Sarecycline hydrochlorideProduct ingredient for Sarecycline
- Name
- Sarecycline hydrochloride
- Drug Entry
- Sarecycline
Sarecycline is a semi-synthetic derivative of tetracycline that was initially discovered by Paratek Pharmaceuticals from Boston, MA but then licensed to Warner Chilcott of Rockaway, NJ in July of 2007 4. After completing various phase-II and phase-III trials demonstrating its effectiveness in treating moderate to severe facial acne vulgaris 2,3 the US Food and Drug Administration approved Barcelona based Almirall, S.A.'s Seysara (sarecylcine) as a new first in class narrow spectrum tetracycline derived oral antibiotic for the treatment of inflammatory lesions of non-nodular moderate to severe acne vulgaris in patients nine years of age and older 5. Seysara (sarecycline) was originally part of Allergan's US Medical Dermatology portfolio, before Almirall acquired the portfolio in the second half of 2018 as a means of consolidating and reinforcing the dermatology-focused pharmaceutical company's presence in the United States 6.
Acne vulgaris itself is a common chronic skin condition associated with the blockage and/or inflammation of hair follicles and their accompanying sebaceous glands 5. The acne often presents physically as a mixture of non-inflammatory and inflammatory lesions mainly on the face but on the back and chest as well 5. Based upon data from Global Burden of Disease studies, the acne vulgaris condition affects up to 85% of young adults aged 12 to 25 years globally - with the possibility of permanent physical and mental scarring resulting from cases of severe acne 5.
Subsequently, while a number of first line tetracycline therapies like doxycycline and minocycline do exist for treating acne vulgaris, sarecycline presents a new and innovative therapy choice because it exhibits the necessary antibacterial activity against relevant pathogens that cause acne vulgaris but also possesses a low propensity for resistance development in such pathogens and a narrower, more specific spectrum of antibacterial activity, resulting in fewer off-target antibacterial effects on endogenous intestinal flora and consequently fewer resultant adverse effects associated with diarrhea, fungal overgrowth, etc.
- Accession Number
- DBSALT002125
- Structure
- Synonyms
- Sarecycline HCl / Sarecycline hydrochloride
- External IDs
- WC3035
- UNII
- 36718856JR
- CAS Number
- 1035979-44-2
- Weight
- Average: 523.97
Monoisotopic: 523.1721426 - Chemical Formula
- C24H30ClN3O8
- InChI Key
- APPRLAGZQKOUFL-FIPJBXKNSA-N
- InChI
- InChI=1S/C24H29N3O8.ClH/c1-26(2)18-13-8-11-7-12-10(9-27(3)35-4)5-6-14(28)16(12)19(29)15(11)21(31)24(13,34)22(32)17(20(18)30)23(25)33;/h5-6,11,13,18,28,30-31,34H,7-9H2,1-4H3,(H2,25,33);1H/t11-,13-,18-,24-;/m0./s1
- IUPAC Name
- (4S,4aS,5aR,12aS)-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-{[methoxy(methyl)amino]methyl}-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride
- SMILES
- Cl.[H][C@@]12CC3=C(CN(C)OC)C=CC(O)=C3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2
- External Links
- ChemSpider
- 28542258
- ChEMBL
- CHEMBL2364633
- Predicted Properties
Property Value Source Water Solubility 2.01 mg/mL ALOGPS logP -0.17 ALOGPS logP -3.1 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 3.31 Chemaxon pKa (Strongest Basic) 8.69 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 173.86 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 127.61 m3·mol-1 Chemaxon Polarizability 49.45 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon