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MedKoo Cat#: 561612 | Name: Oxendolone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxendolone is a steroidal antiandrogen and progestin of the 19-nortestosterone group that has been marketed in Japan by Takeda for the treatment of benign prostatic hyperplasia (BPH) since 1981. It binds to the androgen receptor (AR) (Ki = 320 nM) and progesterone receptor (Ki = 20 nM) and acts as a weak but clinically relevant inhibitor of 5α-reductase.

Chemical Structure

Oxendolone
Oxendolone
CAS#33765-68-3

Theoretical Analysis

MedKoo Cat#: 561612

Name: Oxendolone

CAS#: 33765-68-3

Chemical Formula: C20H30O2

Exact Mass: 302.2246

Molecular Weight: 302.45

Elemental Analysis: C, 79.42; H, 10.00; O, 10.58

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Oxendolone; Prostetin; Roxenone;
IUPAC/Chemical Name
(8R,9S,10R,13S,14S,16S,17S)-16-ethyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
InChi Key
FCKLFGKATYPJPG-SSTBVEFVSA-N
InChi Code
InChI=1S/C20H30O2/c1-3-12-11-18-17-6-4-13-10-14(21)5-7-15(13)16(17)8-9-20(18,2)19(12)22/h10,12,15-19,22H,3-9,11H2,1-2H3/t12-,15-,16+,17+,18-,19-,20-/m0/s1
SMILES Code
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1O)=O
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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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

Preparing Stock Solutions

The following data is based on the product molecular weight 302.45 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
1: Hikichi Y, Yamaoka M, Kusaka M, Hara T. Selective androgen receptor modulator activity of a steroidal antiandrogen TSAA-291 and its cofactor recruitment profile. Eur J Pharmacol. 2015 Oct 15;765:322-31. doi: 10.1016/j.ejphar.2015.08.052. Epub 2015 Sep 1. PubMed PMID: 26335395. 2: Matsuda H, Yamazaki M, Naruo S, Asanuma Y, Kubo M. Anti-androgenic and hair growth promoting activities of Lygodii spora (spore of Lygodium japonicum) I. Active constituents inhibiting testosterone 5alpha-reductase. Biol Pharm Bull. 2002 May;25(5):622-6. PubMed PMID: 12033503. 3: Yamada K, Komatsu H, Ohta A. Effects of 3,6-dimethylpyrazine-2-thiol on reproductive and accessory reproductive organs in male rats. Biol Pharm Bull. 1996 Mar;19(3):360-3. PubMed PMID: 8924900. 4: Iguchi H, Ikeuchi T, Kai Y, Yoshida H. [Influence of anti-androgen therapy for prostatic hypertrophy on lipid metabolism]. Hinyokika Kiyo. 1994 Mar;40(3):215-9. Japanese. PubMed PMID: 7513937. 5: Inoue K, Yamasaki S, Fushiki T, Okada Y, Sugimoto E. Androgen receptor antagonist suppresses exercise-induced hypertrophy of skeletal muscle. Eur J Appl Physiol Occup Physiol. 1994;69(1):88-91. PubMed PMID: 7957162. 6: Yamashita S, Ohno Y, Watanabe Y, Fujimoto Y, Koishi K, Kawashima M, Hosokawa K, Okada H. Antiestrogenic effects of danazol on rabbit uterus. Gynecol Obstet Invest. 1994;38(4):245-8. PubMed PMID: 7851809. 7: Umeda K. [Clinical results and problems of anti-androgen therapy of benign prostatic hypertrophy]. Hinyokika Kiyo. 1991 Nov;37(11):1429-33. Japanese. PubMed PMID: 1722628. 8: Kazama T, Mizuno I, Takamine T, Umeda K, Terada T, Ishikawa S, Fuse H, Katayama T. [Evaluation of anti-androgen therapy for benign prostatic hypertrophy by using transrectal prostatic ultrasonography]. Hinyokika Kiyo. 1990 Dec;36(12):1423-7. Japanese. PubMed PMID: 1706136. 9: Suzuki T, Horibe I, Uchida N, Ezumi K, Uchida K, Takeda K, Tanaka A, Nishizawa Y, Matsumoto K. Effects of antiandrogens on growth of androgen-dependent mouse mammary tumor (Shionogi carcinoma 115) in vivo and in vitro. J Steroid Biochem Mol Biol. 1990 Nov 30;37(4):559-67. PubMed PMID: 2278840. 10: Srivastava A, Maikhuri JP, Setty BS. Effect of TSAA-291 on male reproductive tract and fertility of the rat. Int J Fertil. 1989 May-Jun;34(3):235-9. PubMed PMID: 2567722. 11: Ostri P, Swartz R, Meyhoff HH, Petersen JH, Lindgård G, Frimodt-Møller C, Andersson T, Nielsen MS. Antiandrogenic treatment of benign prostatic hyperplasia: a placebo controlled trial. Urol Res. 1989;17(1):29-33. PubMed PMID: 2466359. 12: Okada K, Oishi K, Yoshida O, Sudo K, Kawase M, Nakayama R. Study of the effect of an anti-androgen (oxendolone) on experimentally induced canine prostatic hyperplasia. II. Endocrinological analysis. Urol Res. 1988;16(2):73-8. PubMed PMID: 2453093. 13: Okada K, Oishi K, Yoshida O, Sudo K, Kawase M, Nakayama R. Study of the effect of an anti-androgen (oxendolone) on experimentally induced canine prostatic hyperplasia. I. Morphological analysis. Urol Res. 1988;16(2):67-72. PubMed PMID: 2453092. 14: Kumamoto Y, Tsukamoto T, Takagi Y, Furuya S, Yokoyama E, Takatsuka K, Tamiya T, Miyamoto S, Aoyama T, Honma A. [Clinical efficacy of oxendolene (antiandrogen) and bunazosin hydrochloride (alpha-adrenergic blocker) in the treatment of prostatism--comparative study of oxendolone, bunazocin hydrochloride and their combination]. Hinyokika Kiyo. 1987 Nov;33(11):1921-41. Japanese. PubMed PMID: 2451412. 15: Bashirelahi N, Ganesan S, Ekiko DB, Young JD Jr, Shida K, Yamanaka H, Takahashi E. Effect of 16 beta-ethyl-17 beta-hydroxy-4-estren-3-one (TSAA-291) on the binding of promegestone (R5020) and methyltrienolone (R1881) to hyperplastic and neoplastic human prostate. J Steroid Biochem. 1986 Sep;25(3):367-74. PubMed PMID: 2430141. 16: Sudo K, Masuoka M, Hiraga K, Yoshida K, Nakayama R. Radioimmunoassay for serum levels of an anti-androgen TSAA-291 (Oxendolone) in rats. J Pharmacobiodyn. 1984 Jun;7(6):378-84. PubMed PMID: 6481613. 17: Yasukawa A, Nihira H, Matsuki S, Fujii M, Fujiwara H, Kitano T, Kodama M, Ukai R, Tado O, Sagami K, et al. [Clinical experience with oxendolone for treatment of benign prostatic hyperplasia. Clinical efficacy and effects on serum lipid and lipoprotein fraction levels]. Hinyokika Kiyo. 1984 Apr;30(4):537-43. Japanese. PubMed PMID: 6207714. 18: Wada F, Nishi N, Matuo Y. Biochemical difference between ventral and dorsolateral prostates: effects of castration and administration of the antiandrogen 16 beta-ethyl-17 beta-hydroxy-4-oestren-3-one on SDS-electrophoretic patterns of subcellular proteins from rat prostates. Prostate. 1984;5(3):285-97. PubMed PMID: 6728729. 19: Goto G, Hiraga K, Miki T, Sumi M. [Alternative synthesis of 16beta-ethyl-17beta-hydroxyester-4-en-3-one (oxendolone)]. Yakugaku Zasshi. 1983 Oct;103(10):1042-5. Japanese. PubMed PMID: 6232373. 20: Midgley I, Fowkes AG, Darragh A, Lambe R, Chasseaud LF, Taylor T. The metabolic fate of the anti-androgenic agent, oxendolone, in man. Steroids. 1983 Apr;41(4):521-36. PubMed PMID: 6419414.

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