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6α-甲基-17α-羟基孕酮

CAS 520-85-4C22H32O3MW 344.5

6α-甲基-17α-羟基孕酮(CAS 520-85-4):分子式 C22H32O3、分子量 344.5。

产品概览

CAS号520-85-4
分子式C22H32O3
分子量344.5
熔点214.5 °C
LogP3.5
应用领域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.

应用领域

登记用途: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.。

技术档案

这个产品是什么

6α-甲基-17α-羟基孕酮 是一种化工化合物,登记 CAS 号为 520-85-4,分子式 C22H32O3(分子量 344.5)。

识别信息

登记 CAS 号:520-85-4

其分子式 C22H32O3 由 22 个碳、32 个氢、3 个氧 组成。

别名/同义词:6α-甲基-17α-羟基孕酮 · 6α-methyl-17α-hydroxyprogesterone

常见问题

6α-甲基-17α-羟基孕酮 的 CAS 号是多少?

6α-甲基-17α-羟基孕酮 的 CAS 登记号为 520-85-4。

6α-甲基-17α-羟基孕酮 的分子式与分子量是多少?

分子式 C22H32O3,分子量 344.5。

6α-甲基-17α-羟基孕酮 还有哪些别名?

别名/同义词:6α-甲基-17α-羟基孕酮、6α-methyl-17α-hydroxyprogesterone。

6α-甲基-17α-羟基孕酮 的登记用途是什么?

登记用途: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.。

PubChem 公开数据

6α-甲基-17α-羟基孕酮(CAS 520-85-4)的独立参考数据,整理自公开化学数据库。

各数据库的登记标识

CAS Registry Number520-85-4
PubChem CID10631
Molecular formulaC22H32O3
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

计算分子描述符

Molecular Weight344.5
XLogP33.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass344.23514488
Monoisotopic Mass344.23514488
Topological Polar Surface Area54.4
Heavy Atom Count25

在册的理化数值

Melting Point214.5 °C

在册的记载用途

    THERAPEUTIC CATEGORY (VETERINARY): Progestogen; estrus regulatorUse (kg; approx.) in Germany (2009): >250

    同义词与商品名

    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

    GHS 危害分类

    Reported hazard statementsH361 (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)

    公开数据库对它的描述

    6α-methyl-17α-hydroxyprogesterone · CAS 520-85-4 · C22H32O3. UNII HSU1C9YRES. Melting Point: 214.5 °C.

    物理形态与操作说明

    数据来源:PubChem / Wikidata;与随货 COA 不一致时以 COA 为准。

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