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Prothionamide

Prothionamide structure

CAS No:
14222-60-7
Formula:
C9H12N2S
Chemical Name:
Prothionamide
Synonyms:
4-Pyridinecarbothioamide,2-propyl-;Isonicotinamide,2-propylthio-;2-Propyl-4-pyridinecarbothioamide;2-Propylthioisonicotinamide;Prothionamide;Trevintix;Ektebin;Protionamid;2-Propylisonicotinylthioamide;9778 R. P.;Tebeform;1321TH;Tuberex;Protion;Protionamide;Protionizina;TH 1321;RP 9778;2-Propylpyridine-4-thiocarboxamide;Peteha;Tuberamin;2-Propylpyridine-4-carboimidothioic acid
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

Protionamide is Yellow Solid

Prothionamide is a member of pyridines.|Prothionamide has been used in trials studying the treatment of MDR-TB and HIV Infections.|Protionamide is a thioamide derivative with antitubercular activity. Protionamide forms a covalent adduct with bacterial nicotinamide adenine dinucleotide (NAD), PTH-NAD, which competitively inhibits 2-trans-enoyl-ACP reductase (inhA), an enzyme essential for mycolic acid synthesis. This results in increased cell wall permeability and decreased resistance against cell injury eventually leading to cell lysis. Mycolic acids, long-chain fatty acids, are essential mycobacterial cell wall components and play a key role in resistance to cell injury and mycobacterial virulence.|Antitubercular agent similar in action and side effects to ETHIONAMIDE. It is used mostly in combination with other agents.

Prothionamide Basic Attributes

Molecular Weight：

180.27

Exact Mass：

180.27

EC Number：

238-093-7

UNII：

76YOO33643

NSC Number：

758962

DSSTox ID：

DTXSID7045940

NCI Thesaurus Code：

C72605

ATC Code：

J - Antiinfectives for systemic use

HScode：

2933399090

Characteristics

PSA：

XLogP3：

1.5

Density：

1.1015 (rough estimate)

Melting Point：

136.7 °C

Boiling Point：

310.4±44.0 °C(Predicted)

Flash Point：

141.5±28.4 °C

Refractive Index：

1.5300 (estimate)

Storage Conditions：

Refrigerator

Toxicity：

LD50 in mice, rats (g/kg): 1.0, 1.32 orally (Il'in)

Collision Cross Section：

141.3 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

RTECS Number：

NS0650000

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 129 companies from 2 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

Drugs used in the treatment of tuberculosis. They are divided into two main classes: "first-line" agents, those with the greatest efficacy and acceptable degrees of toxicity used successfully in the great majority of cases; and "second-line" drugs used in drug-resistant cases or those in which some other patient-related condition has compromised the effectiveness of primary therapy. (See all compounds classified as Antitubercular Agents.)

MeSH Entry Terms：

ektebin

Prothionamide Use and Manufacturing

Methods of Manufacturing

General procedure: THF (5ml/mmol) was added to a flask containing pyridine-4-carboxamide derivative (1 eq) at room temperature under inert atmosphere (argon) and stirring. Lawesson's reagent (1.5 eq) was added to the flask and the solution was stirred at room temperature for 48h-72h. The THF was evaporated under reduce pressure and the residue was partitioned between saturated aqueous NaHCO

Uses

An anti-tuberculosis agent. It has also been used to treat Leprosy. Antibacterial (tuberculostatic).

Computed Properties

Molecular Weight:180.27
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:180.07211956
Monoisotopic Mass:180.07211956
Topological Polar Surface Area:71
Heavy Atom Count:12
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is a derivative of isonicotinic acid. Its mechanism of action is unknown. It may have an inhibitory effect on peptide synthesis. The effect of this product on Mycobacterium tuberculosis depends on the drug concentration at the infected site. It only has an antibacterial effect at low concentrations and a bactericidal effect at high concentrations. It inhibits the synthesis of mycolic acid in Mycobacterium tuberculosis. This product has partial cross-resistance with ethionamide.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Prothionamide Enteric-coated Tablets
Ingredients	Prothionamide.
Indication	1. Taking it together with cycloserine may increase the incidence of central nervous system reactions, especially systemic convulsions. The dose should be adjusted appropriately and the central nervous system toxicity symptoms should be closely monitored. 2. The combination of this product with other anti-tuberculosis drugs may aggravate its adverse reactions. 3. This product is a vitamin B6 antagonist and can increase its renal excretion. Therefore, the requirement for vitamin B6 may increase in patients receiving prothionamide treatment.
Specifications	0.1g
Manufacturer	Liaoning PHARMA-UNION Pharmaceutical Co., Ltd.

Prothionamide

Prothionamide
Specifications	－－－－
Manufacturer	Liaoning PHARMA-UNION Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

Jiangxi Tianxu Pharmaceutical Co., Ltd.

China
Active
Jiangsu Cixing Pharmaceutical Co., Ltd.

China
Active
Liaoning PHARMA-UNION Pharmaceutical Co., Ltd.

China
Active

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