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CAS No. :	187235-37-6
Formula :	C₁₄H₁₂F₃N₃O₅
M.W :	359.26
SMILES Code :	FC(F)(F)OC1=CC=C(C=C1)CO[C@H]2CN3C(OC2)=NC([N+]([O-])=O)=C3
Synonyms :	(S)-PA 824; Pretomanid
MDL No. :	MFCD06809939
InChI Key :	ZLHZLMOSPGACSZ-NSHDSACASA-N
Pubchem ID :	456199

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

IPEC-J2 cells	10, 30, 50 µM	1 hour	Evaluating the antiviral activity of PA-824 in porcine cells, results showed that PA-824 significantly and dose-dependently reduced the expression level of PEDV N.	J Virol. 2024 Jul 23;98(7):e0041323
Vero cells	10 µM	1 hour	Screening for PEDV inhibitors, PA-824 exhibited the highest SI index and lowest price, and was selected for further study.	J Virol. 2024 Jul 23;98(7):e0041323
Mycobacterium tuberculosis (Mtb)	2 to 125 µM	1 week	Evaluate the bactericidal activity of PA-824 against nonreplicating Mtb under hypoxia, showing that PA-824 kills nonreplicating Mtb via NO release	Science. 2008 Nov 28;322(5906):1392-5
Mycobacterium tuberculosis H37Rv	3 μg/ml	21 days	Assessing low-dose PA-824 efficacy, achieving 4.93 ± 0.32 log CFU/ml after 21-day treatment at 3 μg/ml	BMC Microbiol. 2013 Oct 1;13:218
Mycobacterium tuberculosis H37Rv	12.5 μg/ml	21 days	Evaluating bactericidal activity of PA-824 against non-replicating M.tuberculosis under anaerobic conditions, showing 0 CFU/ml after 21-day treatment at 12.5 μg/ml	BMC Microbiol. 2013 Oct 1;13:218
Mycobacterium fortuitum	>32 mg/mL (MIC)	3 days	PA-824 showed no significant inhibitory activity against M. fortuitum	Front Cell Infect Microbiol. 2023 Mar 22;13:1115530
Mycobacterium chelonae	>32 mg/mL (MIC)	3 days	PA-824 showed no significant inhibitory activity against M. chelonae	Front Cell Infect Microbiol. 2023 Mar 22;13:1115530
Mycobacterium abscessus	>32 mg/mL (MIC)	3 days	PA-824 showed no significant inhibitory activity against M. abscessus	Front Cell Infect Microbiol. 2023 Mar 22;13:1115530
Mycobacterium smegmatis	250 µM	3 hours	Investigate the metabolism of PA-824 in M. smegmatis, found that PA-824 was metabolized to six products, but no des-nitro metabolite was detected	Br J Pharmacol. 2011 Jan;162(1):226-36
Mycobacterium tuberculosis	250 µM	3 hours	Investigate the metabolism of PA-824 in M. tuberculosis, found that PA-824 was metabolized to seven products, with the major metabolite being the des-nitro product	Br J Pharmacol. 2011 Jan;162(1):226-36
Human liver S9	250 µM	3 hours	Investigate the metabolism of PA-824 in human liver S9, found that PA-824 was metabolized to four products (M1-M4), but no des-nitro metabolite was detected	Br J Pharmacol. 2011 Jan;162(1):226-36
Mycobacterium tuberculosis H37Rv	1 or 5 µM	4 weeks	To screen PA-824-resistant mutants and analyze their genotypes	Antimicrob Agents Chemother. 2015 Sep;59(9):5316-23
Mycobacterium ulcerans	16 μg/ml	60 days	To evaluate the in vitro activity of PA-824 against 29 clinical isolates of M. ulcerans, showing an MIC90 of 16 μg/ml, significantly higher than other tested drugs.	Antimicrob Agents Chemother. 2006 Jun;50(6):1921-6
Mycobacterium avium	>32 mg/mL (MIC)	7 days	PA-824 showed no significant inhibitory activity against M. avium	Front Cell Infect Microbiol. 2023 Mar 22;13:1115530
Mycobacterium xenopi	3.84 mg/mL (MIC)	7 days	Determine the minimum inhibitory concentration of PA-824 against M. xenopi	Front Cell Infect Microbiol. 2023 Mar 22;13:1115530
Mycobacterium kansasii	1.71 mg/mL (MIC)	7 days	Determine the minimum inhibitory concentration of PA-824 against M. kansasii	Front Cell Infect Microbiol. 2023 Mar 22;13:1115530
Mycobacterium tuberculosis	0.15 μg/mL (MIC99)	7 days	PA-824 showed significant inhibitory activity against M. tuberculosis	Antimicrob Agents Chemother. 2006 Oct;50(10):3350-4
Mycobacterium leprae	0 to 10 μg/ml	7 days	PA-824 had no effect on the metabolic activity of M. leprae at concentrations up to 10 μg/ml	Antimicrob Agents Chemother. 2006 Oct;50(10):3350-4
J774.1 cells	0.13 µM (IC50)	72 hours	Evaluate activity in intracellular infection model	Cell Chem Biol. 2020 Feb 20;27(2):172-185. e11
Leishmania donovani intracellular amastigotes	0.9 ± 0.1 µM (EC50)	72 hours	Evaluate the antileishmanial activity of (R)-PA-824 against L. donovani intracellular amastigotes	Antimicrob Agents Chemother. 2013 Oct;57(10):4699-706
Leishmania donovani promastigotes	0.16 ± 0.03 µM (EC50)	72 hours	Evaluate the antileishmanial activity of (R)-PA-824 against L. donovani promastigotes	Antimicrob Agents Chemother. 2013 Oct;57(10):4699-706
Leishmania donovani intracellular amastigotes	4.9 ± 0.3 µM (EC50)	72 hours	Evaluate the antileishmanial activity of (S)-PA-824 against L. donovani intracellular amastigotes	Antimicrob Agents Chemother. 2013 Oct;57(10):4699-706
Leishmania donovani promastigotes	0.9 ± 0.1 µM (EC50)	72 hours	Evaluate the antileishmanial activity of (S)-PA-824 against L. donovani promastigotes	Antimicrob Agents Chemother. 2013 Oct;57(10):4699-706
Mycobacterium tuberculosis Erdman	2, 10, 50 μg/ml	96 hours	To evaluate the activity of PA-824 against Mycobacterium tuberculosis under low-oxygen conditions. Results showed that PA-824 exhibited significant bactericidal activity at 2, 10, and 50 μg/ml, similar to metronidazole.	Antimicrob Agents Chemother. 2005 Jun;49(6):2294-301
Mycobacterium tuberculosis H37Rv	0.039-0.531 μg/ml	at least 21 days	To evaluate the in vitro activity of PA-824 against drug-sensitive and multidrug-resistant Mycobacterium tuberculosis. Results showed that PA-824 was highly active against all tested strains with MIC ≤1 μg/ml.	Antimicrob Agents Chemother. 2005 Jun;49(6):2294-301

BALB/c mice	Murine models of tuberculosis	Oral	10, 30, 100, 300, or 600 mg/kg	5 days per week for 8 weeks	Evaluate the bactericidal effect of PA-824 as monotherapy in murine models of tuberculosis. Results showed that PA-824 exhibited time- and dose-dependent bactericidal activity, but higher doses (300-600 mg/kg) led to the selection of drug-resistant mutants.	Antimicrob Agents Chemother. 2015 Jan;59(1):129-35
BALB/c mice	M. ulcerans footpad infection model	Oral gavage	100 mg/kg	5 times weekly for 4 weeks	To assess the efficacy of PA-824 monotherapy in M. ulcerans-infected mice, showing no prevention of mortality or reduction in bacterial load.	Antimicrob Agents Chemother. 2006 Jun;50(6):1921-6
BALB/c mice	Murine model of tuberculosis	Oral	100 mg/kg	5 days a week for 2 months	Evaluate the bactericidal and sterilizing activity of PA-824 in combination with moxifloxacin and pyrazinamide, showing that this combination is more effective than the standard regimen.	Antimicrob Agents Chemother. 2008 Apr;52(4):1522-4
BALB/c mice	Experimental tuberculosis model	Oral gavage	100 mg/kg	5 days per week for 6 months	To evaluate the bactericidal and sterilizing activity of PA-824 in combination with standard first-line drugs. Results showed that PA-824 alone had significant bactericidal activity over the first 2 months, but its combination with other drugs did not significantly shorten treatment duration or reduce relapse rates.	Antimicrob Agents Chemother. 2006 Aug;50(8):2621-5
BALB/c mice	Visceral leishmaniasis model	Oral	100 mg/kg	Twice daily for 5 days	Evaluate the efficacy of (R)-PA-824 in the murine model of VL, showing >99% suppression of parasite burden	Antimicrob Agents Chemother. 2013 Oct;57(10):4699-706
BALB/c mice	Murine model of tuberculosis	Oral gavage	12.5 mg/kg/day (MED), 100 mg/kg/day (MBD)	Once daily, 5 days/week, for 4 weeks	Evaluate the bactericidal activity of PA-824 in a murine model of tuberculosis, determine the minimal effective dose and minimal bactericidal dose	Antimicrob Agents Chemother. 2005 Jun;49(6):2289-93
BALB/c mice	Murine model of tuberculosis	Oral	12.5, 25, 50, 100 mg/kg/day	5 days per week for 2 to 6 months	To assess the bactericidal activity of PA-824 in combination with rifampin and/or pyrazinamide. Results showed that PA-824 at 50 and 100 mg/kg/day enhanced the activity of rifampin plus pyrazinamide in a dose-dependent manner. The combination of rifampin, PA-824 (100 mg/kg), and pyrazinamide rendered all mice culture negative after 2 months of treatment and free of relapse after 4 months of treatment.	Antimicrob Agents Chemother. 2008 Oct;52(10):3664-8
BALB/c mice	Murine model of tuberculosis	Oral	144 to 4,608 mg/kg	3, 4, 8, 12, 24, or 48 divided doses over 24 days	To evaluate the time-dependent bactericidal activity of PA-824 in a murine model of tuberculosis, results showed that the bactericidal effect of PA-824 was strongly correlated with free drug T>MIC	Antimicrob Agents Chemother. 2011 Jan;55(1):239-45
BALB/c mice	Non-tuberculous mycobacterial infection model	Oral	200 mg/kg	Once daily for 28 days	Evaluate the in vivo antibacterial activity of PA-824 against four common non-tuberculous mycobacteria. Results showed PA-824 significantly reduced the load of M. abscessus (3.12 and 2.30 log10 CFU reductions in the lungs and spleen, respectively), showed moderate inhibition against M. chelonae and M. fortuitum, but had no inhibitory effect on M. avium.	Front Cell Infect Microbiol. 2023 Mar 22;13:1115530
BALB/c mice and nude mice	Mouse footpad model	Oral	25 mg/kg and 100 mg/kg	4 weeks (5 days/week)	PA-824 had no effect on M. leprae in both BALB/c and nude mouse models	Antimicrob Agents Chemother. 2006 Oct;50(10):3350-4
Piglets	PEDV infection model	Oral	25 mg/kg, 50 mg/kg	Every 6 hours until 66 hours	Evaluating the therapeutic effect of PA-824 in piglets, results showed that PA-824 significantly alleviated clinical signs, intestinal pathological changes, and inflammatory responses.	J Virol. 2024 Jul 23;98(7):e0041323
C3HeB/FeJ mice	Latent tuberculosis infection model	Oral	50 mg/kg	5 times weekly for 2 or 4 months	To evaluate the bactericidal and sterilising activities of PA-824 against LTBI, results showed PA-824 had similar bactericidal activity as isoniazid, but all mice relapsed after 4 months of treatment.	Int J Antimicrob Agents. 2014 Dec;44(6):564-6
BALB/c mice	Murine model of tuberculosis	Oral	50 mg/kg	5 days per week for 2-6 months	To evaluate the bactericidal and sterilizing activity of PA-824 in combination with other drugs in a murine model of tuberculosis. Results showed that the combination of PA-824 with TMC207 exhibited modest antagonism in bactericidal activity, but the combination of PA-824 with PZA and MXF was superior to the standard first-line regimen.	Antimicrob Agents Chemother. 2011 Dec;55(12):5485-92
Mice	Mycobacterium tuberculosis infection model	Oral gavage	50, 100, 300 mg/kg	9 consecutive days	To evaluate the efficacy of PA-824 in a short-course mouse infection model. Results showed that PA-824 exhibited significant antituberculosis activity at all tested doses in a dose-dependent manner. PA-824 at 100 mg/kg in cyclodextrin/lecithin was as active as moxifloxacin at 100 mg/kg and isoniazid at 25 mg/kg and was slightly more active than rifampin at 20 mg/kg.	Antimicrob Agents Chemother. 2005 Jun;49(6):2294-301

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CAS No.: 187235-37-6

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CAS No.: 187235-37-6

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed