Basic information
- Standard SMILES
CON(C)Cc1ccc(O)c2c1C[C@H]1C[C@H]3[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]3(O)C(=O)C1=C2O- InChIKey
PQJQFLNBMSCUSH-SBAJWEJLSA-N- Molecular formula
- C24H29N3O8
- Average molar mass
- 487.5 g/mol
Overview
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. After completing various phase-II and phase-III trials demonstrating its effectiveness in treating moderate to severe facial acne vulgaris 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. 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. Acne vulgaris itself is a common chronic skin condition associated with the blockage and/or inflammation of hair follicles and their accompanying sebaceous glands. 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. 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. 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.
Names & identifiers
- Preferred name
- Sarecycline
- IUPAC
- (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
- English name
- Fosravuconazole bis(L-lysine
- Molecular formula
- C24H29N3O8
- Molecular weight
- 487.5
Names & synonyms
Show more names
Database identifiers
- CAS
1035654-66-0- PubChem CID
- 54681908
- DTXSID
DTXSID001027924- ChEMBL
CHEMBL2364632- UNII
- 94O110CX2E
- Nikkaji
- J3.805.102D
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 174 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 5
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 1,010
Experimental & physicochemical properties
Physicochemical properties
- Boiling point
- 787 · 787.0±70.0 °C(Predicted)
- Density
- 1.53 · 1.53±0.1 g/cm3(Predicted)
- pka
- 4.5 · 4.50±1.00(Predicted)
- FDA UNII
- 94 O110CX2E · 94O110CX2E
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 360 · H360
- REACH Registrations
- Active
Safety & regulation
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- Hazard statements
- H360
- REACH Registrations
- Active
Chemistry & industry
Pharmacology
Pharmacodynamics
Compared to various examples of first-line tetracycline therapies for moderate to severe acne like doxycycline and minocycline, studies have shown that sarecycline can be sixteen to thirty-two fold less active against aerobic Gram-negative bacilli present within the normal human intestinal microbiome. Furthermore, it has also been demonstrated that sarecycline may be four to eight fold less active against various anaerobic bacteria that also comprise the normal human intestinal microbiome. Subsequently, while doxycycline and minocycline typically elicit broad-spectrum antimicrobial activity that can often cause adverse effects like diarrhea, fungal overgrowth, vaginal candidiasis, etc. due to undesirable off-target antibacterial effects on endogenous intestinal flora, sarecycline demonstrates a noticeably more target specific narrow spectrum activity with lower incidence of such side effects. Moreover, sarecycline also shares a relatively low propensity for resistance development in Cutibacterium acnes - one of the principal anaerobic organisms associated with acne lesions - with doxycycline and minocycline treatments.
Mechanism of Action
It has been demonstrated that tetracyclines like sarecycline elicit their antimicrobial action by targeting and inhibiting protein synthesis in microbial agents like Cutibacterium acnes present in acne lesions. In particular, it is believed that sarecycline's mechanism of action revolves around the inhibition of various macromolecular biosynthesis activities like the macromolecular biosynthesis of microbial DNA, RNA, proteins, lipids, and cell wall. Specifically, it has been observed that while sarecycline demonstrates appreciable inhibition of microbial macromolecular DNA and protein synthesis, the compound has little to no effect on lipid biosynthesis, cell wall synthesis, and RNA synthesis. In addition, because Cutibacterium acnes also generates proteins and enzymes that are capable of causing inflammation, it is also believed that tetracyclines like sarecyclines can also affect an anti-inflammatory effect via the inhibition of such microbial protein synthesis.
Absorption, Distribution and Excretion
The median time to peak plasma concentration (Tmax) of sarecycline is 1.5 to 2.0 hours. When the medication is taken with a meal consisting of high fat (about 50% of total caloric content of the meal), high caloric (about 800 to 1000 Kcal), and milk content the Tmax can be delayed by approximately 0.53 hours and the Cmax and AUC can be decreased by 31% and 27%, respectively.
After a single 100 mg oral dose of radiolabeled sarecycline, 42.6% of the dose was recovered in feces (14.9% as unchanged) and 44.1% in urine (24.7% as unchanged).
The mean apparent volume of distribution of sarecycline at steady-state ranges from 91.4 L to 97.0 L.
The mean apparent oral clearance (CL/F) of sarecycline at steady state is about 3 L/h.
Applications
UsesSarecycline-d6 Hydrochloride is a labelled analogue of Sarecycline Hydrochloride(S140525), which is a substituted tetracycline compound used for treatment of bacterial infections and neoplasms.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers33 total
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