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Clindamycin
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| Systematic (IUPAC) name | |
| (2S,4R)-N-((1R)-2-chloro- 1-((3R,4R,5S,6R)-3,4,5-trihydroxy- 6-(methylthio)-tetrahydro-2H-pyran-2-yl)propyl)- 1-methyl-4-propylpyrrolidine-2-carboxamide |
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| Identifiers | |
| CAS number | |
| ATC code | J01 D10AF01 G01AA10 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C18H33ClN2O5S |
| Mol. mass | 424. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug A section of the Anatomical Therapeutic Chemical Classification System. A section of the Anatomical Therapeutic Chemical Classification System. A section of the Anatomical Therapeutic Chemical Classification System. PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The DrugBank database available at the University of Alberta is a unique Bioinformatics and Cheminformatics resource that combines detailed drug (i A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Sulfur or sulphur (ˈsʌlfɚ see spelling below) is the Chemical element that has the Atomic number 16 The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 98 g/mol |
| Synonyms | 7-chloro-lincomycin 7-chloro-7-deoxylincomycin |
| Pharmacokinetic data | |
| Bioavailability | 90% (oral) 4–5% (topical) |
| Protein binding | 90% |
| Metabolism | Hepatic |
| Half life | 2–3 hours |
| Excretion | Biliary and renal (around 20%) |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | Oral, topical, IV, intravaginal |
Clindamycin (rINN; pronounced /klɪndəˈmaɪsɨn/) is a lincosamide antibiotic. This article deals with the general meaning of the term "synonym" In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of A drug's efficiency may be affected by the degree to which it binds to the proteins within Blood plasma. Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems The liver is a vital organ in the human body and is present in Vertebrates and some other animals The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The kidneys are complicated organs that have numerous biological roles The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical if it is used as directed by the mother during For a topic outline on this subject see List of basic Australia topics. The United States of America —commonly referred to as the The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. For a topic outline on this subject see List of basic Australia topics. A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom, the UK or Britain,is a Sovereign state located A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained The United States of America —commonly referred to as the In Pharmacology and Toxicology, a route In Medicine, a topical Medication is applied to body surfaces such as the Skin or Mucous membranes for example the Vagina Intravenous therapy or IV therapy is the giving of Liquid substances directly into a Vein. A pessary is a small Plastic or Silicone medical device or form of Pharmaceutical preparation which is inserted into the Vagina or Rectum An International Nonproprietary Name ( INN; also known as rINN, for recommended International Nonproprietary Name or pINN for proposed Lincosamides (eg Lincomycin, Clindamycin) are a class of drugs which bind to the 23s portion of the 50S subunit of bacterial Ribosomes and inhibit In modern usage an antibiotic is a Chemotherapeutic agent with activity against Microorganisms such as Bacteria, fungi or Protozoa It is usually used to treat infections with anaerobic bacteria but can also be used to treat some protozoal diseases, such as malaria. An infection is the detrimental Colonization of a host Organism by a foreign Species. An anaerobic organism is any Organism that does not require Oxygen for growth and may even die in its presence The Bacteria ( singular: bacterium) are a large group of unicellular Microorganisms Typically a few Micrometres in length bacteria have Protozoa (in Greek πρῶτον proton "first" and ζῷα zoia "animals" are unicellular Eukaryotes (singular Malaria is a vector -borne Infectious disease caused by Protozoan Parasites It is widespread in tropical and subtropical regions including It is a common topical treatment for acne, and can be useful against some methicillin-resistant Staphylococcus aureus (MRSA) infections. In Medicine, a topical Medication is applied to body surfaces such as the Skin or Mucous membranes for example the Vagina Acne vulgaris (commonly called acne) is a Skin disease caused by changes in the Pilosebaceous units (skin structures consisting of a Hair follicle [1]
The most severe common adverse effect of clindamycin is Clostridium difficile-associated diarrhea (the most frequent cause of pseudomembranous colitis). An adverse drug reaction (abbreviated ADR) or adverse drug event (abbreviated ADE) is an expression that describes the unwanted negative consequences Clostridium difficile (pronounced /klɒsˈtrɪdiəm dɪˈfɪsɪli/ also known as CDF/cdf' or 'C In Medicine, diarrhea, also spelled diarrhoea (see spelling differences) is frequent loose or liquid Bowel movements Acute diarrhea Clostridium difficile Pseudomembranous colitis is an infection of the colon often but not always caused by the Bacterium Clostridium difficile Although this side-effect occurs with almost all antibiotics, including beta-lactam antibiotics, it is classically linked to clindamycin use. β-lactam antibiotics are a broad class of Antibiotics that include Penicillin derivatives Cephalosporins Monobactams Carbapenems [2]
Clindamycin is marketed alone and in combination with other drugs under various trade names, including Dalacin and Cleocin (manufactured by Pfizer), in a foam as Evoclin and Duac (with benzoyl peroxide, made by Stiefel), and a gel form by the name of Benzaclin, manufactured by Sanofi Aventis. A trade name, also known as a trading name or a business name, is the name which a Business trades under for commercial purposes although its registered Pfizer Incorporated ( is a major Pharmaceutical company, which ranks number one in the world in sales Benzoyl peroxide (ˈbɛnzɔɪl pəˈrɒksaɪd is a Chemical in the Organic peroxide family Benzaclin is a drug Gel typically prescribed to people suffering from Acne vulgaris. Sanofi-Aventis () headquartered in Paris, France, is a multinational pharmaceutical company It is also available as a generic drug. A generic drug (generic drugs short generics is a drug which is produced and distributed without Patent protection
Contents |
Clindamycin is used primarily to treat infections caused by susceptible anaerobic bacteria, including infections of the respiratory tract, septicemia and peritonitis. An anaerobic organism is any Organism that does not require Oxygen for growth and may even die in its presence The Bacteria ( singular: bacterium) are a large group of unicellular Microorganisms Typically a few Micrometres in length bacteria have In humans the respiratory tract is the part of the Anatomy that has to do with the process of respiration. Sepsis is a serious medical condition characterized by a whole-body inflammatory state (called a Systemic inflammatory response syndrome or SIRS caused Peritonitis is defined as Inflammation of the Peritoneum (the Serous membrane which lines part of the abdominal cavity and some of the Viscera [3] In patients with hypersensitivity to penicillins, clindamycin may be used to treat infections caused by susceptible aerobic bacteria as well. Hypersensitivity (also called hypersensitivity reaction refers to undesirable (damaging discomfort-producing and sometimes fatal reactions produced by the normal immune system Penicillin (sometimes abbreviated PCN or pen) is a group of Beta-lactam antibiotics used in the treatment of Bacterial Infections An aerobic organism or aerobe is an Organism that has an Oxygen based Metabolism. It is also used to treat bone and joint infections, particularly those caused by Staphylococcus aureus. Staphylococcus aureus (ˌstæfɨləˈkɒkəs ˈɔriəs literally "Golden Cluster Seed" and also known as golden staph) is the most common cause of [4][3] Topical application of clindamycin phosphate can be used to treat mild to moderate acne. In Medicine, a topical Medication is applied to body surfaces such as the Skin or Mucous membranes for example the Vagina [5]
Multiple studies have shown the use of clindamycin in conjunction with benzoyl peroxide, which is available both through prescription or over-the-counter, to be more effective in the treatment of acne than the use of either product by itself. Over-the-counter (OTC drugs are medicines that may be sold without a prescription, in contrast to Prescription drugs The name "over-the-counter" [6][7][8] A single-blind study comparing this combination to adapalene, a retinoid, also found it to work faster and be significantly better tolerated than adapalene, as well as more effective. The blind method is a part of the Scientific method, used to prevent research outcomes from being influenced by either the Placebo effect or the Observer Adapalene is a topical Retinoid primarily used in the treatment of acne and is also used ( off-label) to treat Keratosis pilaris as The retinoids are a class of Chemical compounds that are related chemically to Vitamin A. [9]
Clindamycin and adapalene in combination are also more effective than either drug alone, although adverse effects are more frequent;[10] a single study found pretreatment with adapalene (application of adapalene 3–5 minutes before clindamycin) to significantly increase the penetration of clindamycin into the skin, which may enhance efficacy. [11]
Given with chloroquine or quinine, clindamycin is effective and well-tolerated in treating Plasmodium falciparum malaria; the latter combination is particularly useful for children, and is the treatment of choice for pregnant women who become infected in areas where resistance to chloroquine is common. Chloroquine is a 4-aminoquinoline drug used in the treatment or prevention of Malaria. Quinine (ˈkwaɪnaɪn kwɪˈniːn ˈkwiːniːn is a natural white Crystalline Alkaloid having Antipyretic (fever-reducing antimalarial, Plasmodium falciparum is a Protozoan Parasite, one of the species of Plasmodium that cause Malaria in humans Drug resistance is the reduction in effectiveness of a drug in curing a disease or improving a patient's symptoms [12][13] Clindamycin should not be used as an antimalarial by itself, although it appears to be very effective as such, because of its slow action. [12][13]
Clindamycin is used in cases of suspected toxic shock syndrome,[14] often in combination with a bactericidal agent such as vancomycin. Toxic shock syndrome ( TSS) is a rare but potentially fatal disease caused by a bacterial toxin. A bactericide or bacteriocide is a substance that kills bacteria and preferably nothing else Vancomycin ( INN) (ˌvæŋkoʊˈmaɪsɪn is a Glycopeptide Antibiotic used in the Prophylaxis and treatment of infections caused by The rationale for this approach is a presumed synergy between the bactericidal antibiotic, which causes the death of the bacteria by breakdown of the cell membrane, and clindamycin, which is a powerful inhibitor of toxin synthesis. Lysis ( Greek, lysis from lyein = to separate refers to the death of a cell by breaking of the cellular membrane often by viral or osmotic A toxin ( Greek:, toxikon, lit (poison for use on arrows is a Poisonous substance produced by living cells or organisms that is active at very low Both in vitro and in vivo studies have shown that clindamycin reduces the production of exotoxins by staphylococci;[15] it may also induce changes in the surface structure of bacteria that make them more sensitive to immune system attack (opsonization and phagocytosis). In vitro ( Latin: within the glass refers to the technique of performing a given experiment in a controlled environment outside of a living Organism In vivo ( Latin: within the living means that which takes place inside an organism. An exotoxin is a soluble Protein excreted by a Microrganism, including bacteria, Fungi, Algae, and Protozoa. An immune system is a collection of mechanisms within an Organism that protects against Disease by identifying and killing Pathogens and Tumor An opsonin is any molecule that acts as a binding Enhancer for the process of Phagocytosis, for example by coating the negatively-charged molecules on the membrane Phagocytosis is the cellular process of engulfing solid particles by the Cell membrane to form an internal Phagosome, or "food vacuole [16][17]
It can also be useful in skin and soft tissue infections caused by methicillin-resistant Staphylococcus aureus (MRSA);[1] many strains of MRSA are still susceptible to clindamycin. In Medicine, the term soft tissue refers to tissues that connect support or surround other structures and organs of the body
Clindamycin has been proven to decrease the risk of premature births in women diagnosed with bacterial vaginosis during early pregnancy to about a third of the risk of untreated women. Premature birth (also known as preterm birth) is the Birth of a Baby before the standard period of Pregnancy is completed Bacterial vaginosis (BV is the most common cause of vaginal infection ( Vaginitis) [18]
The combination of clindamycin and quinine is the standard treatment for severe babesiosis. Babesiosis is a malaria-like Parasitic disease caused by Babesia, a Genus of Protozoal piroplasms [19] Clindamycin may also be used to treat toxoplasmosis,[20][21][22] and, in combination with primaquine, is effective in treating mild to moderate Pneumocystis jirovecii pneumonia. Toxoplasmosis is a Parasitic disease caused by the Protozoan Toxoplasma gondii. Primaquine (or primaquine phosphate) is a medication used in the treatment of Malaria and Pneumocystis pneumonia. Pneumocystis pneumonia ( PCP) is a form of Pneumonia caused by the yeast-like Fungus, Pneumocystis jirovecii (Jirovecii is pronounced [23]
It is most effective against infections involving the following types of organisms:
Most aerobic gram-negative bacteria (such as Pseudomonas, Legionella, Haemophilus influenzae and Moraxella), as well as the facultative anaerobic Enterobacteriaceae, are resistant to clindamycin. Pseudomonas is a Genus of gamma Proteobacteria, belonging to the larger family of Pseudomonads Recently 16S rRNA sequence Legionella is a Gram negative Bacterium, including species that cause Legionellosis or Legionnaires' disease most notably L Haemophilus influenzae, formerly called Pfeiffer's bacillus or Bacillus influenzae, is a non-motile Gram-negative Coccobacillus Moraxella is a Genus of Gram-negative Bacteria in the Moraxellaceae family A facultative anaerobic organism is an Organism, usually a Bacterium, that makes ATP by Aerobic respiration if Oxygen is present The Enterobacteriaceae are a large family of bacteria, including many of the more familiar Pathogens such as Salmonella and Escherichia [20][24]
Clindamycin preparations for oral administration include capsules (containing clindamycin hydrochloride) and oral suspensions (containing clindamycin palmitate hydrochloride). In chemistry hydrochlorides are salts resulting or regarded as resulting from the reaction of Hydrochloric acid with an organic base (mostly Amines Palmitic acid,CH3(CH214COOH or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated Fatty acids found in animals It is also available for topical administration, in gel form and in a foam delivery system (both containing clindamycin phosphate), primarily as a prescription acne treatment. A gel (from the lat gelu &mdashfreezing cold ice or gelatus &mdashfrozen immobile is an apparently solid jelly-like material formed from a A phosphate, an Inorganic chemical, is a salt of Phosphoric acid. It is also available in the form of vaginal suppositories, in combination with Clotrimazole IP, as in India, sold as "Clinsup-V" and is manufactured by Olive Health Care. The combination of clindamycin and benzoyl peroxide in a single product is also available, as is (in the United States) a combination of clindamycin and tretinoin, sold as Ziana. Tretinoin is the acid form of Vitamin A and so also known as all-trans retinoic acid or ATRA. [25]
Clindamycin is available as a generic drug, for both systemic (oral and intravenous) and topical use. A generic drug (generic drugs short generics is a drug which is produced and distributed without Patent protection
Common adverse drug reactions (ADRs) associated with clindamycin therapy—found in over 1% of patients—include: diarrhea, pseudomembranous colitis, nausea, vomiting, abdominal pain or cramps, rash, and/or itch. An adverse drug reaction (abbreviated ADR) or adverse drug event (abbreviated ADE) is an expression that describes the unwanted negative consequences Clostridium difficile Pseudomembranous colitis is an infection of the colon often but not always caused by the Bacterium Clostridium difficile Nausea ( Latin: Nausea, Greek:, " Sea-sickness " also called wamble) is the sensation of unease and discomfort Vomiting (also called throwing up, emesis) is the forceful expulsion of the contents of one's Stomach through the Mouth and sometimes the In Vertebrates such as Mammals the abdomen (belly constitutes the part of the body between the Thorax (chest and Pelvis. Cramps, sometimes called Charley horses are unpleasant often painful sensations caused by contraction or over shortening of Muscles Cramps can be caused by cold A rash is a change of the Skin which affects its color appearance or Texture. Itch ( Latin: pruritus) is an unpleasant Sensation that evokes the desire or Reflex to scratch High doses (both intravenous and oral) may cause a metallic taste, and topical application may cause contact dermatitis. Contact dermatitis is a term for a Skin reaction resulting from exposure to Allergens (allergic contact dermatitis or irritants (irritant contact dermatitis [26]
Pseudomembranous colitis is a potentially-lethal condition commonly associated with clindamycin, but which also occurs with other antibiotics. Clostridium difficile Pseudomembranous colitis is an infection of the colon often but not always caused by the Bacterium Clostridium difficile [27][2] Overgrowth of Clostridium difficile, which is inherently resistant to clindamycin, results in the production of a toxin that causes a range of adverse effects, from diarrhea to colitis and toxic megacolon. Antibiotic resistance is the ability of a Microorganism to withstand the effects of Antibiotics. Toxic megacolon ( megacolon toxicum) is a life-threatening complication of other intestinal conditions [26]
Rarely—in less than 0. 1% of patients—clindamycin therapy has been associated with anaphylaxis, blood dyscrasias, polyarthritis, jaundice, raised liver enzyme levels and/or hepatotoxicity. Anaphylaxis is an acute systemic (multi-system and severe Type I Hypersensitivity allergic reaction in humans and other Mammals Dyscrasia, is a concept from Ancient Greek Medicine with the word "dyskrasia" meaning bad mixture Polyarthritis is any type of Arthritis which involves five or more joints &mdash an inflammation of two three or four joints is an Oligoarthritis. Jaundice, also known as icterus (attributive adjective "icteric" is yellowish discoloration of the Skin, sclerae (whites of the eyes The presence of elevated transaminases, commonly the transaminases Alanine transaminase (ALT & Aspartate transaminase (AST, may be an indicator Drug metabolism in liver The human body identifies almost all drugs as foreign substances (i [26]
Clindamycin is a semisynthetic derivative of lincomycin, a natural antibiotic produced by the actinobacterium Streptomyces lincolnensis. Lincomycin is a Lincosamide Antibiotic that comes from the actinomyces Streptomyces lincolnensis. Actinobacteria or actinomycetes are a group of Gram-positive bacteria with high G+C ratio. It is obtained by 7(S)-chloro-substitution of the 7(R)-hydroxyl group of lincomycin. Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and In a substitution reaction, a Functional group in a particular Chemical compound is replaced by another group Hydroxyl in Chemistry stands for a molecule consisting of an Oxygen atom and a Hydrogen atom connected by a Covalent bond. [28]
Approximately 90% of an oral dose of clindamycin is absorbed from the gastrointestinal tract and it is widely distributed throughout the body, excluding the central nervous system. In Vertebrates the central nervous system ( CNS) is the part of the Nervous system which is enclosed in the Meninges. Adequate therapeutic concentrations can be achieved in bone. Bones are rigid organs that form part of the Endoskeleton of Vertebrates They function to move support and protect the various organs of the body produce There is also active uptake into white blood cells, most importantly neutrophils. Neutrophil granulocytes, generally referred to as neutrophils, are the most abundant type of White blood cells in humans and form an essential part of the [29]
Clindamycin is extensively metabolised in the liver, probably by CYP3A4;[30][31] some of its metabolites are active, such as N-dimethyl clindamycin and clindamycin sulfoxide. Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems Cytochrome P450 3A4 (abbreviated CYP3A4) ( a member of the Cytochrome P450 mixed-function oxidase system is one of the most important enzymes involved in the metabolism A sulfoxide is a Chemical compound containing a sulfinyl Functional group attached to two carbon atoms The elimination half-life is 1. The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity 5 to 5 hours. Clindamycin is primarily eliminated by hepatic metabolism; after an intravenous dose of clindamycin phosphate, about 4. 5% of the dose is excreted in urine as clindamycin and about 0. 35% as the phosphate salt. [32] The metabolites are excreted primarily in the urine. [33]
Clindamycin has a bacteriostatic effect. Bacteriostatic Antibiotics limit the growth of bacteria by interfering with bacterial Protein production DNA replication or other aspects of It interferes with bacterial protein synthesis (in a similar way to erythromycin, azithromycin and chloramphenicol), by binding preferentially to the 50S subunit of the bacterial ribosome. Protein biosynthesis (synthesis is the process in which cells build Proteins The term is sometimes used to refer only to protein translation but more Erythromycin is a Macrolide Antibiotic that has an antimicrobial spectrum similar to or slightly wider than that of Penicillin, and is often used for people Azithromycin is an Azalide, a subclass of Macrolide Antibiotics. Chloramphenicol is a Bacteriostatic Antimicrobial originally derived from the Bacterium Streptomyces venezuelae, isolated by Note Sometimes the ' 50s is used as shorthand for the 1950s, the 1850s, or other such decades in various centuries Events and Trends Ribosomes ( from ribo nucleic acid and "Greek soma ( meaning body") are complexes of RNA and Protein that [20]
The structures of the complexes between several antibiotics (including clindamycin) and a Deinococcus radiodurans ribosome have been solved by X-ray crystallography by a team from the Max Planck Working Groups for Structural Molecular Biology, and published in the journal Nature. Deinococcus radiodurans is an extremophilic Bacterium, one of the most Radioresistant organisms known X-ray crystallography is a method of determining the arrangement of Atoms within a Crystal, in which a beam of X-rays strikes a crystal and scatters The Max-Planck-Gesellschaft zur Förderung der Wissenschaften e Nature is a prominent Scientific journal, first published on 4 November 1869 [34]
Clindamycin may prolong the effects of neuromuscular-blocking drugs. [35][36][37][38] Its similarity to the mechanism of action of macrolides and chloramphenicol means they should not be given simultaneously, as this causes antagonism[24] and possible cross-resistance. The macrolides are a group of drugs (typically Antibiotics) whose activity stems from the presence of a macrolide ring, a large macrocyclic Cross-resistance is the Tolerance to a usually Toxic substance as a result of Exposure to a similarly acting substance
The veterinary uses of clindamycin are quite similar to its human indications, and include treatment of osteomyelitis,[39] skin infections, and toxoplasmosis, for which it is the drug of choice in dogs and cats. Veterinary medicine the application of medical, diagnostic, and therapeutic principles to companion, domestic, exotic, wildlife Osteomyelitis is an Infection of Bone or Bone marrow, usually caused by Pyogenic Bacteria or Mycobacteria. Toxoplasmosis is a Parasitic disease caused by the Protozoan Toxoplasma gondii. [40] Toxoplasmosis rarely causes symptoms in cats, but can do so in very young or immunocompromised kittens and cats. In Medicine, immunodeficiency (or immune deficiency) is a state in which the Immune system 's ability to fight Infectious disease is compromised Toxoplasmosis is contagious to humans, and therefore cat owners, particularly pregnant women, should take precautions to prevent the spread of the disease.