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Testosterone undecanoate structure
Testosterone undecanoate structure

Testosterone undecanoate

Iupac Name:[(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] undecanoate
CAS No.: 5949-44-0
Molecular Weight:456.70032
Modify Date.: 2022-11-23 06:49
Introduction:

White Solid


Testosterone undecanoate is a steroid ester.|Testosterone undecanoate is the ester prodrug of testosterone and has a midchain fatty acid at the 17Beta position. It is available as an intramuscular injection and as an oral capsule, and is indicated for treatment of testosterone deficiency. It should be noted that testosterone undecanoate is only indicated for treatment of hypogonadal conditions with structural or genetic etiologies and should not be used to manage "age-related hypogonadism".|Testosterone Undecanoate is the undecanoate ester form of the androgen testosterone, with gonadotropin-secretory inhibiting and hormone replacement activity. As testosterone inhibits the secretion of gonadotropins from the pituitary gland, administration of testosterone decreases the secretion of luteinizing hormone (LH). By inhibiting LH secretion, the growth of Leydig cells, which are normally stimulated by LH to produce testosterone, may be suppressed. In addition, this agent promotes the maintenance of male sex characteristics and can be used for testosterone replacement in hypogonadal males.

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1. Names and Identifiers
1.1 Name
Testosterone undecanoate
1.2 Synonyms

(17β)-17-[(1-Oxoundecyl)oxy]androst-4-en-3-one 17-[(1-oxoundecyl)oxy]-androst-4-en-3-one 17-beta-hydroxy-5-alpha-androstan-3-onundecanoate 4-ANDROSTEN-17BETA-OL-3-ONE 17-UNDECANOATE 4-ANDROSTEN-17-BETA-OL-3-ONE UNDECANOATE andriol Andriol Testocaps Androst-4-en-3-one, 17-[(1-oxoundecyl)oxy]-, (17β)- Jatenzo Nebido Org 538 Rextoro Testocaps TESTOSTERONE UNDECANOATE TESTOSTERONE UNDECANOILATE Testosterone undecylate Testosterone, undecanoate testosterone,undecanoate(ester) Undecanoic acid, ester with testosterone Undestor

1.3 CAS No.
5949-44-0
1.4 CID
65157
1.5 EINECS(EC#)
227-712-6
1.6 Molecular Formula
C30H48O3 (isomer)
1.7 Inchi
InChI=1S/C30H48O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h21,24-27H,4-20H2,1-3H3/t24-,25-,26-,27-,29-,30-/m0/s1
1.8 InChkey
UDSFVOAUHKGBEK-CNQKSJKFSA-N
1.9 Canonical Smiles
CCCCCCCCCCC(=O)OC1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
1.10 Isomers Smiles
CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
2. Properties
2.1 Density
1.03
2.1 Melting point
59-61°C
2.1 Boiling point
550.7 °C at 760 mmHg
2.1 Refractive index
1.522
2.1 Flash Point
230.3 °C
2.1 Precise Quality
456.36000
2.1 PSA
43.37000
2.1 logP
7.96090
2.1 Appearance
White crystalline powder
2.2 Storage
Controlled Substance, -20?C Freezer
2.3 Chemical Properties
White Solid
2.4 Color/Form
Powder
2.5 Water Solubility
H2O: Insoluble
2.6 StorageTemp
Controlled Substance, -20C Freezer
3. Use and Manufacturing
3.1 Usage
A metabolite of Testosterone.CONTROLLED SUBSTANC
4. Safety and Handling
4.1 Hazard Codes
Xn; Xi
4.1 Safety Statements
S7-S26-S36/37/39-S45-S37/39-S24-S36/37-S22
4.1 Hazard Declaration
H302
4.1 Caution Statement
P201, P202, P260, P261, P263, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P405, P501
4.1 WGK Germany
3
4.1 RTECS
EN0330050
4.1 Safety
Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating vapors.
4.2 Specification

White Solid
usageEng:A metabolite of Testosterone. CONTROLLED SUBSTANC
4.3 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XA3119700
CHEMICAL NAME :
Testosterone, undecanoate (ester)
CAS REGISTRY NUMBER :
5949-44-0
BEILSTEIN REFERENCE NO. :
3176734
LAST UPDATED :
199712
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C30-H48-O3
MOLECULAR WEIGHT :
456.78

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
288 mg/kg
SEX/DURATION :
male 84 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 18,607,1978
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Carcinogenicity, Category 2

Reproductive toxicity, Category 1A

Reproductive toxicity, Additional category for effects on or via lactation

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H302 Harmful if swallowed

H351 Suspected of causing cancer

H360 May damage fertility or the unborn child

H362 May cause harm to breast-fed children

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P263 Avoid contact during pregnancy and while nursing.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Other Information
7.0 Mesh
Compounds that interact with ANDROGEN RECEPTORS in target tissues to bring about the effects similar to those of TESTOSTERONE. Depending on the target tissues, androgenic effects can be on SEX DIFFERENTIATION; male reproductive organs, SPERMATOGENESIS; secondary male SEX CHARACTERISTICS; LIBIDO; development of muscle mass, strength, and power. (See all compounds classified as Androgens.)
7.1 Absorption
The absorption of testosterone undecanoate varies based on the formulation. The intramuscular formulation of testosterone esters is suspended in oil and is absorbed from the lipid phase. Testosterone is released when tissue esterases cleave the undecanoic acid side chain. The oral formulation of testosterone undecanoate is also formulated as a prodrug, is best absorbed with food and ideal absorption occurs when taken with a meal containing at least 30 g of fat.|The majority (~90%) of an intramuscularly administered dose of testosterone is conjugated and eliminated in the urine. Approximately 6% of the dose is eliminated primarily unconjugated in the feces.
7.2 Metabolism
The side chain of testosterone undecanoate is cleaved by non specific esterases when it enters circulation and the undecanoic acid side chain is metabolized by the beta-oxidation pathway. The resulting Testosterone molecule is then metabolized to dihydrotestosterone (DHT) by the enzyme 5-alpha reductase. DHT is reduced by 3-alpha-hydroxysteroid dehydrogenase (major) and 3-beta-hydroxysteroid dehydrogenase prior to being glucuronidated and cleared by the kidneys. It should be noted that testosterone is metabolized to several other 17-keto steroids in the body.
7.3 Biological Half Life
Based on one source, Testosterone undecanoate in castor oil (for intramuscular injection) has a half life of 33.9 days, allowing it to maintain serum levels in the normal range for over 6 weeks. It should be noted that the half life of testosterone reported in the literature is inconsistent.
7.4 Mesh Entry Terms
Andriol
7.5 Use Classification
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
8. Computational chemical data
  • Molecular Weight: 456.70032g/mol
  • Molecular Formula: C30H48O3
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 456.36034539
  • Monoisotopic Mass: 456.36034539
  • Complexity: 739
  • Rotatable Bond Count: 11
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 43.4
  • Heavy Atom Count: 33
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcfB4MAAAAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGDAAAAAGgAAAAAADxSggAICCAAABACIAqDSCAAAAAAgAAAACAEAAEgAABIAAQACAAAEgAAIAQOIyPCPgAAAAAAAAACAAAQAACAAAIAADAAAAA==
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