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Methenamine hippurate

Methenamine hippurate structure

CAS No:
5714-73-8
Formula:
C9H9NO3.C6H12N4
Chemical Name:
Methenamine hippurate
Synonyms:
Glycine,N-benzoyl-,compd. with 1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane (1:1);Hippuric acid,compd. with hexamethylenetetramine (1:1);Hexamethylenetetramine,monohippurate;1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane,compd. with N-benzoylglycine (1:1);Hexamethylenetetramine hippurate;Hippramine;Hiprex;Methenamine hippurate;Haiprex;Viapta;Hexamethylenetetramine hippuric acid complex;R-657;Urex;Hexamine hippurate
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

Methenamine hippurate (Hexamine hippurate) is an orally active urinary antiseptic agent with a wide antibacterial spectrum. Methenamine hippurate is effective against most common urinary tract pathogens[1][2].

Methenamine hippurate is a N-acylglycine. It derives from a N-benzoylglycine.|Methenamine Hippurate is the hippurate salt form of methenamine, a prodrug and inactive weak base that slowly hydrolyzes in acidic urine to ammonia and the effective, urinary tract antiseptic formaldehyde. Formaldehyde probably exerts its antibacterial effect by denaturation of protein. Depending on the urinary concentrations, formaldehyde is either bactericidal or bacteriostatic. Formaldehyde urinary concentrations are dependent on urine pH, volume, and flow rate. Formaldehyde acts as an antibacterial agent against gram-positive and gram-negative organisms.

Methenamine hippurate Basic Attributes

Molecular Weight：

319.35894

Exact Mass：

319.16400

EC Number：

227-206-5

UNII：

M329791L57

NCI Thesaurus Code：

C47610

HScode：

2933690000

Characteristics

PSA：

79.4

Melting Point：

89-95°C

Flash Point：

234.5ºC

Storage Conditions：

Refrigerator

Safety Information

Transport codes：

NONH for all modes of transport

Precautionary statement(s)：

P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, P501

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (33.33%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

MeSH Entry Terms：

hexamine hippurate

Methenamine hippurate Use and Manufacturing

Uses

Antibacterial (urinary).

Use Classification：

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

Computed Properties

Molecular Weight:319.36
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:319.16443955
Monoisotopic Mass:319.16443955
Topological Polar Surface Area:79.4
Heavy Atom Count:23
Complexity:282
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Drug Function and Efficacy

After entering the body, this product can be hydrolyzed into hippuric acid and formaldehyde under the condition of acidic urine (pH about 6.5). Formaldehyde can denature pathogen proteins and exert nonspecific antibacterial effects. The concentration of formaldehyde in urine has bactericidal or antibacterial effects depending on the pH value, urine volume and excretion rate. Hippuric acid can maintain the acidity of urine and promote the release of formaldehyde. Almost all bacteria and fungi are sensitive to the nonspecific antibacterial effect of formaldehyde produced after the hydrolysis of this product.

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

Hexamethylenetetramine Hippurate Tablets
Ingredients	The main ingredient of this product is hexamethylenetetramine hippurate, and its chemical name is 1,3,5,7-tetraaza-tricyclo[3,3,1,1]decane-mono-N-benzoylglycine salt. Molecular formula: C6H12N4?C9H9NO3 Molecular weight: 319.37
Indication	1. When this product is used in combination with sulfonamides, since this product decomposes into formaldehyde in urine, it can cause some sulfonamides to form insoluble precipitation, increasing the occurrence of crystalluria. 2. Acid-releasing drugs containing magnesium or calcium, carbonic anhydrase inhibitors, citrate, sodium bicarbonate, thiazide diuretics, etc. can make urine alkaline, affecting the efficacy of this product.
Specifications	0.5 g
Manufacturer	Hunan Mingrui Pharmaceutical Co., Ltd.

Hexamethylenetetramine hippurate
Manufacturer	Hunan Mingrui Pharmaceutical Co., Ltd.

Registered Holders

SS PHARMA LLC

United States
Active
MICRO LABS LTD

United States
Active
FAR SPECIALTY PRODUCTS INC DBA FAR CHEMICAL

United States
Active

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