Sarecycline

Sarecycline
Names
Pronunciationsar"e sye' kleen
Trade namesSeysara
Other namesP-005672
IUPAC name
  • (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
Clinical data
Drug classTetracycline[1]
Main usesAcne[1]
Side effectsNausea, sunburns, dizziness, Clostridium difficile infection[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • US: N (Not classified yet)
    Typical dose60 to 150 mg OD[1]
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa618068
    Legal
    License data
    Legal status
    Chemical and physical data
    FormulaC24H29N3O8
    Molar mass487.509 g·mol−1
    3D model (JSmol)
    SMILES
    • 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 is an antibiotic used to treat acne.[1] Specifically it is used for moderate to severe acne of the non-nodular type.[1] It is taken by mouth.[1]

    Common side effects include nausea.[1] Other side effects may include sunburns, dizziness, Clostridium difficile infections.[1] Use during pregnancy may harm the baby.[1] It is in the tetracycline class.[1]

    Sarecycline was approved for medical use in the United States in 2018.[2] In the United States it costs about 750 USD per month as of 2021.[3] It is not available in Europe or the United Kingdom as of 2021.[4]

    Medical uses

    The spectrum of activity is limited to clinically relevant Gram-positive bacteria, mainly Cutibacterium acnes, with little or no activity against Gram-negative bacterial microflora commonly found in the human gastrointestinal tract.[5] Sarecycline has not been tested in spirochetes.

    Dosage

    It is taken at a dose of 60 to 150 mg once per day depending on a person's weight.[1]

    Chemistry

    Unlike other tetracycline-class antibiotics, sarecycline has a long C7 moiety that extends into and directly interact with the bacterial messenger RNA (mRNA).[6]

    References

    1. 1 2 3 4 5 6 7 8 9 10 11 12 "Sarecycline Monograph for Professionals". Drugs.com. Archived from the original on 21 January 2021. Retrieved 10 October 2021.
    2. ↑ "FDA-approved Labeling-Package Insert for Seysara" (PDF). Drugs@FDA. June 2020. Archived (PDF) from the original on June 7, 2020. Retrieved September 5, 2020.
    3. ↑ "Seysara Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 10 October 2021.
    4. ↑ "Sarecycline". SPS - Specialist Pharmacy Service. 30 March 2017. Archived from the original on 11 October 2021. Retrieved 10 October 2021.
    5. ↑ Zhanel, George; Critchley, Ian; Lin, Lynn-Yao; Alvandi, Nancy (2019-01-01). "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. ISSN 0066-4804. PMC 6325184. PMID 30397052.
    6. ↑ Batool, Zahra; Lomakin, Ivan B.; Polikanov, Yury S.; Bunick, Christopher G. (2020-08-25). "Sarecycline interferes with tRNA accommodation and tethers mRNA to the 70S ribosome". Proceedings of the National Academy of Sciences. 117 (34): 20530–20537. doi:10.1073/pnas.2008671117. ISSN 0027-8424. PMC 7456112. PMID 32817463.
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