V7A

Sarecycline


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Chemical Component Summary

NameSarecycline
Synonyms(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
Identifiers(4~{S},4~{a}~{S},5~{a}~{R},12~{a}~{S})-4-(dimethylamino)-7-[[methoxy(methyl)amino]methyl]-3,10,12,12~{a}-tetrakis(oxidanyl)-1,11-bis(oxidanylidene)-4~{a},5,5~{a},6-tetrahydro-4~{H}-tetracene-2-carboxamide
FormulaC24 H29 N3 O8
Molecular Weight487.502
TypeNON-POLYMER
Isomeric SMILESCN(C)[C@H]1[C@@H]2C[C@@H]3Cc4c(ccc(c4C(=O)C3=C([C@@]2(C(=O)C(=C1O)C(=O)N)O)O)O)CN(C)OC
InChIInChI=1S/C24H29N3O8/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)/t11-,13-,18-,24-/m0/s1
InChIKeyPQJQFLNBMSCUSH-SBAJWEJLSA-N

Chemical Details

Formal Charge0
Atom Count64
Chiral Atom Count4
Bond Count67
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB12035 
NameSarecycline
Groups
  • approved
  • investigational
DescriptionSarecycline 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 [A40005]. After completing various phase-II and phase-III trials demonstrating its effectiveness in treating moderate to severe facial acne vulgaris [A39993, A39994] 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 [L4814]. 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 [L4815]. Acne vulgaris itself is a common chronic skin condition associated with the blockage and/or inflammation of hair follicles and their accompanying sebaceous glands [L4814]. 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 [L4814]. 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 [L4814]. 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.
Synonyms
  • Sareciclina
  • Sarecycline
  • Sarecycline hydrochloride
  • Sarécycline
  • Sarecyclinum
Brand NamesSeysara
IndicationSarecycline is a tetracycline-class drug indicated for the treatment of inflammatory lesions of non-nodular moderate to severe acne vulgaris in patients 9 years of age and older [FDA Label].
Categories
  • Anti-Acne Preparations
  • Anti-Acne Preparations for Systemic Use
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
ATC-Code
  • J01AA14
  • J01AA20
CAS number1035654-66-0

Drug Targets

NameTarget SequencePharmacological ActionActions
P-glycoprotein 1MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...unknowninhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682