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
ChemSpider
28542258
ChEMBL
CHEMBL2364633
Predicted Properties
PropertyValueSource
Water Solubility2.01 mg/mLALOGPS
logP-0.17ALOGPS
logP-3.1Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.31Chemaxon
pKa (Strongest Basic)8.69Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area173.86 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity127.61 m3·mol-1Chemaxon
Polarizability49.45 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon