6-Methylene-4-pregnene-3,20-dione

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

MedKoo CAT#: 529169

CAS#: 19457-57-9

Description: 6-Methylene-4-pregnene-3,20-dione has reproductive effect.


Chemical Structure

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6-Methylene-4-pregnene-3,20-dione
CAS# 19457-57-9

Theoretical Analysis

MedKoo Cat#: 529169
Name: 6-Methylene-4-pregnene-3,20-dione
CAS#: 19457-57-9
Chemical Formula: C22H30O2
Exact Mass: 326.2246
Molecular Weight: 326.48
Elemental Analysis: C, 80.94; H, 9.26; O, 9.80

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: 6-Methylene-4-pregnene-3,20-dione

IUPAC/Chemical Name: Pregn-4-ene-3,20-dione, 6-methylene-

InChi Key: BKWJSCFKITXBBM-NTNOATJHSA-N

InChi Code: InChI=1S/C22H30O2/c1-13-11-16-18-6-5-17(14(2)23)21(18,3)10-8-19(16)22(4)9-7-15(24)12-20(13)22/h12,16-19H,1,5-11H2,2-4H3/t16-,17+,18-,19-,21+,22+/m0/s1

SMILES Code: CC([C@H]1CC[C@@]2([H])[C@]3([H])CC(C4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O)=C)=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: >3 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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 326.48 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

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1: Roberson KM, Padilla GM, Schmidt JM, Petrow V, Robertson CN. 6-Methylene progesterone is cytotoxic to human cancer cell lines independent of its 5-alpha-reductase activity. Prostate. 1995 Jan;26(1):28-34. PubMed PMID: 7845864.

2: Neubauer BL, Best KL, Blohm TR, Gates C, Goode RL, Hirsch KS, Laughlin ME, Petrow V, Smalstig EB, Stamm NB, et al. LY207320 (6-methylene-4-pregnene-3,20-dione) inhibits testosterone biosynthesis, androgen uptake, 5 alpha-reductase, and produces prostatic regression in male rats. Prostate. 1993;23(3):181-99. PubMed PMID: 8234065.

3: Damber JE, Bergh A, Daehlin L, Petrow V, Landström M. Effects of 6-methylene progesterone on growth, morphology, and blood flow of the Dunning R3327 prostatic adenocarcinoma. Prostate. 1992;20(3):187-97. PubMed PMID: 1574466.

4: Iguchi T, Uesugi Y, Takasugi N, Petrow V. Quantitative analysis of the development of genital organs from the urogenital sinus of the fetal male mouse treated prenatally with a 5 alpha-reductase inhibitor. J Endocrinol. 1991 Mar;128(3):395-401. PubMed PMID: 2013746.

5: Toomey RE, Goode RL, Petrow V, Neubauer BL. In vivo assay for conversion of testosterone to dihydrotestosterone by rat prostatic steroid 5 alpha-reductase and comparison of two inhibitors. Prostate. 1991;19(1):63-72. PubMed PMID: 1876537.

6: Sikes RA, Thomsen S, Petrow V, Neubauer BL, Chung LW. Inhibition of experimentally induced mouse prostatic hyperplasia by castration or steroid antagonist administration. Biol Reprod. 1990 Aug;43(2):353-62. PubMed PMID: 1696141.

7: Gałdecki Z, Grochulski P, Wawrzak Z, Duax WL, Strong PD. Structure of 6-methylene-4-pregnene-3,20-dione. Acta Crystallogr C. 1990 May 15;46 ( Pt 5):941-3. PubMed PMID: 2378699.

8: Robertson WR, Lambert A, Mitchell R, Kendle K, Petrow V. The effect of some antiprostatic steroids upon cortisol production by guinea-pig adrenal cells stimulated by ACTH. Biochem Pharmacol. 1989 Nov 1;38(21):3669-71. PubMed PMID: 2557025.

9: Ito YZ, Nakazato Y, Petrow V. A new approach to prostate cancer. J Pharm Pharmacol. 1989 Jul;41(7):488-9. PubMed PMID: 2570857.

10: Petrow V, Padilla GM, McPhail AT, Bruchovsky N, Schneider SL. Prostate. III--A structural feature characteristic of the rat prostate 5 alpha-reductase active site. J Steroid Biochem. 1989 Mar;32(3):399-407. PubMed PMID: 2704237.

11: Iguchi T, Todoroki R, Takasugi N, Petrow V. The effects of an aromatase inhibitor and a 5 alpha-reductase inhibitor upon the occurrence of polyovular follicles, persistent anovulation, and permanent vaginal stratification in mice treated neonatally with testosterone. Biol Reprod. 1988 Oct;39(3):689-97. PubMed PMID: 3196799.

12: Uilenbroek JT, Woutersen PJ. Inhibition of 5 alpha-reductase activity in prepubertal female rats: effect on the timing of first ovulation. Acta Endocrinol (Copenh). 1988 Apr;117(4):451-6. PubMed PMID: 3389038.

13: Marts SA, Padilla GM, Petrow V. A comparison of the effects of castration and 6-methylene progesterone, a 5 alpha-reductase inhibitor, on the rat ventral prostate. Biochem Cell Biol. 1987 Jul;65(7):626-34. PubMed PMID: 3435660.

14: Zama S, Akimoto S, Yazawa S, Ichikawa T, Hayata I, Petrow V, Shimazaki J. Androgen receptor, testosterone uptake and karyotype in androgen-dependent mouse tumor (SC 115) and its androgen-independent subline (CS 2). Endocrinol Jpn. 1987 Apr;34(2):279-89. PubMed PMID: 3622394.

15: Collins RH, Lack L, Killenberg PG. Rat hepatic bile acid sulfotransferase: enzyme response to androgens and estrogens. Am J Physiol. 1987 Feb;252(2 Pt 1):G276-80. PubMed PMID: 2435165.

16: McKinney SC, Collins RH, Killenberg PG, Lack L. Effect of 6-methylene-4-pregnene-3,20-dione treatment on hepatic bile acid sulfotransferase activity in male rats. Biochem Pharmacol. 1986 Mar 15;35(6):1050-2. PubMed PMID: 3456744.

17: Petrow V. The dihydrotestosterone (DHT) hypothesis of prostate cancer and its therapeutic implications. Prostate. 1986;9(4):343-61. Review. PubMed PMID: 3537993.

18: Padilla GM, Petrow V, Marts SA, Mukherji S. Approaches to prostatic cancer chemotherapy using the Dunning R3327H prostatic adenocarcinoma. Prostate. 1985;6(2):129-43. PubMed PMID: 3975175.

19: MacIndoe JH, West ER, Petrow V. Comparative studies of 5 alpha-reductase inhibitors within MCF-7 human breast cancer cells. J Steroid Biochem. 1984 May;20(5):1095-100. PubMed PMID: 6727360.

20: Petrow V, Padilla GM, Mukherji S, Marts SA. Endocrine dependence of prostatic cancer upon dihydrotestosterone and not upon testosterone. J Pharm Pharmacol. 1984 May;36(5):352-3. PubMed PMID: 6145781.