Tromethamine

Identification

Summary

Tromethamine is a proton acceptor used for the prevention and correction of metabolic acidosis associated with various clinical conditions, such as cardiac bypass surgery.

Generic Name
Tromethamine
DrugBank Accession Number
DB03754
Background

An organic amine proton acceptor. It is used in the synthesis of surface-active agents and pharmaceuticals; as an emulsifying agent for cosmetic creams and lotions, mineral oil and paraffin wax emulsions, as a biological buffer, and used as an alkalizer. (From Merck, 11th ed; Martindale, The Extra Pharmacopoeia, 30th ed, p1424)

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 121.135
Monoisotopic: 121.073893223
Chemical Formula
C4H11NO3
Synonyms
  • 1,1,1-tris(hydroxymethyl)methanamine
  • 2-Amino-2-(hydroxymethyl)-1,3-propanediol
  • aminotris(hydroxymethyl)methane
  • THAM
  • Tris
  • Tris(hydroxymethyl)aminomethane
  • Trometamol
  • Tromethamine
External IDs
  • NSC-6365

Pharmacology

Indication

For the prevention and correction of metabolic acidosis.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Prevention ofMetabolic acidosis•••••••••••••••••••••• ••••••••
Treatment ofMetabolic acidosis•••••••••••••••••••••• ••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAmyloid beta A4 protein
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
FlecainideThe serum concentration of Flecainide can be increased when it is combined with Tromethamine.
Food Interactions
No interactions found.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ThamInjection, solution3.6 g/100mLIntravenousHospira, Inc.2020-06-24Not applicableUS flag
Tham Solution 36mg/mlSolution36 mg / mLIntravenousHospira Healthcare Ulc1972-12-312018-10-03Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Sooryehan Hyo Fermented Sun BlockTromethamine (2.63 mL/100mL) + Amiloxate (1.6 mL/100mL) + Bemotrizinol (1 mL/100mL) + Diethylamino hydroxybenzoyl hexyl benzoate (1 mL/100mL) + Ensulizole (3.9 mL/100mL) + Octinoxate (7 mL/100mL) + Titanium dioxide (2.52 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2011-09-27Not applicableUS flag

Categories

ATC Codes
B05XX02 — TrometamolB05BB03 — Trometamol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
1,2-aminoalcohols
Alternative Parents
Primary alcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
1,2-aminoalcohol / Alcohol / Aliphatic acyclic compound / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Organopnictogen compound / Primary alcohol / Primary aliphatic amine / Primary amine
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
primary amino compound, triol (CHEBI:9754) / a small molecule (TRIS)
Affected organisms
Not Available

Chemical Identifiers

UNII
023C2WHX2V
CAS number
77-86-1
InChI Key
LENZDBCJOHFCAS-UHFFFAOYSA-N
InChI
InChI=1S/C4H11NO3/c5-4(1-6,2-7)3-8/h6-8H,1-3,5H2
IUPAC Name
2-amino-2-(hydroxymethyl)propane-1,3-diol
SMILES
NC(CO)(CO)CO

References

Synthesis Reference

Jean Bourguignon, Marcel-Xavier Sion, Michel Moreau, "Preparation of tris(hydroxymethyl)aminomethane." U.S. Patent US4233245, issued August, 1959.

US4233245
General References
Not Available
Human Metabolome Database
HMDB0240288
KEGG Drug
D00396
KEGG Compound
C07182
PubChem Compound
6503
PubChem Substance
46506027
ChemSpider
6257
RxNav
10865
ChEBI
9754
ChEMBL
CHEMBL1200391
ZINC
ZINC000000896695
PDBe Ligand
TRS
Wikipedia
Tris
FDA label
Download (88.7 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CreamTopical
Injection, solutionIntravenous3.6 g/100mL
SolutionIntravenous36 mg / mL
Injection, solutionIntravenous; Parenteral3.6 %
SolutionIntravenous3.6 %
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility695.0 mg/mLALOGPS
logP-2.1ALOGPS
logP-2.7Chemaxon
logS0.76ALOGPS
pKa (Strongest Acidic)14.16Chemaxon
pKa (Strongest Basic)8.95Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area86.71 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity28.36 m3·mol-1Chemaxon
Polarizability12.02 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.52
Blood Brain Barrier-0.6989
Caco-2 permeable-0.6613
P-glycoprotein substrateNon-substrate0.6664
P-glycoprotein inhibitor INon-inhibitor0.9749
P-glycoprotein inhibitor IINon-inhibitor0.9671
Renal organic cation transporterNon-inhibitor0.9239
CYP450 2C9 substrateNon-substrate0.8432
CYP450 2D6 substrateNon-substrate0.8337
CYP450 3A4 substrateNon-substrate0.8096
CYP450 1A2 substrateNon-inhibitor0.8179
CYP450 2C9 inhibitorNon-inhibitor0.9095
CYP450 2D6 inhibitorNon-inhibitor0.9027
CYP450 2C19 inhibitorNon-inhibitor0.895
CYP450 3A4 inhibitorNon-inhibitor0.9568
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9686
Ames testNon AMES toxic0.9257
CarcinogenicityNon-carcinogens0.7844
BiodegradationReady biodegradable0.582
Rat acute toxicity1.5129 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9739
hERG inhibition (predictor II)Non-inhibitor0.9664
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-53da6b0f35ab1e8e8a57
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0pi0-7900000000-244b89c0e2e656701b1d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-9000000000-a468801012da982d3bac
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-9000000000-eb66f99d48d2027e0fb2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-9000000000-2983a91b4350760fab44
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-5900000000-4d44f73244a275768005
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-4900000000-7cc13727c3c08c282ed2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fki-7900000000-45788fffce8e42246e79
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-6efd8f2c26b19f375624
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-f9b5a0ac4652a0aa4196
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-2108be11fdf60bbbbc8f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-120.305657
predicted
DarkChem Lite v0.1.0
[M-H]-127.053345
predicted
DeepCCS 1.0 (2019)
[M+H]+120.570657
predicted
DarkChem Lite v0.1.0
[M+H]+129.05507
predicted
DeepCCS 1.0 (2019)
[M+Na]+120.176757
predicted
DarkChem Lite v0.1.0
[M+Na]+137.35686
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transition metal ion binding
Specific Function
Functions as a cell surface receptor and performs physiological functions on the surface of neurons relevant to neurite growth, neuronal adhesion and axonogenesis. Involved in cell mobility and tra...
Gene Name
APP
Uniprot ID
P05067
Uniprot Name
Amyloid beta A4 protein
Molecular Weight
86942.715 Da
References
  1. Arispe N, Rojas E, Pollard HB: Alzheimer disease amyloid beta protein forms calcium channels in bilayer membranes: blockade by tromethamine and aluminum. Proc Natl Acad Sci U S A. 1993 Jan 15;90(2):567-71. doi: 10.1073/pnas.90.2.567. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48