MedKoo Cat#: 461129 | Name: Rogletimide

Description:

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

Rogletimide is a selective aromatase inhibitor. Rogletimide is related to the drug aminoglutethimide, but with no significant sedative effect. It potentially useful in the treatment of some forms of cancer.

Chemical Structure

Rogletimide
Rogletimide
CAS#92788-10-8

Theoretical Analysis

MedKoo Cat#: 461129

Name: Rogletimide

CAS#: 92788-10-8

Chemical Formula: C12H14N2O2

Exact Mass: 218.1055

Molecular Weight: 218.25

Elemental Analysis: C, 66.04; H, 6.47; N, 12.84; O, 14.66

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
Rogletimide; 3-PYG; 3 PYG; 3PYG; Pyridoglutethimide;
IUPAC/Chemical Name
(R)-3-ethyl-3-(pyridin-4-yl)piperidine-2,6-dione
InChi Key
QXKJWHWUDVQATH-GFCCVEGCSA-N
InChi Code
InChI=1S/C12H14N2O2/c1-2-12(9-4-7-13-8-5-9)6-3-10(15)14-11(12)16/h4-5,7-8H,2-3,6H2,1H3,(H,14,15,16)/t12-/m1/s1
SMILES Code
O=C(CC1)NC([C@@]1(CC)c2ccncc2)=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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 218.25 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: Etienne MC, Oster W, Milano G. Development and validation of a chiral high-performance liquid chromatography assay for rogletimide and rogletimide-N-oxide isomers in plasma. Cancer Chemother Pharmacol. 1996;38(4):343-8. PubMed PMID: 8674157. 2: Newton CJ, Mehta A, Dowsett M. The effect of the aromatase inhibitor, rogletimide (pyridoglutethimide), on guinea pig adrenal cell steroidogenesis and placental microsomal aromatase activity: comparison with aminoglutethimide and CGS 16949A. J Steroid Biochem Mol Biol. 1991 Nov;39(5A):723-7. PubMed PMID: 1659868. 3: MacNeill FA, Jones AL, Jacobs S, Lønning PE, Powles TJ, Dowsett M. The influence of aminoglutethimide and its analogue rogletimide on peripheral aromatisation in breast cancer. Br J Cancer. 1992 Oct;66(4):692-7. PubMed PMID: 1419608; PubMed Central PMCID: PMC1977412. 4: McCague R, Rowlands MG. Conformational analysis of the aromatase inhibitor 3-ethyl-3-(4-pyridyl)piperidine-2,6-dione (rogletimide) and discovery of potent 5-alkyl derivatives. J Med Chem. 1992 Oct 2;35(20):3699-704. PubMed PMID: 1433182. 5: van Bakergem E, van der Hoeven RA, Niessen WM, Tjaden UR, van der Greef J, Poon GK, McCague R. On-line continuous-flow dialysis thermospray tandem mass spectrometry for quantitative screening of drugs in plasma: rogletimide. J Chromatogr. 1992 May 15;598(2):189-94. PubMed PMID: 1618979. 6: Feutrie ML, Bonneterre J. [Aromatase inhibitors]. Bull Cancer. 1999 Oct;86(10):821-7. Review. French. PubMed PMID: 10572233. 7: Poon GK, McCague R, Griggs LJ, Jarman M, Lewis IA. Characterisation of metabolites of 3-ethyl-3-(4-pyridyl)-piperidine-2,6-dione, a potential breast cancer drug. J Chromatogr. 1991 Dec 6;572(1-2):143-57. PubMed PMID: 1818050. 8: Ogbunude PO, Aboul-Enein HY. In vitro inhibition of aromatase by the enantiomers of aminoglutethimide and analogs. Chirality. 1994;6(8):623-6. PubMed PMID: 7857773. 9: Vanden Bossche HV, Moereels H, Koymans LM. Aromatase inhibitors--mechanisms for non-steroidal inhibitors. Breast Cancer Res Treat. 1994;30(1):43-55. Review. PubMed PMID: 7949204. 10: Dowsett M, Lønning PE. Anastrozole--a new generation in aromatase inhibition: clinical pharmacology. Oncology. 1997;54 Suppl 2:11-4. Review. PubMed PMID: 9394854. 11: Kitawaki J, Yamamoto T, Urabe M, Tamura T, Inoue S, Honjo H, Okada H. Selective aromatase inhibition by pyridoglutethimide, an analogue of aminoglutethimide. Acta Endocrinol (Copenh). 1990 May;122(5):592-8. PubMed PMID: 2353556. 12: Njar VC, Brodie AM. Comprehensive pharmacology and clinical efficacy of aromatase inhibitors. Drugs. 1999 Aug;58(2):233-55. Review. PubMed PMID: 10473018. 13: Roseman BJ, Buzdar AU, Singletary SE. Use of aromatase inhibitors in postmenopausal women with advanced breast cancer. J Surg Oncol. 1997 Nov;66(3):215-20. Review. PubMed PMID: 9369969. 14: Seago A, Goss PE, Griggs LJ, Jarman M. Pyridoglutethimide [3-ethyl-3-(4-pyridyl)-piperidine-2,6-dione], an analogue of aminoglutethimide. Metabolism and pharmacokinetics. Biochem Pharmacol. 1986 Sep 1;35(17):2911-6. PubMed PMID: 3741481. 15: Dowsett M, MacNeill F, Mehta A, Newton C, Haynes B, Jones A, Jarman M, Lonning P, Powles TJ, Coombes RC. Endocrine, pharmacokinetic and clinical studies of the aromatase inhibitor 3-ethyl-3-(4-pyridyl)piperidine-2,6-dione ('pyridoglutethimide') in postmenopausal breast cancer patients. Br J Cancer. 1991 Nov;64(5):887-94. PubMed PMID: 1931611; PubMed Central PMCID: PMC1977449. 16: Kelloff GJ, Lubet RA, Lieberman R, Eisenhauer K, Steele VE, Crowell JA, Hawk ET, Boone CW, Sigman CC. Aromatase inhibitors as potential cancer chemopreventives. Cancer Epidemiol Biomarkers Prev. 1998 Jan;7(1):65-78. Review. PubMed PMID: 9456245. 17: Aboul-Enein HY, Serignese V, Minguillón C, Oliveros L. Enantioselective separation of several piperidine-2, 6-diones on a covalently bonded cellulose 3,5-dimethylphenyl carbamate/10-undecenoate chiral selector. Biomed Chromatogr. 1997 Sep-Oct;11(5):303-6. Erratum in: Biomed Chromatogr 1998 Jan-Feb;12(1):45. PubMed PMID: 9376714. 18: Lønning PE, Dowsett M, Powles TJ. Postmenopausal estrogen synthesis and metabolism: alterations caused by aromatase inhibitors used for the treatment of breast cancer. J Steroid Biochem. 1990 Mar;35(3-4):355-66. Review. PubMed PMID: 2139151. 19: Dowsett M. Clinical development of aromatase inhibitors for the treatment of breast and prostate cancer. J Steroid Biochem Mol Biol. 1990 Dec 20;37(6):1037-41. Review. PubMed PMID: 2149504. 20: Yamamoto T, Urabe M, Tamura T, Kitawaki J, Honjo H, Okada H. Antitumor effect of pyridoglutethimide, an aromatase inhibitor, on 7,12-dimethylbenz(a)anthracene-induced mammary tumors of rat. Anticancer Res. 1991 Nov-Dec;11(6):1999-2002. PubMed PMID: 1776832.