CYP2C19 and CYP3A4 are inhibited by secnidillo (RP-14539) (0-5000 μM; 5 or 10 minutes), with IC50 values of 3873 μM and 3722 μM, respectively [2]. Regarding time-dependent inhibition, secnidazole (0-5000 μM; 5 or 10 minutes) shows no evidence [2]. With an apparent IC50 value of 503 μM, secnidazole (0-5000 μM; 5 or 10 minutes) directly inhibits human ALDH2 [2]. Secnidazole (0-5000 μM; 5 or 10 minutes) inhibits several CYP isomers, including CYP2A6, CYP2B6, and CYP2D6, at higher dosages in a concentration-dependent manner [2]. The growth of Serratia marcescens is inhibited by secnidazole (10 μL; 20 hours; serially dilute the secnidazole solution two-fold using Mueller-Hinton broth to generate dilutions from 80 to 0.3125 mg/mL); the MIC50 value is 10 mg/mL[3].

Secnidazole (100 μL; intraperitoneal injection; 5 days) can lessen Salmonella marcescens pathogenesis in mice and has preventive action against its pathogenesis [3].

Cell Viability Assay[3]
Cell Types: S.marcescens
Tested Concentrations: 10 μL (Secnidazole solution was serially diluted two-fold using Mueller-Hinton broth to obtain dilutions from 80 to 0.3125 mg/mL)
Incubation Duration: 20 h
Experimental Results: 2 mg/mL (equivalent to 1/5 MIC) has no inhibitory effect on the growth of Serratia marcescens.

Animal/Disease Models: Female healthy albino mouse[3]
Doses: 100 μL Administration
Doses: 100 μL; intellectual property. ; Results for 5 days: Dramatically diminished the ability of bacteria to kill mice.

Absorption, Distribution and Excretion
Secnidazole is rapidly and completely absorbed after oral administration. Following administration of a single oral dose of 2 g in healthy adult female subjects, the mean (SD) Cmax was 45.4 (7.64) mcg/mL and mean (SD) systemic exposure (AUC0-inf) was 1331.6 (230.16) mcg x hr/mL. Tmax ranged from three to four hours. Food has negligible effects on drug absorption and systemic exposure.
Following oral administration of a 2 g oral dose of secnidazole, approximately 15% of the drug was excreted as unchanged secnidazole in the urine.
The apparent volume of distribution of secnidazole is approximately 42 L.
The total body clearance of secnidazole is approximately 25 mL/min. The renal clearance is approximately 3.9 mL/min.

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Metabolism / Metabolites
The metabolism of secnidazole has not been fully characterized. According to _in vitro_ studies, secnidazole is metabolized by hepatic CYP450 enzymes, with less than or equal to 1% of the parent drug converted to metabolites. Secnidazole was found to be metabolized by CYP3A4 and CYP3A5 but to a limited extent. Secnidazole most likely undergoes oxidation. A hydroxymethyl metabolite and glucuronide conjugates of secnidazole have been detected in urine.

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Biological Half-Life
The plasma elimination half-life for secnidazole is approximately 17 hours.

Hepatotoxicity
Secnidazole is typically given as a single oral dose and, in follow up, de novo serum enzyme elevations occur rarely, overall rates being less than 0.5% of participants. In prelicensure studies, there were no reported cases of clinically apparent liver injury. Furthermore, despite considerable use worldwide, secnidazole has not been linked convincingly to instances of clinically apparent liver injury with jaundice.
Likelihood score: E (unlikely cause of clinically apparent liver injury).

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Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
No information is available on the clinical use of secnidazole during breastfeeding and no studies have evaluated adverse effects of secnidazole on the infant during breastfeeding, but presumably they are similar to those of the closely related drug, metronidazole, such as increased risk of oral and rectal Candida infections.
As with metronidazole, concern has been raised about exposure of healthy infants to secnidazole via breastmilk, because of possible mutagenicity and carcinogenicity. Based on the elimination half-life of secnidazole of approximately 17 hours, the manufacturer recommends avoidance of breastfeeding for 96 after a single dose. Other drugs are available for bacterial vaginosis, and can be given vaginally, which should result in lower amounts in breastmilk.
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.

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Protein Binding
The plasma protein binding of secnidazole is less than 5%.

[1]. Secnidazole. LiverTox: Clinical and Research Information on Drug-Induced Liver Injury, National Institute of Diabetes and Digestive and Kidney Diseases, 25 February 2020.
[2]. Helen S Pentikis, et al. 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.
[3]. Ahdab N Khayyat, et al. Secnidazole Is a Promising Imidazole Mitigator of Serratia marcescens Virulence. Microorganisms. 2021 Nov 11;9(11):2333.

Secnidazole is a C-nitro compound that is 5-nitroimidazole in which the hydrogens at positions 1 and 2 are replaced by 2-hydroxypropyl and methyl groups, respectively. It has a role as an epitope. It is a C-nitro compound, a member of imidazoles and a secondary alcohol.
Secnidazole is a second-generation 5-nitroimidazole antimicrobial agent. It is structurally related to other 5-nitroimidazoles, including [DB00916] and [DB00911], but displays improved oral absorption and a longer terminal elimination half-life than other drugs in this class. Secnidazole is selective against many anaerobic Gram-positive and Gram-negative bacteria as well as protozoa. Once it enters bacteria and parasites, secnidazole is activated by bacterial or parasitic enzymes to form a radical anion, thereby damaging and killing the target pathogen. Secnidazole has been available in many other countries in Europe, Asia, South America, and Africa for decades. In September 2017, FDA approved secnidazole under the market name Solosec for the treatment of trichomoniasis and bacterial vaginosis.
Secnidazole is a Nitroimidazole Antimicrobial.
Secnidazole is an orally available, broad spectrum antimicrobial agent used in the treatment of bacterial vaginosis. Secnidazole is a nitroimidazole similar to metronidazole but is used as a single dose and, unlike metronidazole, has not been linked to serum enzyme elevations during therapy or to cases of clinically apparent acute liver injury.

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Drug Indication
Secnidazole is indicated for treating trichomoniasis and bacterial vaginosis in patients 12 years of age and older. In other countries, it is also available as a combination product with other antibacterial drugs, such as [itraconazole].

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Mechanism of Action
Like other 5-nitroimidazole antimicrobials, the antimicrobial and antiprotozoal activity of secnidazole is accounted for by the nitro group in the imidazole ring. Upon entering the target pathogen, the nitro group of secnidazole is reduced by bacterial or parasitic nitroreductase enzymes, producing radical anions and reactive intermediates. Radical anions and reactive intermediates cause the depletion of thiols, DNA helix damage, disruption of bacterial or parasitic protein synthesis and replication, and ultimately, cell death of susceptible isolates of Gram positive bacteria, Gram negative bacteria and _T. vaginalis_.

C7H11N3O3

185.18

185.08

3366-95-8

Secnidazole hemihydrate;227622-73-3;Secnidazole-d6;1346603-27-7;Secnidazole-13C2, 15N2;Secnidazole-d4

71815

White to off-white solid powder

1.4±0.1 g/cm3

396.1±22.0 °C at 760 mmHg

76ºC

193.4±22.3 °C

0.0±1.0 mmHg at 25°C

1.598

0.33

1

4

2

13

194

0

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

KPQZUUQMTUIKBP-UHFFFAOYSA-N

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

1-(2-methyl-5-nitroimidazol-1-yl)propan-2-ol

SYM 1219 SYM1219 SYM-1219PM 185184, RP 14539 PM185184, RP14539 PM-185184, RP-14539

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ≥ 30 mg/mL (~162.00 mM)
H2O : ~25 mg/mL (~135.00 mM)

Solubility in Formulation 1: 50 mg/mL (270.01 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

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 (Please use freshly prepared in vivo formulations for optimal results.)