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Manufacturer supply Steroids Hormone Megestrol Acetate
Cas No: 595-33-5
USD $ 15.0-30.0 / Kilogram 1 Kilogram 5000 Kilogram/Month Xi'an Julong Bio-Tech Co., Ltd. Contact Supplier
Steroids Hormone Raw Material Powder Megestrol Acetate CAS 595-33-5
Cas No: 595-33-5
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megestrol acetate
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Megestrol acetate
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595-33-5 Usage

Description

Megestrol Acetate is the acetate salt form of megestrol, a synthetic derivative of the naturally occurring female sex hormone progesterone with potential anti-estrogenic and antineoplastic activity.Megestrol acetate, a progestational agent, is frequently used in the treatment of patients with metastatic breast cancer. It is generally well tolerated, except that it may cause undesirable weight gain. Subsequently, it was shown that megestrol acetate produced weight gain in a variety of cachectic cancer patients. Significant reduction inserum levels of IL-1a and b,IL-2,IL-6, and TNF-o were observed in cancer patientstreated with megestrol acetate which may bear on the mechanism of improved appetite and body weight gain.It has also been postulated that the effect is, at least in part,mediated by NPY,a potent central appetite stimulant.

Chemical Properties

Crystalline Solid

Originator

Megestat,Bristol,W. Germany,1964

Uses

Megestrol acetate USP (Megace) is used to treat Carcinoma of the breast or endorometrium.

Uses

Megestrol acetate (Megace), a semi-synthetic progestational steroid, is the most effective known appetite stimulant at present. Previously used in patients with cancer and acquired immunodeficiency syndrome, only a few studies have considered the applicability of this drug in malnourished older persons. Megestrol acetate is useful if profound anorexia is the main manifestation of cachexia and if expected survival is weeks to months. Megace has been shown to significantly increase appetite, but not survival. In patients with a shorter predicted survival, a brief course of corticosteroids may be useful to stimulate appetite and have positive effects on nausea, pain, and asthenia.

Definition

ChEBI: Megestrol acetate is a steroid ester resulting from the formal condensation of the hydroxy group of megestrol with the carboxy group of acetic acid. It is an appetite stimulant used for the treatment of anorexia and cachexia. Also used for birth control and for the treatment of breast cancer. It has a role as an antineoplastic agent, an appetite enhancer, a contraceptive drug, a progestin and a synthetic oral contraceptive. It is a steroid ester, an acetate ester, a 20-oxo steroid and a 3-oxo-Delta(4) steroid. It derives from a megestrol.

Manufacturing Process

The following preparation is given in US Patent 3,356,573. 17α-Acetoxy-3βhydroxy-6-methylpregn-5-ene-20-one (1 g), aluminum tert-butoxide (1 g) and p-benzoquinone (6 g) were dissolved in dry benzene (100 ml) and the mixture was heated under reflux for 30 minutes. The reaction mixture was cooled and washed with potassium hydroxide solution until the benzene layer was colorless. The benzene was washed with water, dried and evaporated to dryness under reduced pressure. The residue crystallized from aqueous methanol to give 17α-acetoxy-6-methylpregna-4,6-diene-3,20-dione, needles, MP 214° to 216°C.

Brand name

Megace (Bristol-Myers Squibb); Megace (Par).

Therapeutic Function

Cancer chemotherapy

General Description

Megestrol acetate, 17-hydroxy-6-methylpregna-4,6-diene-3,20-dione acetate(Megace), is a progestin used primarily for the palliativemanagement of recurrent, inoperable, or metastatic endometrialor breast carcinoma. Megestrol acetate has also beenindicated for appetite enhancement in patients with AIDS.The biochemical basis for this use of megestrol is unclear.

Clinical Use

Progestin activity is further enhanced when a double bond is introduced between positions 6 and 7, as is found in megestrol acetate. Megestrol is used primarily in the treatment of breast and endometrial carcinomas and in postmenopausal women with advanced hormone-dependent carcinoma.

Safety Profile

Suspected carcinogen with experimental carcinogenic and teratogenic data. Poison by intravenous route. Human reproductive effects bp ingestion and implant routes: effects on ovaries and fallopian tubes, menstrual cycle changes, and female fertility index changes. Mutation data reported. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. An FDA proprietary drug used to treat endometriosis and breast cancer. A steroid.

Veterinary Drugs and Treatments

Megestrol acetate (Ovaban?—Schering) is approved by FDA for use in dogs only for the postponement of estrus and the alleviation of false pregnancy. In male dogs, it has been used for benign prostatic hypertrophy. It is used clinically for many dermatologic and behavior- related conditions, primarily in the cat. See the Dosage section for specific indications and dosages for both dogs and cats. Megestrol acetate is indicated in humans for the palliative treatment of advanced carcinoma of the breast or endometrium.

Drug interactions

Potentially hazardous interactions with other drugs Antibacterials: metabolism of progestogens accelerated by griseofulvin and rifamycins. Anticoagulants: progestogens antagonise anticoagulant effect of phenindione; may enhance or reduce anticoagulant effect of coumarins. Antiepileptics: metabolism accelerated by carbamazepine, eslicarbazepine, fosphenytoin, oxcarbazepine, phenobarbital, phenytoin, primidone, rufinamide and topiramate; concentration of lamotrigine reduced; concentration reduced by high dose perampanel. Antivirals: metabolism accelerated by nevirapine. Ciclosporin: progestogens inhibit metabolism of ciclosporin (increased plasma concentration). Dopaminergics: concentration of selegiline increased - avoid.

Metabolism

Less than 10% of an oral dose undergoes metabolism. Several major metabolites appear in the urine (e.g., 2-hydroxy and 6-hydroxymethyl megestrol and their glucuronide conjugates).
InChI:InChI=1/C23H30O4/c1-14(24)23(27-15(2)25)12-9-20-18-6-5-16-13-17(26)7-10-21(16,3)19(18)8-11-22(20,23)4/h5-6,13,18-20H,7-12H2,1-4H3/t18-,19+,20+,21+,22+,23+/m1/s1

595-33-5 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (M1949)  Megestrol Acetate  >96.0%(HPLC) 595-33-5 1g 295.00CNY Detail
TCI America (M1949)  Megestrol Acetate  >96.0%(HPLC) 595-33-5 5g 896.00CNY Detail
Sigma-Aldrich (Y0001514)  Megestrolacetate  European Pharmacopoeia (EP) Reference Standard 595-33-5 Y0001514 1,880.19CNY Detail
Sigma-Aldrich (Y0001507)  Megestrol acetate for peak identification  European Pharmacopoeia (EP) Reference Standard 595-33-5 Y0001507 1,880.19CNY Detail
Sigma-Aldrich (Y0001524)  Megestrol acetate for system suitability  European Pharmacopoeia (EP) Reference Standard 595-33-5 Y0001524 1,880.19CNY Detail

595-33-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name megestrol acetate

1.2 Other means of identification

Product number -
Other names Megestrol acetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:595-33-5 SDS

595-33-5Synthetic route

methyl bromide
74-83-9

methyl bromide

C27H38O7

C27H38O7

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Stage #1: methyl bromide; C27H38O7 With magnesium In tetrahydrofuran at 30 - 55℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 60 - 65℃;
69.8%
methoxymethyl acetate
4382-76-7

methoxymethyl acetate

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
With sodium acetate; trichlorophosphate In chloroform at 70℃; for 0.166667h;51%
With sodium acetate; trichlorophosphate In chloroform
Medroxyprogesterone acetate
71-58-9

Medroxyprogesterone acetate

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
With chloranil
With 2-methyl-propan-1-ol; chloranil Heating;
With chloranil
Multi-step reaction with 2 steps
1: TsOH / dioxane
2: (tBuO)2CrO2, Ac2O / CCl4
View Scheme
Medroxyprogesterone acetate
71-58-9

Medroxyprogesterone acetate

chloranil
118-75-2

chloranil

acetic acid
64-19-7

acetic acid

ethyl acetate
141-78-6

ethyl acetate

Megestrol acetate
595-33-5

Megestrol acetate

Medroxyprogesterone acetate
71-58-9

Medroxyprogesterone acetate

chloranil
118-75-2

chloranil

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Megestrol acetate
595-33-5

Megestrol acetate

3-Methoxy-17α-acetoxy-6-methyl-pregnadien-(3,5)-on-(20)
1104-99-0

3-Methoxy-17α-acetoxy-6-methyl-pregnadien-(3,5)-on-(20)

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
With acetic anhydride In tetrachloromethane
6-methylpregn-5-ene-3β,17α-diol-20-one 17-acetate
2381-48-8

6-methylpregn-5-ene-3β,17α-diol-20-one 17-acetate

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
With aluminum tri-tert-butoxide; p-benzoquinone
3β-acetoxy-17α-hydroxy-5-pregnen-20-one
1863-39-4

3β-acetoxy-17α-hydroxy-5-pregnen-20-one

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: benzene; toluene-4-sulfonic acid
2: peroxybenzoic acid; chloroform
3: benzene; diethyl ether
4: aqueous methanol.H2SO4
5: CrO3; pyridine
6: aqueous HCl
7: acetic acid; toluene-4-sulfonic acid
8: tetrachloro-<1,4>benzoquinone
View Scheme
Medroxyprogesterone
520-85-4

Medroxyprogesterone

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; toluene-4-sulfonic acid
2: tetrachloro-<1,4>benzoquinone
View Scheme
3β,5,17-trihydroxy-6β-methyl-5α-pregnan-20-one
113665-92-2

3β,5,17-trihydroxy-6β-methyl-5α-pregnan-20-one

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: CrO3; pyridine
2: aqueous HCl
3: acetic acid; toluene-4-sulfonic acid
4: tetrachloro-<1,4>benzoquinone
View Scheme
5,17-dihydroxy-6β-methyl-5α-pregnane-3,20-dione
23706-51-6

5,17-dihydroxy-6β-methyl-5α-pregnane-3,20-dione

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous HCl
2: acetic acid; toluene-4-sulfonic acid
3: tetrachloro-<1,4>benzoquinone
View Scheme
20,20-ethanediyldioxy-6β-methyl-5α-pregnane-3β,5,17-triol
19699-76-4

20,20-ethanediyldioxy-6β-methyl-5α-pregnane-3β,5,17-triol

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: aqueous methanol.H2SO4
2: CrO3; pyridine
3: aqueous HCl
4: acetic acid; toluene-4-sulfonic acid
5: tetrachloro-<1,4>benzoquinone
View Scheme
3β-acetoxy-20,20-ethanediyldioxy-pregn-5-en-17-ol
19699-74-2

3β-acetoxy-20,20-ethanediyldioxy-pregn-5-en-17-ol

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: peroxybenzoic acid; chloroform
2: benzene; diethyl ether
3: aqueous methanol.H2SO4
4: CrO3; pyridine
5: aqueous HCl
6: acetic acid; toluene-4-sulfonic acid
7: tetrachloro-<1,4>benzoquinone
View Scheme
3β-acetoxy-20,20-ethanediyldioxy-5,6α-epoxy-5α-pregnan-17-ol
19699-75-3

3β-acetoxy-20,20-ethanediyldioxy-5,6α-epoxy-5α-pregnan-17-ol

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: benzene; diethyl ether
2: aqueous methanol.H2SO4
3: CrO3; pyridine
4: aqueous HCl
5: acetic acid; toluene-4-sulfonic acid
6: tetrachloro-<1,4>benzoquinone
View Scheme
17α-Acetoxy-6-methylene-pregn-4-ene-3,20-dione
32634-95-0

17α-Acetoxy-6-methylene-pregn-4-ene-3,20-dione

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
With sodium acetate; palladium on activated charcoal; 4-methylcyclohexene In ethanol Heating / reflux;
Megestrol acetate
595-33-5

Megestrol acetate

17α-acetoxy-3-β-hydroxy-6-methylpregna-4,6-dien-20-one
2233-58-1

17α-acetoxy-3-β-hydroxy-6-methylpregna-4,6-dien-20-one

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 5h;97%
With sodium tetrahydroborate In methanol for 0.5h;94.5%
With lithium tri(t-butoxy)aluminum hydride In tetrahydrofuran at 0℃;
Megestrol acetate
595-33-5

Megestrol acetate

megestrol
3562-63-8

megestrol

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 1.5h; Heating;94%
With sodium methylate
With sodium hydroxide In methanol; water
Megestrol acetate
595-33-5

Megestrol acetate

6-Methyl-1,4,6-pregnatrien-17α-ol-3,20-dione Acetate

6-Methyl-1,4,6-pregnatrien-17α-ol-3,20-dione Acetate

Conditions
ConditionsYield
With bunazosin In 1,4-dioxane; ethyl acetate90%
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