U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C43H51N3O11
Molecular Weight 785.8785
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIFAXIMIN

SMILES

CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C4=C(C(O)=C3C)C(O)=C(NC(=O)C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C5=C4N=C6C=C(C)C=CN56

InChI

InChIKey=NZCRJKRKKOLAOJ-XRCRFVBUSA-N
InChI=1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/cdi/rifaximin.html http://www.rxlist.com/xifaxan-drug.htm http://www.wikidoc.org/index.php/Special:Search?search=RIFAXIMIN

Rifaximin is a structural analog of rifampin and a non-systemic, gastrointestinal site-specific antibiotic. Rifaximin acts by inhibiting bacterial ribonucleic acid (RNA) synthesis and contributes to restore intestinal microflora imbalance. It is FDA approved for the treatment of travelers’ diarrhea, reduction in risk of overt hepatic encephalopathy (HE) recurrence and treatment of irritable bowel syndrome with diarrhea. More common side effects are: black, tarry stools; dizziness or lightheadedness; muscle spasm; rapid breathing; shortness of breath; trouble sleeping. Co-administration of cyclosporine, with XIFAXAN resulted in 83-fold and 124-fold increases in rifaximin mean Cmax in healthy subjects.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
25.0 µM [IC50]
Target ID: P0A8V2
Gene ID: 948488.0
Gene Symbol: rpoB
Target Organism: Escherichia coli (strain K12)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
XIFAXAN

Approved Use

To reduce the development of drug-resistant bacteria and maintain the effectiveness of XIFAXAN and other antibacterial drugs, XIFAXAN when used to treat infection should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. XIFAXAN is a rifamycin antibacterial indicated for: The treatment of patients (≥ 12 years of age) with travelers’ diarrhea (TD) caused by noninvasive strains of ( ) Escherichia coli 1.1 Reduction in risk of overt hepatic encephalopathy (HE) recurrence in patients ≥ 18 years of age ( ) 1.2 Limitations of Use TD: Do not use in patients with diarrhea complicated by fever or blood in the stool or diarrhea due to pathogens other than ( ) Escherichia coli 1.1 1.1 Travelers’ Diarrhea XIFAXAN 200 mg is indicated for the treatment of patients (≥ 12 years of age) with travelers’ diarrhea caused by noninvasive strains of Escherichia coli [see Warnings and Precautions ( ), Clinical Pharmacology ( ) and Clinical Studies ( )

Launch Date

2004
Preventing
XIFAXAN

Approved Use

To reduce the development of drug-resistant bacteria and maintain the effectiveness of XIFAXAN and other antibacterial drugs, XIFAXAN when used to treat infection should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. XIFAXAN is a rifamycin antibacterial indicated for: The treatment of patients (≥ 12 years of age) with travelers’ diarrhea (TD) caused by noninvasive strains of ( ) Escherichia coli 1.1 Reduction in risk of overt hepatic encephalopathy (HE) recurrence in patients ≥ 18 years of age ( ) 1.2 Limitations of Use TD: Do not use in patients with diarrhea complicated by fever or blood in the stool or diarrhea due to pathogens other than ( ) Escherichia coli 1.1 1.1 Travelers’ Diarrhea XIFAXAN 200 mg is indicated for the treatment of patients (≥ 12 years of age) with travelers’ diarrhea caused by noninvasive strains of Escherichia coli [see Warnings and Precautions ( ), Clinical Pharmacology ( ) and Clinical Studies ( )

Launch Date

2004
Primary
XIFAXAN

Approved Use

To reduce the development of drug-resistant bacteria and maintain the effectiveness of XIFAXAN and other antibacterial drugs, XIFAXAN when used to treat infection should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. XIFAXAN is a rifamycin antibacterial indicated for: The treatment of patients (≥ 12 years of age) with travelers’ diarrhea (TD) caused by noninvasive strains of ( ) Escherichia coli 1.1 Reduction in risk of overt hepatic encephalopathy (HE) recurrence in patients ≥ 18 years of age ( ) 1.2 Limitations of Use TD: Do not use in patients with diarrhea complicated by fever or blood in the stool or diarrhea due to pathogens other than ( ) Escherichia coli 1.1 1.1 Travelers’ Diarrhea XIFAXAN 200 mg is indicated for the treatment of patients (≥ 12 years of age) with travelers’ diarrhea caused by noninvasive strains of Escherichia coli [see Warnings and Precautions ( ), Clinical Pharmacology ( ) and Clinical Studies ( )

Launch Date

2004
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.1 ng/mL
550 mg single, oral
dose: 550 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RIFAXIMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
3.4 ng/mL
550 mg 2 times / day steady-state, oral
dose: 550 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
RIFAXIMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.8 ng/mL
550 mg single, oral
dose: 550 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RIFAXIMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11.1 ng × h/mL
550 mg single, oral
dose: 550 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RIFAXIMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
12.3 ng × h/mL
550 mg 2 times / day steady-state, oral
dose: 550 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
RIFAXIMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
22.5 ng × h/mL
550 mg single, oral
dose: 550 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RIFAXIMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.8 h
550 mg single, oral
dose: 550 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RIFAXIMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
4.8 h
550 mg single, oral
dose: 550 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RIFAXIMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
32.5%
550 mg single, oral
dose: 550 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RIFAXIMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
200 mg 3 times / day multiple, oral
Recommended
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources: Page: p.4
unhealthy, 18-79
n = 320
Health Status: unhealthy
Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli
Age Group: 18-79
Sex: M+F
Population Size: 320
Sources: Page: p.4
Disc. AE: Taste loss, Dysentery...
AEs leading to
discontinuation/dose reduction:
Taste loss
Dysentery
Weight decrease
Anorexia
Nausea
Nasal passage irritation
Sources: Page: p.4
1200 mg 2 times / day multiple, oral
Highest studied dose
Dose: 1200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 2 times / day
Sources: Page: p.478
unhealthy, 18–73
n = 99
Health Status: unhealthy
Condition: Crohn's disease
Age Group: 18–73
Sex: M+F
Population Size: 99
Sources: Page: p.478
800 mg 3 times / day multiple, oral
Highest studied dose
Dose: 800 mg, 3 times / day
Route: oral
Route: multiple
Dose: 800 mg, 3 times / day
Sources: Page: p.207
unhealthy, 32-82
n = 17
Health Status: unhealthy
Condition: Hepatic Encephalopathy
Age Group: 32-82
Sex: M+F
Population Size: 17
Sources: Page: p.207
550 mg 3 times / day multiple, oral
Studied dose
Dose: 550 mg, 3 times / day
Route: oral
Route: multiple
Dose: 550 mg, 3 times / day
Sources: Page: p.1119
unhealthy, 46.4
n = 2579
Health Status: unhealthy
Condition: Diarrhea-Predominant Irritable Bowel Syndrome
Age Group: 46.4
Sex: M+F
Population Size: 2579
Sources: Page: p.1119
AEs

AEs

AESignificanceDosePopulation
Anorexia Disc. AE
200 mg 3 times / day multiple, oral
Recommended
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources: Page: p.4
unhealthy, 18-79
n = 320
Health Status: unhealthy
Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli
Age Group: 18-79
Sex: M+F
Population Size: 320
Sources: Page: p.4
Dysentery Disc. AE
200 mg 3 times / day multiple, oral
Recommended
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources: Page: p.4
unhealthy, 18-79
n = 320
Health Status: unhealthy
Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli
Age Group: 18-79
Sex: M+F
Population Size: 320
Sources: Page: p.4
Nasal passage irritation Disc. AE
200 mg 3 times / day multiple, oral
Recommended
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources: Page: p.4
unhealthy, 18-79
n = 320
Health Status: unhealthy
Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli
Age Group: 18-79
Sex: M+F
Population Size: 320
Sources: Page: p.4
Nausea Disc. AE
200 mg 3 times / day multiple, oral
Recommended
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources: Page: p.4
unhealthy, 18-79
n = 320
Health Status: unhealthy
Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli
Age Group: 18-79
Sex: M+F
Population Size: 320
Sources: Page: p.4
Taste loss Disc. AE
200 mg 3 times / day multiple, oral
Recommended
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources: Page: p.4
unhealthy, 18-79
n = 320
Health Status: unhealthy
Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli
Age Group: 18-79
Sex: M+F
Population Size: 320
Sources: Page: p.4
Weight decrease Disc. AE
200 mg 3 times / day multiple, oral
Recommended
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources: Page: p.4
unhealthy, 18-79
n = 320
Health Status: unhealthy
Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli
Age Group: 18-79
Sex: M+F
Population Size: 320
Sources: Page: p.4
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
no
no
no
no
no
no
no
no
yes
weak (co-administration study)
Comment: Mean AUC of midazolam was 3.8% and 8.8% lower, respectively, after rifaximin was administered 3x a day for 7 days and 14 days, respectively.
Page: 30.0
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Rifaximin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic potential in conditions mediated by gastrointestinal bacteria.
1995 Mar
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Rifaximin, a poorly absorbed antibiotic: pharmacology and clinical potential.
2005
Rifaximin: a new treatment for travelers' diarrhea.
2005 Feb
Rifaximin for the treatment of hepatic encephalopathy.
2008 Aug
Rifaximin pharmacology and clinical implications.
2009 Jun
Rifaximin: a nonsystemic rifamycin antibiotic for gastrointestinal infections.
2010 Jul
Pharmacotherapy of hepatic encephalopathy in cirrhosis.
2010 Jun
Review article: rifaximin, a minimally absorbed oral antibacterial, for the treatment of travellers' diarrhoea.
2010 Jun
Solomonsterols A and B from Theonella swinhoei. The first example of C-24 and C-23 sulfated sterols from a marine source endowed with a PXR agonistic activity.
2011 Jan 13
Total synthesis and pharmacological characterization of solomonsterol A, a potent marine pregnane-X-receptor agonist endowed with anti-inflammatory activity.
2011 Jul 14
Patents

Sample Use Guides

Travelers’ Diarrhea: The recommended dose is one 200 mg tablet taken orally three times a day for 3 days. Hepatic Encephalopathy: The recommended dose is one 550 mg tablet taken orally two times a day. Irritable Bowel Syndrome with Diarrhea: The recommended dose is one 550 mg tablet taken orally three times a day for 14 days. It can be taken with or without food.
Route of Administration: Oral
The activities of rifaximin against enteropathogens were found to be as follows: a MIC50 of 4 to 8 μg/ml and a MIC90 of >8 μg/ml.
Name Type Language
RIFAXIMIN
EP   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
(2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-25-(ACETYLOXY)-5,6,21,23-TETRAHYDROXY-27-METHOXY-2,4,11,16,20,22,24,26-OCTAMETHYL-2,7-(EPOXYPENTADECA(1,11,13)TRIENIMINO)BENZOFURO(4,5-E)PYRIDO(1,2-A)BENZIMIDAZOLE-1,15(2H)-DIONE
Common Name English
RIFAXIMIN [USAN]
Common Name English
rifaximin [INN]
Common Name English
NSC-758957
Code English
RIFAXIMIN [VANDF]
Common Name English
RIFAXIMIN [EP IMPURITY]
Common Name English
RIFAXIMIN [ORANGE BOOK]
Common Name English
RIFAMYCIN L 105
Common Name English
RIFAXIDIN
Common Name English
L-105
Common Name English
RIFAXIMIN [EP MONOGRAPH]
Common Name English
Rifaximin [WHO-DD]
Common Name English
RIFAXIMIN [MART.]
Common Name English
RIFAXIMIN [MI]
Common Name English
XIFAXSAN
Brand Name English
2,7-(EPOXYPENTADECA(1,11,13)TRIENIMINO)BENZOFURO(4,5-E)PYRIDO(1,2-A)BENZIMIDAZOLE-1,15(2H)-DIONE, 25-(ACETYLOXY)-5,6,21,23-TETRAHYDROXY-27-METHOXY-2,4,11,16,20,22,24,26-OCTAMETHYL-, (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-
Systematic Name English
RIFAXIMIN [JAN]
Common Name English
4-DEOXY-4'-METHYLPYRIDO(1',2'-1,2)IMIDAZO(5,4-C)RIFAMYCIN SV
Common Name English
Classification Tree Code System Code
WHO-ATC D06AX11
Created by admin on Fri Dec 15 15:44:56 GMT 2023 , Edited by admin on Fri Dec 15 15:44:56 GMT 2023
NDF-RT N0000007911
Created by admin on Fri Dec 15 15:44:56 GMT 2023 , Edited by admin on Fri Dec 15 15:44:56 GMT 2023
NDF-RT N0000007911
Created by admin on Fri Dec 15 15:44:56 GMT 2023 , Edited by admin on Fri Dec 15 15:44:56 GMT 2023
WHO-VATC QD06AX11
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FDA ORPHAN DRUG 778520
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NDF-RT N0000007911
Created by admin on Fri Dec 15 15:44:56 GMT 2023 , Edited by admin on Fri Dec 15 15:44:56 GMT 2023
WHO-VATC QA07AA11
Created by admin on Fri Dec 15 15:44:56 GMT 2023 , Edited by admin on Fri Dec 15 15:44:56 GMT 2023
NCI_THESAURUS C258
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FDA ORPHAN DRUG 109497
Created by admin on Fri Dec 15 15:44:56 GMT 2023 , Edited by admin on Fri Dec 15 15:44:56 GMT 2023
WHO-VATC QJ51XX01
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WHO-VATC QG51AA06
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NDF-RT N0000175500
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WHO-ATC A07AA11
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NDF-RT N0000007911
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LIVERTOX NBK548082
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Code System Code Type Description
SMS_ID
100000091946
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PRIMARY
INN
5244
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PRIMARY
RXCUI
35619
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PRIMARY RxNorm
CAS
80621-81-4
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PRIMARY
LACTMED
Rifaximin
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PRIMARY
EVMPD
SUB10312MIG
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PRIMARY
FDA UNII
L36O5T016N
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PRIMARY
DAILYMED
L36O5T016N
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PRIMARY
MERCK INDEX
m9615
Created by admin on Fri Dec 15 15:44:56 GMT 2023 , Edited by admin on Fri Dec 15 15:44:56 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1617
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PRIMARY
CHEBI
75246
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PRIMARY
USAN
EE-33
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PRIMARY
NCI_THESAURUS
C61926
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PRIMARY
NSC
758957
Created by admin on Fri Dec 15 15:44:56 GMT 2023 , Edited by admin on Fri Dec 15 15:44:56 GMT 2023
PRIMARY
DRUG CENTRAL
2379
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PRIMARY
EPA CompTox
DTXSID7045998
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PRIMARY
DRUG BANK
DB01220
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PRIMARY
MESH
C042734
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PRIMARY
PUBCHEM
6436173
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PRIMARY
WIKIPEDIA
RIFAXIMIN
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PRIMARY