[(6S,10R,13S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate

Base Information

• Chemical Name: [(6S,10R,13S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
• CAS No.: 71-58-9
• Molecular Formula: C24H34O4
• Molecular Weight: 386.532
• Hs Code.: 29372390
• NSC Number: 757095
• ChEMBL ID: CHEMBL305242
• Mol file: 71-58-9.mol

Synonyms:[(6S,10R,13S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate;Spectrum_000895;Spectrum2_000147;Spectrum3_000487;Spectrum4_000039;Spectrum5_000944;Medroxyprogestesterone acetate;BSPBio_001953;KBioGR_000477;KBioSS_001375;DivK1c_000487;SPECTRUM1500379;SPBio_000254;CHEMBL305242;HMS501I09;KBio1_000487;KBio2_001375;KBio2_003943;KBio2_006511;KBio3_001453;CHEBI:145457;NINDS_000487;HMS1920J19;HMS2091B10;Pharmakon1600-01500379;CCG-38954;NSC757095;NSC-757095;IDI1_000487;NCGC00178899-01;SBI-0051434.P003;AB00052034_02;SR-05000002023;SR-05000002023-1;BRD-A61221616-001-02-7

Chemical Property of [(6S,10R,13S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.85E-10mmHg at 25°C
• Melting Point: 206-207 °C(lit.)
• Refractive Index: 48 ° (C=1, Dioxane)
• Boiling Point: 496.4 °C at 760 mmHg
• Flash Point: 213.2 °C
• PSA: 60.44000
• Density: 1.13 g/cm³
• LogP: 4.51270
• Storage Temp.: Refrigerator
• Solubility.: Practically insoluble in water, freely soluble in methylene chloride, soluble in acetone, sparingly soluble in ethanol (96 per cent)
• Water Solubility.: <0.1 g/100 mL at 23℃
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 386.24570956
• Heavy Atom Count: 28
• Complexity: 767

Purity/Quality:

99.00% ^*data from raw suppliers

Medroxy Progesterone 17-acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40-48
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC2C(CCC3(C2CCC3(C(=O)C)OC(=O)C)C)C4(C1=CC(=O)CC4)C
• Isomeric SMILES: C[C@H]1CC2C(CC[C@]3(C2CC[C@@]3(C(=O)C)OC(=O)C)C)[C@@]4(C1=CC(=O)CC4)C
• Description: Medroxyprogesterone 17-acetate is a synthetic progestogen.,, It prevents fertilization and increases the rate of transport of eggs from the fallopian tubes to the uterus in female ferrets when administered prior to ovulation. Medroxyprogesterone 17-acetate reversibly blocks ovulation in rats when injected on the last day of diestrus. It also has anti-androgenic activity in rats, decreasing plasma testosterone (Item Nos. 15645 | ISO60154) levels via induction of hepatic testosterone reductase activity. Medroxyprogesterone 17-acetate exhibits immunosuppressive effects in vitro and in vivo, inhibiting the production of IFN-γ by CD2/CD3/CD28-stimulated peripheral blood mononuclear cells (PBMCs) at concentrations ≥10 nM and extending the survival of rabbit skin allografts., Injectable formulations containing medroxyprogesterone 17-acetate have been used as contraceptives.
• Uses: Progestogen; an injectable contraceptive. Medroxyprogesterone Acetate is a synthetic progesterone receptor agonist that is used to treat amenorrhea (unusual stopping of menstrual periods) and abnormal uterine bleeding.
• Therapeutic Function: Progestin
• Clinical Use: Progestogen: Cachexia (unlicensed), contraception, epilepsy, male hypersexuality, malignant neoplasms, respiratory disorders, sickle-cell disease, dysfunctional uterine bleeding, endometriosis
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: metabolism of progestogens accelerated by griseofulvin and rifamycins (reduced contraceptive effect). Anticoagulants: progestogens antagonise anticoagulant effect of phenindione and may enhance or reduce effect of coumarins. Antidepressants: contraceptive effect reduced by St John’s Wort - avoid. Antiepileptics: metabolism accelerated by carbamazepine, eslicarbazepine, fosphenytoin, lamotrigine, oxcarbazepine, perampanel, phenytoin, phenobarbital, primidone, rufinamide and topiramate (reduced contraceptive effect); concentration of lamotrigine reduced. Antivirals: contraceptive effect possibly reduced by efavirenz; metabolism accelerated by nevirapine (reduced contraceptive effect). Aprepitant: possible contraceptive failure. Bosentan: possible contraceptive failure. Ciclosporin: progestogens inhibit metabolism of ciclosporin (increased plasma concentration). Cytotoxics: possibly reduced contraceptive effect with crizotinib dabrafenib, olaparib and vemurafenib. Dopaminergics: concentration of selegiline increased - avoid. Fosaprepitant: possible contraceptive failure. Lumacaftor: possible contraceptive failure. Ulipristal: contraceptive effect possibly reduced

Technology Process of [(6S,10R,13S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate

There total 28 articles about [(6S,10R,13S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.5%

17α-Acetoxy-6-methylene-pregn-4-ene-3,20-dione (32634-95-0) → Medroxyprogesterone acetate (71-58-9)

Guidance literature:

With ethanol; 5%-palladium/activated carbon; In cyclohexene; at 75 - 78 ℃; for 5h; Reagent/catalyst; Temperature;

Reference yield: 81.0%

3-cycloethylenedioxy-6-methyl-17α-acetoxy-pregn-5-ene-20-one (809-01-8) → Medroxyprogesterone acetate (71-58-9)

Guidance literature:

With silica gel; copper(II) sulfate; In chloroform; for 2h; Heating;

DOI:10.1080/00397919508011371

Reference yield:

3,17-diacetoxy-6-methyl-pregna-3,5-dien-20-one (986-96-9) → Medroxyprogesterone acetate (71-58-9)

Guidance literature:

With hydrogenchloride;

upstream raw materials:

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

3,17-diacetoxy-6-methyl-pregna-3,5-dien-20-one

Medroxyprogesterone

acetic anhydride

Downstream raw materials:

6α-Methyl-17α-hydroxy-1,4-pregnadien-3,20-dion

17α-Acetoxy-6-methyl-Δ⁵-pregnen-3,20-dion

17-acetoxy-6-methyl-pregna-1,4,6-triene-3,20-dione

megestrol

Refernces

• 1、 -. "Preparation method of palace progesterone". Paragraph 0115; 0121; 0124; 0130-0131; 0137. . Retrieved 2021/11/03.
• 2、 -. "THERAPEUTIC FOR HEPATIC CANCER". . . Retrieved 2011/02/18.