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Secnidazole

Secnidazole structure

CAS No:
3366-95-8
Formula:
C7H11N3O3
Chemical Name:
Secnidazole
Synonyms:
1H-Imidazole-1-ethanol,α,2-dimethyl-5-nitro-;Imidazole-1-ethanol,α,2-dimethyl-5-nitro-;α,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol;Secnidazole;RP 14539;Flagentyl;PM 185184;1-(2-Methyl-5-nitroimidazol-1-yl)-2-propanol;Secnol;Sabima;SYM 1219;Deprozol;Solosec;1-(2-Methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol;56274-78-3
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Secnidazole is a nitroimidazole anti-infective drug.

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 that is structurally related to other 5-nitroimidazoles including [DB00916] and [DB00911], but displays improved oral absorption and longer terminal elimination half-life than antimicrobial agents in this class. Secnidazole is selective against many anaerobic Gram-positive and Gram-negative bacteria and protozoa. In September 2017, FDA granted approval to secnidazole under the market name Solosec as a single-dose oral treatment for bacterial vaginosis, which is a common vaginal infection in women aged 15 to 44 years. The antimicrobial therapy is only intended to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria.|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.

Secnidazole Basic Attributes

Molecular Weight：

185.18

Exact Mass：

185.18

EC Number：

222-134-0

NSC Number：

759812

DSSTox ID：

DTXSID3045934

ATC Code：

P01AB07|P - Antiparasitic products, insecticides and repellents

HScode：

2933290090

Characteristics

PSA：

83.9

XLogP3：

0.2

Appearance：

Crystalline solid

Density：

1.4±0.1 g/cm3

Melting Point：

76 °C

Boiling Point：

396.1°C at 760 mmHg

Flash Point：

193.4±22.3 °C

Refractive Index：

1.598

Water Solubility：

>27.8 [ug/mL]

Storage Conditions：

Refrigerator

Collision Cross Section：

135.2 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|138.6 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]

Safety Information

Precautionary statement(s)：

P261, P264, P270, P271, P301+P312, P304+P312, P304+P340, P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P301+P312, P304+P312, P304+P340, P312, P330, and P501|Aggregated GHS information provided by 8 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Oral LD50 in mouse, rabbit and rat is 300 mg/kg, 3200 mg/kg and 980 mg/kg, in a respective order [MSDS]. Secnidazole was positive in the Bacterial Reverse Mutation Assay, but was negative for the rat micronucleus test and mouse lymphoma test. No parental toxicity or signs of reproductive toxicity were observed in female rat fertility studies at doses of up to the maximum tolerated dose of 300 mg/kg/day.

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.

Protein Binding：

The plasma protein binding of secnidazole is < 5-15%.

Drug Information

Drug Indication：

Indicated for the treatment of bacterial vaginosis in adult women .|FDA Label

LiverTox Summary：

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.

Drug Classes：

Antiinfective Agents

Pharmacology：

Secnidazole is a nitroimidazole antimicrobial drug that displays selectivity against many anaerobic Gram-positive and Gram-negative bacteria and protozoa. In vitro studies demonstrates the effectiveness of the drug against *Bacteroides fragilis*, *Trichomonas vaginalis*, *Entamoeba histolytica* and *Giardia lamblia*. There is no significant bacterial or protozoal resistance reported from secnidazole treatment.

MeSH：

Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

Absorption：

Secnidazole is rapidly and completely absorbed after oral administration. Following a single oral dose of 2 g in healthy adult female subjects, the mean (SD) secnidazole peak plasma concentration (Cmax) of 45.4 (7.64) mcg/mL and mean (SD) systemic exposure (AUC0-inf) of 1331.6 (230.16) mcg x hr/mL was reached. Median (range) time to peak concentration (Tmax) was 4.0 (3.0-4.0) hours.|The predominant route of elimination is renal elimination. Following a single oral dose of 2g secnidazole, approximately 15% of the drug is excreted as unchanged compoung in the urine.|The apparent volume of distribution of secnidazole is approximately 42-49 L.|The total body clearance of secnidazole is approximately 25 mL/min. The renal clearance of secnidazole is approximately 3.9 mL/min.

Metabolism/Metabolites：

According to *in vitro* studies, secnidazole is metabolized via oxidation by human hepatic CYP450 enzyme system with ≤ 1% conversion to metabolites.

Biological Half-Life：

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

Mechanism of Action：

Secnidazole enters the bacterial cell as a prodrug without an antimicrobial activity. The drug is converted to an active form via reduction of nitro groups to radical anions by bacterial enzymes. The radical anions are thought to interfere with bacterial DNA synthesis of susceptible isolates.

MeSH Entry Terms：

1-(2'-hydroxypropyl)-2-methyl-5- nitroimidazole

Secnidazole Use and Manufacturing

Uses

antiameobic, antitrichomonas

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:185.18
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:185.08004122
Monoisotopic Mass:185.08004122
Topological Polar Surface Area:83.9
Heavy Atom Count:13
Complexity:194
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is a 5-nitroimidazole antiprotozoan and anaerobic drug, which acts on the growth period of protozoa or anaerobic bacteria, destroys DNA chains or inhibits DNA synthesis, leading to the death of protozoa and anaerobic bacteria. This product has a strong killing effect on urogenital Trichomonas, intestinal and tissue amoeba and Giardia.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Secnidazole capsules
Ingredients	Secnidazole.
Indication	When used in combination with anticoagulants such as warfarin, the efficacy of the anticoagulants can be enhanced. Careful observation of the prothrombin time should be made and the dosage adjusted.
Specifications	0.25 g
Manufacturer	Jiangxi Yaodu Renhe Pharmaceutical Co., Ltd.

Secnidazole tablets
Ingredients	The main ingredient is: Secnidazole. The chemical name is: 1-(2-hydroxypropyl)-2-methyl-5-nitroimidazole hemihydrate.
Indication	1. This product can cause delirium or mental disorder when taken together with disulfiram (also known as anabolic sulfamethoxazole). Do not drink alcohol during treatment with this product or at least within one day after taking the medicine to avoid disulfiram-like reactions. 2. This product has a strong inhibitory effect on the anticoagulant effect of warfarin, so patients with a history of abnormal blood counts should not take it.
Specifications	0.5g

Secnidazole tablets
Ingredients	The main ingredient is: Secnidazole. The chemical name is: 1-(2-hydroxypropyl)-2-methyl-5-nitroimidazole hemihydrate.
Indication	1. This product can cause delirium or mental disorder when taken together with disulfiram (also known as anabolic sulfamethoxazole). Do not drink alcohol during treatment with this product or at least within one day after taking the medicine to avoid disulfiram-like reactions. 2. This product has a strong inhibitory effect on the anticoagulant effect of warfarin, so patients with a history of abnormal blood counts should not take it.
Specifications	0.5g (calculated as C7H11N3O3)
Manufacturer	Fujian Quanzhou Straits Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

CORDEN PHARMA BERGAMO S.P.A.

Italy
Active
Hunan Dino Pharmaceutical Co., Ltd.

China
Active
Hunan Jiudian HONGYANG Pharmaceutical Co., Ltd.

China
Active

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