Names | |
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Preferred IUPAC name 3-(2-Chlorophenothiazin-10-yl)-N,N-diethylpropan-1-amine | |
Other names RP-4909 | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.373 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C19H23ClN2S | |
Molar mass | 346.91732 g/mol |
Pharmacology | |
N05AA07 ( WHO ) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Chlorproethazine, sold under the brand name Neuriplege, is a drug of the phenothiazine group described as a muscle relaxant or tranquilizer which is or has been marketed in Europe as a topical cream for the treatment of muscle pain. [1] [2] [3] [4] [5] It has been associated with photoallergic contact dermatitis. [6] [7]
Chlorproethazine can be synthesized from a diphenylsulfide derivative. The general scheme is sufficiently flexible to permit the interchange of the order of some of the steps.
Thus alkylation of 2-(2-bromo-phenylsulfanyl)-5-chloro-aniline [105790-02-1] (1) with 3-chloro-1-diethylaminopropane [104-77-8] (2) leads to the intermediate (3). Ring closure as above by nucleophilic aromatic displacement leads to the antipsychotic drug chlorproethazine (4).
The last step uses copper powder and is a form of the Ullmann condensation (i.e. the Goldberg reaction).
Metenolone, or methenolone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as metenolone acetate and metenolone enanthate. Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure. Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.
Aminoglutethimide (AG), sold under the brand names Elipten, Cytadren, and Orimeten among others, is a medication which has been used in the treatment of seizures, Cushing's syndrome, breast cancer, and prostate cancer, among other indications. It has also been used by bodybuilders, athletes, and other men for muscle-building and performance- and physique-enhancing purposes. AG is taken by mouth three or four times per day.
Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is given by injection into muscle. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market. A related drug, metenolone acetate, is taken by mouth.
Mitotane, sold under the brand name Lysodren, is a steroidogenesis inhibitor and cytostatic antineoplastic medication which is used in the treatment of adrenocortical carcinoma and Cushing's syndrome. It is a derivative of the early insecticide DDT and an isomer of p,p'-DDDTooltip dichlorodiphenyldichloroethane (4,4'-dichlorodiphenyldichloroethane) and is also known as 2,4'-(dichlorodiphenyl)-2,2-dichloroethane (o,p'-DDD).
Propiomazine, sold under the brand name Propavan among others, is an antihistamine which is used to treat insomnia and to produce sedation and relieve anxiety before or during surgery or other procedures and in combination with analgesics as well as during labor. Propiomazine is a phenothiazine, but is not used therapeutically as a neuroleptic because it does not block dopamine receptors well.
Oxatomide, sold under the brand name Tinset among others, is a antihistamine of the diphenylmethylpiperazine family which is marketed in Europe, Japan, and a number of other countries. It was discovered at Janssen Pharmaceutica in 1975. Oxatomide lacks any anticholinergic effects. In addition to its H1 receptor antagonism, it also possesses antiserotonergic activity similarly to hydroxyzine. Oxatomide was also found to have antiviral activity against Venezuelan equine encephalitis virus (VEEV).
Tuaminoheptane is a sympathomimetic agent and vasoconstrictor which was formerly used as a nasal decongestant. It is still used in France as a nasal decongestant but its use is not recommended by the health authorities due to the lack of evidence of its effectiveness. It has also been used as a stimulant.
Dixyrazine, also known as dixypazin (oxalate), sold under the brand names Ansiolene, Esocalm, Esucos, Metronal, and Roscal, is a typical antipsychotic of the phenothiazine group described as a neuroleptic and antihistamine. It was first introduced in Germany in 1969. It is used as a neuroleptic, anxiolytic, and antihistamine in doses between 12.5 and 75 mg a day.
Thioproperazine, sold under the brand name Majeptil, is a typical antipsychotic of the phenothiazine group which is used as a tranquilizer, antiemetic, sedative, and in the treatment of schizophrenia and manic phase of bipolar disorder. Majeptil is available in 10 mg tablets.
Prothipendyl, also known as azapromazine or phrenotropin, is an anxiolytic, antiemetic, and antihistamine of the azaphenothiazine group which is marketed in Europe and is used to treat anxiety and agitation in psychotic syndromes. It differs from promazine only by the replacement of one carbon atom with a nitrogen atom in the tricyclic ring system. Prothipendyl is said to not possess antipsychotic effects, and in accordance, appears to be a weaker dopamine receptor antagonist than other phenothiazines.
Norclostebol is a synthetic androgen and anabolic steroid (AAS) that was derived from nandrolone. It was described in the literature in 1957. Norclostebol is also used as an ester, norclostebol acetate.
Carfenazine (INN), or carphenazine (BAN), also known as carphenazine maleate (USAN), is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.
Testosterone decanoate is an androgen and anabolic steroid and a testosterone ester. It is a component of Sustanon, along with testosterone propionate, testosterone phenylpropionate, and testosterone isocaproate. The medication has not been marketed as a single-drug preparation. Testosterone decanoate has been investigated as a potential long-acting injectable male contraceptive. It has a longer duration of action than testosterone enanthate, but its duration is not as prolonged as that of testosterone undecanoate.
Trengestone, sold under the brand names Reteroid, Retroid, and Retrone, is a progestin medication which was formerly used to treat menstrual disorders but is now no longer marketed. It is taken by mouth.
Zoxazolamine is a muscle relaxant that is no longer marketed. It was synthesized in 1953 and introduced clinically in 1955 but was withdrawn due to hepatotoxicity. One of its active metabolites, chlorzoxazone, was found to show less toxicity, and was subsequently marketed in place of zoxazolamine. These drugs activate IKCa channels.
Flugestone acetate (FGA), sold under the brand name Cronolone among others, is a progestin medication which is used in veterinary medicine.
Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone enanthate, is given by injection into muscle.
Nisterime acetate (USAN) (developmental code name ORF-9326), also known as 2α-chloro-4,5α-dihydrotestosterone O-(p-nitrophenyl)oxime 17β-acetate or as 2α-chloro-5α-androstan-17β-ol-3-one O-(p-nitrophenyl)oxime 17β-acetate, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a derivative of dihydrotestosterone (DHT) that was developed as a postcoital contraceptive but was never marketed. It is an androgen ester – specifically, the C17α acetate ester of nisterime. Unlike antiprogestogens like mifepristone, nisterime acetate does not prevent implantation and instead induces embryo resorption as well as interrupts the post-implantation stage of pregnancy.
Droloxifene, also known as 3-hydroxytamoxifen, is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was developed originally in Germany and later in Japan for the treatment of breast cancer, osteoporosis in men and postmenopausal women, and cardiovascular disorders but was abandoned and never marketed. It reached phase II and phase III clinical trials for these indications before development was discontinued in 2000. The drug was found to be significantly less effective than tamoxifen in the treatment of breast cancer in two phase III clinical trials.
Androstenediol dipropionate, or 5-androstenediol 3β,17β-dipropionate, also known as androst-5-ene-3β,17β-diol 3β,17β-dipropionate, is a synthetic anabolic–androgenic steroid and an androgen ester – specifically, the dipropionate diester of 5-androstenediol (androst-5-ene-3β,17β-diol) – which has been marketed in Europe, including in Spain, Italy, and Austria.