Synonym
Metyrapone, Metopirone, SU 4885, Methbipyranone, Methopyrapone
IUPAC/Chemical Name
2-methyl-1,2-dipyridin-3-ylpropan-1-one
InChi Key
FJLBFSROUSIWMA-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H14N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10H,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
Biological target:
Metyrapone (Su-4885) is a potent and orally active 11β-hydroxylase inhibitor and an autophagy activator, also inhibits the production of aldosterone.
In vitro activity:
The omega/omega-1 hydroxylase activities of both NPE and PE cells require NADPH and molecular oxygen, are associated with the microsomal fraction, respond to inducers such as clofibrate, and are inhibited by metyrapone and SKF525 A (inhibitors of P450 enzymes). These results support the suggestion that PG omega/omega-1 hydroxylations by NPE and PE are cytochrome P450-mediated reactions.
Reference: Exp Eye Res. 1992 Aug;55(2):377-84. https://pubmed.ncbi.nlm.nih.gov/1426070/
In vivo activity:
The purpose of the present study was to use different doses of the 11-beta-hydroxylase inhibitor metyrapone to produce dose-dependent inhibition of the synthesis of corticosterone and examine the consequences of that on several cognitive and emotional parameters. Systemic (SC) injections of metyrapone (25 or 50 mg/kg) dose-dependently suppressed increases in plasma concentrations of corticosterone induced by spatial training in a water maze, but did not affect plasma corticosterone levels in non-stressed rats.
Reference: Psychoneuroendocrinology. 1996 Nov;21(8):681-93. https://pubmed.ncbi.nlm.nih.gov/9247987/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
30.0 |
132.58 |
|
| DMSO |
50.9 |
224.85 |
|
| Ethanol |
30.0 |
132.58 |
|
| PBS (pH 7.2) |
5.0 |
22.10 |
|
| Water |
20.1 |
88.96 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
226.27
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 |
Formulation protocol:
1. Asakura T, Shichi H. Cytochrome P450-mediated prostaglandin omega/omega-1 hydroxylase activities in porcine ciliary body epithelial cells. Exp Eye Res. 1992 Aug;55(2):377-84. doi: 10.1016/0014-4835(92)90202-4. PMID: 1426070.
2. Hays SJ, Tobes MC, Gildersleeve DL, Wieland DM, Beierwaltes WH. Structure-activity relationship study of the inhibition of adrenal cortical 11 beta-hydroxylase by new metyrapone analogues. J Med Chem. 1984 Jan;27(1):15-9. doi: 10.1021/jm00367a004. PMID: 6606707.
3. Tanriverdi AM, Aydin B, Bebitoglu BT, Cabadak H, Goren MZ. The behavioral and neurochemical effects of methylprednisolone or metyrapone in a post-traumatic stress disorder rat model. North Clin Istanb. 2019 Jul 17;6(4):327-333. doi: 10.14744/nci.2019.69345. PMID: 31909376; PMCID: PMC6936935.
4. Roozendaal B, Bohus B, McGaugh JL. Dose-dependent suppression of adrenocortical activity with metyrapone: effects on emotion and memory. Psychoneuroendocrinology. 1996 Nov;21(8):681-93. doi: 10.1016/s0306-4530(96)00028-5. PMID: 9247987.
In vitro protocol:
1. Asakura T, Shichi H. Cytochrome P450-mediated prostaglandin omega/omega-1 hydroxylase activities in porcine ciliary body epithelial cells. Exp Eye Res. 1992 Aug;55(2):377-84. doi: 10.1016/0014-4835(92)90202-4. PMID: 1426070.
2. Hays SJ, Tobes MC, Gildersleeve DL, Wieland DM, Beierwaltes WH. Structure-activity relationship study of the inhibition of adrenal cortical 11 beta-hydroxylase by new metyrapone analogues. J Med Chem. 1984 Jan;27(1):15-9. doi: 10.1021/jm00367a004. PMID: 6606707.
In vivo protocol:
1. Tanriverdi AM, Aydin B, Bebitoglu BT, Cabadak H, Goren MZ. The behavioral and neurochemical effects of methylprednisolone or metyrapone in a post-traumatic stress disorder rat model. North Clin Istanb. 2019 Jul 17;6(4):327-333. doi: 10.14744/nci.2019.69345. PMID: 31909376; PMCID: PMC6936935.
2. Roozendaal B, Bohus B, McGaugh JL. Dose-dependent suppression of adrenocortical activity with metyrapone: effects on emotion and memory. Psychoneuroendocrinology. 1996 Nov;21(8):681-93. doi: 10.1016/s0306-4530(96)00028-5. PMID: 9247987.
1: Ferrier IN, Anderson IM, Barnes J, Gallagher P, Grunze HCR, Haddad PM, House AO, Hughes T, Lloyd AJ, Mamasoula C, McColl E, Pearce S, Siddiqi N, Sinha B, Speed C, Steen N, Wainwright J, Watson S, Winter FH, McAllister-Williams RH. Randomised controlled trial of Antiglucocorticoid augmentation (metyrapone) of antiDepressants in Depression (ADD Study). Southampton (UK): NIHR Journals Library; 2015 Jun. PubMed PMID: 26086063.
2: Goeders NE, Guerin GF, Schmoutz CD. The combination of metyrapone and oxazepam for the treatment of cocaine and other drug addictions. Adv Pharmacol. 2014;69:419-79. doi: 10.1016/B978-0-12-420118-7.00011-1. Review. PubMed PMID: 24484984.
3: Hána V, Dokoupilová M, Marek J, Plavka R. Recurrent ACTH-independent Cushing's syndrome in multiple pregnancies and its treatment with metyrapone. Clin Endocrinol (Oxf). 2001 Feb;54(2):277-81. Review. PubMed PMID: 11207645.
4: Tanaka K, Toriumi M, Itoh S, Ogino Y. [Metyrapone test]. Nihon Rinsho. 1997 Apr;55 Suppl 2:349-52. Review. Japanese. PubMed PMID: 9172545.
5: Hildebrandt AG. The binding of metyrapone to cytochrome P-450 and its inhibitory action on microsomal hepatic mixed function oxidation reactions. Biochem Soc Symp. 1972;34:79-102. Review. PubMed PMID: 4570969.
