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
Following oral administration of secnidazole, the drug is rapidly and completely absorbed. In healthy adult female subjects, after a single oral dose of 2 g secnidazole, the mean (standard deviation) peak plasma concentration (Cmax) was 45.4 (7.64) mcg/mL, and the mean (standard deviation) systemic exposure (AUC0-inf) was 1331.6 (230.16) mcg·hr/mL. The time to peak concentration (Tmax) was 3 to 4 hours. The effect of food on drug absorption and systemic exposure was negligible. Approximately 15% of the drug is excreted unchanged in the urine after oral administration of 2 g secnidazole. The apparent volume of distribution of secnidazole is approximately 42 liters. The systemic clearance of secnidazole is approximately 25 mL/min. The renal clearance is approximately 3.9 mL/min. Metabolism/Metabolites The metabolism of secnidazole has not been fully elucidated. In vitro studies have shown that secnidazole is primarily metabolized by hepatic CYP450 enzymes, with only ≤1% of the parent drug converted to metabolites. Secnidazole can also be metabolized by CYP3A4 and CYP3A5, but to a limited extent. Secnidazole is highly susceptible to oxidation. Hydroxymethyl metabolites and glucuronide conjugates of secnidazole have been detected in urine.

---

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

Hepatotoxicity
Secnidazole is usually administered orally as a single dose. New-onset elevations of serum enzymes are rare during follow-up, with an overall incidence of less than 0.5%. No clinically significant liver injury cases were reported in premarketing studies. Furthermore, despite its widespread use globally, there is no conclusive evidence linking secnidazole to clinically significant liver injury with jaundice. Probability Score: E (Unlikely a cause of clinically significant liver injury). Pregnancy and Lactation Effects ◉ Overview of Use During Lactation There is currently no clinical information regarding the use of secnidazole during lactation, and no studies have evaluated adverse reactions of secnidazole in breastfed infants. However, it is speculated that adverse reactions are similar to those of the closely related drug metronidazole, such as an increased risk of oral and rectal candidiasis. As with metronidazole, concerns exist regarding the potential mutagenicity and carcinogenicity of secnidazole, leading to exposure of healthy infants to secnidazole through breast milk. Based on the approximately 17-hour elimination half-life of secnidazole, the manufacturer recommends avoiding breastfeeding for 96 hours after a single dose. Other medications used to treat bacterial vaginosis can be administered vaginally, thus reducing drug concentrations in breast milk.
◉ Effects on breastfed infants
No published information found as of the revision date.
◉ Effects on lactation and breast milk
No published information found as of the revision date.

---

Protein binding
Secnidazole has a plasma protein binding rate of 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, a derivative of 5-nitroimidazole, with its hydrogen atoms at positions 1 and 2 replaced by 2-hydroxypropyl and methyl groups, respectively. It is an epitope compound. Secnidazole belongs to the imidazole class of compounds and is also a secondary alcohol. Secnidazole is a second-generation 5-nitroimidazole antibacterial drug. Its structure is similar to other 5-nitroimidazole drugs (including [DB00916] and [DB00911]), but it has a higher oral absorption rate and a longer terminal elimination half-life compared to similar drugs. Secnidazole is selective against a variety of anaerobic Gram-positive and Gram-negative bacteria, as well as protozoa. After entering bacteria and parasites, secnidazole is activated by bacterial or parasite enzymes to form free radical anions, thereby destroying and killing the target pathogens. Secnidazole has been marketed for decades in many other countries in Europe, Asia, South America, and Africa. In September 2017, the U.S. Food and Drug Administration (FDA) approved secnidazole, marketed under the brand name Solosec, for the treatment of trichomoniasis and bacterial vaginosis. Secinnidazole is a nitroimidazole antibiotic. It is an oral, broad-spectrum antibiotic used to treat bacterial vaginosis. Similar to metronidazole, secnidazole requires only a single dose and, unlike metronidazole, has not been found to cause elevated serum enzymes or clinically significant acute liver injury during treatment. Indications: Secinnidazole is indicated for the treatment of trichomoniasis and bacterial vaginosis in patients 12 years of age and older. In other countries, secnidazole is also used in combination with other antibiotics, such as itraconazole, in combination formulations. Mechanism of Action: Like other 5-nitroimidazole antibiotics, the antibacterial and antiprotozoal activity of secnidazole derives primarily from the nitro group on the imidazole ring. When secnidazole enters the target pathogen, its nitro group is reduced by nitroreductases in bacteria or parasites, producing free radical anions and reactive intermediates. These free radical anions and reactive intermediates lead to thiol depletion, DNA helix damage, and inhibition of bacterial or parasite protein synthesis and replication, ultimately resulting in cell death in secnidazole-sensitive Gram-positive bacteria, Gram-negative bacteria, and Trichomonas 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.

---

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