Sarecycline free base | P005672 | CAS#1035979-44-2 | 1035654-66-0 | tetracycline antibiotic

MedKoo Cat#: 329881 | Name: Sarecycline free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Sarecycline, also known as WC-3035 and P005672, is a novel, tetracycline-derived, narrow-spectrum antibiotic being developed for use as an oral once daily antibiotic treatment for patients suffering from moderate to severe acne vulgaris. Sarecycline was designed by Paratek as a narrow-spectrum antibiotic with anti-inflammatory activity and the potential for a favorable tolerability profile.

Chemical Structure

Sarecycline free base

CAS#1035654-66-0 (free base)

Theoretical Analysis

MedKoo Cat#: 329881

Name: Sarecycline free base

CAS#: 1035654-66-0 (free base)

Chemical Formula: C24H29N3O8

Exact Mass: 487.1955

Molecular Weight: 487.51

Elemental Analysis: C, 59.13; H, 6.00; N, 8.62; O, 26.25

Price and Availability

Size	Price	Availability
10mg	USD 250.00	2 Weeks
25mg	USD 450.00	2 Weeks
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
200mg	USD 1,950.00	2 Weeks
500mg	USD 2,950.00	2 Weeks
1g	USD 4,650.00	2 Weeks
2g	USD 7,350.00	2 Weeks

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Related CAS #

1035979-44-2 (HCl) 1035654-66-0 (free base)

Synonym

WC-3035; WC 3035; WC3035; P005672; P-005672; P 005672; P005672; Sarecycline; Seysara.

IUPAC/Chemical 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

InChi Key

PQJQFLNBMSCUSH-SBAJWEJLSA-N

InChi Code

InChI=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

SMILES Code

O=C(C1=C(O)[C@@H](N(C)C)[C@@](C[C@@]2([H])C(C(C3=C(O)C=CC(CN(OC)C)=C3C2)=O)=C4O)([H])[C@@]4(O)C1=O)N

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sarecycline is a tetracycline-class antibiotic.

In vitro activity:

In three in vitro models of the human colon, sarecycline had minimal and transient impact on the gut microbiota composition and diversity, when compared to minocycline and doxycycline. Sarecycline caused a slight decline in bacterial diversity at the start of treatment, but abundances of most families remained stable during treatment. All populations recovered to pre-antibiotic levels after sarecycline exposure. These results suggest that sarecycline has minimal off-target effects and negative gastrointestinal sequelae. Reference: Front Microbiol. 2022 May 31;13:901911. https://pubmed.ncbi.nlm.nih.gov/35711781/

In vivo activity:

Sarecycline, compared with other tetracyclines, has low rates of vestibular-related adverse events. In rats, sarecycline was not detected in brain samples postdosing. In the octanol/water solvent system, sarecycline had a numerically lower lipophilicity profile than minocycline and doxycycline at pH 5.5 and 7.4. Reference: Front Med (Lausanne). 2022 Dec 8;9:1033980. https://pubmed.ncbi.nlm.nih.gov/36569144/

Preparing Stock Solutions

The following data is based on the product molecular weight 487.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Moura IB, Grada A, Spittal W, Clark E, Ewin D, Altringham J, Fumero E, Wilcox MH, Buckley AM. Profiling the Effects of Systemic Antibiotics for Acne, Including the Narrow-Spectrum Antibiotic Sarecycline, on the Human Gut Microbiota. Front Microbiol. 2022 May 31;13:901911. doi: 10.3389/fmicb.2022.901911. PMID: 35711781; PMCID: PMC9194605. 2. Ghannoum MA, Long L, Bunick CG, Del Rosso JQ, Gamal A, Tyring SK, McCormick TS, Grada A. Sarecycline Demonstrated Reduced Activity Compared to Minocycline against Microbial Species Representing Human Gastrointestinal Microbiota. Antibiotics (Basel). 2022 Feb 28;11(3):324. doi: 10.3390/antibiotics11030324. PMID: 35326788; PMCID: PMC8944611. 3. Grada A, Del Rosso JQ, Moore AY, Stein Gold L, Harper J, Damiani G, Shaw K, Obagi S, Salem RJ, Tanaka SK, Bunick CG. Reduced blood-brain barrier penetration of acne vulgaris antibiotic sarecycline compared to minocycline corresponds with lower lipophilicity. Front Med (Lausanne). 2022 Dec 8;9:1033980. doi: 10.3389/fmed.2022.1033980. PMID: 36569144; PMCID: PMC9773825. 4. Zhanel G, Critchley I, Lin LY, Alvandi N. Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris. Antimicrob Agents Chemother. 2018 Dec 21;63(1):e01297-18. doi: 10.1128/AAC.01297-18. PMID: 30397052; PMCID: PMC6325184.

In vitro protocol:

In vivo protocol:

1. Grada A, Del Rosso JQ, Moore AY, Stein Gold L, Harper J, Damiani G, Shaw K, Obagi S, Salem RJ, Tanaka SK, Bunick CG. Reduced blood-brain barrier penetration of acne vulgaris antibiotic sarecycline compared to minocycline corresponds with lower lipophilicity. Front Med (Lausanne). 2022 Dec 8;9:1033980. doi: 10.3389/fmed.2022.1033980. PMID: 36569144; PMCID: PMC9773825. 2. Zhanel G, Critchley I, Lin LY, Alvandi N. Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris. Antimicrob Agents Chemother. 2018 Dec 21;63(1):e01297-18. doi: 10.1128/AAC.01297-18. PMID: 30397052; PMCID: PMC6325184.

1: Kaul G, Saxena D, Dasgupta A, Chopra S. Sarecycline hydrochloride for the treatment of acne vulgaris. Drugs Today (Barc). 2019 Oct;55(10):615-625. doi: 10.1358/dot.2019.55.10.3045040. Review. PubMed PMID: 31720559. 2: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548293/ PubMed PMID: 31643616. 3: Hussar DA, Chahine EB. Omadacycline tosylate, Sarecycline hydrochloride, Rifamycin sodium, and Moxidectin. J Am Pharm Assoc (2003). 2019 Sep - Oct;59(5):756-760. doi: 10.1016/j.japh.2019.07.016. PubMed PMID: 31522740. 4: Moore AY, Charles JEM, Moore S. Sarecycline: a narrow spectrum tetracycline for the treatment of moderate-to-severe acne vulgaris. Future Microbiol. 2019 Sep;14:1235-1242. doi: 10.2217/fmb-2019-0199. Epub 2019 Sep 2. PubMed PMID: 31475868; PubMed Central PMCID: PMC6802708. 5: Haidari W, Bruinsma R, Cardenas-de la Garza JA, Feldman SR. Sarecycline Review. Ann Pharmacother. 2019 Aug 28:1060028019873111. doi: 10.1177/1060028019873111. [Epub ahead of print] PubMed PMID: 31462063. 6: Deeks ED. Correction to: Sarecycline: First Global Approval. Drugs. 2019 May;79(7):795. doi: 10.1007/s40265-019-01122-z. PubMed PMID: 31037601; PubMed Central PMCID: PMC6520308. 7: Sarecycline (Seysara) - another oral tetracycline for acne. Med Lett Drugs Ther. 2019 Mar 25;61(1568):43-44. Review. PubMed PMID: 31022156. 8: Deeks ED. Sarecycline: First Global Approval. Drugs. 2019 Feb;79(3):325-329. doi: 10.1007/s40265-019-1053-4. Review. Erratum in: Drugs. 2019 Apr 29;:. PubMed PMID: 30659422; PubMed Central PMCID: PMC6505496. 9: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK535605/ PubMed PMID: 30601614. 10: Zhanel G, Critchley I, Lin LY, Alvandi N. Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris. Antimicrob Agents Chemother. 2018 Dec 21;63(1). pii: e01297-18. doi: 10.1128/AAC.01297-18. Print 2019 Jan. PubMed PMID: 30397052; PubMed Central PMCID: PMC6325184. 11: Moore A, Green LJ, Bruce S, Sadick N, Tschen E, Werschler P, Cook-Bolden FE, Dhawan SS, Forsha D, Gold MH, Guenthner S, Kempers SE, Kircik LH, Parish JL, Rendon MI, Rich P, Stein-Gold L, Tyring SK, Weiss RA, Nasir A, Schmitz C, Boodhoo TI, Kaoukhov A, Berk DR. Once-Daily Oral Sarecycline 1.5 mg/kg/day Is Effective for Moderate to Severe Acne Vulgaris: Results from Two Identically Designed, Phase 3, Randomized, Double-Blind Clinical Trials. J Drugs Dermatol. 2018 Sep 1;17(9):987-996. PubMed PMID: 30235387. 12: Leyden JJ, Sniukiene V, Berk DR, Kaoukhov A. Efficacy and Safety of Sarecycline, a Novel, Once-Daily, Narrow Spectrum Antibiotic for the Treatment of Moderate to Severe Facial Acne Vulgaris: Results of a Phase 2, Dose-Ranging Study. J Drugs Dermatol. 2018 Mar 1;17(3):333-338. PubMed PMID: 29537451.