristics.5,14,15,16,17,18,19,20 The duration of action of testosterone is variable from patient to patient with a half life of 10-100 minutes.14,15,16,17,18,19,20 The therapeutic index is wide considering the normal testosterone levels in an adult man range from 300-1000ng/dL.14,16,17,18,19,20 Counsel patients regarding the risk of secondary exposure of testosterone topical products to children.14,16,17,18,19

Mechanism of action

The androgen receptor exists in the cytoplasm bound to the heat shock proteins HSP90, HSP70, and other chaperones.5 After binding to an androgen, the androgen receptor dissociates from HSP90 and undergoes a conformational change to slow the rate of dissociation from the androgen receptor.5 The androgen-receptor complex is transported into the nucleus where it binds to DNA and recruits other transcriptional regulators to form a pre-initiation complex and eventually induce expression of specific genes.5

Testosterone and its active metabolite dihydrotestosterone (DHT) antagonize the androgen receptor to develop masculine sex organs including the prostate, seminal vesicles, penis, and scrotum.4,14,15,16,17,18,19,20

Antagonism of the androgen receptor is also responsible for the development of secondary sexual characteristics including facial and body hair, enlargement of the larynx, thickening of the vocal cords, and changes in muscle and fat distribution.4,14,15,16,17,18,19,20

TargetActionsOrganism
AAndrogen receptor
agonist
Humans
UEstrogen receptor alpha
inhibitor
Humans
UMineralocorticoid receptor
ligand
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

A single 100mg topical dose of testosterone has an AUC of 10425±5521ng*h/dL and a Cmax of 573±284ng/dL.14 Testosterone is approximately 10% bioavailable topically.14,16,19

Volume of distribution

The volume of distribution of testosterone in elderly men is 80.36±24.51L.2

Protein binding

Testosterone is 40% bound to sex hormone binding globulin, 2% unbound, and the remainder is bound to albumin and other proteins.14,15,16,17,18,19,20

Metabolism

Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).14,15,16,17,18,19,20

Testosterone can be hydroxylated at a number of positions by CYP3A4, CYP2B6, CYP2C9, and CYP2C19;6,8 glucuronidated by UGT2B17;11,12 sulfated;12 converted to estradiol by aromatase;10 converted to dihydrotestosterone (DHT) by 5α-reductase;7 metabolized to androstenedione by CYP3A4, CYP2C9, and CYP2C19;6 or converted to DHT glucuronide.13

Androstenedione undergoes metabolism by aromatase to form estrone,10 which undergoes a reversible reaction to form estradiol.13 Androstenedione can also be converted to 5α-androstanedione7 by 5α-reductase,9 which can be further metabolized to 5α-androsterone.7

DHT can be glucuronidated13 or sulfated, or metabolized to 5α-androstanediol,7 androstane-3α,17β-diol, or androstane-3β,17β-diol.10 DHT can also be reversibly converted to 5α-androstanedione.7

Route of elimination

90% of an intramuscular dose is eliminated in urine, mainly as glucuronide and sulfate conjugates.14,15,16,17,18,19,20 6% is eliminated in feces, mostly as unconjugated metabolites.14,15,16,17,18,19,20

Half life

The half life of testosterone is highly variable, ranging from 10-100 minutes.14,15,16,17,18,19,20

Clearance

The mean metabolic clearance in middle aged men is 812±64L/day.3

Toxicity

Data regarding an overdose with a topical testosterone product is not readily available.14,15,16,17,18,19,20 In the case of overdose with an injectable product, patients may present with a cerebrovascular event.14,15,16,17,18,19,20 Treat overdoses by stopping testosterone products, washing off any topical products with soap and water, and initiating symptomatic and supportive treatments.14,15,16,17,18,19,20

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
17-beta Hydroxysteroid Dehydrogenase III DeficiencyDisease
Androstenedione MetabolismMetabolic
Androgen and Estrogen MetabolismMetabolic
Aromatase DeficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Testosterone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Testosterone.
2,4-thiazolidinedioneTestosterone may increase the hypoglycemic activities of 2,4-thiazolidinedione.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Testosterone.
4-hydroxycoumarinTestosterone may increase the anticoagulant activities of 4-hydroxycoumarin.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Testosterone.
6-Deoxyerythronolide BThe metabolism of Testosterone can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased when combined with Testosterone.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be increased when combined with Testosterone.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be increased when combined with Testosterone.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
Not Available

References

Synthesis Reference

Merle G. Wovcha, Frederick J. Antosz, John M. Beaton, Alfred B. Garcia, Leo A. Kominek, "Process for preparing 9.alpha.-OH testosterone." U.S. Patent US4221868, issued November, 1977.

US4221868
General References
  1. Nieschlag E, Nieschlag S: ENDOCRINE HISTORY: The history of discovery, synthesis and development of testosterone for clinical use. Eur J Endocrinol. 2019 Jun 1;180(6):R201-R212. doi: 10.1530/EJE-19-0071. [PubMed:30959485]
  2. White CM, Ferraro-Borgida MJ, Moyna NM, McGill CC, Ahlberg AW, Thompson PD, Chow MS, Heller GV: The pharmacokinetics of intravenous testosterone in elderly men with coronary artery disease. J Clin Pharmacol. 1998 Sep;38(9):792-7. [PubMed:9753206]
  3. Wang C, Catlin DH, Starcevic B, Leung A, DiStefano E, Lucas G, Hull L, Swerdloff RS: Testosterone metabolic clearance and production rates determined by stable isotope dilution/tandem mass spectrometry in normal men: influence of ethnicity and age. J Clin Endocrinol Metab. 2004 Jun;89(6):2936-41. doi: 10.1210/jc.2003-031802. [PubMed:15181080]
  4. Handelsman DJ: Mechanisms of action of testosterone--unraveling a Gordian knot. N Engl J Med. 2013 Sep 12;369(11):1058-9. doi: 10.1056/NEJMe1305307. [PubMed:24024843]
  5. Ferraldeschi R, Welti J, Luo J, Attard G, de Bono JS: Targeting the androgen receptor pathway in castration-resistant prostate cancer: progresses and prospects. Oncogene. 2015 Apr 2;34(14):1745-57. doi: 10.1038/onc.2014.115. Epub 2014 May 19. [PubMed:24837363]
  6. Choi MH, Skipper PL, Wishnok JS, Tannenbaum SR: Characterization of testosterone 11 beta-hydroxylation catalyzed by human liver microsomal cytochromes P450. Drug Metab Dispos. 2005 Jun;33(6):714-8. doi: 10.1124/dmd.104.003327. Epub 2005 Mar 11. [PubMed:15764715]
  7. Price VH: Testosterone metabolism in the skin. A review of its function in androgenetic alopecia, acne vulgaris, and idiopathic hirsutism including recent studies with antiandrogens. Arch Dermatol. 1975 Nov;111(11):1496-1502. doi: 10.1001/archderm.111.11.1496. [PubMed:128323]
  8. Ekins S, Vandenbranden M, Ring BJ, Gillespie JS, Yang TJ, Gelboin HV, Wrighton SA: Further characterization of the expression in liver and catalytic activity of CYP2B6. J Pharmacol Exp Ther. 1998 Sep;286(3):1253-9. [PubMed:9732386]
  9. Weisser H, Krieg M: Kinetic analysis of androstenedione 5 alpha-reductase in epithelium and stroma of human prostate. Steroids. 1997 Aug-Sep;62(8-9):589-94. doi: 10.1016/s0039-128x(97)00042-1. [PubMed:9432753]
  10. Ishikawa T, Glidewell-Kenney C, Jameson JL: Aromatase-independent testosterone conversion into estrogenic steroids is inhibited by a 5 alpha-reductase inhibitor. J Steroid Biochem Mol Biol. 2006 Feb;98(2-3):133-8. doi: 10.1016/j.jsbmb.2005.09.004. Epub 2005 Dec 28. [PubMed:16386416]
  11. Sten T, Bichlmaier I, Kuuranne T, Leinonen A, Yli-Kauhaluoma J, Finel M: UDP-glucuronosyltransferases (UGTs) 2B7 and UGT2B17 display converse specificity in testosterone and epitestosterone glucuronidation, whereas UGT2A1 conjugates both androgens similarly. Drug Metab Dispos. 2009 Feb;37(2):417-23. doi: 10.1124/dmd.108.024844. Epub 2008 Nov 20. [PubMed:19022937]
  12. Gomes RL, Meredith W, Snape CE, Sephton MA: Analysis of conjugated steroid androgens: deconjugation, derivatisation and associated issues. J Pharm Biomed Anal. 2009 Jul 12;49(5):1133-40. doi: 10.1016/j.jpba.2009.01.027. Epub 2009 Jan 31. [PubMed:19304432]
  13. Ishimaru T, Edmiston A, Pages L, Horton R: Direct conversion of testosterone to dihydrotestosterone glucuronide in man. J Clin Endocrinol Metab. 1978 Dec;47(6):1282-6. doi: 10.1210/jcem-47-6-1282. [PubMed:263350]
  14. FDA Approved Drug Products: Vogelxo Testosterone Gel [Link]
  15. FDA Approved Drugs: Natesto [Link]
  16. FDA Approved Drugs: Testim [Link]
  17. FDA Approved Drug Products: Fortesta Testosterone Topical Gel [Link]
  18. FDA Approved Drug Products: Androgel 1.62% Testosterone Topical Gel [Link]
  19. FDA Approved Drug Products: Androgel 1% Testosterone Topical Gel [Link]
  20. FDA Approved Drug Products: Androderm Testosterone Transdermal System [Link]
External Links
Human Metabolome Database
HMDB0000234
KEGG Drug
D00075
KEGG Compound
C00535
PubChem Compound
6013
PubChem Substance
46505691
ChemSpider
5791
BindingDB
8885
ChEBI
17347
ChEMBL
CHEMBL386630
Therapeutic Targets Database
DAP000841
PharmGKB
PA451627
Guide to Pharmacology
GtP Drug Page
HET
TES
RxList
RxList Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Testosterone
ATC Codes
G03BA03 — TestosteroneG03EA02 — Testosterone and estrogen
AHFS Codes
  • 68:08.00 — Androgens
PDB Entries
1afs / 1i9j / 1j96 / 1jtv / 1q13 / 1vpo / 2am9 / 2q7i / 2q7j / 2q7k
show 17 more
FDA label
Download (738 KB)
MSDS
Download (49.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingOtherInsulin Resistance1
0Active Not RecruitingTreatmentHealth Services for Transgender Persons / Transgender Persons1
0CompletedBasic SciencePolycystic Ovaries Syndrome1
0CompletedTreatmentCancer, Breast / Painful Intercourse / Sexual Health Quality of Life / Vaginal Dryness1
0RecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC) / Prostate Cancer1
0TerminatedSupportive CareAging1
0TerminatedTreatmentErectile Dysfunction (ED) / Hypogonadism1
0WithdrawnTreatmentHypogonadism / Priapism / Sickle Cell Disorders1
1Active Not RecruitingTreatmentPeyronie's Disease1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableHypergonadism1
1CompletedNot AvailableHypogonadism2
1CompletedBasic ScienceAging1
1CompletedBasic ScienceBMI >30 kg/m21
1CompletedBasic ScienceHealthy Participants1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceNormal Healthy Volunteers1
1CompletedDiagnosticContraception1
1CompletedDiagnosticLocalized Prostate Cancer / Prostate Cancer1
1CompletedDiagnosticMuscle Anabolism1
1CompletedDiagnosticSkin Androgenization1
1CompletedHealth Services ResearchHealthy Volunteers1
1CompletedOtherHealthy Men / Healthy Women / Male Contraception / Product Transference1
1CompletedOtherHealthy Volunteers1
1CompletedOtherHypogonadism1
1CompletedPreventionContraception1
1CompletedPreventionHypogonadism1
1CompletedPreventionMammographic Density1
1CompletedSupportive CareCachexia / Cervical Cancers / Squamous Cell Carcinoma (SCC)1
1CompletedTreatmentAging1
1CompletedTreatmentConstitutional Delay in Growth and Puberty (CDGP) / Primary or Secondary Hypogonadism1
1CompletedTreatmentContraception / Hypogonadism2
1CompletedTreatmentFemale Sexual Dysfunction (FSD)1
1CompletedTreatmentHealthy Volunteers / Pharmacokinetics1
1CompletedTreatmentHormone Deficiency / Pharmacokinetics1
1CompletedTreatmentHypogonadism3
1CompletedTreatmentHypogonadism / Testicular Hypogonadism1
1CompletedTreatmentMuscle Anabolism1
1CompletedTreatmentProstate Cancer2
1RecruitingOtherHypogonadism1
1RecruitingTreatmentAging1
1RecruitingTreatmentProstate Cancer1
1TerminatedBasic ScienceIdiopathic Hypogonadotropic Hypogonadism / Olfacto genital dysplasia1
1TerminatedPreventionHypoactive Sexual Desire Disorder (HSDD)1
1TerminatedTreatmentHypogonadism1
1WithdrawnOtherPost-menopausal Period1
1WithdrawnTreatmentHypogonadism1
1, 2CompletedNot AvailableDisseminated Sclerosis1
1, 2CompletedPreventionContraception2
1, 2CompletedTreatmentAndrogen Deficiency / BMI >30 kg/m2 / Insulin Resistance / Metabolic Diseases / Type 2 Diabetes Mellitus1
1, 2CompletedTreatmentGender Dysphoria1
1, 2CompletedTreatmentHealthy Males2
1, 2CompletedTreatmentHypogonadism1
1, 2Not Yet RecruitingTreatmentSpinal Cord Injuries (SCI)1
1, 2RecruitingTreatmentFemale Infertility Due to Diminished Ovarian Reserve / Primary Ovarian Insufficiency1
1, 2SuspendedTreatmentNeoplasms, Breast / Painful Intercourse / Vaginal Inflammation1
1, 2Unknown StatusTreatmentOpioid Addiction / Pain, Chronic / Symptomatic Hypogonadism1
2Active Not RecruitingPreventionBrca1 Mutation Carrier / Brca2 Mutation Carrier / Cancer, Breast1
2CompletedNot AvailableHypogonadism1
2CompletedBasic ScienceAthletic Performance / Testosterone / Women's Health: Female Athlete/Female Athlete Triad1
2CompletedPreventionHealthy Volunteers1
2CompletedSupportive CareSexual Dysfunction, Physiological1
2CompletedTreatmentAIDS Wasting Syndrome1
2CompletedTreatmentAging / BMI >30 kg/m2 / Hypogonadism / Insulin Resistance1
2CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS) / Spinal Muscular Atrophy (SMA) / Spinobulbar Muscular Atrophy1
2CompletedTreatmentAnorexia Nervosa (AN) / Anxiety / Depression / Eating Disorder1
2CompletedTreatmentCachexia / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentConstitutional Delay in Growth and Puberty (CDGP) / Primary or Secondary Hypogonadism1
2CompletedTreatmentContraception / Hypogonadism1
2CompletedTreatmentDepression / Diabetes Mellitus (DM) / Hypogonadism / Osteoporosis / Sarcopenia1
2CompletedTreatmentEjaculatory Dysfunction / Hypogonadism1
2CompletedTreatmentErectile Dysfunction (ED)1
2CompletedTreatmentFrailty / Muscle Weakness / Sarcopenia1
2CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentHip Fractures / Muscle Weakness / Testosterone Deficiency1
2CompletedTreatmentHormonal Cycling / Malignancies / Prostate1
2CompletedTreatmentHuman Growth Hormone Deficiency / Hypogonadism / Hypopituitarism1
2CompletedTreatmentHypoactive Sexual Desire Disorder (HSDD)3
2CompletedTreatmentHypogonadal Males1
2CompletedTreatmentHypogonadism9
2CompletedTreatmentHypogonadism / Low Testosterone1
2CompletedTreatmentHypogonadism / Nonalcoholic Steatohepatitis1
2CompletedTreatmentHypogonadism / Testicular Hypogonadism1
2CompletedTreatmentHypogonadism / Type 2 Diabetes Mellitus1
2CompletedTreatmentMeibomian Gland Dysfunction (MGD)1
2CompletedTreatmentObesity in Men1
2CompletedTreatmentOvarian Diseases1
2CompletedTreatmentProstate Cancer1
2CompletedTreatmentRecurrent Prostate Cancer1
2CompletedTreatmentSex Behavior1
2CompletedTreatmentTesticular Hypogonadism1
2CompletedTreatmentSecondary Hypogonadotrophic hypogonadism3
2Enrolling by InvitationPreventionHypogonadotropism1
2Enrolling by InvitationTreatmentHypogonadotropism1
2Not Yet RecruitingOtherHealthy Volunteers / Male Contraception / Men1
2Not Yet RecruitingTreatmentDisseminated Sclerosis1
2Not Yet RecruitingTreatmentFunctional Disability After ICU / Hypermetabolism in ICU / ICU Acquired Hypogonadism / Loss of muscle mass / Treatment With Testosterone Gel in ICU1
2Not Yet RecruitingTreatmentPituitary gonadotropin hypofunction1
2Not Yet RecruitingTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
2RecruitingPreventionTesticular Cancer1
2RecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC) / Homologous Recombination Deficiency1
2RecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC) / Metastatic Hormone Refractory Prostate Cancer / Prostate Cancer1
2RecruitingTreatmentMenopause1
2RecruitingTreatmentSpinal Cord Injuries (SCI)1
2SuspendedTreatmentHypogonadism / Osteopenia / Osteoporosis1
2TerminatedTreatmentHealthy Volunteers1
2TerminatedTreatmentHeart Failure2
2TerminatedTreatmentHormone Deficiency1
2TerminatedTreatmentHypogonadism1
2TerminatedTreatmentIdiopathic Hypogonadotropic Hypogonadism / Type 2 Diabetes Mellitus1
2TerminatedTreatmentProstate Cancer1
2Unknown StatusTreatmentArthralgia/joint pain / Cancer, Breast / Osteoporosis1
2Unknown StatusTreatmentHypogonadism / Pain NOS1
2WithdrawnTreatmentDisseminated Sclerosis / Multiple Sclerosis, Primary Progressive / Relapsing Remitting Multiple Sclerosis (RRMS) / Secondary Progressive Multiple Sclerosis (SPMS)1
2WithdrawnTreatmentMetabolic Syndromes1
2WithdrawnTreatmentProstate Cancer1
2, 3CompletedHealth Services ResearchSpinal Cord Injuries (SCI)1
2, 3CompletedTreatmentAnorexia Nervosa (AN)1
2, 3CompletedTreatmentConstitutional Delay of Growth and Puberty1
2, 3CompletedTreatmentHealthy Volunteers2
2, 3CompletedTreatmentHypergonadotropic Azospermia / Hypergonadotropic Cryptozoospermia / Hypergonadotropic Hypogonadism / Klinefelter's Syndrome1
2, 3CompletedTreatmentHypogonadism / Spinal Cord Injuries (SCI)1
2, 3CompletedTreatmentMinor burns1
2, 3RecruitingTreatmentAcute Myocardial Infarction: Rehabilitation Phase / Hypogonadism1
2, 3RecruitingTreatmentCritical Illness Polyneuropathies1
2, 3RecruitingTreatmentLeydig Cell Failure in Adult / Metabolic Syndromes / Testicular Cancer1
2, 3RecruitingTreatmentMuscle Weakness1
2, 3RecruitingTreatmentMinor burns1
3Active Not RecruitingBasic ScienceMuscle Hypotrophy / Muscle Wasting / Sarcopenia1
3Active Not RecruitingSupportive CareArthralgia/joint pain / Cancer, Breast / Menopausal Hot Flushes / Musculoskeletal Complications / Sexual Dysfunctions1
3Active Not RecruitingTreatmentObesity and Hypogonadism1
3CompletedNot AvailableOvarian Response1
3CompletedBasic ScienceHypogonadism1
3CompletedSupportive CareCancer Survivors / Sexual Dysfunctions / Sexuality and Reproductive Issues / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedTreatmentAdult Male Hypogonadism2
3CompletedTreatmentAdult Male Hypogonadism / Testicular Hypogonadism1
3CompletedTreatmentAlzheimer's Disease (AD) / Mild Cognitive Impairment (MCI)1
3CompletedTreatmentAndrogens (Deficiency) / Males1
3CompletedTreatmentAndropause1
3CompletedTreatmentBMI >30 kg/m2 / Hypogonadism1
3CompletedTreatmentCancer, Advanced1
3CompletedTreatmentCoronary Artery Disease1
3CompletedTreatmentElective Hip Replacement / Frailty / Hip Arthroplasty / Hip Fractures / Hypogonadism / Physical Frailty1
3CompletedTreatmentErectile Dysfunction (ED) / Hypogonadism1
3CompletedTreatmentHypergonadotropic Hypogonadism / Idiopathic Hypogonadotropic Hypogonadism1
3CompletedTreatmentHypoactive Sexual Desire Disorder (HSDD)12
3CompletedTreatmentHypogonadism8
3CompletedTreatmentInfertility, Female1
3CompletedTreatmentSubfertility1
3CompletedTreatmentTesticular Hypogonadism5
3CompletedTreatmentSecondary Hypogonadotrophic hypogonadism3
3Not Yet RecruitingTreatmentFertility Disorders1
3Not Yet RecruitingTreatmentHypogonadism1
3RecruitingPreventionChronic Renal Failure (CRF)1
3RecruitingTreatmentFrailty / Hip Fractures / Sarcopenia1
3RecruitingTreatmentHypogonadism / Pre-frail Seniors1
3RecruitingTreatmentInfertilities / Poor Ovarian Response1
3RecruitingTreatmentTesticular Hypogonadism1
3Unknown StatusTreatmentACL Reconstruction / Muscle Wasting / Osteoarthritis (OA) / Traumas1
3Unknown StatusTreatmentHypogonadism2
3Unknown StatusTreatmentHypogonadism / Metabolic Syndromes1
3Unknown StatusTreatmentMetabolic Syndromes1
4Active Not RecruitingTreatmentKlinefelter's Syndrome1
4CompletedNot AvailableHypogonadism1
4CompletedNot AvailableMuscle Weakness / Muscular Atrophy1
4CompletedBasic ScienceAbuse of Anabolic Steroids / Steroid Doping1
4CompletedBasic SciencePlacebos / Testosterone1
4CompletedBasic ScienceTranssexualism1
4CompletedPreventionCaloric Restriction / Exercise1
4CompletedPreventionDrug-induced QT Interval Prolongation / Long qt Syndrome / Prolonged QT Interval in EKG and Sudden Death1
4CompletedScreeningHypogonadism3
4CompletedTreatmentAging / Frailty / Osteoporosis1
4CompletedTreatmentAngina Pectoris1
4CompletedTreatmentBMI >30 kg/m2 / Erectile Dysfunction (ED) / Hypogonadism / Metabolic Syndromes1
4CompletedTreatmentBMI >30 kg/m2 / Hypogonadism1
4CompletedTreatmentBMI >30 kg/m2 / Testicular Hypogonadism / Type 2 Diabetes Mellitus1
4CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Hypogonadism1
4CompletedTreatmentBrain Injury / Testosterone / Traumas1
4CompletedTreatmentDiabetes Mellitus (DM) / Erectile Dysfunction (ED) / Testosterone Deficiency1
4CompletedTreatmentDiabetes Mellitus (DM) / Hypogonadism1
4CompletedTreatmentDiabetes Mellitus (DM) / Peripheral Vascular Disease (PVD)1
4CompletedTreatmentErectile Dysfunction (ED) / Hypogonadism1
4CompletedTreatmentFrailty / Sarcopenia1
4CompletedTreatmentHeart Failure1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHypogonadism4
4CompletedTreatmentHypogonadism / Lower Urinary Tract Symptoms (LUTS) / Prostatic Hyperplasia1
4CompletedTreatmentHypogonadism / Type 2 Diabetes Mellitus1
4CompletedTreatmentHypogonadotrophic Hypogonadism2
4CompletedTreatmentIdiopathic Hypogonadotropic Hypogonadism1
4CompletedTreatmentMajor Depressive Disorder (MDD)1
4CompletedTreatmentSarcopenia1
4CompletedTreatmentTesticular Hypogonadism / Testosterone Deficiency1
4CompletedTreatmentSecondary Hypogonadotrophic hypogonadism1
4Not Yet RecruitingPreventionBMI >30 kg/m2 / Fatty Liver / Testicular Hypogonadism / Type2 Diabetes Mellitus1
4RecruitingBasic ScienceGender Dysphoria1
4RecruitingTreatmentCardiovascular (CV) Disease / Cardiovascular Disease (CVD) / Hypogonadism1
4RecruitingTreatmentHypogonadism1
4RecruitingTreatmentHypogonadism / Type 2 Diabetes Mellittus / Type 2 Diabetes Mellitus1
4RecruitingTreatmentInfertility, Female1
4RecruitingTreatmentTesticular Hypogonadism1
4TerminatedSupportive CareAssess the Effects of a the 90-day Oral TS Study Regimen on PSA, IPSS, Haemoglobin and Haematocrit, and to Assess Adverse and Serious Adverse Events1
4TerminatedTreatmentHypogonadism1
4TerminatedTreatmentHypogonadism / Muscular Diseases / Sarcopenia1
4TerminatedTreatmentHypogonadism / Type 2 Diabetes Mellitus1
4Unknown StatusDiagnosticType 2 Diabetes Mellitus1
4Unknown StatusSupportive CareHypoactive Sexual Desire Disorder (HSDD)1
4Unknown StatusTreatmentAtherosclerosis / Hypogonadism1
4Unknown StatusTreatmentErectile Dysfunction (ED) / Hypogonadotrophic Males1
4Unknown StatusTreatmentHypogonadism / Metabolic Syndromes1
4Unknown StatusTreatmentHypogonadism / Peripheral Vascular Disease (PVD) / Type 2 Diabetes Mellitus1
4Unknown StatusTreatmentPanhypopituitarism1
4WithdrawnTreatmentDiabetes Mellitus (DM) / Hypogonadism1
4WithdrawnTreatmentHypogonadism2
4WithdrawnTreatmentHypogonadism / Low Testosterone / Pain NOS1
4WithdrawnTreatmentSarcopenia1
Not AvailableActive Not RecruitingNot AvailableDuchenne's Muscular Dystrophy (DMD)1
Not AvailableActive Not RecruitingBasic ScienceAging / Insulin Resistance1
Not AvailableActive Not RecruitingTreatmentCircadian / Exercise / Testosterone1
Not AvailableCompletedNot AvailableBone Density / Hypogonadism / Osteoporosis / Paraplegia1
Not AvailableCompletedNot AvailableCancer, Breast1
Not AvailableCompletedNot AvailableHypogonadism3
Not AvailableCompletedNot AvailableHypogonadism / Males1
Not AvailableCompletedNot AvailableIdiopathic Hypogonadotropic Hypogonadism1
Not AvailableCompletedNot AvailableTestosterone Deficiency1
Not AvailableCompletedBasic ScienceAnxiety1
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Menopausal Syndromes1
Not AvailableCompletedBasic ScienceHealthy Volunteers / Volunteers1
Not AvailableCompletedBasic ScienceTestosterone's Effects on Threat Perception/Response1
Not AvailableCompletedDiagnosticHealthy Volunteers1
Not AvailableCompletedOtherBMI >30 kg/m2 / Obstructive Sleep Apnea (OSA) / Polycystic Ovaries Syndrome / Polycystic Ovary Syndrome (PCOS)1
Not AvailableCompletedScreeningOther Diseases or Conditions1
Not AvailableCompletedScreeningPuberty, Precocious1
Not AvailableCompletedTreatmentAlzheimer's Disease (AD) / Hypogonadism1
Not AvailableCompletedTreatmentDepression2
Not AvailableCompletedTreatmentDepressive Disorders / Gonadal Disorders / Hypogonadism1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHypogonadism1
Not AvailableCompletedTreatmentHypogonadism / Pain NOS1
Not AvailableCompletedTreatmentHysterectomy / Menopause / Oophorectomy / Testosterone Deficiency1
Not AvailableCompletedTreatmentKidney Diseases / Renal Failure1
Not AvailableCompletedTreatmentKlinefelter's Syndrome1
Not AvailableCompletedTreatmentProstate Cancer1
Not AvailableCompletedTreatmentStress Urinary Incontinence (SUI)1
Not AvailableEnrolling by InvitationTreatmentOlfacto genital dysplasia1
Not AvailableRecruitingOtherHypogonadism1
Not AvailableRecruitingTreatmentLiver Cirrhosis1
Not AvailableRecruitingTreatmentType 2 Diabetic Male With Hypogonadotrophic Hypogonadism1
Not AvailableSuspendedTreatmentMetabolic Syndromes1
Not AvailableTerminatedNot AvailableCongestive Heart Failure (CHF)1
Not AvailableTerminatedSupportive CareBrain and Central Nervous System Tumors / Musculoskeletal Complications1
Not AvailableTerminatedTreatmentCognition Disorders / Moods Disorders1
Not AvailableUnknown StatusNot AvailableHypogonadism1
Not AvailableUnknown StatusTreatmentBMI >30 kg/m2 / Insulin Resistance1
Not AvailableUnknown StatusTreatmentHeart Failure / Hypogonadism1
Not AvailableUnknown StatusTreatmentMetabolic Syndromes1
Not AvailableUnknown StatusTreatmentOther Complications Associated With Artificial Fertilization1
Not AvailableUnknown StatusTreatmentMinor burns1
Not AvailableWithdrawnOtherHigh Blood Pressure (Hypertension)1
Not AvailableWithdrawnTreatmentInfertilities1

Pharmacoeconomics

Manufacturers
  • Heather drug co inc
  • Valeant pharmaceuticals international
  • Schering corp sub schering plough corp
  • Novartis pharmaceuticals corp
  • Impax laboratories inc
  • Eli lilly and co
  • Purepac pharmaceutical co
  • Private formulations inc
  • Tablicaps inc
  • Usl pharma inc
  • Inwood laboratories inc sub forest laboratories inc
  • Kv pharmaceutical co
  • Lannett co inc
  • Parke davis div warner lambert co
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Alza corp
  • Unimed pharmaceuticals inc
  • Auxilium pharmaceuticals
  • Par pharmaceutical
  • Watson laboratories
  • Slate pharmaceuticals inc
  • Columbia laboratories inc
  • Pharmacia and upjohn co
  • Bedford laboratories div ben venue laboratories inc
  • Paddock laboratories inc
  • Sandoz canada inc
  • Synerx pharma llc
  • Endo pharmaceutical solutions inc
  • Solvay Pharmaceuticals, Inc.
Packagers
  • Abraxis BioScience Inc.
  • Amneal Pharmaceuticals
  • Andapharm
  • Anip Acquisition Co.
  • A-S Medication Solutions LLC
  • Auxilium Pharmaceuticals
  • Bartor Pharmaceutical
  • Breckenridge Pharmaceuticals
  • C.O. Truxton Inc.
  • Carlisle Laboratories Inc.
  • Columbia Labs
  • Contract Pharm
  • Creekwood Pharmaceutical Inc.
  • Cutis Pharma Inc.
  • Darby Dental Supply Co. Inc.
  • Dispensing Solutions
  • DPT Laboratories Ltd.
  • Endo Pharmaceuticals Inc.
  • Glenmark Generics Ltd.
  • Global Pharmaceuticals
  • Indevus Pharmaceuticals
  • Laboratoires Besins International
  • Lannett Co. Inc.
  • Lunsco Inc.
  • Marlex Pharmaceuticals
  • Martica Enterprises Inc.
  • Martin Surgical Supply
  • Medisca Inc.
  • Merit Pharmaceuticals
  • Microtest Laboratories Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • National Pharmaceuticals
  • Paddock Labs
  • Pharmaceutics International Inc.
  • Pharmacia Inc.
  • Pharmaforce Inc.
  • Pharmascience Inc.
  • Physicians Total Care Inc.
  • Prasco Labs
  • Primedics Laboratories
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Schering-Plough Inc.
  • Schwarz Pharma Inc.
  • Slate Pharmaceuticals Inc.
  • Solvay Pharmaceuticals
  • Southwood Pharmaceuticals
  • Star Pharmaceuticals Inc.
  • Stat Rx Usa
  • Syntho Pharmaceuticals Inc.
  • Teva Pharmaceutical Industries Ltd.
  • UNIMED
  • Unimed Pharmaceuticals Inc.
  • Valeant Ltd.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
PatchTransdermal12.2 mg/1
PatchTransdermal2 mg/1d
PatchTransdermal2.5 mg/1d
PatchTransdermal2.5 mg
PatchTransdermal24.3 mg/1
PatchTransdermal4 mg/1d
PatchTransdermal5 mg
PatchTransdermal5 mg/1d
GelTransdermal1 %
GelTransdermal10 mg/1g
GelTransdermal12.5 mg
GelTransdermal16.2 mg/1g
SolutionTopical30 mg/1.5mL
SolutionTransdermal30 mg
Gel, meteredTopical10 mg/0.5g
PatchTransdermal300 micrograms/24hours
SuspensionIntramuscular
GelNasal4.5 %
GelNasal5.5 mg/1
Gel, meteredNasal5.5 mg/0.122g
TabletBuccal30 mg/1
GelTopical50 mg/5g
GelTransdermal50 mg/5g
GelTransdermal
Pellet, implantableSubcutaneous100 mg/1
PelletSubcutaneous75 mg/1
GelTopical10 mg/1g
GelTopical12.5 mg/1.25g
GelTopical16.2 mg/1g
GelTopical20.25 mg/1.25g
GelTopical40.5 mg/2.5g
GelTransdermal25 mg/2.5g
Gel, meteredTopical12.5 mg/1
Gel, meteredTopical20.25 mg/1.25g
Gel, meteredTransdermal1.62 mg/1g
PelletOral100 mg/1
PelletOral200 mg/1
PelletOral25 mg/1
PelletOral37.5 mg/1
PelletOral50 mg/1
PelletOral87.5 mg/1
PelletOral
PowderNot applicable1 g/1g
Prices
Unit descriptionCostUnit
AndroGel Pump 1% Gel (1 Box Contains Two 75 gm Bottles)290.63USD box
Androderm 60 2.5 mg/24hr Patches 1 Box = 60 Patches278.56USD box
Androderm 30 5 mg/24hr Patches 1 Box = 30 Patches277.53USD box
AndroGel (each Box Contains Thirty - 50 mg/5 gm Packets) 150 gm Box274.58USD box
AndroGel (each Box Contains Thirty - 25 mg/2.5 gm Packets) 75 gm Box270.61USD box
Delatestryl 200 mg/ml Oil 5ml Vial93.98USD vial
Testosterone Cypionate 200 mg/ml Oil 10ml Vial88.99USD vial
Testosterone Cypionate 100 mg/ml Oil 10ml Vial57.99USD vial
Depo-Testosterone 200 mg/ml Oil 1ml Vial34.99USD vial
Testosterone cypionate powd32.74USD g
Testosterone Cypionate 200 mg/ml Oil 1ml Vial28.99USD vial
Depo-testosterone 200 mg/ml28.63USD ml
Testopel 75 mg pellets27.5USD pellet
Testosterone cyp 200 mg/ml23.18USD ml
Delatestryl 200 mg/ml vial19.86USD ml
Testred 10 mg capsule17.6USD capsule
Testosterone enan 200 mg/ml16.99USD ml
Testosterone Enanthate 200 mg/ml Oil16.66USD ml
Depo-Testosterone 200 mg/ml Oil13.23USD ml
Android 10 mg capsule11.91USD capsule
Delatestryl 200 mg/ml10.75USD ml
Testim 1% Gel 5 gm Tube10.08USD tube
Androderm 5 mg/24hr patch10.06USD patch
Methyltestosterone powder8.54USD g
Depo-Testosterone 100 mg/ml Oil7.87USD ml
Depo-testosterone 100 mg/ml vial7.67USD ml
Testosterone powder6.25USD g
Testosterone propionate powder6.25USD g
Testosterone cyp 100 mg/ml5.91USD ml
Androderm 2.5 mg/24hr patch5.03USD patch
Methitest 10 mg tablet4.84USD tablet
Striant 30 mg Miscellaneous4.32USD ea
Striant 30 mg mucoadhesive4.31USD each
Depo-Testosterone Cypionate 100 mg/ml2.98USD ml
Testim 1%(50 mg) gel2.47USD g
Testosterone Cypionate 100 mg/ml2.23USD ml
Androgel 1% gel pump1.92USD g
First-testosterone mc 2% cr0.91USD g
First 2% testosterone oint0.88USD g
First-Testosterone 2% Ointment0.86USD gm
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5152997No1992-10-062010-12-11Us
CA2366856No2006-05-162020-03-27Canada
CA1332570No1994-10-182011-10-18Canada
US6348210No2002-02-192019-11-10Us
US5840327No1998-11-242016-08-15Us
US6503894Yes2003-01-072021-03-01Us
US9132089Yes2015-09-152021-03-02Us
US9125816Yes2015-09-082021-03-02Us
US6299900No2001-10-092017-02-19Us
US6818226No2004-11-162017-02-19Us
US6923983No2005-08-022017-02-19Us
US7320968No2008-01-222025-01-18Us
US7608605No2009-10-272023-04-21Us
US7608606No2009-10-272023-04-21Us
US7608607No2009-10-272023-04-21Us
US7608608No2009-10-272023-04-21Us
US7608609No2009-10-272023-04-21Us
US7608610No2009-10-272023-04-21Us
US7935690No2011-05-032023-04-21Us
US8063029No2011-11-222023-04-21Us
US8178518No2012-05-152023-04-21Us
US6319913No2001-11-202018-11-09Us
US6579865No2003-06-172018-11-09Us
US6248358No2001-06-192019-08-23Us
US8466138No2013-06-182026-10-12Us
US8466137No2013-06-182026-10-12Us
US8741881No2014-06-032026-10-12Us
US8729057No2014-05-202026-10-12Us
US8759329No2014-06-242026-10-12Us
US8466136No2013-06-182026-10-12Us
US8486925No2013-07-162026-10-12Us
US8754070No2014-06-172026-10-12Us
US9289586No2016-03-222027-02-26Us
US9180194No2015-11-102026-06-02Us
US8071075No2011-12-062017-02-19Us
US8419307No2013-04-162027-02-26Us
US8784878No2014-07-222023-07-13Us
US8807861No2014-08-192027-02-26Us
US8435944No2013-05-072027-09-27Us
US8993520No2015-03-312026-06-02Us
US8877230No2014-11-042024-02-04Us
US8784882No2014-07-222024-02-04Us
US8574622No2013-11-052024-02-04Us
US8784869No2014-07-222024-02-04Us
US8338395No2012-12-252026-02-27Us
US7718640No2010-05-182027-03-14Us
US9295675No2016-03-292034-02-11Us
US8785426No2014-07-222034-02-11Us
US9622340No2017-04-112034-02-11Us
US9662340No2017-05-302034-02-11Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)155 °CPhysProp
water solubility23.4 mg/L (at 25 °C)YALKOWSKY,SH & HE,Y (2003)
logP3.32HANSCH,C ET AL. (1995)
Caco2 permeability-4.34ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0333 mg/mLALOGPS
logP2.99ALOGPS
logP3.37ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)18.52ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.43 m3·mol-1ChemAxon
Polarizability33.88 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.973
Caco-2 permeable+0.8984
P-glycoprotein substrateSubstrate0.6498
P-glycoprotein inhibitor IInhibitor0.5489
P-glycoprotein inhibitor IINon-inhibitor0.8923
Renal organic cation transporterNon-inhibitor0.7324
CYP450 2C9 substrateNon-substrate0.8167
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7739
CYP450 1A2 substrateNon-inhibitor0.9005
CYP450 2C9 inhibitorNon-inhibitor0.95
CYP450 2D6 inhibitorNon-inhibitor0.9452
CYP450 2C19 inhibitorNon-inhibitor0.6668
CYP450 3A4 inhibitorNon-inhibitor0.8812
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8683
Ames testNon AMES toxic0.9382
CarcinogenicityNon-carcinogens0.9483
BiodegradationNot ready biodegradable0.9174
Rat acute toxicity1.6259 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8938
hERG inhibition (predictor II)Non-inhibitor0.7163
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (13.5 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-004i-3910000000-d6ace9b7f8aff4dd46d0
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-053u-1920200000-db3504f562c54e6e1bbb
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-004l-3910000000-b43cd1ee268a855c8aa0
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-004l-3910000000-356ddfa8ddf8e551278d
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0597-7920000000-dde7fba02fcbcec2d665
GC-MS Spectrum - EI-BGC-MSsplash10-05fs-4920000000-ccd839134de79f179f9e
GC-MS Spectrum - EI-BGC-MSsplash10-00ds-0950000000-c65fc8043083ad93d169
GC-MS Spectrum - GC-MSGC-MSsplash10-004i-3910000000-d6ace9b7f8aff4dd46d0
GC-MS Spectrum - GC-MSGC-MSsplash10-053u-1920200000-db3504f562c54e6e1bbb
GC-MS Spectrum - GC-MSGC-MSsplash10-004l-3910000000-b43cd1ee268a855c8aa0
GC-MS Spectrum - GC-MSGC-MSsplash10-004l-3910000000-356ddfa8ddf8e551278d
Mass Spectrum (Electron Ionization)MSsplash10-00dv-5940000000-5e22fba0c369374c75df
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0090000000-914b212f1dbb7fb7b1ac
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-052b-9800000000-d2e38d44d2f16d0a4203
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-052b-9300000000-6830823fa12b40e784a2
MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , PositiveLC-MS/MSsplash10-0597-7920000000-dde7fba02fcbcec2d665
MS/MS Spectrum - EI-B (HITACHI RMU-6E) , PositiveLC-MS/MSsplash10-05fs-4920000000-ccd839134de79f179f9e
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-00ds-0950000000-48c1f79091d708072f30
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
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4j-6900000000-3d818ffe03ecd499e078
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4j-7900000000-6db3d23d98d548cbbfaa
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ukj-2690000000-14b953cb16c53d1e2744
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uka-2790000000-dcd6839af64c3ef6006e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0090000000-b5f0189f1d6f21b90673
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0090000000-21e1bde01931b051a4a3
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Secondary alcohols / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-skeleton / 3-oxo-delta-4-steroid / 3-oxosteroid / Hydroxysteroid / Oxosteroid / 17-hydroxysteroid / Delta-4-steroid / Cyclohexenone / Cyclic alcohol / Secondary alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo steroid, 17beta-hydroxy steroid, androstanoid (CHEBI:17347) / androstane, C19 steroids (androgens) and derivatives, Androstane and derivatives, Androgens (C00535) / C19 steroids (androgens) and derivatives (LMST02020002)

Targets

Details
1. 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. [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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Details
2. Estrogen receptor alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Kojima H, Iida M, Katsura E, Kanetoshi A, Hori Y, Kobayashi K: Effects of a diphenyl ether-type herbicide, chlornitrofen, and its amino derivative on androgen and estrogen receptor activities. Environ Health Perspect. 2003 Apr;111(4):497-502. [PubMed:12676605]
  2. Zhou J, Ng S, Adesanya-Famuiya O, Anderson K, Bondy CA: Testosterone inhibits estrogen-induced mammary epithelial proliferation and suppresses estrogen receptor expression. FASEB J. 2000 Sep;14(12):1725-30. doi: 10.1096/fj.99-0863com. [PubMed:10973921]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
General Function
Zinc ion binding
Specific Function
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
Gene Name
NR3C2
Uniprot ID
P08235
Uniprot Name
Mineralocorticoid receptor
Molecular Weight
107066.575 Da
References
  1. Takeda AN, Pinon GM, Bens M, Fagart J, Rafestin-Oblin ME, Vandewalle A: The synthetic androgen methyltrienolone (r1881) acts as a potent antagonist of the mineralocorticoid receptor. Mol Pharmacol. 2007 Feb;71(2):473-82. Epub 2006 Nov 14. [PubMed:17105867]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
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. Zhang T, Zhu Y, Gunaratna C: Rapid and quantitative determination of metabolites from multiple cytochrome P450 probe substrates by gradient liquid chromatography-electrospray ionization-ion trap mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 25;780(2):371-9. [PubMed:12401364]
  2. Kandel SE, Han LW, Mao Q, Lampe JN: Digging Deeper into CYP3A Testosterone Metabolism: Kinetic, Regioselectivity, and Stereoselectivity Differences between CYP3A4/5 and CYP3A7. Drug Metab Dispos. 2017 Dec;45(12):1266-1275. doi: 10.1124/dmd.117.078055. Epub 2017 Oct 6. [PubMed:28986474]
  3. Usmani KA, Tang J: Human cytochrome P450: metabolism of testosterone by CYP3A4 and inhibition by ketoconazole. Curr Protoc Toxicol. 2004 Jun;Chapter 4:Unit4.13. doi: 10.1002/0471140856.tx0413s20. [PubMed:20945304]
  4. Han JH, Lee YS, Kim HJ, Lee SY, Myung SC: Association between cytochrome CYP17A1, CYP3A4, and CYP3A43 polymorphisms and prostate cancer risk and aggressiveness in a Korean study population. Asian J Androl. 2015 Mar-Apr;17(2):285-91. doi: 10.4103/1008-682X.133320. [PubMed:25337833]
  5. Flockhart Table of Drug Interactions [Link]
  6. Source [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Niwa T, Narita K, Okamoto A, Murayama N, Yamazaki H: Comparison of Steroid Hormone Hydroxylations by and Docking to Human Cytochromes P450 3A4 and 3A5. J Pharm Pharm Sci. 2019;22(1):332-339. doi: 10.18433/jpps30558. [PubMed:31339834]
  2. Han JH, Lee YS, Kim HJ, Lee SY, Myung SC: Association between cytochrome CYP17A1, CYP3A4, and CYP3A43 polymorphisms and prostate cancer risk and aggressiveness in a Korean study population. Asian J Androl. 2015 Mar-Apr;17(2):285-91. doi: 10.4103/1008-682X.133320. [PubMed:25337833]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Ohmori S, Fujiki N, Nakasa H, Nakamura H, Ishii I, Itahashi K, Kitada M: Steroid hydroxylation by human fetal CYP3A7 and human NADPH-cytochrome P450 reductase coexpressed in insect cells using baculovirus. Res Commun Mol Pathol Pharmacol. 1998 Apr;100(1):15-28. [PubMed:9644715]
  2. Han JH, Lee YS, Kim HJ, Lee SY, Myung SC: Association between cytochrome CYP17A1, CYP3A4, and CYP3A43 polymorphisms and prostate cancer risk and aggressiveness in a Korean study population. Asian J Androl. 2015 Mar-Apr;17(2):285-91. doi: 10.4103/1008-682X.133320. [PubMed:25337833]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Monooxygenase activity
Specific Function
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name
CYP3A43
Uniprot ID
Q9HB55
Uniprot Name
Cytochrome P450 3A43
Molecular Weight
57669.21 Da
References
  1. Han JH, Lee YS, Kim HJ, Lee SY, Myung SC: Association between cytochrome CYP17A1, CYP3A4, and CYP3A43 polymorphisms and prostate cancer risk and aggressiveness in a Korean study population. Asian J Androl. 2015 Mar-Apr;17(2):285-91. doi: 10.4103/1008-682X.133320. [PubMed:25337833]
Details
5. Cytochrome P450 19A1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Morale MC, L'Episcopo F, Tirolo C, Giaquinta G, Caniglia S, Testa N, Arcieri P, Serra PA, Lupo G, Alberghina M, Harada N, Honda S, Panzica GC, Marchetti B: Loss of aromatase cytochrome P450 function as a risk factor for Parkinson's disease? Brain Res Rev. 2008 Mar;57(2):431-43. doi: 10.1016/j.brainresrev.2007.10.011. Epub 2007 Nov 7. [PubMed:18063054]
  2. Wang ZJ, Jeffs B, Ito M, Achermann JC, Yu RN, Hales DB, Jameson JL: Aromatase (Cyp19) expression is up-regulated by targeted disruption of Dax1. Proc Natl Acad Sci U S A. 2001 Jul 3;98(14):7988-93. doi: 10.1073/pnas.141543298. Epub 2001 Jun 26. [PubMed:11427738]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Sjoberg RL, Ducci F, Barr CS, Newman TK, Dell'osso L, Virkkunen M, Goldman D: A non-additive interaction of a functional MAO-A VNTR and testosterone predicts antisocial behavior. Neuropsychopharmacology. 2008 Jan;33(2):425-30. Epub 2007 Apr 11. [PubMed:17429405]
  2. Hoff KM: Interaction of testosterone with monoamineoxidase in mouse brain maturation. Gen Pharmacol. 1977;8(1):55-7. [PubMed:590724]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name
CYP11A1
Uniprot ID
P05108
Uniprot Name
Cholesterol side-chain cleavage enzyme, mitochondrial
Molecular Weight
60101.87 Da
References
  1. Kostic TS, Stojkov NJ, Bjelic MM, Mihajlovic AI, Janjic MM, Andric SA: Pharmacological doses of testosterone upregulated androgen receptor and 3-Beta-hydroxysteroid dehydrogenase/delta-5-delta-4 isomerase and impaired leydig cells steroidogenesis in adult rats. Toxicol Sci. 2011 Jun;121(2):397-407. doi: 10.1093/toxsci/kfr063. Epub 2011 Apr 6. [PubMed:21427060]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-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 oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Schwarz D, Kisselev P, Schunck WH, Chernogolov A, Boidol W, Cascorbi I, Roots I: Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. Pharmacogenetics. 2000 Aug;10(6):519-30. [PubMed:10975606]
  2. Urban P, Truan G, Pompon D: High-throughput functional screening of steroid substrates with wild-type and chimeric P450 enzymes. Biomed Res Int. 2014;2014:764102. doi: 10.1155/2014/764102. Epub 2014 Aug 26. [PubMed:25243177]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Shimada T, Watanabe J, Kawajiri K, Sutter TR, Guengerich FP, Gillam EM, Inoue K: Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13. doi: 10.1093/carcin/20.8.1607. [PubMed:10426814]
  2. Zhang H, Li L, Xu Y: CYP1B1 polymorphisms and susceptibility to prostate cancer: a meta-analysis. PLoS One. 2013 Jul 4;8(7):e68634. doi: 10.1371/journal.pone.0068634. Print 2013. [PubMed:23861929]
  3. Pingili AK, Thirunavukkarasu S, Kara M, Brand DD, Katsurada A, Majid DS, Navar LG, Gonzalez FJ, Malik KU: 6beta-Hydroxytestosterone, a Cytochrome P450 1B1-Testosterone-Metabolite, Mediates Angiotensin II-Induced Renal Dysfunction in Male Mice. Hypertension. 2016 May;67(5):916-26. doi: 10.1161/HYPERTENSIONAHA.115.06936. Epub 2016 Feb 29. [PubMed:26928804]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-s...
Gene Name
CYP2A13
Uniprot ID
Q16696
Uniprot Name
Cytochrome P450 2A13
Molecular Weight
56687.095 Da
References
  1. von Weymarn LB, Zhang QY, Ding X, Hollenberg PF: Effects of 8-methoxypsoralen on cytochrome P450 2A13. Carcinogenesis. 2005 Mar;26(3):621-9. doi: 10.1093/carcin/bgh348. Epub 2004 Dec 3. [PubMed:15579482]
  2. Gene cards, CYP2A13 [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Ekins S, Vandenbranden M, Ring BJ, Gillespie JS, Yang TJ, Gelboin HV, Wrighton SA: Further characterization of the expression in liver and catalytic activity of CYP2B6. J Pharmacol Exp Ther. 1998 Sep;286(3):1253-9. [PubMed:9732386]
  2. Rendic S, Nolteernsting E, Schanzer W: Metabolism of anabolic steroids by recombinant human cytochrome P450 enzymes. Gas chromatographic-mass spectrometric determination of metabolites. J Chromatogr B Biomed Sci Appl. 1999 Nov 26;735(1):73-83. [PubMed:10630892]
  3. Yang TJ, Krausz KW, Shou M, Yang SK, Buters JT, Gonzalez FJ, Gelboin HV: Inhibitory monoclonal antibody to human cytochrome P450 2B6. Biochem Pharmacol. 1998 May 15;55(10):1633-40. doi: 10.1016/s0006-2952(98)00018-5. [PubMed:9633999]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Zhang JG, Dehal SS, Ho T, Johnson J, Chandler C, Blanchard AP, Clark RJ Jr, Crespi CL, Stresser DM, Wong J: Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7. Epub 2006 Feb 24. [PubMed:16501008]
  2. Yamazaki H, Shimada T: Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9. doi: 10.1006/abbi.1997.0302. [PubMed:9328296]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
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. Pardridge WM: Serum bioavailability of sex steroid hormones. Clin Endocrinol Metab. 1986 May;15(2):259-78. [PubMed:3521955]
  2. Guechot J, Loric S, Vaubourdolle M, Chretien Y, Giboudeau J, Poupon R: Effect of protein binding on testosterone extraction by human cirrhotic liver: evidence for a dissociation-limited uptake. J Clin Endocrinol Metab. 1989 Jul;69(1):200-3. doi: 10.1210/jcem-69-1-200. [PubMed:2732295]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
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. Pardridge WM: Serum bioavailability of sex steroid hormones. Clin Endocrinol Metab. 1986 May;15(2):259-78. [PubMed:3521955]
  2. Guechot J, Loric S, Vaubourdolle M, Chretien Y, Giboudeau J, Poupon R: Effect of protein binding on testosterone extraction by human cirrhotic liver: evidence for a dissociation-limited uptake. J Clin Endocrinol Metab. 1989 Jul;69(1):200-3. doi: 10.1210/jcem-69-1-200. [PubMed:2732295]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Kobayashi Y, Hirokawa N, Ohshiro N, Sekine T, Sasaki T, Tokuyama S, Endou H, Yamamoto T: Differential gene expression of organic anion transporters in male and female rats. Biochem Biophys Res Commun. 2002 Jan 11;290(1):482-7. [PubMed:11779196]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
References
  1. Kobayashi Y, Hirokawa N, Ohshiro N, Sekine T, Sasaki T, Tokuyama S, Endou H, Yamamoto T: Differential gene expression of organic anion transporters in male and female rats. Biochem Biophys Res Commun. 2002 Jan 11;290(1):482-7. [PubMed:11779196]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Virus receptor activity
Specific Function
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
Gene Name
SLC10A1
Uniprot ID
Q14973
Uniprot Name
Sodium/bile acid cotransporter
Molecular Weight
38118.64 Da
References
  1. Schroeder A, Eckhardt U, Stieger B, Tynes R, Schteingart CD, Hofmann AF, Meier PJ, Hagenbuch B: Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells. Am J Physiol. 1998 Feb;274(2 Pt 1):G370-5. [PubMed:9486191]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Janvilisri T, Venter H, Shahi S, Reuter G, Balakrishnan L, van Veen HW: Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51. Epub 2003 Mar 28. [PubMed:12668685]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Cho E, Montgomery RB, Mostaghel EA: Minireview: SLCO and ABC transporters: a role for steroid transport in prostate cancer progression. Endocrinology. 2014 Nov;155(11):4124-32. doi: 10.1210/en.2014-1337. Epub 2014 Aug 22. [PubMed:25147980]
  2. Sharifi N, Hamada A, Sissung T, Danesi R, Venzon D, Baum C, Gulley JL, Price DK, Dahut WL, Figg WD: A polymorphism in a transporter of testosterone is a determinant of androgen independence in prostate cancer. BJU Int. 2008 Aug 5;102(5):617-21. doi: 10.1111/j.1464-410X.2008.07629.x. Epub 2008 Jun 4. [PubMed:18537956]

Drug created on June 13, 2005 07:24 / Updated on October 20, 2019 02:47