Sarecycline

Last updated

Sarecycline
Sarecycline.svg
Clinical data
Pronunciationsar"e sye' kleen
Trade names Seysara
Other namesP-005672
AHFS/Drugs.com Monograph
MedlinePlus a618068
License data
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Identifiers
  • (4S,4aS,5aR,12aR)-4-(Dimethylamino)-1,10,11,12a-tetrahydroxy-7-[[methoxy(methyl)amino]methyl]-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
PDB ligand
ECHA InfoCard 100.241.852 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C24H29N3O8
Molar mass 487.509 g·mol−1
3D model (JSmol)
  • CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)CN(C)OC

Sarecycline, sold under the brand name Seysara, is a narrow-spectrum tetracycline-derived antibiotic medication. [2] [3] It is specifically designed for the treatment of acne, and was approved by the FDA in October 2018 for the treatment of inflammatory lesions of non-nodular moderate to severe acne vulgaris in patients 9 years of age and older. [1] Two randomized and well-controlled clinical trials reported efficacy data on both facial and truncal acne (back and chest). [4] Efficacy was assessed in a total of 2002 subjects 9 years of age and older. [1] Unlike other tetracycline-class antibiotics, sarecycline has a long C7 moiety that extends into and directly interact with the bacterial messenger RNA (mRNA). [5] The spectrum of activity is limited to clinically relevant Gram-positive bacteria, mainly Cutibacterium acnes , with little or no activity against Gram-negative bacteria l microflora commonly found in the human gastrointestinal tract. [6]

Medical uses

Sarecycline, is indicated for the treatment of inflammatory lesions of non-nodular moderate to severe acne vulgaris. [1]

Related Research Articles

<span class="mw-page-title-main">Acne</span> Skin condition characterized by pimples

Acne, also known as acne vulgaris, is a long-term skin condition that occurs when dead skin cells and oil from the skin clog hair follicles. Typical features of the condition include blackheads or whiteheads, pimples, oily skin, and possible scarring. It primarily affects skin with a relatively high number of oil glands, including the face, upper part of the chest, and back. The resulting appearance can lead to lack of confidence, anxiety, reduced self-esteem, and, in extreme cases, depression or thoughts of suicide.

<span class="mw-page-title-main">Minocycline</span> Antibiotic medication

Minocycline, sold under the brand name Minocin among others, is a tetracycline antibiotic medication used to treat a number of bacterial infections such as pneumonia. It is generally less preferred than the tetracycline doxycycline. Minocycline is also used for the treatment of acne and rheumatoid arthritis. It is taken by mouth or applied to the skin.

<span class="mw-page-title-main">Broad-spectrum antibiotic</span> Treatment for a wide range of bacteria

A broad-spectrum antibiotic is an antibiotic that acts on the two major bacterial groups, Gram-positive and Gram-negative, or any antibiotic that acts against a wide range of disease-causing bacteria. These medications are used when a bacterial infection is suspected but the group of bacteria is unknown or when infection with multiple groups of bacteria is suspected. This is in contrast to a narrow-spectrum antibiotic, which is effective against only a specific group of bacteria. Although powerful, broad-spectrum antibiotics pose specific risks, particularly the disruption of native, normal bacteria and the development of antimicrobial resistance. An example of a commonly used broad-spectrum antibiotic is ampicillin.

<i>Cutibacterium acnes</i> Species of bacterium

Cutibacterium acnes is the relatively slow-growing, typically aerotolerant anaerobic, gram-positive bacterium (rod) linked to the skin condition of acne; it can also cause chronic blepharitis and endophthalmitis, the latter particularly following intraocular surgery. Its genome has been sequenced and a study has shown several genes can generate enzymes for degrading skin and proteins that may be immunogenic.

<span class="mw-page-title-main">Clindamycin</span> Antibiotic

Clindamycin is a lincosamide antibiotic medication used for the treatment of a number of bacterial infections, including osteomyelitis (bone) or joint infections, pelvic inflammatory disease, strep throat, pneumonia, acute otitis media, and endocarditis. It can also be used to treat acne, and some cases of methicillin-resistant Staphylococcus aureus (MRSA). In combination with quinine, it can be used to treat malaria. It is available by mouth, by injection into a vein, and as a cream or a gel to be applied to the skin or in the vagina.

<span class="mw-page-title-main">Doxycycline</span> Tetracycline-class antibiotic

Doxycycline is a broad-spectrum antibiotic of the tetracycline class used in the treatment of infections caused by bacteria and certain parasites. It is used to treat bacterial pneumonia, acne, chlamydia infections, Lyme disease, cholera, typhus, and syphilis. It is also used to prevent malaria. Doxycycline may be taken by mouth or by injection into a vein.

<span class="mw-page-title-main">Rosacea</span> Skin condition resulting in redness, pimples and swelling, usually on the face

Rosacea is a long-term skin condition that typically affects the face. It results in redness, pimples, swelling, and small and superficial dilated blood vessels. Often, the nose, cheeks, forehead, and chin are most involved. A red, enlarged nose may occur in severe disease, a condition known as rhinophyma.

<span class="mw-page-title-main">Fusidic acid</span> Antibiotic

Fusidic acid, sold under the brand names Fucidin among others, is an antibiotic that is often used topically in creams or ointments and eyedrops but may also be given systemically as tablets or injections.
As of October 2008, the global problem of advancing antimicrobial resistance has led to a renewed interest in its use.

<span class="mw-page-title-main">Demeclocycline</span> Chemical compound

Demeclocycline is a tetracycline antibiotic which was derived from a mutant strain of Streptomyces aureofaciens.

<span class="mw-page-title-main">Tigecycline</span> Chemical compound

Tigecycline, sold under the brand name Tygacil, is a tetracycline antibiotic medication for a number of bacterial infections. It is a glycylcycline administered intravenously. It was developed in response to the growing rate of antibiotic resistant bacteria such as Staphylococcus aureus, Acinetobacter baumannii, and E. coli. As a tetracycline derivative antibiotic, its structural modifications has expanded its therapeutic activity to include Gram-positive and Gram-negative organisms, including those of multi-drug resistance.

<span class="mw-page-title-main">Lincosamides</span> Group of antibiotics

Lincosamides are a class of antibiotics, which include lincomycin, clindamycin, and pirlimycin.

<span class="mw-page-title-main">Tetracycline antibiotics</span> Type of broad-spectrum antibiotic

Tetracyclines are a group of broad-spectrum antibiotic compounds that have a common basic structure and are either isolated directly from several species of Streptomyces bacteria or produced semi-synthetically from those isolated compounds. Tetracycline molecules comprise a linear fused tetracyclic nucleus to which a variety of functional groups are attached. Tetracyclines are named after their four ("tetra-") hydrocarbon rings ("-cycl-") derivation ("-ine"). They are defined as a subclass of polyketides, having an octahydrotetracene-2-carboxamide skeleton and are known as derivatives of polycyclic naphthacene carboxamide. While all tetracyclines have a common structure, they differ from each other by the presence of chloro, methyl, and hydroxyl groups. These modifications do not change their broad antibacterial activity, but do affect pharmacological properties such as half-life and binding to proteins in serum.

<span class="mw-page-title-main">Sparfloxacin</span> Chemical to treat bacterial infections

Sparfloxacin is a fluoroquinolone antibiotic used in the treatment of bacterial infections. It has a controversial safety profile.

<span class="mw-page-title-main">Cefoxitin</span> Chemical compound

Cefoxitin is a second-generation cephamycin antibiotic developed by Merck & Co., Inc. from Cephamycin C in the year following its discovery, 1972. It was synthesized in order to create an antibiotic with a broader spectrum. It is often grouped with the second-generation cephalosporins. Cefoxitin requires a prescription and as of 2010 is sold under the brand name Mefoxin by Bioniche Pharma, LLC. The generic version of cefoxitin is known as cefoxitin sodium.

<span class="mw-page-title-main">Ceftobiprole</span> Chemical compound

Ceftobiprole (Zevtera/Mabelio) is a fifth-generation cephalosporin for the treatment of hospital-acquired pneumonia and community-acquired pneumonia. It is marketed by Basilea Pharmaceutica in the United Kingdom, Germany, Switzerland and Austria under the trade name Zevtera, in France and Italy under the trade name Mabelio. Like other cephalosporins, ceftobiprole exerts its antibacterial activity by binding to important penicillin-binding proteins and inhibiting their transpeptidase activity which is essential for the synthesis of bacterial cell walls. Ceftobiprole has high affinity for penicillin-binding protein 2a of methicillin-resistant Staphylococcus aureus strains and retains its activity against strains that express divergent mecA gene homologues. Ceftobiprole also binds to penicillin-binding protein 2b in Streptococcus pneumoniae (penicillin-intermediate), to penicillin-binding protein 2x in Streptococcus pneumoniae (penicillin-resistant), and to penicillin-binding protein 5 in Enterococcus faecalis.

Infantile acne is a form of acneiform eruption that occurs in infants from 6 weeks to 1 year of age. Typical symptoms include inflammatory and noninflammatory lesions, papules and pustules most commonly present on the face. No cause of infantile acne has been established but it may be caused by increased sebaceous gland secretions due to elevated androgens, genetics and the fetal adrenal gland causing increased sebum production. Infantile acne can resolve by itself by age 1 or 2. However, treatment options include topical benzyl peroxide, topical retinoids and topical antibiotics in most cases.

<span class="mw-page-title-main">Solithromycin</span> Chemical compound

Solithromycin is a ketolide antibiotic undergoing clinical development for the treatment of community-acquired pneumonia and other infections.

<span class="mw-page-title-main">Nemonoxacin</span> Chemical compound

Nemonoxacin is a non-fluorinated quinolone antibiotic undergoing clinical trials. It has the same mechanism of action as fluouroquinolones; it inhibits DNA gyrase, preventing DNA synthesis, gene duplication, and cell division. At the end of 2016, it had reached market in Taiwan, Russia, the Commonwealth Independent States, Turkey, mainland China, and Latin America under the brand name Taigexyn. Nemonoxacin has completed phase 2 trials in the US and has moved on to phase 3 trials. The U.S. Food and Drug Administration (FDA) has granted nemonoxacin qualified infectious disease product (QIDP) and fast track designations for community-acquired bacterial pneumonia (CAP) and acute bacterial skin and skin-structure infections (ABSSSI).

<span class="mw-page-title-main">Omadacycline</span> Chemical compound

Omadacycline, sold under the brand name Nuzyra, is a broad spectrum antibiotic medication belonging to the aminomethylcycline subclass of tetracycline antibiotics. In the United States, it was approved in October 2018, for the treatment of community-acquired bacterial pneumonia and acute skin and skin structure infections.

<span class="mw-page-title-main">Antimicrobial spectrum</span> Method of assessing antibiotics

The antimicrobial spectrum of an antibiotic means the range of microorganisms it can kill or inhibit. Antibiotics can be divided into broad-spectrum antibiotics, extended-spectrum antibiotics and narrow-spectrum antibiotics based on their spectrum of activity. Detailedly, broad-spectrum antibiotics can kill or inhibit a wide range of microorganisms; extended-spectrum antibiotic can kill or inhibit Gram positive bacteria and some Gram negative bacteria; narrow-spectrum antibiotic can only kill or inhibit limited species of bacteria.

References

  1. 1 2 3 4 "Seysara- sarecycline hydrochloride tablet, coated". DailyMed. U.S. National Library of Medicine. 1 August 2021. Retrieved 31 March 2023.
  2. Zhanel G, Critchley I, Lin LY, Alvandi N (January 2019). "Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris". Antimicrobial Agents and Chemotherapy. 63 (1). doi:10.1128/AAC.01297-18. PMC   6325184 . PMID   30397052.
  3. "Sarecycline". PubChem. U.S. National Library of Medicine. Retrieved 5 September 2020.
  4. Moore A, Green LJ, Bruce S, Sadick N, Tschen E, Werschler P, et al. (September 2018). "Once-Daily Oral Sarecycline 1.5 mg/kg/day Is Effective for Moderate to Severe Acne Vulgaris: Results from Two Identically Designed, Phase 3, Randomized, Double-Blind Clinical Trials". Journal of Drugs in Dermatology. 17 (9): 987–996. PMID   30235387.
  5. Batool Z, Lomakin IB, Polikanov YS, Bunick CG (August 2020). "Sarecycline interferes with tRNA accommodation and tethers mRNA to the 70S ribosome". Proceedings of the National Academy of Sciences of the United States of America. 117 (34): 20530–20537. Bibcode:2020PNAS..11720530B. doi: 10.1073/pnas.2008671117 . PMC   7456112 . PMID   32817463.
  6. Zhanel G, Critchley I, Lin LY, Alvandi N (January 2019). "Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris". Antimicrobial Agents and Chemotherapy. 63 (1). doi: 10.1128/AAC.01297-18 . PMC   6325184 . PMID   30397052.