hexamethylenetetramine
Approved
Jul 5, 1967
Methenamine is an antibacterial agent for preventing recurrent urinary tract infection. It can be used as methenamine hippurate or methenamine mandelate preparations and is United States Food and Drug Administration-approved. Methenamine exerts its activity because it is hydrolyzed to formaldehyde in acid urine. — NCATS
Clinical trial activity
5 trials · 6 clinical orgs · 14 marketing orgs
Earliest trial started Dec 1, 2014 (NCT02358993)
Timeline
1960s
- Jul 5, 1967
Earliest FDA Approval
- Jul 5, 1967
County Line — NDA Secondary Org
- Jul 5, 1967
Alvogen — Marketing Organization
- Jul 5, 1967
Alvogen — NDA Secondary Org
- Jul 5, 1967
Quagen Pharma — Marketing Organization
1970s
- Sep 9, 1976
Validus Pharmaceuticals — Marketing Organization
- Sep 9, 1976
Validus Pharmaceuticals — NDA Secondary Org
- Sep 9, 1976
ESJAY PHARMA — Marketing Organization
2000s
- Jun 20, 2003
Impax Laboratories — Marketing Organization
2010s
- Jan 1, 2016
Earliest Phase 3 Sponsor(trial)
- Jul 5, 2016
Aurobindo Pharma — Marketing Organization
- Aug 1, 2019
Micro Labs Ltd India — Marketing Organization
2020s
- Nov 27, 2020
RiconPharma — Marketing Organization
- Nov 27, 2020
Novast Labs — Marketing Organization
- Nov 27, 2020
Ingenus Pharmaceuticals — Marketing Organization
- Dec 1, 2023
Jubilant Innovation Ltd. — Marketing Organization
- Mar 10, 2025
Zydus Discovery DMCC — Marketing Organization
Indications
Approved for
Studied for
Mechanism of action
- DNAINHIBITOR
DNA inhibitor
Causes cross-linking of proteins and nucleic acids (PMID: 9880479).
Approval history
- approvedJul 5, 1967
Chemistry & pharmacology
SMILES
C1N2CN3CN1CN(C2)C3- Mol. weight
- 140.1863 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Prescription Only
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaHexamethylenetetramine ↗
- NCATSJ50OIX95QV ↗
- ChEMBLCHEMBL1201270 ↗
- ChEMBLCHEMBL1201104 ↗
Also known as
- 1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane
- 1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane
- 3m brand 1 of methenamine hippurate
- 3m brand 2 of methenamine hippurate
- e239
- e239
- hexamethylenamine
- hexamethylenamine
- hexamethylenamine
- hexamethylenamine
- hexamethylenetetramine
- hexamethylenetetramine
- hexamethylenetetramine
- hexamethylenetetramine
- hexamethylenetetramine
- hexamethylenetetramine
- hexamethylenetetramine
- hexamethylene tetramine
- hexamethylene tetramine
- hexamethylene tetramine hippurate
- hexamethylenetetramine hippurate
- hexamethylenetetramine hippuric acid complex
- hexamethylentetramin
- hexamethylentetramin
- hexamethylentetraminum
- hexamethylentetraminum
- hexamine
- hexamine
- hexamine
- hexamine
- hexamine hippurate
- hexamine hippurate
- hexamine hippurate
- hexaminum
- hexaminum
- hiprex
- hiprex
- hiprex
- hip-rex
- hmt
- hmt
- hmta
- hmta
- metenamina
- metenamina
- methenamin
- methenamine
- methenamine
- methenamine
- methenamine
- methenamine
- methenamine
- methenamine
- méthénamine
- méthénamine
- methenamine hippurate
- methenamine hippurate
- methenamine hippurate
- methenamine hippurate
- methenamine hippurate
- methenamine hippurate
- methenaminum
- methenaminum
- united drug brand of methenamine hippurate
- urex
- urex
- urex
- urex
- urex
- uritone
- uritone
- urotractan
- urotropin
- urotropin
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT04709601 | Phase 4 | Jan 4, 2021 | The University of Texas, Dallas |
| NCT03077711 | Phase 4 | Jun 1, 2016 | University of Chicago |
| NCT01657448 | Phase 3 | Jan 1, 2016 | EMS S/A |
| NCT02430246 | N/A | Jan 1, 2016 | Emek Medical Center, Technion University |
| NCT02358993 | N/A | Dec 1, 2014 | University of Pennsylvania |
Organizations
Research & Development (6)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Emek Medical Center | Academic/Hospital | 1 | 1 | 1 | 2016 |
| EMS S/A | For profit | 1 | 1 | 1 | 2016 |
| Technion University | Academic/Hospital | 1 | 0 | 1 | 2016 |
| The University of Texas, Dallas | Academic/Hospital | 1 | 1 | 1 | 2021 |
| University of Chicago | Academic/Hospital | 1 | 1 | 1 | 2016 |
| University of Pennsylvania | Academic/Hospital | 1 | 1 | 1 | 2014 |
Marketing (16)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| 3M | For profit | NDA | — |
| Alvogen | For profit | MKTG | Jul 5, 1967 |
| Alvogen | For profit | NDA2 | Jul 5, 1967 |
| Aurobindo Pharma | For profit | MKTG | Jul 5, 2016 |
| County Line | For profit | NDA2 | Jul 5, 1967 |
| ESJAY PHARMA | For profit | MKTG | Sep 9, 1976 |
| Impax Laboratories | For profit | MKTG | Jun 20, 2003 |
| Ingenus Pharmaceuticals | For profit | MKTG | Nov 27, 2020 |
| Jubilant Innovation Ltd. | For profit | MKTG | Dec 1, 2023 |
| Micro Labs Ltd India | For profit | MKTG | Aug 1, 2019 |
| Novast Labs | For profit | MKTG | Nov 27, 2020 |
| Quagen Pharma | For profit | MKTG | Jul 5, 1967 |
| RiconPharma | For profit | MKTG | Nov 27, 2020 |
| Validus Pharmaceuticals | For profit | MKTG | Sep 9, 1976 |
| Validus Pharmaceuticals | For profit | NDA2 | Sep 9, 1976 |
| Zydus Discovery DMCC | For profit | MKTG | Mar 10, 2025 |