6α-methyl-17α-hydroxyprogesterone (CAS 520-85-4) — formula C22H32O3, molecular weight 344.5; category organic chemicals.
| CAS Number | 520-85-4 |
|---|---|
| Molecular Formula | C22H32O3 |
| Molecular Weight | 344.5 |
| Melting Point | 214.5 °C |
| LogP | 3.5 |
| Applications | Uses: THERAPEUTIC CATEGORY (VETERINARY): Progestogen, estrus regulator, MEDICATION, MEDICATION (VET), Use (kg, approx.) in Germany (2009): >250, Use (kg) in USA (2002): 3340, Consumption (g per capita, approx.) in Germany (2009): 0.00305, Consumption (g per capita) in the USA (2002): 0.0118, Calculated removal (%): 25.1, Use Classification: Pharmaceuticals -> Animal Drugs -> Approved in Taiwan, Methods of Manufacturing: From 17alpha-hydroxyprogesterone by first forming the 3, 21-bisethylene acetal with ethylene glycol, then treating with peracetic acid to give a mixture of the 5alpha, 6alpha- and 5beta, 6beta-epoxides. With methyl magnesium iodide the alpha-epoxide isomer yields the 5alpha-hydroxy-6beta-methyl derivative, which dehydrates and epimerizes with hydrogen chloride in chloroform to the delta4-6alpha-methyl compound, medroxyprogesterone. Acylation with acetic anhydride and p-toluenesulfonic acid in acetic acid gives medroxyprogesterone acetate., The bisethylene acetal of 17alpha-hydroxyprogesterone was treated with peracetic acid to give a mixture of 5alpha, 6alpha-epoxy-17alpha-hydroxypregnane-3, 20-dione bisethylene acetal and the corresponding 5beta, 6beta-epoxide. The 5alpha, 6alpha-epoxide was refluxed with methylmagnesium bromide in tetrahydrofuran to afford the bisethylene acetal of 5alpha, 17alpha- dihydroxy-6beta-methylpregnane-3, 20-dione. Dehydration by dilute sodium hydroxide in pyridine produced 6beta-methyl-17alpha-hydroxyprogesterone which was epimerized in chloroform saturated with gaseous hydrogen chloride to 6alpha-methyl-17alpha-hydroxyprogesterone. Alternatively, dehydration and epimerization of 5alpha, 17beta-dihydroxy-6beta-methylpregnane- 3, 20-dione bisethylene acetal could be effected directly with chloroform or hydrogen chloride. Acylation with acetic anhydride, acetic acid and para-toluenesulfonic acid produced medroxyprogesterone acetate., Medroxyprogesterone acetate, Impurities: Reported impurities include: 6alpha, 17a-dimethyl-3, 17-dioxo-D-homoandrost-4-en-17aalpha- yl acetate, 6beta-hydroxy-6-methyl-3, 20-dioxopregn-4-en-17-yl acetate (6beta-hydroxymedroxyprogesterone acetate), 17-hydroxy-6alpha-methylpregn-4-ene-3, 20-dione (medroxyprogesterone), 6-methyl-3, 20-dioxopregna-4, 6-dien-17-yl acetate, 6alpha-methyl-3, 20-dioxo-5beta-pregnan-17-yl acetate (4, 5beta-dihydromedroxyprogesterone acetate), 6beta-methyl-3, 20-dioxopregn- 4-en-17-yl acetate (6-epimedroxyprogesterone acetate) and 6-methylene-3, 20-dioxopregn- 4-en-17-yl acetate., Formulations, Preparations: Medroxyprogesterone acetate is available commercially as single-ingredient tablets, as combination tablets with conjugated estrogens, estradiol or estradiol cypionate and as sterile suspensions., General Manufacturing Information: ...Used in human medicine in US for treatment of endometriosis, habitual abortion and threatened abortion. ...in Oct 1973 US Food & Drug Administration announced plans to withdraw approval for certain strengths and vial sizes ... destined for these applications ..., ...In Oct 1973 US Food & Drug Administration proposed to restrict approved uses of medroxyprogesterone acetate tablets to treatment of endometriosis, secondary amenorrhea and abnormal uterine bleeding due to hormonal imbalance, in absence of organ pathology such as submucous fibroids or uterine cancer..., From 1964 until late 1970...product was withdrawn from US market, medroxyprogesterone acetate was used in us as component of oral contraceptives. ... Product was removed...because studies showed that breast nodules developed in beagles given high doses of medroxyprogesterone acetate. |
| Category | Organic Chemicals |
Documented applications: Uses: THERAPEUTIC CATEGORY (VETERINARY): Progestogen, estrus regulator, MEDICATION, MEDICATION (VET), Use (kg, approx.) in Germany (2009): >250, Use (kg) in USA (2002): 3340, Consumption (g per capita, approx.) in Germany (2009): 0.00305, Consumption (g per capita) in the USA (2002): 0.0118, Calculated removal (%): 25.1, Use Classification: Pharmaceuticals -> Animal Drugs -> Approved in Taiwan, Methods of Manufacturing: From 17alpha-hydroxyprogesterone by first forming the 3, 21-bisethylene acetal with ethylene glycol, then treating with peracetic acid to give a mixture of the 5alpha, 6alpha- and 5beta, 6beta-epoxides. With methyl magnesium iodide the alpha-epoxide isomer yields the 5alpha-hydroxy-6beta-methyl derivative, which dehydrates and epimerizes with hydrogen chloride in chloroform to the delta4-6alpha-methyl compound, medroxyprogesterone. Acylation with acetic anhydride and p-toluenesulfonic acid in acetic acid gives medroxyprogesterone acetate., The bisethylene acetal of 17alpha-hydroxyprogesterone was treated with peracetic acid to give a mixture of 5alpha, 6alpha-epoxy-17alpha-hydroxypregnane-3, 20-dione bisethylene acetal and the corresponding 5beta, 6beta-epoxide. The 5alpha, 6alpha-epoxide was refluxed with methylmagnesium bromide in tetrahydrofuran to afford the bisethylene acetal of 5alpha, 17alpha- dihydroxy-6beta-methylpregnane-3, 20-dione. Dehydration by dilute sodium hydroxide in pyridine produced 6beta-methyl-17alpha-hydroxyprogesterone which was epimerized in chloroform saturated with gaseous hydrogen chloride to 6alpha-methyl-17alpha-hydroxyprogesterone. Alternatively, dehydration and epimerization of 5alpha, 17beta-dihydroxy-6beta-methylpregnane- 3, 20-dione bisethylene acetal could be effected directly with chloroform or hydrogen chloride. Acylation with acetic anhydride, acetic acid and para-toluenesulfonic acid produced medroxyprogesterone acetate., Medroxyprogesterone acetate, Impurities: Reported impurities include: 6alpha, 17a-dimethyl-3, 17-dioxo-D-homoandrost-4-en-17aalpha- yl acetate, 6beta-hydroxy-6-methyl-3, 20-dioxopregn-4-en-17-yl acetate (6beta-hydroxymedroxyprogesterone acetate), 17-hydroxy-6alpha-methylpregn-4-ene-3, 20-dione (medroxyprogesterone), 6-methyl-3, 20-dioxopregna-4, 6-dien-17-yl acetate, 6alpha-methyl-3, 20-dioxo-5beta-pregnan-17-yl acetate (4, 5beta-dihydromedroxyprogesterone acetate), 6beta-methyl-3, 20-dioxopregn- 4-en-17-yl acetate (6-epimedroxyprogesterone acetate) and 6-methylene-3, 20-dioxopregn- 4-en-17-yl acetate., Formulations, Preparations: Medroxyprogesterone acetate is available commercially as single-ingredient tablets, as combination tablets with conjugated estrogens, estradiol or estradiol cypionate and as sterile suspensions., General Manufacturing Information: ...Used in human medicine in US for treatment of endometriosis, habitual abortion and threatened abortion. ...in Oct 1973 US Food & Drug Administration announced plans to withdraw approval for certain strengths and vial sizes ... destined for these applications ..., ...In Oct 1973 US Food & Drug Administration proposed to restrict approved uses of medroxyprogesterone acetate tablets to treatment of endometriosis, secondary amenorrhea and abnormal uterine bleeding due to hormonal imbalance, in absence of organ pathology such as submucous fibroids or uterine cancer..., From 1964 until late 1970...product was withdrawn from US market, medroxyprogesterone acetate was used in us as component of oral contraceptives. ... Product was removed...because studies showed that breast nodules developed in beagles given high doses of medroxyprogesterone acetate..
6α-methyl-17α-hydroxyprogesterone is a carbon-based organic compound with CAS registry number 520-85-4 and molecular formula C22H32O3 (molecular weight 344.5), belonging to the organic chemicals segment of chemical raw materials.
CAS number: 520-85-4
Its molecular formula C22H32O3 comprises 22 C, 32 H, 3 O atoms.
Also known as: 6α-methyl-17α-hydroxyprogesterone · 6α-甲基-17α-羟基孕酮
Category: organic chemicals
The CAS registry number of 6α-methyl-17α-hydroxyprogesterone is 520-85-4.
Molecular formula C22H32O3, molecular weight 344.5.
It is also registered under: 6α-methyl-17α-hydroxyprogesterone, 6α-甲基-17α-羟基孕酮.
Recorded applications: Uses: THERAPEUTIC CATEGORY (VETERINARY): Progestogen, estrus regulator, MEDICATION, MEDICATION (VET), Use (kg, approx.) in Germany (2009): >250, Use (kg) in USA (2002): 3340, Consumption (g per capita, approx.) in Germany (2009): 0.00305, Consumption (g per capita) in the USA (2002): 0.0118, Calculated removal (%): 25.1, Use Classification: Pharmaceuticals -> Animal Drugs -> Approved in Taiwan, Methods of Manufacturing: From 17alpha-hydroxyprogesterone by first forming the 3, 21-bisethylene acetal with ethylene glycol, then treating with peracetic acid to give a mixture of the 5alpha, 6alpha- and 5beta, 6beta-epoxides. With methyl magnesium iodide the alpha-epoxide isomer yields the 5alpha-hydroxy-6beta-methyl derivative, which dehydrates and epimerizes with hydrogen chloride in chloroform to the delta4-6alpha-methyl compound, medroxyprogesterone. Acylation with acetic anhydride and p-toluenesulfonic acid in acetic acid gives medroxyprogesterone acetate., The bisethylene acetal of 17alpha-hydroxyprogesterone was treated with peracetic acid to give a mixture of 5alpha, 6alpha-epoxy-17alpha-hydroxypregnane-3, 20-dione bisethylene acetal and the corresponding 5beta, 6beta-epoxide. The 5alpha, 6alpha-epoxide was refluxed with methylmagnesium bromide in tetrahydrofuran to afford the bisethylene acetal of 5alpha, 17alpha- dihydroxy-6beta-methylpregnane-3, 20-dione. Dehydration by dilute sodium hydroxide in pyridine produced 6beta-methyl-17alpha-hydroxyprogesterone which was epimerized in chloroform saturated with gaseous hydrogen chloride to 6alpha-methyl-17alpha-hydroxyprogesterone. Alternatively, dehydration and epimerization of 5alpha, 17beta-dihydroxy-6beta-methylpregnane- 3, 20-dione bisethylene acetal could be effected directly with chloroform or hydrogen chloride. Acylation with acetic anhydride, acetic acid and para-toluenesulfonic acid produced medroxyprogesterone acetate., Medroxyprogesterone acetate, Impurities: Reported impurities include: 6alpha, 17a-dimethyl-3, 17-dioxo-D-homoandrost-4-en-17aalpha- yl acetate, 6beta-hydroxy-6-methyl-3, 20-dioxopregn-4-en-17-yl acetate (6beta-hydroxymedroxyprogesterone acetate), 17-hydroxy-6alpha-methylpregn-4-ene-3, 20-dione (medroxyprogesterone), 6-methyl-3, 20-dioxopregna-4, 6-dien-17-yl acetate, 6alpha-methyl-3, 20-dioxo-5beta-pregnan-17-yl acetate (4, 5beta-dihydromedroxyprogesterone acetate), 6beta-methyl-3, 20-dioxopregn- 4-en-17-yl acetate (6-epimedroxyprogesterone acetate) and 6-methylene-3, 20-dioxopregn- 4-en-17-yl acetate., Formulations, Preparations: Medroxyprogesterone acetate is available commercially as single-ingredient tablets, as combination tablets with conjugated estrogens, estradiol or estradiol cypionate and as sterile suspensions., General Manufacturing Information: ...Used in human medicine in US for treatment of endometriosis, habitual abortion and threatened abortion. ...in Oct 1973 US Food & Drug Administration announced plans to withdraw approval for certain strengths and vial sizes ... destined for these applications ..., ...In Oct 1973 US Food & Drug Administration proposed to restrict approved uses of medroxyprogesterone acetate tablets to treatment of endometriosis, secondary amenorrhea and abnormal uterine bleeding due to hormonal imbalance, in absence of organ pathology such as submucous fibroids or uterine cancer..., From 1964 until late 1970...product was withdrawn from US market, medroxyprogesterone acetate was used in us as component of oral contraceptives. ... Product was removed...because studies showed that breast nodules developed in beagles given high doses of medroxyprogesterone acetate..
Category: Organic Chemicals.
Independent reference data for 6α-methyl-17α-hydroxyprogesterone (CAS 520-85-4), compiled from public chemistry databases.
| CAS Registry Number | 520-85-4 |
|---|---|
| PubChem CID | 10631 |
| Molecular formula | C22H32O3 |
| IUPAC name | (6S,8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one |
| UNII (FDA) | HSU1C9YRES |
| Molecular Weight | 344.5 |
|---|---|
| XLogP3 | 3.5 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Exact Mass | 344.23514488 |
| Monoisotopic Mass | 344.23514488 |
| Topological Polar Surface Area | 54.4 |
| Heavy Atom Count | 25 |
| Melting Point | 214.5 °C |
|---|
medroxyprogesterone; 520-85-4; Medroxyprogesteron; Medroxiprogesterona; Medroxyprogesteronum; Medrossiprogesterone; 6alpha-Methyl-17alpha-hydroxyprogesterone; 17-Hydroxy-6alpha-methylprogesterone; 17alpha-Hydroxy-6alpha-methylprogesterone; Farlutal inyectable; DTXSID0036508; 6alpha-Methyl-4-pregnen-17alpha-ol-3,20-dione; 17-Hydroxy-6alpha-methyl-pregn-4-ene-3,20-dione; HSU1C9YRES; U 8840; (6alpha)-17-hydroxy-6-methylpregn-4-ene-3,20-dione
| Reported hazard statements | H361 (92.9%) |
|---|
H361 (92.9%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
6α-methyl-17α-hydroxyprogesterone · CAS 520-85-4 · C22H32O3. UNII HSU1C9YRES. Melting Point: 214.5 °C.
Source: PubChem / Wikidata; the batch COA governs where values differ.
Supplier: Jinan Shenghe Chemical Co., Ltd.
中文页面: 6α-甲基-17α-羟基孕酮