TESTOSTERONE CYPIONATE

First marketed in 1937

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H40O3
Molecular Weight	412.6047
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2OC(=O)CCC5CCCC5

InChI

InChIKey=HPFVBGJFAYZEBE-ZLQWOROUSA-N

InChI=1S/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/m0/s1

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB00624
Curator's Comment: Description was created based on several sources, including

Testosterone is a steroid sex hormone found in both men and women. In men, testosterone is produced primarily by the Leydig (interstitial) cells of the testes when stimulated by luteinizing hormone (LH). It functions to stimulate spermatogenesis, promote physical and functional maturation of spermatozoa, maintain accessory organs of the male reproductive tract, support development of secondary sexual characteristics, stimulate growth and metabolism throughout the body and influence brain development by stimulating sexual behaviors and sexual drive. In women, testosterone is produced by the ovaries (25%), adrenals (25%) and via peripheral conversion from androstenedione (50%). Testerone in women functions to maintain libido and general wellbeing. Testosterone exerts a negative feedback mechanism on pituitary release of LH and follicle-stimulating hormone (FSH). Testosterone may be further converted to dihydrotestosterone or estradiol depending on the tissue. 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 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. Testosterone is used as hormone replacement or substitution of diminished or absent endogenous testosterone. Use in males: For management of congenital or acquired hypogonadism, hypogonadism associated with HIV infection, and male climacteric (andopause). Use in females: For palliative treatment of androgen-responsive, advanced, inoperable, metastatis (skeletal) carcinoma of the breast in women who are 1-5 years postmenopausal; testosterone esters may be used in combination with estrogens in the management of moderate to severe vasomotor symptoms associated with menopause in women who do not respond to adequately to estrogen therapy alone.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen receptor 42 Target ID: P10275 Gene ID: 367.0 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17635942	Agonist 2752
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19856921	Agonist 2752		3.16 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypogonadism 29 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/203098s006lbl.pdf	Primary		Approved 8583	TESTOSTERONE Approved Use Testosterone is an androgen indicated for replacement therapy in males for conditions associated with a deficiency or absence of endogenous testosterone: • Primary Hypogonadism (Congenital or Acquired) (1) • Hypogonadotropic Hypogonadism (Congenital or Acquired) Launch Date 2013

C_max

Value	Dose	Analyte	Population
930.1 ng/dL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01386606	5 g 1 times / day multiple, topical dose: 5 g route of administration: topical experiment type: multiple co-administered:	TESTOSTERONE plasma	Homo sapiens
231 ng/dL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01725451	30 mg single, topical dose: 30 mg route of administration: topical experiment type: single co-administered:	TESTOSTERONE serum	Homo sapiens population: healthy age: sex: food status:
214 ng/dL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01725451	30 mg single, topical dose: 30 mg route of administration: topical experiment type: single co-administered:	TESTOSTERONE serum	Homo sapiens population: healthy age: sex: food status:
13.1 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10902784/	8.2 mg single, topical dose: 8.2 mg route of administration: Topical experiment type: SINGLE co-administered:	TESTOSTERONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
3110 ng*h/dL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01725451	30 mg single, topical dose: 30 mg route of administration: topical experiment type: single co-administered:	TESTOSTERONE serum	Homo sapiens population: healthy age: sex: food status:
2120 ng*h/dL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01725451	30 mg single, topical dose: 30 mg route of administration: topical experiment type: single co-administered:	TESTOSTERONE serum	Homo sapiens population: healthy age: sex: food status:
948 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10902784/	8.2 mg single, topical dose: 8.2 mg route of administration: Topical experiment type: SINGLE co-administered:	TESTOSTERONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10902784/	8.2 mg single, topical dose: 8.2 mg route of administration: Topical experiment type: SINGLE co-administered:		TESTOSTERONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
13% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10902784/	8.2 mg single, topical dose: 8.2 mg route of administration: Topical experiment type: SINGLE co-administered:		TESTOSTERONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 910 P-gp 1741 MRP2 499	UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A5 56 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A10 331 UGT2A1 39 UGT2A2 49 UGT2A3 49 UGT2B4 278 UGT2B7 456 UGT2B10 131 UGT2B15 236 UGT2B17 237 UGT2B28 65 CYP3A5 446 CYP3A7 109 P-gp 2052	MCT4 19 P-gp 301

Drug as perpetrator

Target	Modality	Activity
BCRP 985	inhibitor 4027 Sources: https://link.springer.com/article/10.1007/s11095-009-9896-0 Page: -	no
MRP2 625	inhibitor 4027 Sources: https://link.springer.com/article/10.1007/s11095-009-9896-0 Page: -	no
P-gp 1932	inhibitor 4027 Sources: https://link.springer.com/article/10.1007/s11095-009-9896-0 Page: -	no
MCT4 31	inducer 1966 Sources: https://physoc.onlinelibrary.wiley.com/doi/full/10.1113/jphysiol.2006.115436 Page: -	yes
P-gp 1932	inducer 1966 Sources: https://www.sciencedirect.com/science/article/pii/S0024320506000786 Page: -	yes

Drug as victim

Target	Modality	Activity
UGT2B17 237	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	major [Km 10 uM]
UGT2A1 39	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	major [Km 38.7 uM]
UGT1A10 331	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A3 470	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A4 399	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A8 323	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A9 423	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT2A2 49	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT2B15 236	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT2B7 456	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A1 479	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT1A5 56	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT1A6 343	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT1A7 249	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2A3 49	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2B10 131	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2B28 65	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2B4 278	substrate 4014 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
CYP3A4 1946	substrate 4014 Sources: https://jpet.aspetjournals.org/content/299/3/825.short Page: -	yes
CYP3A5 446	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5697443/ Page: -	yes
CYP3A7 109	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5697443/ Page: -	yes
P-gp 2052	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0006291X19317887 Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:17347	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17347
ChemicalBook	CB5380541	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5380541
eMolecules	511977	https://www.emolecules.com/cgi-bin/more?vid=511977
ZINC	ZINC000118912393	http://zinc15.docking.org/substances/ZINC000118912393

PubMed

Title	Date	PubMed
Effects of estrogenic (o,p'-DDT; octylphenol) and anti-androgenic (p,p'-DDE) chemicals on indicators of endocrine status in juvenile male summer flounder (Paralichthys dentatus).	2001-04	11164537
Changes in androgenic steroid profile due to urine contamination by microorganisms: a prospective study in the context of doping control.	2001-02-15	11161304
Luteinizing hormone-dependent activity and luteinizing hormone-independent differentiation of rat fetal Leydig cells.	2001-02-14	11165053
Porcine gonadal and placental isozymes of aromatase cytochrome P450: sub-cellular distribution and support by NADPH-cytochrome P450 reductase.	2001-02-14	11165045
Testosterone concentrations in women aged 25-50 years: associations with lifestyle, body composition, and ovarian status.	2001-02-01	11157413
Neuronal size in the spinal nucleus of the bulbocavernosus: direct modulation by androgen in rats with mosaic androgen insensitivity.	2001-02-01	11157092
Psychophysiological responses to the Stroop Task after a maximal cycle ergometry in elite sportsmen and physically active subjects.	2001-02	11166107
Spz1, a novel bHLH-Zip protein, is specifically expressed in testis.	2001-02	11165476
Effects of the anti-androgen finasteride on the modulatory actions of oestradiol on androgen metabolism by human gingival fibroblasts.	2001-02	11163318
Androgens and the role of female "hyperaggressiveness" in spotted hyenas (Crocuta crocuta).	2001-02	11161886
Interactions among paternal behavior, steroid hormones, and parental experience in male marmosets (Callithrix kuhlii).	2001-02	11161885
Castration in Gambel's and Scaled Quail: ornate plumage and dominance persist, but courtship and threat behaviors do not.	2001-02	11161878
cDNA cloning and initial characterization of CYP3A43, a novel human cytochrome P450.	2001-02	11160876
Modulation of P450 CYP3A4-dependent metabolism by P-glycoprotein: implications for P450 phenotyping.	2001-02	11160617
Claudin-1 is not restricted to tight junctions in the rat epididymis.	2001-02	11159859
Relative enzymatic activity, protein stability, and tissue distribution of human steroid-metabolizing UGT2B subfamily members.	2001-02	11159850
Effects of organic solvents on the activities of cytochrome P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes.	2001-02	11159803
Performance characteristics of a carbon isotope ratio method for detecting doping with testosterone based on urine diols: controls and athletes with elevated testosterone/epitestosterone ratios.	2001-02	11159778
Photoperiod-induced testicular apoptosis in European starlings (Sturnus vulgaris).	2001-02	11159376
Neuroendocrine regulation of sexually dimorphic brain structure and associated sexual behavior in male rats is genetically controlled.	2001-02	11159360
Influence of the degree of stimulation of the pituitary by gonadotropin-releasing hormone on the action of inhibin and testosterone to suppress the secretion of the gonadotropins in rams.	2001-02	11159349
Follicular-fluid factors and granulosa-cell gene expression associated with follicle deviation in cattle.	2001-02	11159344
Substitution mutation C268Y causes 17 beta-hydroxysteroid dehydrogenase 3 deficiency.	2001-02	11158067
Sex differences in androgen receptors of the human mamillary bodies are related to endocrine status rather than to sexual orientation or transsexuality.	2001-02	11158052
Plasma melatonin concentration before and during testosterone replacement in Klinefelter's syndrome: relation to hepatic indolamine metabolism and sympathoadrenal activity.	2001-02	11158039
Longitudinal effects of aging on serum total and free testosterone levels in healthy men. Baltimore Longitudinal Study of Aging.	2001-02	11158037
Evidence that cyproterone acetate improves psychological symptoms and enhances the activity of the dopaminergic system in postmenopause.	2001-02	11158017
Androgen deficiency in women with hypopituitarism.	2001-02	11158009
Muting of androgen negative feedback unveils impoverished gonadotropin-releasing hormone/luteinizing hormone secretory reactivity in healthy older men.	2001-02	11158004
Polycystic ovary syndrome is associated with obstructive sleep apnea and daytime sleepiness: role of insulin resistance.	2001-02	11158002
Disparate response of wild-type and variant forms of LH to GnRH stimulation in individuals heterozygous for the LHbeta variant allele.	2001-02	11157812
Estrogen and androgen elicit growth hormone release via dissimilar patterns of hypothalamic neuropeptide secretion.	2001-02	11146085
Sex difference in the phosphorylation of cAMP response element binding protein (CREB) in neonatal rat brain.	2001-01-26	11164773
Testosterone modulates the dendritic architecture of arcuate neuroendocrine neurons in adult male rats.	2001-01-26	11164770
Expression of the 17beta-hydroxysteroid dehydrogenase type 5 mRNA in the human brain.	2001-01-22	11165025
Distribution of 17beta-hydroxysteroid dehydrogenases in human osteoblast-like cells.	2001-01-22	11165024
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.	2001-01-22	11165023
Structure-function aspects and inhibitor design of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3).	2001-01-22	11165022
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.	2001-01-22	11165020
Pan1b (17betaHSD11)-enzymatic activity and distribution in the lung.	2001-01-22	11165019
17beta-Hydroxysteroid dehydrogenase type 9 and other short-chain dehydrogenases/reductases that catalyze retinoid, 17beta- and 3alpha-hydroxysteroid metabolism.	2001-01-22	11165018
Type 5 17beta-hydroxysteroid dehydrogenase: its role in the formation of androgens in women.	2001-01-22	11165014
Induction of nuclear transcription factors, cytochrome P450 monooxygenases, and glutathione S-transferase alpha gene expression in Aroclor 1254-treated rat hepatocyte cultures.	2001-01-15	11163329
Reproductive effects of valproate, carbamazepine, and oxcarbazepine in men with epilepsy.	2001-01-09	11148232
Progressive decrease in bone density over 10 years of androgen deprivation therapy in patients with prostate cancer.	2001-01	11164157
Long-term remission of ovarian hyperandrogenism after short-term treatment with a gonadotropin-releasing hormone agonist.	2001-01	11163817
Prevalence of polycystic ovary syndrome (PCOS) in first-degree relatives of patients with PCOS.	2001-01	11163816
Concentrations of steroid hormones in layers and biopsies of chelonian egg yolks.	2001-01	11161774
Insulin action and insulin secretion in polycystic ovary syndrome treated with ethinyl oestradiol/cyproterone acetate.	2001-01	11161134
Androgenic anabolic steroids and arterial structure and function in male bodybuilders.	2001-01	11153743

Patents

Sample Use Guides

In Vivo Use Guide

Starting dose of testosterone gel is 50 mg of testosterone (4 pump actuations, two 25 mg packets, or one 50 mg packet), applied once daily in the morning.

Route of Administration: Topical

In Vitro Use Guide

10 nM Testosterone significantly reduced secretion of BDNF in in human airway smooth muscle

Name

Type

Language

TESTOSTERONE CIPIONATE

Preferred Name

English

TESTOSTERONE CYPIONATE

Common Name

English

DEPO-TESTOSTERONE

Brand Name

English

Testosterone cipionate [WHO-DD]

Common Name

English

TESTOSTERONE CYPIONATE [VANDF]

Common Name

English

DEPO-TESTADIOL COMPONENT TESTOSTERONE CYPIONATE

Common Name

English

NSC-9157

Code

English

TESTOSTERONE 17.BETA.-CYCLOPENTANEPROPIONATE [MI]

Common Name

English

TESTOSTERONE CIPIONATE [MART.]

Common Name

English

Testosterone cyclopentanepropionate

Common Name

English

ANDROST-4-EN-3-ONE, 17-(3-CYCLOPENTYL-1-OXOPROPOXY)-, (17.BETA.)-

Systematic Name

English

TESTOSTERONE 17.BETA.-CYCLOPENTANEPROPIONATE

Common Name

English

TESTOSTERONE CYPIONATE CIII [USP-RS]

Common Name

English

TESTOSTERONE CYPIONATE [USP MONOGRAPH]

Common Name

English

TESTOSTERONE CYPIONATE [ORANGE BOOK]

Common Name

English

TESTOSTERONE CYPIONATE CIII

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C862