71-58-9 Usage
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.
Chemical Properties
White or almost white, crystalline powder.
Uses
Different sources of media describe the Uses of 71-58-9 differently. You can refer to the following data:
1. Progestogen; an injectable contraceptive.
2. Medroxyprogesterone Acetate is a synthetic progesterone receptor agonist that is used to treat amenorrhea (unusual stopping of menstrual periods) and abnormal uterine bleeding.
Definition
ChEBI: Medroxyprogesterone acetate is an acetate ester resulting from the formal condensation of the 17alpha-hydroxy group of medroxyprogesterone with the carboxy group of acetic acid. A widely used progestin in menopausal hormone therapy and in progestogen-only birth control. It has a role as a progestin, an androgen, a female contraceptive drug, a synthetic oral contraceptive, an adjuvant, an inhibitor, an antioxidant and an antineoplastic agent. It is a steroid ester, an acetate ester, a 20-oxo steroid, a 3-oxo-Delta(4) steroid and a corticosteroid. It is functionally related to a medroxyprogesterone.
Brand name
Amen (Amarin);
Curretab (Solvay Pharmaceuticals); Cycrin (ESI); Provera
(Pharmacia & Upjohn);Clinovie;Cliovir;Dep0-clinover;Dep0-map;Depcorlutin;Depo-prodasone;Depo-progevera;Depo-promone;Deporone;Dugen;Farlurin;Farlutale;Gesinal;Gestapuran;Gestapuron;G-farlutal;Hysron;Intex;Luteocrin orale;Luteodione;Luteos;Lutoporal;Metigestene;Nadigest;Nogest;Onco-provera;Perlutest;Petogen;Piermap;Povera;Promone-e;Pronone;Proverone;Provest;Sindomens;Sodelut "g";Supprestal;Verafen;Veramix plus v.
Therapeutic Function
Progestin
World Health Organization (WHO)
A depot preparation containing 150 mg medroxyprogesterone
acetate was introduced over 20 years ago for use as a long-acting injectable
contraceptive. Subsequently, positive results of carcinogenicity studies carried out
in beagle bitches led to refusal of registration in the United States. These findings
were later considered irrelevant to contraceptive use in women and the drug was
approved by the Food and Drug Administration. Menstrual irregularities are the
most common adverse effect associated with depot medroxyprogesterone acetate.
Risk-benefit judgements differ significantly from country to country, having regard
to differing national circumstances. The preparation is, however, widely available
and is included in the WHO Model List of Essential Drugs.
(Reference: (WHTAC4) The Use of Essential Drugs, 4th Report of the WHO Expert
Committee, 796, , 1990)
General Description
Medroxyprogesterone acetate is an odorless white to off-white microcrystalline powder. It?is a synthetic, acetate derivative of the sex hormone progesterone. (NTP, 1992)
Air & Water Reactions
Medroxyprogesterone 17-acetate is sensitive to prolonged exposure to air and light. Insoluble in water.
Hazard
Possible carcinogen.
Fire Hazard
Flash point data for Medroxyprogesterone 17-acetate are not available; however, Medroxyprogesterone 17-acetate is probably combustible.
Biochem/physiol Actions
Medroxyprogesterone 17-acetate (MPA) is a synthetic progestin used as a contraceptive, in hormone replacement therapy and for the treatment of endometriosis. It is a more potent progestin that the nonacetylated form.
Clinical Use
Progestogen:
Cachexia (unlicensed), contraception, epilepsy, male
hypersexuality, malignant neoplasms, respiratory
disorders, sickle-cell disease, dysfunctional uterine
bleeding, endometriosis
Safety Profile
Suspected carcinogen
with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data.
Human systemic effects by intravenous
route: increased intraocular pressure. Human teratogenic effects by an unspecified
route: developmental abnormalities of the
urogenital system. Human reproductive
effects by multiple routes:
spermatogenesis, menstrual cycle changes or
dlsorders, postpartum effects, female fertility
effects, abortion, newborn behavioral
effects. Human mutation data reported.
Experimental reproductive effects. A drug
for the treatment of secondary amenorrhoea
and dysfunctional uterine bleeding. When
heated to decomposition it emits acrid
smoke and irritating fumes.
Veterinary Drugs and Treatments
In cats, MPA has been used when either castration is ineffective or
undesirable to treat sexually dimorphic behavior problems such as
roaming, inter-male aggressive behaviors, spraying, mounting, etc.
MPA has also been used as a tranquilizing agent to treat syndromes
such as feline psychogenic dermatitis and alopecia, but treatment
with “true” tranquilizing agents may be preferable.
In humans, parenteral MPA has been used as a long-acting
contraceptive in females, to decrease sexually deviant behavior in
males, and as an antineoplastic agent for some carcinomas (see
Pharmacology section above). Oral MPA is used in human females
to treat secondary amenorrhea and to treat abnormal uterine bleeding
secondary to hormone imbalances.
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
Metabolism
Among the first of these substituted 17α-acetoxyprogesterone analogues to be utilized therapeutically was medroxyprogesterone
acetate, a 6α-methyl progesterone analogue. This analogue is 25-fold more active than ethisterone. Following oral
administration, medroxyprogesterone acetate is completely and rapidly deacetylated by first-pass metabolism to
medroxyprogesterone. Medroxyprogesterone is extensively metabolized via pathways similar to those for progesterone, except for
6α-hydroxylation. Most medroxyprogesterone acetate metabolites are excreted in the urine, primarily as glucuronide conjugates.
Plasma protein binding for medroxyprogesterone is approximately 86%, primarily to serum albumin, with no binding to SHBG.
Check Digit Verification of cas no
The CAS Registry Mumber 71-58-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 1 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 71-58:
(4*7)+(3*1)+(2*5)+(1*8)=49
49 % 10 = 9
So 71-58-9 is a valid CAS Registry Number.
InChI:InChI=1/C24H34O4/c1-13-10-17-18(23(4)8-6-16(27)11-19(13)23)7-9-24(5)20(17)12-21(28-15(3)26)22(24)14(2)25/h11,13,17-18,20-22H,6-10,12H2,1-5H3
71-58-9Relevant articles and documents
Preparation method of medroxyprogesterone acetate for perimenopausal syndrome
-
, (2022/03/17)
The invention relates to a preparation method of medroxyprogesterone acetate for perimenopausal syndrome. Compared with the prior art, the preparation method disclosed by the invention has the advantages of few steps, simplicity in operation, short total reaction time, high yield, less raw material consumption, low cost, good product quality and the like. The preparation method of medroxyprogesterone acetate has high economic value and is suitable for industrial application.
Preparation method of medroxyprogesterone acetate
-
Paragraph 0012; 0028; 0033; 0036-0040, (2018/03/26)
The invention provides a preparation method of medroxyprogesterone acetate. The preparation method comprises the following steps: using 6-methylene pregna-4-alkene-3, 20-diketone-17 alpha-acetic esteras a raw material, performing a hydrogenation reaction on the 6-methylene pregna-4-alkene-3, 20-diketone-17 alpha-acetic ester and cyclohexene in an alcohols solvent under the catalytic action of 5%palladium on carbon, and filtering and recovering palladium on carbon from reaction solution after the reaction is complete; performing transposition on the reaction solution with hydrochloric acid, adjusting the pH value of the reaction solution to 6-7, concentrating the reaction solution at normal pressure, as well as cooling, filtering, washing and drying the reaction solution, so as to obtaina medroxyprogesterone acetate crude product; finally, performing recrystallization with a mixed solvent of methanol and dichloromethane, so as to obtain a medroxyprogesterone acetate competitive product. According to the preparation method of the medroxyprogesterone acetate provided by the invention, the process method is simple, the alcohols solvent is adopted for the hydrogenation reaction, andthen the transposition is performed with hydrochloric acid, so that the content of the generated impurity F is low, the yield of a target product is high, the product cost is low, and the output of chemical pollutants is less, so that the preparation method is suitable for industrial production.
Anti-Claudin 3 Monoclonal Antibody and Treatment and Diagnosis of Cancer Using the Same
-
, (2010/05/13)
Monoclonal antibodies that bind specifically to Claudin 3 expressed on cell surface are provided. The antibodies of the present invention are useful for diagnosis of cancers that have enhanced expression of Claudin 3, such as ovarian cancer, prostate cancer, breast cancer, uterine cancer, liver cancer, lung cancer, pancreatic cancer, stomach cancer, bladder cancer, and colon cancer. The present invention provides monoclonal antibodies showing cytotoxic effects against cells of these cancers. Methods for inducing cell injury in Claudin 3-expressing cells and methods for suppressing proliferation of Claudin 3-expressing cells by contacting Claudin 3-expressing cells with a Claudin 3-binding antibody are disclosed. The present application also discloses methods for diagnosis or treatment of cancers.
