An enantiopure drug is a pharmaceutical that is available in one specific enantiomeric form. Most biological molecules (proteins, sugars, etc.) are present in only one of many chiral forms, so different enantiomers of a chiral drug molecule bind differently (or not at all) to target receptors. Chirality can be observed when the geometric properties of an object is not superimposable with its mirror image. Two forms of a molecule are formed (both mirror images) from a chiral carbon, these two forms are called enantiomers. One enantiomer of a drug may have a desired beneficial effect while the other may cause serious and undesired side effects, or sometimes even beneficial but entirely different effects.[1] The desired enantiomer is known as an eutomer while the undesired enantiomer is known as the distomer.[2] When equal amounts of both enantiomers are found in a mixture, the mixture is known as a racemic mixture. If a mixture for a drug does not have a 1:1 ratio of its enantiomers it is a candidate for an enantiopure drug. Advances in industrial chemical processes have made it economical for pharmaceutical manufacturers to take drugs that were originally marketed as a racemic mixture and market the individual enantiomers, either by specifically manufacturing the desired enantiomer or by resolving a racemic mixture. On a case-by-case basis, the U.S. Food and Drug Administration (FDA) has allowed single enantiomers of certain drugs to be marketed under a different name than the racemic mixture.[3] Also case-by-case, the United States Patent Office has granted patents for single enantiomers of certain drugs. The regulatory review for marketing approval (safety and efficacy) and for patenting (proprietary rights) is independent, and differs country by country.
^Ariëns EJ (1984-11-01). "Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology". European Journal of Clinical Pharmacology. 26 (6): 663–668. doi:10.1007/BF00541922. ISSN 1432-1041. PMID 6092093. S2CID 30916093.
^Novotna A, Kamenickova A, Pecova M, Korhonova M, Bartonkova I, Dvorak Z (2014-02-05). "Profiling of enantiopure drugs towards aryl hydrocarbon (AhR), glucocorticoid (GR) and pregnane X (PXR) receptors in human reporter cell lines". Chemico-Biological Interactions. 208: 64–76. doi:10.1016/j.cbi.2013.11.018. ISSN 0009-2797. PMID 24316275.
^Research Cf (2020-04-28). "Development of New Stereoisomeric Drugs". U.S. Food and Drug Administration. Retrieved 2022-11-17.
An enantiopuredrug is a pharmaceutical that is available in one specific enantiomeric form. Most biological molecules (proteins, sugars, etc.) are present...
have improved therapeutic efficacy. The switch from a racemic drug to an enantiopuredrug is called a chiral switch. In many cases, the enantiomers have...
purity. Assessing the purity of a unichiral drug or enantiopuredrug is of great importance from a drug safety and efficacy perspective. Chirality (chemistry)...
the amphetamine molecule. While pharmaceutical formulations containing enantiopure levoamphetamine are no longer manufactured, levomethamphetamine (levmetamfetamine)...
Armodafinil (trade name Nuvigil) is the enantiopure compound of the eugeroic modafinil (Provigil). It consists of only the (R)-(−)-enantiomer of the racemic...
infection appears mild, moderate or severe. Despite having a lower than optimum drug penetration into bone ratio of 10–20%, flucloxacillin appears effective in...
better therapeutic value.[1] Such a switching from a racemic drug to an enantiopuredrug is called a chiral switch. The naturally occurring plant form...
analgesic action, it possesses central analgesic action. Chiral switch Enantiopuredrug Chirality "Medicinal products authorised in Estonia". State Agency...
sample with only a single enantiomer is an enantiomerically pure or enantiopure compound. From racemic acid found in grapes; from Latin racemus, meaning...
United States, with more than 2 million prescriptions. Ramipril is a pro-drug. The molecule must be hydrolyzed by the esterase at the OCH2CH3 and form...
dexfenfluramine hydrochloride under the name Redux, is a serotonergic anorectic drug: it reduces appetite by increasing the amount of extracellular serotonin...
Lisinopril is a medication belonging to the drug class of angiotensin-converting enzyme (ACE) inhibitors and is used to treat hypertension (high blood...
unclear. Levofloxacin is a broad-spectrum antibiotic of the fluoroquinolone drug class. It usually results in death of the bacteria. It is the left-handed...
enantiomer, arketamine (R-ketamine), has never been marketed as an enantiopuredrug for clinical use. While S-ketamine is more effective as an analgesic...
CYP3A4, thereby making the medication susceptible to grapefruit-drug interactions. The drug has an elimination half-life of approximately 12 hours, allowing...
Organization's List of Essential Medicines. Levetiracetam is effective as single-drug treatment for newly diagnosed focal epilepsy in adults. It reduces focal...
ten hours. Trandolaprilat has about eight times the activity of its parent drug. About one-third of trandolapril and its metabolites are excreted in the...
Analogue-based Drug Discovery. John Wiley & Sons. p. 491. ISBN 9783527607495. "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration...
symptoms of Parkinson's disease. It is most often used as an adjunct to drugs such as levodopa (L-DOPA), although it has been used off-label as a monotherapy...
protect the heart against the cardiotoxic side effects of chemotherapeutic drugs such as anthracyclines, such as daunorubicin or doxorubicin or other chemotherapeutic...
hyperreactivity and inflammation. Potential formulation of the R form as an enantiopuredrug is complicated by the fact that the stereochemistry is not stable,...
therefore interact with drugs that depend on it for metabolism, such as diazepam and warfarin; the concentrations of these drugs may increase if they are...
its large R chain, which does not allow the beta-lactamases to bind. This drug has a weaker antibacterial activity than benzylpenicillin, and is devoid...
Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019. "Benazepril Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved...
1969 and 1970 under the names Keflex and Ceporex, among others. Generic drug versions are available under other trade names and are inexpensive. It is...
Dexmedetomidine, sold under the trade name Precedex among others, is a drug used in humans for sedation. Veterinarians use dexmedetomidine for similar...
000 patients who took the drug (ages 18-64), and only 4.1 cases of TdP for every 100,000 elderly patients who took the drug (ages 65 and up). Of the 9...
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