Synonym
SU-5236; SU5236; SU 5236; Metyrapol
IUPAC/Chemical Name
2-methyl-1,2-di(pyridin-3-yl)propan-1-ol
InChi Key
DDFNHFXLQJLFSX-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H16N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10,13,17H,1-2H3
SMILES Code
CC(C1=CC=CN=C1)(C)C(C2=CC=CN=C2)O
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, not in water
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
228.30
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.
| 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: Berger ML, Hammerschmidt F, Qian R, Hahner S, Schirbel A, Stichelberger M, Schibli R, Yu J, Arion VB, Woschek A, Öhler E, Zolle IM. [(3)H]metyrapol and 4-[(131)i]iodometomidate label overlapping, but not identical, binding sites on rat adrenal membranes. Mol Pharm. 2013 Mar 4;10(3):1119-30. doi: 10.1021/mp3006227. Epub 2013 Feb 20. PubMed PMID: 23343186.
2: Hotham NJ, Ilett KF, Hackett LP, Morton MR, Muller P, Hague WM. Transfer of metyrapone and its metabolite, rac-metyrapol, into breast milk. J Hum Lact. 2009 Nov;25(4):451-4. doi: 10.1177/0890334409345496. Epub 2009 Sep 16. PubMed PMID: 19759353.
3: Cassiano NM, Cass QB, Degani AL, Wainer IW. Determination of the plasma levels of metyrapone and its enantiomeric metyrapol metabolites by direct plasma injection and multidimensional achiral-chiral chromatography. Chirality. 2002 Oct;14(9):731-5. PubMed PMID: 12237834.
4: Nagamine S, Horisaka E, Fukuyama Y, Maetani K, Matsuzawa R, Iwakawa S, Asada S. Stereoselective reductive metabolism of metyrapone and inhibitory activity of metyrapone metabolites, metyrapol enantiomers, on steroid 11 beta-hydroxylase in the rat. Biol Pharm Bull. 1997 Feb;20(2):188-92. PubMed PMID: 9057984.
5: Chiarotto JA, Wainer IW. Determination of metyrapone and the enantiomers of its chiral metabolite metyrapol in human plasma and urine using coupled achiral-chiral liquid chromatography. J Chromatogr B Biomed Appl. 1995 Mar 10;665(1):147-54. PubMed PMID: 7795785.
6: Usansky JI, Damani LA. The urinary metabolic profile of metyrapone in the rat. Identification of two novel isomeric metyrapol N-oxide metabolites. Drug Metab Dispos. 1992 Jan-Feb;20(1):64-9. PubMed PMID: 1346999.
7: Usansky JI, Damani LA. Assay of metyrapone, metyrapol and the isomeric mono-N-oxides of metyrapone in biological fluids by high-performance liquid chromatography. J Chromatogr. 1991 Feb 15;563(2):283-98. PubMed PMID: 2055992.
8: Maser E, Legrum W. Alteration of the inhibitory effect of metyrapone by reduction to metyrapol during the metabolism of methacetin in vivo in mice. Naunyn Schmiedebergs Arch Pharmacol. 1985 Nov;331(2-3):283-9. PubMed PMID: 3937061.
9: Damani LA, Crooks PA, Cowan DA. Metabolism of metyrapone. 2-Chromatographic and mass spectral properties of the N-oxides of metyrapone and metyrapol. Biomed Mass Spectrom. 1981 Jun;8(6):270-7. PubMed PMID: 7260343.
10: Satre M, Vignais PV. Steroid 11beta-hydroxylation in beef adrenal cortex mitochondria. Binding affinity and capacity of specific (14C)steroids and for (3H)metyrapol, an inhibitor of the 11beta-hydroxylation reaction. Biochemistry. 1974 May 7;13(10):2201-9. PubMed PMID: 4826891.
11: Satre M, Lunardi J, Vignais PV. ( 3 H)metyrapol as a tool for studies of interactions of deoxycorticosterone with adrenal cortex mitochondria. FEBS Lett. 1972 Oct 1;26(1):193-6. PubMed PMID: 4636729.
