Secnidazole | SYM-1219 | CAS#3366-95-8 | anti-infective

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

MedKoo CAT#: 319558

CAS#: 3366-95-8

Description: Secnidazole, also known as SYM-1219, is a nitroimidazole anti-infective. Effectiveness in the treatment of dientamoebiasis has been reported. It has also been tested against Atopobium vaginae.

Chemical Structure

Secnidazole

CAS# 3366-95-8

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319558
Name: Secnidazole
CAS#: 3366-95-8
Chemical Formula: C7H11N3O3
Exact Mass: 185.08
Molecular Weight: 185.180
Elemental Analysis: C, 45.40; H, 5.99; N, 22.69; O, 25.92

Price and Availability

Size	Price	Availability
5g	USD 250	2 weeks
25g	USD 550	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: PM 185184; PM-185184; PM185184; RP 14539; RP-14539; RP14539; SYM-1219; SYM1219; SYM 1219; Secnidazole, trade name: Flagentyl, Secnol, Deprozol, Sabima; Sindose, Secnil.

IUPAC/Chemical Name: 1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol

InChi Key: KPQZUUQMTUIKBP-UHFFFAOYSA-N

InChi Code: InChI=1S/C7H11N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3,5,11H,4H2,1-2H3

SMILES Code: OC(C)CN1C([N+]([O-])=O)=CN=C1C

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 water

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:

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Biological target:	Secnidazole effectively inhibits QS resulting in the attenuation of Pseudomonas aeruginosa pathogenesis. Secnidazole has antimicrobial activity against many anaerobic Gram-negative and Gram-positive bacterial species in vitro.
In vitro activity:	This study reports the metabolism and drug-drug interaction profile for secnidazole and demonstrates that it has minimal to no potential drug interactions of concern. Secnidazole exhibited very low metabolism in human liver microsomes at concentrations up to 6400 µmol/L. Secnidazole inhibited CYP2C19 and CYP3A4, with IC50 values of 3873 and 3722 µmol/L, respectively. There was no inhibition observed for any other CYP enzyme or with human recombinant aldehyde dehydrogenase 2 (ALDH2). Reference: Pharmacol Res Perspect. 2020 Aug;8(4):e00634. https://pubmed.ncbi.nlm.nih.gov/32776491/
In vivo activity:	Single-dose oral secnidazole 2 g was highly efficacious in curing trichomoniasis in women co-infected with bacterial vaginosis (BV). Microbiological cure rates for trichomoniasis at test of cure were 97.7% (42/43) for secnidazole and 0% (0/36) for placebo. Reference: BMJ Open. 2023 Aug 7;13(8):e072071. https://pubmed.ncbi.nlm.nih.gov/37550019/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Water	25.0	135.00

Preparing Stock Solutions

The following data is based on the product molecular weight 185.18 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. Khayyat AN, Abbas HA, Khayat MT, Shaldam MA, Askoura M, Asfour HZ, Khafagy ES, Abu Lila AS, Allam AN, Hegazy WAH. Secnidazole Is a Promising Imidazole Mitigator of Serratia marcescens Virulence. Microorganisms. 2021 Nov 11;9(11):2333. doi: 10.3390/microorganisms9112333. PMID: 34835458; PMCID: PMC8617784. 2. Pentikis HS, Adetoro N, Kaufman G. In vitro metabolic profile and drug-drug interaction assessment of secnidazole, a high-dose 5-nitroimidazole antibiotic for the treatment of bacterial vaginosis. Pharmacol Res Perspect. 2020 Aug;8(4):e00634. doi: 10.1002/prp2.634. PMID: 32776491; PMCID: PMC7416039. 3. Muzny CA, Van Gerwen OT, Kaufman G, Chavoustie S. Efficacy of single-dose oral secnidazole for the treatment of trichomoniasis in women co-infected with trichomoniasis and bacterial vaginosis: a post hoc subgroup analysis of phase 3 clinical trial data. BMJ Open. 2023 Aug 7;13(8):e072071. doi: 10.1136/bmjopen-2023-072071. PMID: 37550019; PMCID: PMC10407359. 4. Jiménez JC, Pinon A, Dive D, Capron M, Dei-Cas E, Convit J. Antibody response in children infected with Giardia intestinalis before and after treatment with Secnidazole. Am J Trop Med Hyg. 2009 Jan;80(1):11-5. PMID: 19141831.
In vitro protocol:	1. Khayyat AN, Abbas HA, Khayat MT, Shaldam MA, Askoura M, Asfour HZ, Khafagy ES, Abu Lila AS, Allam AN, Hegazy WAH. Secnidazole Is a Promising Imidazole Mitigator of Serratia marcescens Virulence. Microorganisms. 2021 Nov 11;9(11):2333. doi: 10.3390/microorganisms9112333. PMID: 34835458; PMCID: PMC8617784. 2. Pentikis HS, Adetoro N, Kaufman G. In vitro metabolic profile and drug-drug interaction assessment of secnidazole, a high-dose 5-nitroimidazole antibiotic for the treatment of bacterial vaginosis. Pharmacol Res Perspect. 2020 Aug;8(4):e00634. doi: 10.1002/prp2.634. PMID: 32776491; PMCID: PMC7416039.
In vivo protocol:	1. Muzny CA, Van Gerwen OT, Kaufman G, Chavoustie S. Efficacy of single-dose oral secnidazole for the treatment of trichomoniasis in women co-infected with trichomoniasis and bacterial vaginosis: a post hoc subgroup analysis of phase 3 clinical trial data. BMJ Open. 2023 Aug 7;13(8):e072071. doi: 10.1136/bmjopen-2023-072071. PMID: 37550019; PMCID: PMC10407359. 2. Jiménez JC, Pinon A, Dive D, Capron M, Dei-Cas E, Convit J. Antibody response in children infected with Giardia intestinalis before and after treatment with Secnidazole. Am J Trop Med Hyg. 2009 Jan;80(1):11-5. PMID: 19141831.

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1: 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/NBK548222/ PubMed PMID: 31643547.

2: Abd El Aziz MA, Sharifipour F, Abedi P, Jahanfar S, Judge HM. Secnidazole for treatment of bacterial vaginosis: a systematic review. BMC Womens Health. 2019 Oct 21;19(1):121. doi: 10.1186/s12905-019-0822-2. PubMed PMID: 31638955; PubMed Central PMCID: PMC6802328.

3: Cheung W, Russo C, Maher S, Malik R, Šlapeta J. Successful use of secnidazole to manage a giardiosis outbreak in a shelter. Vet Parasitol. 2019 Oct;274:108911. doi: 10.1016/j.vetpar.2019.08.005. Epub 2019 Aug 14. PubMed PMID: 31499401.

4: Leggit JC, Saguil A. Secnidazole (Solosec) for Bacterial Vaginosis. Am Fam Physician. 2019 Aug 15;100(4):242-243. PubMed PMID: 31414782.

5: Elghazaly SM, Hamam KM, Badawy MM, Yakoub Agha NA, Samy A, Abbas AM. Efficacy and safety of single dose of oral secnidazole 2 g in treatment of bacterial vaginosis: A systematic review and meta-analysis. Eur J Obstet Gynecol Reprod Biol. 2019 Jul;238:125-131. doi: 10.1016/j.ejogrb.2019.05.013. Epub 2019 May 14. Review. PubMed PMID: 31129560.

6: Escobedo AA, Almirall P, Chirino E, Pacheco F, Duque A, Avila I. Treatment of refractory paediatric giardiasis using secnidazole plus albendazole: a case series. Infez Med. 2018 Dec 1;26(4):379-384. PubMed PMID: 30555145.

7: Saleh MM, Abbas HA, Askoura MM. Repositioning secnidazole as a novel virulence factors attenuating agent in Pseudomonas aeruginosa. Microb Pathog. 2019 Feb;127:31-38. doi: 10.1016/j.micpath.2018.11.042. Epub 2018 Nov 27. PubMed PMID: 30500409.

8: Lin X, Ruan Q, Zhang X, Duan X, Teng Y, Zhang J. (99m)Tc labelled complexes with secnidazole xanthate: Synthesis and evaluation as potential radiotracers to target tumor hypoxia. Appl Radiat Isot. 2018 Oct;140:289-293. doi: 10.1016/j.apradiso.2018.07.036. Epub 2018 Jul 30. PubMed PMID: 30092554.

9: Nespoulous L, Matei I, Charissoux A, Bédane C, Assikar S. Symmetrical drug-related intertriginous and flexural exanthema (SDRIFE) associated with pristinamycin, secnidazole, and nefopam, with a review of the literature. Contact Dermatitis. 2018 Dec;79(6):378-380. doi: 10.1111/cod.13084. Epub 2018 Jul 30. Review. PubMed PMID: 30062790.

10: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK500938/ PubMed PMID: 29999997.

11: Volpato A, Fortuoso BF, Campigotto G, Glombowsky P, Bottari NB, Lopes LS, Da Silva AS. Secnidazole for control of giardiasis in dairy calves. Exp Parasitol. 2018 Jun;189:16-18. doi: 10.1016/j.exppara.2018.04.008. Epub 2018 Apr 11. PubMed PMID: 29684664.

12: Secnidazole (Solosec) for bacterial vaginosis. Med Lett Drugs Ther. 2018 Mar 26;60(1543):52-53. PubMed PMID: 29635264.

13: Hussar DA, Walter MA. Delafloxacin meglumine, Meropenem trihydrate/vaborbactam, Secnidazole, and Benznidazole. J Am Pharm Assoc (2003). 2018 Mar - Apr;58(2):223-227. doi: 10.1016/j.japh.2018.01.007. PubMed PMID: 29506662.

14: Ghosh AP, Aycock C, Schwebke JR. In Vitro Study of the Susceptibility of Clinical Isolates of Trichomonas vaginalis to Metronidazole and Secnidazole. Antimicrob Agents Chemother. 2018 Mar 27;62(4). pii: e02329-17. doi: 10.1128/AAC.02329-17. Print 2018 Apr. PubMed PMID: 29439963; PubMed Central PMCID: PMC5913958.

15: Nyirjesy P, Schwebke JR. Secnidazole: next-generation antimicrobial agent for bacterial vaginosis treatment. Future Microbiol. 2018 Apr;13:507-524. doi: 10.2217/fmb-2017-0270. Epub 2018 Jan 12. PubMed PMID: 29327947.

16: Chavoustie SE, Gersten JK, Samuel MJ, Schwebke JR. A Phase 3, Multicenter, Prospective, Open-Label Study to Evaluate the Safety of a Single Dose of Secnidazole 2 g for the Treatment of Women and Postmenarchal Adolescent Girls with Bacterial Vaginosis. J Womens Health (Larchmt). 2018 Apr;27(4):492-497. doi: 10.1089/jwh.2017.6500. Epub 2018 Jan 11. PubMed PMID: 29323627.

17: Pentikis HS, Adetoro N. Two Phase 1, Open-Label, Single-Dose, Randomized, Crossover Studies to Assess the Pharmacokinetics, Safety, and Tolerability of Orally Administered Granules of Secnidazole (2 g) in Healthy Female Volunteers Under Different Administration Conditions. Clin Pharmacol Drug Dev. 2018 Jun;7(5):543-553. doi: 10.1002/cpdd.406. Epub 2017 Nov 10. PubMed PMID: 29125715; PubMed Central PMCID: PMC6033001.

18: Darpo B, Xue H, Adetoro N, Matthews BG, Pentikis HS. Thorough QT/QTc Evaluation of the Cardiac Safety of Secnidazole at Therapeutic and Supratherapeutic Doses in Healthy Individuals. J Clin Pharmacol. 2018 Mar;58(3):286-293. doi: 10.1002/jcph.1014. Epub 2017 Oct 2. PubMed PMID: 28967984; PubMed Central PMCID: PMC5836856.

19: Schwebke JR, Morgan FG Jr, Koltun W, Nyirjesy P. A phase-3, double-blind, placebo-controlled study of the effectiveness and safety of single oral doses of secnidazole 2 g for the treatment of women with bacterial vaginosis. Am J Obstet Gynecol. 2017 Dec;217(6):678.e1-678.e9. doi: 10.1016/j.ajog.2017.08.017. Epub 2017 Sep 1. Erratum in: Am J Obstet Gynecol. 2018 Jul;219(1):110. PubMed PMID: 28867602.

20: Hillier SL, Nyirjesy P, Waldbaum AS, Schwebke JR, Morgan FG, Adetoro NA, Braun CJ. Secnidazole Treatment of Bacterial Vaginosis: A Randomized Controlled Trial. Obstet Gynecol. 2017 Aug;130(2):379-386. doi: 10.1097/AOG.0000000000002135. PubMed PMID: 28697102.

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