Etiocholanolone
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MedKoo CAT#: 464829

CAS#: 53-42-9

Description: Etiocholanolone is an androgenically inactive metabolite of testosterone and androstenedione and the 5β epimer of androsterone. It increases the frequency of long channel openings and potentiates GABA-induced chloride currents in HEK293 cells expressing rat α1β2γ2L subunit-containing GABAA receptors when used at a concentration of 10 µM. Etiocholanolone is protective against seizures induced by 6 Hz electroshock or pentylenetetrazol (PTZ; ED50s = 76.9 and 139 mg/kg, respectively). It is also pyretic in an IL-1-dependent manner, inducing increases in body temperature in rhesus macaques but not squirrel monkeys that lack testosterone and androstenedione metabolizing enzymes.

Chemical Structure

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Etiocholanolone
CAS# 53-42-9
Instruction

Theoretical Analysis

MedKoo Cat#: 464829
Name: Etiocholanolone
CAS#: 53-42-9
Chemical Formula: C19H30O2
Exact Mass: 290.22
Molecular Weight: 290.447
Elemental Analysis: C, 78.57; H, 10.41; O, 11.02

Price and Availability

Size Price Availability Quantity
10mg USD 285 2 Weeks
25mg USD 515 2 Weeks
50mg USD 850 2 Weeks
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Synonym: Etiocholanolone; 5β-Androsterone; 5β Androsterone; 5βAndrosterone; 3α-Etiocholanolone; 3αEtiocholanolone; 3α Etiocholanolone; NSC 50908; NSC50908; NSC-50908;

IUPAC/Chemical Name: (3R,5R,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one

InChi Key: QGXBDMJGAMFCBF-BNSUEQOYSA-N

InChi Code: InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1

SMILES Code: C[C@@]12[C@@]3([C@]([H])([C@]4([C@](C(CC4)=O)(C)CC3)[H])CC[C@@]1(C[C@H](O)CC2)[H])[H]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Chloroform 10.0 34.43

Preparing Stock Solutions

The following data is based on the product molecular weight 290.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Marzuki NS, Idris FP, Kartapradja H, Renata S, Harahap A, Batubara JRL. Accuracy of Urinary Etiocholanolone/Androsterone Ratio as Alternative to Serum Testosterone/Dihydrotestosterone Ratio for Diagnosis of 5 Alpha-reductase Type 2 Deficiency Patients and Carriers in Indonesia. Int J Endocrinol Metab. 2021 Apr 18;19(2):e109510. doi: 10.5812/ijem.109510. PMID: 34149847; PMCID: PMC8198621.

2: Honesova L, Van Eenoo P, Polet M. A uniform sample preparation procedure for gas chromatography combustion isotope ratio mass spectrometry for all human doping control relevant anabolic steroids using online 2/3-dimensional liquid chromatography fraction collection. Anal Chim Acta. 2021 Jul 11;1168:338610. doi: 10.1016/j.aca.2021.338610. Epub 2021 May 6. PMID: 34051993.

3: Fuster DG, Morard GA, Schneider L, Mattmann C, Lüthi D, Vogt B, Dhayat NA. Association of urinary sex steroid hormones with urinary calcium, oxalate and citrate excretion in kidney stone formers. Nephrol Dial Transplant. 2020 Dec 9:gfaa360. doi: 10.1093/ndt/gfaa360. Epub ahead of print. PMID: 33295624.

4: Stoll A, Iannone M, De Gregorio G, Molaioni F, de la Torre X, Botrè F, Parr MK. Influence of Indomethacin on Steroid Metabolism: Endocrine Disruption and Confounding Effects in Urinary Steroid Profiling of Anti-Doping Analyses. Metabolites. 2020 Nov 14;10(11):463. doi: 10.3390/metabo10110463. PMID: 33202527; PMCID: PMC7698016.

5: Wang R, Hartmann MF, Wudy SA. Targeted LC-MS/MS analysis of steroid glucuronides in human urine. J Steroid Biochem Mol Biol. 2021 Jan;205:105774. doi: 10.1016/j.jsbmb.2020.105774. Epub 2020 Oct 22. PMID: 33172831.

6: Martinez-Brito D, Notarianni ML, Iannone M, de la Torre X, Botrè F. Validation of steroid sulfates deconjugation for metabolic studies. Application to human urine samples. J Pharmacol Toxicol Methods. 2020 Nov-Dec;106:106938. doi: 10.1016/j.vascn.2020.106938. Epub 2020 Oct 17. PMID: 33080389.

7: Milani C, Rota A, Olsson U, Paganotto A, Holst BS. Serum concentration of mineralocorticoids, glucocorticoids, and sex steroids in peripartum bitches. Domest Anim Endocrinol. 2021 Jan;74:106558. doi: 10.1016/j.domaniend.2020.106558. Epub 2020 Sep 4. PMID: 32980594.

8: Li CY, Gupta A, Gáborik Z, Kis E, Prasad B. Organic Anion Transporting Polypeptide-Mediated Hepatic Uptake of Glucuronide Metabolites of Androgens. Mol Pharmacol. 2020 Sep;98(3):234-242. doi: 10.1124/mol.120.119891. Epub 2020 Jun 25. PMID: 32587096.

9: Volfova M, Machovcova Z, Voslarova E, Bedanova I, Vecerek V. Comparison of the Glucocorticoid Concentrations between Three Species of Lemuridae Kept in a Temporary Housing Facility. Animals (Basel). 2020 Jun 10;10(6):1013. doi: 10.3390/ani10061013. PMID: 32532091; PMCID: PMC7341240.

10: PouralijanAmiri M, Khoshkam M, Madadi R, Kamali K, Faghanzadeh Ganji G, Salek R, Ramazani A. NMR-based plasma metabolic profiling in patients with unstable angina. Iran J Basic Med Sci. 2020 Mar;23(3):311-320. doi: 10.22038/IJBMS.2020.39979.9475. PMID: 32440317; PMCID: PMC7229510.

11: Chioncel O, Collins SP, Butler J. Istaroxime in acute heart failure: the holy grail is at HORIZON? Eur J Heart Fail. 2020 Sep;22(9):1694-1697. doi: 10.1002/ejhf.1843. Epub 2020 May 6. PMID: 32374050.

12: Engelhart DC, Granados JC, Shi D, Saier Jr MH Jr, Baker ME, Abagyan R, Nigam SK. Systems Biology Analysis Reveals Eight SLC22 Transporter Subgroups, Including OATs, OCTs, and OCTNs. Int J Mol Sci. 2020 Mar 5;21(5):1791. doi: 10.3390/ijms21051791. PMID: 32150922; PMCID: PMC7084758.

13: Campbell NA, Angles R, Bowden RM, Casto JM, Paitz RT. Characterizing the timing of yolk testosterone metabolism and the effects of etiocholanolone on development in avian eggs. J Exp Biol. 2020 Feb 20;223(Pt 4):jeb210427. doi: 10.1242/jeb.210427. PMID: 32001543.

14: Carubelli V, Zhang Y, Metra M, Lombardi C, Felker GM, Filippatos G, O'Connor CM, Teerlink JR, Simmons P, Segal R, Malfatto G, La Rovere MT, Li D, Han X, Yuan Z, Yao Y, Li B, Lau LF, Bianchi G, Zhang J; Istaroxime ADHF Trial Group. Treatment with 24 hour istaroxime infusion in patients hospitalised for acute heart failure: a randomised, placebo-controlled trial. Eur J Heart Fail. 2020 Sep;22(9):1684-1693. doi: 10.1002/ejhf.1743. Epub 2020 Jan 23. PMID: 31975496.

15: Marzuki NS, Idris FP, Kartapradja HD, Harahap AR, Batubara JRL. Characterising SRD5A2 Gene Variants in 37 Indonesian Patients with 5-Alpha-Reductase Type 2 Deficiency. Int J Endocrinol. 2019 Dec 1;2019:7676341. doi: 10.1155/2019/7676341. PMID: 31885560; PMCID: PMC6914983.

16: DE Luca S, Amante E, Fiori C, Alleva G, Alladio E, Marini F, Garrou D, Manfredi M, Amparore D, Checcucci E, Pruner S, Salomone A, Scarpa RM, Vincenti M, Porpiglia F. Prospective evaluation of urinary steroids and prostate carcinoma-induced deviation: preliminary results. Minerva Urol Nephrol. 2021 Feb;73(1):98-106. doi: 10.23736/S0393-2249.19.03529-X. Epub 2019 Dec 11. PMID: 31833333.

17: Pussard E, Travers S, Bouvattier C, Xue QY, Cosson C, Viengchareun S, Martinerie L, Lombès M. Urinary steroidomic profiles by LC-MS/MS to monitor classic 21-Hydroxylase deficiency. J Steroid Biochem Mol Biol. 2020 Apr;198:105553. doi: 10.1016/j.jsbmb.2019.105553. Epub 2019 Nov 26. PMID: 31778802.

18: Elmongy H, Masquelier M, Ericsson M. Development and validation of a UHPLC- HRMS method for the simultaneous determination of the endogenous anabolic androgenic steroids in human serum. J Chromatogr A. 2020 Feb 22;1613:460686. doi: 10.1016/j.chroma.2019.460686. Epub 2019 Nov 6. PMID: 31735349.

19: Järvinen E, Kidron H, Finel M. Human efflux transport of testosterone, epitestosterone and other androgen glucuronides. J Steroid Biochem Mol Biol. 2020 Mar;197:105518. doi: 10.1016/j.jsbmb.2019.105518. Epub 2019 Nov 6. PMID: 31704245.

20: Putz M, Piper T, Dubois M, Delahaut P, Thevis M. Analysis of endogenous steroids in urine by means of multi-immunoaffinity chromatography and isotope ratio mass spectrometry for sports drug testing. Anal Bioanal Chem. 2019 Nov;411(28):7563-7571. doi: 10.1007/s00216-019-02169-3. Epub 2019 Nov 15. PMID: 31641821.