METYRAPONE
- CAS No.
- 54-36-4
- Chemical Name:
- METYRAPONE
- Synonyms
- Metapyron;Metopirone;su4885;Su 4885;su-4885;Metopiron;Metyrapon;NSC-25265;ETYRAPONE;Metapyrone
- CBNumber:
- CB8329426
- Molecular Formula:
- C14H14N2O
- Molecular Weight:
- 226.27
- MOL File:
- 54-36-4.mol
- MSDS File:
- SDS
- Modify Date:
- 2025/1/27 9:38:02
| Melting point | 52-55 °C(lit.) |
|---|---|
| Boiling point | 367.89°C (rough estimate) |
| Density | 1.0852 (rough estimate) |
| refractive index | 1.6419 (estimate) |
| Flash point | >230 °F |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | H2O: soluble (sparingly) |
| form | solid |
| pka | 4.61±0.10(Predicted) |
| color | White |
| Merck | 13,6181 |
| BRN | 163023 |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months. |
| EPA Substance Registry System | Metyrapone (54-36-4) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H315-H319-H335 | |||||||||
| Precautionary statements | P261-P264-P270-P301+P312-P302+P352-P305+P351+P338 | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 22-36/37/38 | |||||||||
| Safety Statements | 26 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | UC3050000 | |||||||||
| HS Code | 2933399090 | |||||||||
| Hazardous Substances Data | 54-36-4(Hazardous Substances Data) | |||||||||
| Toxicity | A well-known inhibitor of monooxygenase reactions and can also, under some circumstances, stimulate metabolism of xenobiotics in vitro. In either case, the effect is non-competitive, in that the KM does not change whereas Vmax does, decreasing in the case of inhibition and increasing in the case of stimulation. | |||||||||
| NFPA 704 |
|
METYRAPONE price More Price(4)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | M2696 | Metyrapone ≥98% (HPLC), solid | 54-36-4 | 10MG | ₹7339.35 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | M2696 | Metyrapone ≥98% (HPLC), solid | 54-36-4 | 50MG | ₹26477.95 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 856525 | 2-Methyl-1,2-di-3-pyridyl-1-propanone 96% | 54-36-4 | 250MG | ₹2305.73 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 856525 | 2-Methyl-1,2-di-3-pyridyl-1-propanone 96% | 54-36-4 | 1G | ₹8237.83 | 2022-06-14 | Buy |
METYRAPONE Chemical Properties,Uses,Production
Uses
Metyrapone acts as a glucocorticoid synthesis inhibitor, maintaining stress-hormone levels.
Biological Activity
Cytochrome P450 inhibitor. Blocks glucocorticoid synthesis via inhibition of steroid 11- β hydroxylase (CYP11B1) activity (IC 50 = 7.83 μ M). Also inhibits CYP3A4 and cytochrome P450-mediated ω / ω -1 hydroxylase activity.
Mechanism of action
Metyrapone (Metopirone) produces its primary pharmacological effect by inhibiting 11-β-hydroxylase, thereby causing diminished production and release of cortisol. The resulting reduction in the negative feedback of cortisol on the hypothalamus and pituitary causes an increase in corticotrophin release and in the secretion of precursor 11-deoxysteroids.
Clinical Use
Metyrapone is used in the differential diagnosis of both
adrenocortical insufficiency and Cushing’s syndrome
(hypercortisolism). The drug tests the functional competence
of the hypothalamic–pituitary axis when the
adrenals are able to respond to corticotrophin; that is,
when primary adrenal insufficiency has been ruled out.
After metyrapone administration, a patient with a
disease of pituitary origin cannot achieve a compensatory
increase in the urinary excretion of 17-hydroxycorticosteroids
or 11-deoxysteroids. Moreover, if pituitary
corticotrophin is suppressed by an autonomously secreting
adrenal carcinoma, there will be no increase in response
to metyrapone. On the other hand, if pituitary
corticotrophin secretion is maintained, as occurs in adrenal
hyperplasia, the inhibition of corticoid synthesis produced
by metyrapone will stimulate corticotrophin secretion
and the release of metabolites of precursor urinary
steroids, which can be measured as 17-hydroxycorticosteroids.
Metyrapone is now used less frequently in the
differential diagnosis of Cushing’s syndrome because of
the ability to measure plasma corticotrophin directly.
The steroid-inhibiting properties of metyrapone
have also been used in the treatment of Cushing’s syndrome,
and it remains one of the more effective drugs
used to treat this syndrome. However, the compensatory
rise in corticotrophin levels in response to falling
cortisol levels tends to maintain adrenal activity.This requires
that glucocorticoids be administered concomitantly
to suppress hypothalamic–pituitary activity.
Although metyrapone interferes with 11β- and 18-
hydroxylation reactions and thereby inhibits aldosterone
synthesis, it may not cause mineralocorticoid deficiency
because of the compensatory increased production
of 11-desoxycorticosterone.
Side effects
Side effects associated with the use of metyrapone include gastrointestinal distress, dizziness, headache, sedation, and allergic rash. The drug should not be used in cases of adrenocortical insufficiency or when hypersensitivity reactions can be expected. When administered to pregnant women during the second or third trimesters, the drug may impair steroid biosynthesis in the fetus. Because metyrapone is relatively nontoxic, it is used in combination therapy with the more toxic aminoglutethimide to reduce its dosage.
METYRAPONE Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6257 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6100 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6739 | 58 | Inquiry |
| career henan chemical co | +86-0371-86658258 +8613203830695 | China | 29859 | 58 | Inquiry |
| SHANDONG ZHI SHANG CHEMICAL CO.LTD | +86 18953170293 | China | 2930 | 58 | Inquiry |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | United States | 32159 | 58 | Inquiry |
| Hefei TNJ Chemical Industry Co.,Ltd. | +86-0551-65418671 +8618949823763 | China | 34563 | 58 | Inquiry |
| Shaanxi Dideu Medichem Co. Ltd | +86-029-89586680 +86-18192503167 | China | 7859 | 58 | Inquiry |
| AFINE CHEMICALS LIMITED | +86-0571-85134551 | China | 15349 | 58 | Inquiry |
| Zhejiang J&C Biological Technology Co.,Limited | +1-2135480471 +1-2135480471 | China | 10473 | 58 | Inquiry |
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