Methenamine Hippurate
Basic information
- CAS
5714-73-8- Standard SMILES
C1N2CN3CN1CN(C2)C3.O=C(O)CNC(=O)c1ccccc1- InChIKey
ROAIXOJGRFKICW-UHFFFAOYSA-N- Molecular formula
- C15H21N5O3
- Average molar mass
- 319.36 g/mol
- Monoisotopic mass
- 319.16443955
Overview
Methenamine hippurate is a N-acylglycine. It is functionally related to a N-benzoylglycine.
Names & identifiers
- Preferred name
- Methenamine Hippurate
- IUPAC
- 2-benzamidoacetic acid;1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane
- English name
- Methenamine hippurate
- Molecular formula
- C15H21N5O3
- Molecular weight
- 319.37
Names & synonyms
Methenamine hippurate5714-73-8Viaptahexamine hippurateHippramineHexamethylene tetramine hippurateM329791L57Hip-RexRefChem:55599Glycine, N-benzoyl, compound with 1,3,5,7-tetraazatricyclo(3.3.1.1(sup 3,7))decane(1:1)UrexHiprex
Show more names
Methenamine Hippuric acidr-657Urex (tn)cane(1:1)Hiprex (tn)
Hexamethylenetetramine monohippurate1,3,5,7-tetraazaadamantane benzoylglycinateMethenamine (hippurate)2-benzamidoacetic acid;1,3,5,7-tetrazatricyclo[3.3.1.13,7]decaneHaiprexD00855Hexamethylenetetramine hippurate1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane, compd. with N-benzoylglycine (1:1)
Database identifiers
- CAS
5714-73-8- PubChem CID
- 21945
- DTXSID
DTXSID10972603- ChEMBL
CHEMBL1201104- ChEBI
CHEBI:6825- UNII
- M329791L57
- EC Number
- 227-206-5
Properties
Computed structural properties
- Topological polar surface area
- 79.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 282
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Anti-Infective Agents, Urinary
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 89 · 89-95°C
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- color
- White to Off-White
- Water Solubility
- 2 O: · H2O: 2mg/mL, clear
- InChI
- 1S/C9H9NO3.C6H12N4/c11-8(12)6-10-9(13)7-4-2-1-3-5-7;1-7-2-9-4-8(1)5-10(3-7)6-9/h1-5H,6H2,(H,10,13)(H,11,12);1-6H2
- InChIKey
- ROAIXOJGRFKICW-UHFFFAOYSA-N
- SMILES
- OC(CNC(C1=CC=CC=C1)=O)=O.N2(CN(C3)C4)CN3CN4C2
- FDA UNII
- 329791 L57 · M329791L57
- UNSPSC Code
- 41116107 · 41116107
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (33.3%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Methenamine hippurate
Ambiguous-DILI-concern
3
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- WGK 3
- hs_code
- 2933690000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P321-P332+P313-P337+P313-P362
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
Substances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionMethenamine hippurate is a broad-spectrum urinary antiseptic agent. Under acidic conditions, methenamine hippurate is hydrolyzed to formaldehyde and ammonia, which exerts an antibacterial effect. It is effective against a wide range of bacteria but lacks activity against Proteus and other bacteria that increase urine alkalinity. Formulations containing methenamine hippurate have been used to treat urinary tract infections.
UsesAntibacterial (urinary).
General DescriptionMethenamine hippurate (Hiprex) is the hippuric acid salt ofmethenamine. It is readily absorbed after oral administrationand is concentrated in the urinary bladder, where it exerts itsantibacterial activity. Its activity is increased in acid urine.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Methenamine hippurate is a N-acylglycine. It is functionally related to a N-benzoylglycine.
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