Tromethamine

Identification

Name
Tromethamine
Accession Number
DB03754  (EXPT03072)
Type
Small Molecule
Groups
Approved
Description

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)

Structure
Thumb
Synonyms
  • 1,1,1-tris(hydroxymethyl)methanamine
  • 2-Amino-2-(hydroxymethyl)-1,3-propanediol
  • aminotris(hydroxymethyl)methane
  • THAM
  • Tris
  • Tris(hydroxymethyl)aminomethane
  • Trometamol
External IDs
NSC-6365
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ThamInjection, solution3.6 g/100mLIntravenousHospira, Inc.2005-11-302017-06-01Us
Tham Solution 36mg/mlSolution36 mgIntravenousHospira, Inc.1972-12-31Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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
Categories
UNII
023C2WHX2V
CAS number
77-86-1
Weight
Average: 121.135
Monoisotopic: 121.073893223
Chemical Formula
C4H11NO3
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

Pharmacology

Indication

For the prevention and correction of metabolic acidosis.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAutolysinNot AvailableStreptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
UCytochrome c4Not AvailablePseudomonas stutzeri
USoluble calcium-activated nucleotidase 1Not AvailableHuman
ULipoprotein NlpINot AvailableEscherichia coli (strain K12)
UDNA protection during starvation proteinNot AvailableAgrobacterium tumefaciens (strain C58 / ATCC 33970)
UPutative glucose-6-phosphate 1-epimeraseNot AvailableHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
UEndonuclease 8-like 1Not AvailableHuman
UCholera enterotoxin subunit BNot AvailableVibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
US-adenosylmethionine decarboxylase proenzymeNot AvailableHuman
UBiotin synthaseNot AvailableEscherichia coli (strain K12)
UVascular endothelial growth factor ANot AvailableHuman
U6-phosphogluconolactonaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UDecorinNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AtazanavirTromethamine can cause a decrease in the absorption of Atazanavir resulting in a reduced serum concentration and potentially a decrease in efficacy.
Bismuth subcitrate potassiumThe therapeutic efficacy of Bismuth Subcitrate can be decreased when used in combination with Tromethamine.
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Tromethamine.
CefditorenThe serum concentration of Cefditoren can be decreased when it is combined with Tromethamine.
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be decreased when it is combined with Tromethamine.
DabrafenibThe serum concentration of Dabrafenib can be decreased when it is combined with Tromethamine.
DasatinibTromethamine can cause a decrease in the absorption of Dasatinib resulting in a reduced serum concentration and potentially a decrease in efficacy.
Ferric CarboxymaltoseTromethamine can cause a decrease in the absorption of Ferric Carboxymaltose resulting in a reduced serum concentration and potentially a decrease in efficacy.
Ferric pyrophosphateTromethamine can cause a decrease in the absorption of Ferric pyrophosphate resulting in a reduced serum concentration and potentially a decrease in efficacy.
FlecainideThe serum concentration of Flecainide can be increased when it is combined with Tromethamine.
Food Interactions
Not Available

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
External Links
Human Metabolome Database
HMDB0240288
KEGG Drug
D00396
KEGG Compound
C07182
PubChem Compound
6503
PubChem Substance
46506027
ChemSpider
6257
ChEBI
9754
ChEMBL
CHEMBL1200391
HET
TRS
Wikipedia
Tris
ATC Codes
B05BB03 — TrometamolB05XX02 — Trometamol
AHFS Codes
  • 40:08.00 — Alkalinizing Agents
FDA label
Download (88.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingPreventionCystic Fibrosis (CF) / Healthy Volunteers1
2, 3RecruitingTreatmentPain, Acute1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CreamTopical
Injection, solutionIntravenous3.6 g/100mL
SolutionIntravenous36 mg
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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

Taxonomy

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 / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Primary amine / Primary alcohol / Organooxygen compound / Primary aliphatic amine / Alcohol / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
primary amino compound, triol (CHEBI:9754) / a small molecule (TRIS)

Targets

Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Unknown
General Function
N-acetylmuramoyl-l-alanine amidase activity
Specific Function
Autolysins are involved in some important biological processes such as cell separation, cell-wall turnover, competence for genetic transformation, formation of the flagella and sporulation. Autolys...
Gene Name
lytA
Uniprot ID
P06653
Uniprot Name
Autolysin
Molecular Weight
36544.235 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Pseudomonas stutzeri
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Diheme, high potential cytochrome c believed to be an intermediate electron donor to terminal oxidation systems.
Gene Name
cc4
Uniprot ID
Q52369
Uniprot Name
Cytochrome c4
Molecular Weight
21741.505 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Uridine-diphosphatase activity
Specific Function
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards...
Gene Name
CANT1
Uniprot ID
Q8WVQ1
Uniprot Name
Soluble calcium-activated nucleotidase 1
Molecular Weight
44839.24 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Not Available
Specific Function
May be involved in cell division. May play a role in bacterial septation or regulation of cell wall degradation during cell division. Negatively controls the production of extracellular DNA (eDNA).
Gene Name
nlpI
Uniprot ID
P0AFB1
Uniprot Name
Lipoprotein NlpI
Molecular Weight
33620.395 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Agrobacterium tumefaciens (strain C58 / ATCC 33970)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, oxidizing metal ions
Specific Function
Protects DNA from oxidative damage by sequestering intracellular Fe(2+) ion and storing it in the form of Fe(3+) oxyhydroxide mineral, which can be released after reduction. It efficiently inhibits...
Gene Name
dps
Uniprot ID
Q8UCK6
Uniprot Name
DNA protection during starvation protein
Molecular Weight
17822.915 Da
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Carbohydrate binding
Gene Name
Not Available
Uniprot ID
P44160
Uniprot Name
Putative glucose-6-phosphate 1-epimerase
Molecular Weight
Not Available
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
NEIL1
Uniprot ID
Q96FI4
Uniprot Name
Endonuclease 8-like 1
Molecular Weight
43683.625 Da
Kind
Protein
Organism
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
Pharmacological action
Unknown
General Function
Host cell surface binding
Specific Function
The B subunit pentameric ring directs the A subunit to its target by binding to the GM1 gangliosides present on the surface of the intestinal epithelial cells. It can bind five GM1 gangliosides. It...
Gene Name
ctxB
Uniprot ID
P01556
Uniprot Name
Cholera enterotoxin subunit B
Molecular Weight
13957.055 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Putrescine binding
Specific Function
Essential for biosynthesis of the polyamines spermidine and spermine. Promotes maintenance and self-renewal of embryonic stem cells, by maintaining spermine levels (By similarity).
Gene Name
AMD1
Uniprot ID
P17707
Uniprot Name
S-adenosylmethionine decarboxylase proenzyme
Molecular Weight
38339.335 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Catalyzes the conversion of dethiobiotin (DTB) to biotin by the insertion of a sulfur atom into dethiobiotin via a radical-based mechanism.
Gene Name
bioB
Uniprot ID
P12996
Uniprot Name
Biotin synthase
Molecular Weight
38647.785 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Vascular endothelial growth factor receptor binding
Specific Function
Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of...
Gene Name
VEGFA
Uniprot ID
P15692
Uniprot Name
Vascular endothelial growth factor A
Molecular Weight
27042.205 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
6-phosphogluconolactonase activity
Specific Function
Hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate.
Gene Name
pgl
Uniprot ID
Q9X0N8
Uniprot Name
6-phosphogluconolactonase
Molecular Weight
25324.955 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Poly(a) rna binding
Specific Function
May affect the rate of fibrils formation.
Gene Name
DCN
Uniprot ID
P07585
Uniprot Name
Decorin
Molecular Weight
39746.43 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2018 20:32