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MedKoo Cat#: 414089 | Name: Spirorenone

Description:

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

Spirorenone is an androstadienone derivative patented by Schering A.-G as a highly effective aldosterone antagonist. Spirorenone is 8.6 times as potent as spironolactone, but showed a lower affinity for the mineralocorticoid receptors. In phase I clinical trials Spirorenone was absorbed with a half-life of 20-30 min, achieving maximum concentrations of about 100 ng/ml (10 mg) and 260 ng/ml (40 mg) after 1-2 h. Disposition of the parent drug was biphasic with half-lives of 50-60 min (distribution) and 5-6 h (elimination). Neither significant accumulation nor enzyme induction was observed after prolonged treatment.

Chemical Structure

Spirorenone
Spirorenone
CAS#74220-07-8

Theoretical Analysis

MedKoo Cat#: 414089

Name: Spirorenone

CAS#: 74220-07-8

Chemical Formula: C24H28O3

Exact Mass: 364.2038

Molecular Weight: 364.49

Elemental Analysis: C, 79.09; H, 7.74; O, 13.17

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
Spirorenone; Espirorenona; Spirorenonum
IUPAC/Chemical Name
(4aR,4bS,6aS,7S,7aS,8aS,8bS,8cR,8dR,9aR)-4a,6a-dimethyl-3',4b,4',5,6,6a,7a,8,8a,8b,8c,8d,9,9a-tetradecahydro-5'H-spiro[cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthrene-7,2'-furan]-2,5'(4aH)-dione
InChi Key
NZUIUYWHFPQZBH-HXCATZOESA-N
InChi Code
InChI=1S/C24H28O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h3,6,9,13-16,18,20-21H,4-5,7-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1
SMILES Code
C[C@]12CC[C@H]3[C@H]([C@@H]1[C@@H]4C[C@@H]4[C@@]25CCC(O5)=O)[C@H]6C[C@H]6C7=CC(C=C[C@]37C)=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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 364.49 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: Losert W, Casals-Stenzel J, Buse M. Progestogens with antimineralocorticoid activity. Arzneimittelforschung. 1985;35(2):459-71. PMID: 4039568. 2: Krause W, Sack C, Seifert W. Pharmacokinetics of the new aldosterone antagonist, spirorenone, in healthy volunteers after single and repeated daily doses. Eur J Clin Pharmacol. 1983;25(2):231-6. doi: 10.1007/BF00543796. PMID: 6628506. 3: Krause W, Kühne G. Isolation and identification of spirorenone metabolites from the monkey (Macaca fascicularis). Steroids. 1982 Jul;40(1):81-90. doi: 10.1016/0039-128x(82)90114-3. PMID: 7157447. 4: Krause W, Jakobs U. Determination of plasma levels of spirorenone, a new aldosterone antagonist, and one of its metabolites by high-performance liquid chromatography. J Chromatogr. 1982 Jun 11;230(1):37-45. doi: 10.1016/s0378-4347(00)81428-0. PMID: 7107766. 5: Nickisch K, Bittler D, Casals-Stenzel J, Laurent H, Nickolson R, Nishino Y, Petzoldt K, Wiechert R. Aldosterone antagonists. 1. Synthesis and activities of 6 beta,7 beta:15 beta,16 beta-dimethylene steroidal spirolactones. J Med Chem. 1985 May;28(5):546-50. doi: 10.1021/jm50001a002. PMID: 3989815. 6: Casals-Stenzel J, Buse M, Wambach G, Losert W. The renal action of spirorenone and other 6 beta,7 beta; 15 beta,16 beta- dimethylene-17-spirolactones, a new type of steroidal aldosterone antagonists. Arzneimittelforschung. 1984;34(3):241-6. PMID: 6329237. 7: Larik FA, Saeed A, Shahzad D, Faisal M, El-Seedi H, Mehfooz H, Channar PA. Synthetic approaches towards the multi target drug spironolactone and its potent analogues/derivatives. Steroids. 2017 Feb;118:76-92. doi: 10.1016/j.steroids.2016.12.010. Epub 2016 Dec 29. PMID: 28041953. 8: Krause W, Karras J, Jakobs U. Determination of canrenone, the major metabolite of spironolactone, in plasma and urine by high-performance liquid chromatography. J Chromatogr. 1983 Oct 14;277:191-9. doi: 10.1016/s0378-4347(00)84836-7. PMID: 6643605. 9: Yakushiji E, Ayaori M, Nishida T, Shiotani K, Takiguchi S, Nakaya K, Uto- Kondo H, Ogura M, Sasaki M, Yogo M, Komatsu T, Lu R, Yokoyama S, Ikewaki K. Probucol-Oxidized Products, Spiroquinone and Diphenoquinone, Promote Reverse Cholesterol Transport in Mice. Arterioscler Thromb Vasc Biol. 2016 Apr;36(4):591-7. doi: 10.1161/ATVBAHA.115.306376. Epub 2016 Feb 4. PMID: 26848156. 10: Losert W, Bittler D, Buse M, Casals-Stenzel J, Haberey M, Laurent H, Nickisch K, Schillinger E, Wiechert R. Mespirenone and other 15,16-methylene-17-spirolactones, a new type of steroidal aldosterone antagonists. Arzneimittelforschung. 1986 Nov;36(11):1583-600. PMID: 3028435.