Prodrugs

Dydrogesterone, sold under the brand name Duphaston among others, is a progestin medication which is used for a variety of indications, including threatened or recurrent miscarriage during pregnancy, dysfunctional bleeding, infertility due to luteal insufficiency, dysmenorrhea, endometriosis, secondary amenorrhea, irregular cycles, premenstrual syndrome, and as a component of menopausal hormone therapy. It is taken by mouth.

Fospropofol (INN), often used as the disodium salt (trade name Lusedra), is an intravenous sedative-hypnotic agent. It is currently approved for use in sedation of adult patients undergoing diagnostic or therapeutic procedures such as endoscopy.

Tybamate (INN; Solacen, Tybatran, Effisax) is an anxiolytic of the carbamate family. It is a prodrug for meprobamate in the same way as the better known drug carisoprodol. It has liver enzyme inducing effects similar to those of phenobarbital but much weaker.

pharmaceutical drug

chemical compound

chemical compound

Aceglutamide (brand name Neuramina), or aceglutamide aluminium (brand name Glumal), also known as acetylglutamine, is a psychostimulant, nootropic, and antiulcer agent that is marketed in Spain and Japan. It is an acetylated form of the amino acid L-glutamine, the precursor of glutamate in the body and brain. Aceglutamide functions as a prodrug to glutamine with improved potency and stability.

chemical compound

Fosaprepitant, sold under the brand names Emend (US) and Ivemend (EU) among others, is an antiemetic medication, administered intravenously. It is a prodrug of aprepitant.

Equilin is a naturally occurring estrogen sex hormone found in horses as well as a medication. It is one of the estrogens present in the estrogen combination drug preparations known as conjugated estrogens (CEEs; e.g. Premarin) and esterified estrogens (EEs; e.g. Estratab, Menest). CEEs is the most commonly used form of estrogen medications in hormone replacement therapy (HRT) for menopausal symptoms in the United States. Estrone sulfate is the major estrogen in CEEs (about 50%) while equilin sulfate is the second major estrogen in the formulation, present as about 25% of the total.

chemical compound

Oxyfedrine, sold under the brand names Ildamen and Myofedrin among others, is a sympathomimetic agent and coronary vasodilator which is used in the treatment of coronary heart disease, angina pectoris, and acute myocardial infarction. It is taken by mouth or intravenously.

chemical compound

Fursultiamine (INN; chemical name thiamine tetrahydrofurfuryl disulfide or TTFD; brand names Adventan, Alinamin-F, Benlipoid, Bevitol Lipophil, Judolor, Lipothiamine) is a medication and vitamin used to treat thiamine deficiency. Chemically, it is a disulfide derivative of thiamine and is similar in structure to allithiamine.

chemical compound

Chlorotrianisene (CTA), also known as 'tri-p-anisylchloroethylene (TACE) and sold under the brand name Tace' among others, is a nonsteroidal estrogen related to diethylstilbestrol (DES) which was previously used in the treatment of menopausal symptoms and estrogen deficiency in women and prostate cancer in men, among other indications, but has since been discontinued and is now no longer available. It is taken by mouth.

chemical compound

chemical compound

Lofepramine, sold under the brand names Gamanil, Lomont, and Tymelyt among others, is a tricyclic antidepressant (TCA) which is used to treat depression. The TCAs are so named as they share the common property of having three rings in their chemical structure. Like most TCAs lofepramine is believed to work in relieving depression by increasing concentrations of the neurotransmitters norepinephrine and serotonin in the synapse, by inhibiting their reuptake. It is usually considered a third-generation TCA, as unlike the first- and second-generation TCAs it is relatively safe in overdose and has

Picamilon (also known as '''N-nicotinoyl-GABA, pycamilon, and pikamilon''') is a drug formed by a synthetic combination of niacin and γ-aminobutyric acid (GABA). It was developed in the Soviet Union in 1969 and further studied in both Russia and Japan as a prodrug of GABA.

chemical compound

chemical compound

Alatrofloxacin (Trovan IV) is a fluoroquinolone antibiotic developed by Pfizer, delivered as a mesylate salt.

chemical compound

Quingestanol (, ), also known as norethisterone 3-cyclopentyl enol ether, is a progestin of the 19-nortestosterone group which was never marketed. It is a prodrug of norethisterone. An acylated derivative, quingestanol acetate, is used as a pharmaceutical drug.

Norgestimate, sold under the brand name Ortho Tri-Cyclen among others, is a progestin medication which is used in birth control pills for women and in menopausal hormone therapy. The medication is available in combination with an estrogen and is not available alone. It is taken by mouth.

Fosfestrol, sold under the brand name Honvan and also known as diethylstilbestrol diphosphate (DESDP), is an estrogen medication which is used in the treatment of prostate cancer in men. It is given by slow intravenous infusion once per day to once per week or by mouth once per day.

chemical compound

Mebolazine (; brand names Dostalon and Roxilon; also known as dimethazine, dymethazine, di(methasterone) azine, or 2α,17α-dimethyl-5α-androstan-17β-ol-3-one azine) is a synthetic, orally active androgen/anabolic steroid (AAS) and a 17α-alkylated derivative of dihydrotestosterone (DHT) which is no longer marketed. It has a unique and unusual chemical structure, being a dimer of methasterone linked at the 3-position of the A-ring by an azine group, and reportedly acts as a prodrug of methasterone.

Quinbolone (, ), sold under the brand names Anabolicum and Anabolvis, is an androgen and anabolic steroid (AAS) which was previously marketed in Italy. It was developed by Parke-Davis as a viable orally administered AAS with little or no liver toxicity.

chemical compound

Omidenepag, sold under the brand name Eybelis among others, is a medication used for the treatment of glaucoma and ocular hypertension.

Clofibride is a fibrate. Clofibride is a derivative of clofibrate. In the body it is converted into 4-chlorophenoxyisobutyric acid (clofibric acid), which is the true hypolipidemic agent. So clofibride, just like clofibrate is a prodrug of clofibric acid.

11-Nor-9-carboxy-Δ9-tetrahydrocannabinol (11-COOH-THC or THC-COOH), often referred to as 11-nor-9-carboxy-THC or THC-11-oic acid, is the main secondary metabolite of tetrahydrocannabinol (THC) which is formed in the body after cannabis is consumed.

Tebipenem (brand name Orapenem) is a broad-spectrum orally-administered antibiotic, from the carbapenem subgroup of β-lactam antibiotics. It was developed as a replacement drug to combat bacteria that had acquired antibiotic resistance to commonly used antibiotics. Tebipenem is formulated as the ester tebipenem pivoxil due to the better absorption and improved bioavailability of this form. It has performed well in clinical trials for ear infection and looks likely to be further developed in future. It is only marketed in Japan. Tebipenem is the first carbapenem whose prodrug form, the pivalyl

Bolazine (), also known as 2α-methyl-5α-androstan-17β-ol-3-one azine, is a synthetic androgen/anabolic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed. It is not orally active and is used as the ester prodrug bolazine capronate (brand name Roxilon Inject) via depot intramuscular injection. Bolazine has a unique and unusual chemical structure, being a dimer of drostanolone linked at the C3 position of the A-ring by an azine group, and reportedly acts as a prodrug of drostanolone.

Mepitiostane, sold under the brand name Thioderon, is an orally active antiestrogen and anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which is marketed in Japan as an antineoplastic agent for the treatment of breast cancer. It is a prodrug of epitiostanol. The drug was patented and described in 1968.

chemical compound

Amlodipine/benazepril, sold under the brand name Lotrel among others, is a fixed-dose combination medication used to treat high blood pressure. It is a combination of amlodipine, as the besilate, a calcium channel blocker, and benazepril, an angiotensin converting enzyme inhibitor. It may be used if a single agent is not sufficient. It is taken by mouth.

Etilevodopa (developmental code name TV-1203) is a dopaminergic agent which was developed as a treatment for Parkinson's disease. It is the ethyl ester of levodopa. It was never marketed.

Ibopamine is a sympathomimetic drug, designed as a prodrug of epinine (deoxyepinephrine or N-methyldopamine), used in ophthalmology. It induces mydriasis. It also has been investigated for use in the treatment of congestive heart failure.

chemical compound

Fosfluconazole () is a water-soluble phosphate prodrug of fluconazole — a triazole antifungal drug used in the treatment and prevention of superficial and systemic fungal infections.

Taribavirin (rINN; also known as viramidine, codenamed ICN 3142) is an antiviral drug in Phase III human trials, but not yet approved for pharmaceutical use. It is a prodrug of ribavirin, active against a number of DNA and RNA viruses. Taribavirin has better liver-targeting than ribavirin, and has a shorter life in the body due to less penetration and storage in red blood cells. It is expected eventually to be the drug of choice for viral hepatitis syndromes in which ribavirin is active. These include hepatitis C and perhaps also hepatitis B and yellow fever.

Valofane is a sedative drug structurally related to the barbiturates and similar drugs such as primidone. It is metabolized once inside the body to form the barbiturate proxibarbital (proxibarbal) and is thus a prodrug.

Etynodiol, or ethynodiol, is a steroidal progestin of the 19-nortestosterone group which was never marketed. A diacylated derivative, etynodiol diacetate, is used as a hormonal contraceptive. Etynodiol is sometimes used as a synonym for etynodiol diacetate.

Progabide, sold under the brand name Gabrene, is a GABA receptor agonist which is used in the treatment of epilepsy. It is an analogue of γ-aminobutyric acid (GABA) and acts both via a metabolite and as a prodrug of GABA, in turn behaving as an agonist of the GABA receptors.

chemical compound

'THC-O-phosphate' is a water-soluble organophosphate ester derivative of tetrahydrocannabinol (THC), which functions as a metabolic prodrug for THC itself. It was invented in 1978 in an attempt to get around the poor water solubility of THC and make it easier to inject for the purposes of animal research into its pharmacology and mechanism of action. The main disadvantage of THC phosphate ester is the slow rate of hydrolysis of the ester link, resulting in delayed onset of action and lower potency than the parent drug. Pharmacologically, it is comparable to the action of psilocybin as a metabo

Pirisudanol (Mentis, Menthen, Mentium, Nadex, Nadexen, Nadexon, Pridana, Stivane), also known as pyrisuccideanol, is the succinic acid ester of pyridoxine (a form of vitamin B6) and of deanol (DMAE). It has been used in Europe in the treatment of mild cognitive impairment as well as fatigue and depression. ==Synthesis== Pirisudanol is synthesized by the following method: class=skin-invert-image|center|500px Cyclic ketal formation between pyridoxine [33605-94-6] HCl: [58-56-0] (1) and acetone resulted in alpha4,3-O-Isopropylidene Pyridoxine [1136-52-3] (2). In the other arm of the synthesis suc

Silandrone (, ) (developmental code name SC-16148), also known as testosterone 17β-trimethylsilyl ether or 17β-trimethylsilyltestosterone, as well as 17β-(trimethylsiloxy)androst-4-en-3-one, is a synthetic anabolic-androgenic steroid (AAS) and an androgen ether – specifically, the 17β-trimethylsilyl ether of testosterone – which was developed by the G. D. Searle & Company in the 1960s but was never marketed. It has a very long duration of action when given via subcutaneous or intramuscular injection, as well as significantly greater potency than that of testosterone propionate. In addition, si

THC-O-acetate (THC acetate ester, O-acetyl-THC, THC-O, AcO-THC) is the acetate ester of THC. The term THC-O-acetate is commonly used for two different isomers of this substance, dependent on which isomer of THC it is synthesized from. The difference between Δ8-THC and Δ9-THC is the location of the double bond within the cyclohexene ring system. In naming the esters of THC, the "-O-" is superfluous.

Sibrafiban (Ro 48–3657, proposed brand name Xubix) is the double prodrug of Ro-44-3888, which is a platelet aggregation inhibitor. It was being developed for secondary prevention of arterial thrombosis following unstable angina pectoris and acute myocardial infarction (MI). On August 6, 1999, Hoffmann-La Roche announced that the preliminary results from Phase III clinical trials had not shown that sibrafiban was better than aspirin in preventing recurrent ischemic events in patients with acute coronary syndrome. The development of sibrafiban was terminated.

Aeruginascin, also known as '4-phosphoryloxy-N,N,N-trimethyltryptamine (4-PO-TMT'), is an indoleamine derivative which occurs naturally within the mushrooms Inocybe aeruginascens, Pholiotina cyanopus, and Psilocybe cubensis. It was discovered by Jochen Gartz.

Cloforex (Oberex) is an anorectic of the amphetamine class. It is a prodrug to chlorphentermine. It never became a mass produced drug in part due to the side effects found in mice. Mice who consumed 75 mg of cloforex a day experienced weight loss along with pulmonary hypertension and hair loss.

Mesabolone, also known as 1-testosterone 17β-methoxycyclopentyl ether, is a synthetic anabolic–androgenic steroid (AAS) that was never marketed. It is the 17β-(1-methoxycyclohexane) ether of 1-testosterone (dihydroboldenone).

chemical compound

chemical compound

Fladrafinil (developmental code name CRL-40,941), also known as fluorafinil or as bisfluoroadrafinil, is a wakefulness-promoting agent related to modafinil that was never marketed. It is sold online and used non-medically as a nootropic (cognitive enhancer).

Cyprodenate (Actebral) is a stimulant drug. It was used for counteracting the effects of benzodiazepine tranquillizer drugs before the development of newer antidotes such as flumazenil. It produces dimethylethanolamine as a metabolite.