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Details

Stereochemistry ACHIRAL
Molecular Formula C7H7NO3.C6H7N3O
Molecular Weight 290.2747
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PASINIAZID

SMILES

NNC(=O)C1=CC=NC=C1.NC2=CC=C(C(O)=O)C(O)=C2

InChI

InChIKey=RKPHTRVPGYGVQD-UHFFFAOYSA-N
InChI=1S/C7H7NO3.C6H7N3O/c8-4-1-2-5(7(10)11)6(9)3-4;7-9-6(10)5-1-3-8-4-2-5/h1-3,9H,8H2,(H,10,11);1-4H,7H2,(H,9,10)

HIDE SMILES / InChI

Molecular Formula C7H7NO3
Molecular Weight 153.1354
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H7N3O
Molecular Weight 137.1393
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/13595397 | https://www.drugs.com/international/pasiniazid.html | https://www.ncbi.nlm.nih.gov/pubmed/28131606 | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1553312b-ed76-421c-a055-2579bdcf366c#i4i_indications_id_indications | http://www.drugbank.ca/drugs/DB00233 | https://www.ncbi.nlm.nih.gov/pubmed/15151838

Pasiniazid is a composition of isoniazid and 4-aminosalicylic acid, that has mutual effects coupling isoniazid and 4-aminosalicylic acid for use in tuberculosis patients. Isoniazid is a bactericidal agent active against organisms of the genus Mycobacterium, specifically M. tuberculosis, M. bovis and M. kansasii. Isoniazid is a prodrug and must be activated by bacterial catalase. Isoniazid inhibits InhA, the enoyl reductase from Mycobacterium tuberculosis, by forming a covalent adduct with the NAD cofactor. 4-Aminosalicylic acid is an anti-tuberculosis drug used to treat tuberculosis in combination with other active agents. There are two mechanisms responsible for aminosalicylic acid's bacteriostatic action against Mycobacterium tuberculosis. Firstly, aminosalicylic acid inhibits folic acid synthesis (without potentiation with antifolic compounds). The binding of para-aminobenzoic acid to pteridine synthetase acts as the first step in the folic acid synthesis. Aminosalicylic acid binds pteridine synthetase with greater affinity than para-aminobenzoic acid, effectively inhibiting the synthesis of folic acid. As bacteria are unable to use external sources of folic acid, cell growth and multiplication slow. Secondly, the aminosalicylic acid may inhibit the synthesis of the cell wall component, mycobactin, thus reducing iron uptake by M. tuberculosis.

Originator

Sources: Bulletin de la Societe Chimique de France, Volume 47, Pages 290, Journal

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.75 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Jieheqing

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A comparison of isoniazid-cycloserine with isoniazid-PAS in the therapy of cavitary pulmonary tuberculosis. X. A report of the Veterans Administration-Armed Forces cooperative study.
1960 Jun
Patents

Patents

Sample Use Guides

A single oral dose of 1200 mg pasiniazide and dipasic tablets was given according to a cross over design.
Route of Administration: Oral
Minimum inhibitory concentration (MIC) determination. Inocula were prepared from actively growing bacteria collected from LJ slants or Middlebrook 7H10 agar plates. Inocula were adjusted with saline to a cell density of 1.5 x 10^8 cells/mL (0.5 McFarland standard) and were then diluted (1:200) using CA-MHB for RGM or CAMHB+ 5% ADC supplement (CA-MHB-S) for SGM. Dipasic (Pasiniazid) were serially diluted two-fold in 100 μL of CA-MHB or CA-MHB-S. The final reaction volume was 200 μL (100 μL of the antibiotic solution and 100 μL of the bacterial suspension). Three negative controls were used as part of this study: medium without antibiotics was used to determine the addition time for alamarBlue; Medium without inoculum was used to determine the interference to alamarBlue by the medium; and a series of concentration gradients for Dipasic were used to determine the interference to alamarBlue by the drug–medium mixture colour. The plates were sealed in individual Ziploc bags and were incubated at 37 °C. After 24 h for RGM or 6 days for SGM, the first drug-free growth control wells were examined using an indicator (20 μL of alamarBlue and 50 μL of sterile 5% Tween-80). The plateswere then re-incubated for 24 h. If the control well changed to a pink colour, all of the wells containing drugs were supplemented with the indicator. After a further 24 h of incubation, the colour of all of the wells was recorded. Each MIC for the tested drug was recorded on a daily basis between the third and sixth days for RGM and between the seventh and eleventh days for SGM. The MIC was defined as the lowest drug concentration that prevented a change in colour.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:00:12 UTC 2023
Edited
by admin
on Fri Dec 15 15:00:12 UTC 2023
Record UNII
83J17CN0MN
Record Status Validated (UNII)
Record Version
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Name Type Language
PASINIAZID
INN   WHO-DD  
INN  
Official Name English
FINTOZID
Brand Name English
ISONIAZID P-AMINO-SALICYLATE
Common Name English
ISONICOTINIC ACID HYDRAZIDE, MONO(4-AMINOSALICYLATE)
Common Name English
NSC-758447
Code English
ISONIAZID 4-AMINOSALICYLATE [MI]
Common Name English
PASINIAZIDE
Common Name English
P-AMINOSALICYLIC ACID ISONICOTINYL HYDRAZIDE
Common Name English
PARANIAZIDE
Common Name English
ISONIAZID 4-AMINOSALICYLATE
MI  
Common Name English
GEWO-399
Code English
PASHAIN
Brand Name English
ISONICOTINIC ACID HYDRAZIDE P-AMINOSALICYLATE
Common Name English
RD 328
Code English
4-PYRIDINECARBOXYLIC ACID, HYDRAZIDE, MONO(4-AMINO-2-HYDROXYBENZOATE)
Common Name English
SALICYLIC ACID, 4-AMINO-, COMPD. WITH ISONICOTINIC ACID HYDRAZIDE
Common Name English
BENZOIC ACID, 4-AMINO-2-HYDROXY-, COMPD. WITH 4-PYRIDINECARBOXYLIC ACID HYDRAZIDE (1:1)
Common Name English
PARASAL INH
Common Name English
4-PYRIDINECARBOXYLIC ACID, HYDRAZIDE, COMPD. WITH 4-AMINO-2-HYDROXYBENZOATE (1:1)
Common Name English
RD-328
Code English
NIDRAPAS
Brand Name English
DIPASIC
Brand Name English
PAS-HIDRACIDA
Common Name English
Pasiniazid [WHO-DD]
Common Name English
SALICYLIC ACID, 4-AMINO-, COMPD. WITH ISONICOTINIC ACID HYDRAZIDE (1:1)
Common Name English
pasiniazid [INN]
Common Name English
PASCIDABER
Brand Name English
Code System Code Type Description
SMS_ID
100000083000
Created by admin on Fri Dec 15 15:00:12 UTC 2023 , Edited by admin on Fri Dec 15 15:00:12 UTC 2023
PRIMARY
FDA UNII
83J17CN0MN
Created by admin on Fri Dec 15 15:00:12 UTC 2023 , Edited by admin on Fri Dec 15 15:00:12 UTC 2023
PRIMARY
PUBCHEM
16367
Created by admin on Fri Dec 15 15:00:12 UTC 2023 , Edited by admin on Fri Dec 15 15:00:12 UTC 2023
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MERCK INDEX
m6502
Created by admin on Fri Dec 15 15:00:12 UTC 2023 , Edited by admin on Fri Dec 15 15:00:12 UTC 2023
PRIMARY Merck Index
MESH
C008767
Created by admin on Fri Dec 15 15:00:12 UTC 2023 , Edited by admin on Fri Dec 15 15:00:12 UTC 2023
PRIMARY
ECHA (EC/EINECS)
218-183-2
Created by admin on Fri Dec 15 15:00:12 UTC 2023 , Edited by admin on Fri Dec 15 15:00:12 UTC 2023
PRIMARY
INN
472
Created by admin on Fri Dec 15 15:00:12 UTC 2023 , Edited by admin on Fri Dec 15 15:00:12 UTC 2023
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NSC
758447
Created by admin on Fri Dec 15 15:00:12 UTC 2023 , Edited by admin on Fri Dec 15 15:00:12 UTC 2023
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EPA CompTox
DTXSID50174700
Created by admin on Fri Dec 15 15:00:12 UTC 2023 , Edited by admin on Fri Dec 15 15:00:12 UTC 2023
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NCI_THESAURUS
C175185
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CAS
2066-89-9
Created by admin on Fri Dec 15 15:00:12 UTC 2023 , Edited by admin on Fri Dec 15 15:00:12 UTC 2023
PRIMARY
EVMPD
SUB09635MIG
Created by admin on Fri Dec 15 15:00:12 UTC 2023 , Edited by admin on Fri Dec 15 15:00:12 UTC 2023
PRIMARY
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